Updated on 2024/04/10

写真a

 
ABE Hiroshi
 
Organization
Institute for Glyco-core Research Professor
Graduate School of Science Professor
Graduate School
Graduate School of Science
Title
Professor
External link

Degree 1

  1. 博士(薬学) ( 2001.3   北海道大学 ) 

Research Areas 1

  1. Life Science / Bioorganic chemistry

Research History 10

  1. 名古屋大学大学院理学研究科物質理学専攻(化学系)生物化学研究室・教授

    2015.3

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    Country:Japan

  2. Nagoya University   大学院理学研究科 物質理学専攻化学系   教授

    2015.3

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  3. 北海道大学大学院薬学研究院・准教授

    2013.8 - 2015.3

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    Country:Japan

  4. 科学技術振興機構 研究領域:「脳神経回路の形成・動作と制御」・さきがけ研究員

    2011.10 - 2015.3

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    Country:Japan

  5. 科学技術振興機構   さきがけ研究員

    2011.10 - 2015.3

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  6. 独立行政法人理化学研究所   専任研究員

    2009.4 - 2013.8

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  7. 独立行政法人理化学研究所・専任研究員

    2009.4 - 2013.7

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    Country:Japan

  8. 独立行政法人理化学研究所・研究員

    2005.6 - 2009.3

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    Country:Japan

  9. 独立行政法人理化学研究所   研究員

    2005.6 - 2009.3

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  10. 米国スタンフォード大学   化学科   博士研究員

    2002.4 - 2005.5

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Education 2

  1. Hokkaido University   Graduate School, Division of Pharmaceutical Sciences

    1998.4 - 2001.3

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    Country: Japan

  2. Hokkaido University   Faculty of Pharmaceutical Science

    1988.4 - 1991.3

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    Country: Japan

Professional Memberships 2

  1. 日本薬学会

  2. 日本化学会

Committee Memberships 1

  1. 日本核酸医薬学会   幹事  

       

Awards 4

  1. 学術賞

    2021.6   日本核酸医薬学会  

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  2. 長瀬研究振興賞

    2014.4  

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  3. 第58回高分子研究発表会(神戸) ヤングサイエンティスト講演賞

    2012.7  

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  4. 理化学研究所 研究奨励賞

    2012.3  

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Papers 238

  1. Structural optimization of pseudorotaxane-forming oligonucleotides for efficient and stable complex formation

    Onizuka Kazumitsu, Miyashita Takuya, Chikuni Tomoko, Ozawa Mamiko, Abe Hiroshi, Nagatsugi Fumi

    NUCLEIC ACIDS RESEARCH   Vol. 46 ( 17 ) page: 8710 - 8719   2018.9

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1093/nar/gky744

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  2. MGST1, a GSH transferase/peroxidase essential for development and hematopoietic stem cell differentiation

    Brautigam Lars, Zhang Jie, Dreij Kristian, Spahiu Linda, Holmgren Arne, Abe Hiroshi, Tew Kenneth D., Townsend Danyelle M., Kelner Michael J., Morgenstern Ralf, Johansson Katarina

    REDOX BIOLOGY   Vol. 17   page: 171 - 179   2018.7

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    DOI: 10.1016/j.redox.2018.04.013

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  3. Chemical ligation reaction for oligonucleotides based on electrophilic phosphorothioester

    Kimura Yasuaki, Maruyama Hideto, Oikawa Ryota, Hayakawa Mayu, Abe Naoko, Tsuji Genichiro, Matsuda Akira, Shuto Satoshi, Ito Yoshihiro, Abe Hiroshi

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   Vol. 255   page: .   2018.3

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  4. Effect of sigma-pi conjugation between Si-Si bond and pyridine ring in tris(trimethylsilyl) silylpyridine on its spectroscopic property and SN2 reaction with methyl iodide

    Ichinose Wataru, Abe Hiroshi, Shuto Satoshi

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   Vol. 251   2016.3

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  5. Sustained delivery of siRNA from dopamine-coated stainless steel surfaces (vol 9, pg 6753, 2013)

    Joddar Binata, Albayrak Aydin, Kang Jeonghwa, Nishihara Mizuki, Abe Hiroshi, Ito Yoshihiro

    ACTA BIOMATERIALIA   Vol. 10 ( 8 ) page: 3811 - 3811   2014.8

  6. Development of rapid DNA templated reaction based on nucleophilic aromatic substitution reaction

    Shibata Aya, Abe Hiroshi, Uzawa Takanori, Nakano Yukiko, Shuto Satoshi, Ito Yoshihiro

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   Vol. 247   2014.3

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  7. Synthesis of active siRNA species via chemical ligation

    Maruyama Hideto, Matsuda Akira, Shuto Satoshi, Ito Yoshihiro, Abe Hiroshi

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   Vol. 247   2014.3

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  8. PEGylated antibodies and DNA in organic media and genetic PEGylation

    Tada S., Abe H., Ito Y.

    ACS Symposium Series   Vol. 1144   page: 223 - 233   2013.11

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    Publisher:ACS Symposium Series  

    Polyethylene glycol (PEG) is an amphiphilic polymer that is soluble in both water and organic media and can add many functions to biopolymers by conjugation. Here, PEG was coupled to antibodies or oligonucleotides for solubilization into organic media. The former interacted with antigens and the latter formed specific structures and had catalytic activity in organic media. In addition, we attempted to incorporate PEG genetically into a polypeptide. Although the PEG incorporation ratio decreased as the molecular weight of PEG was increased, PEG with a molecular weight of ≤1000 Da was incorporated successfully. The potential applications of PEGylated biopolymers and the methodology for gene PEGylation are discussed. © 2013 American Chemical Society.

    DOI: 10.1021/bk-2013-1144.ch016

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  9. PEGylated Antibodies and DNA in Organic Media and Genetic PEGylation

    Tada Seiichi, Abe Hiroshi, Ito Yoshihiro

    GREEN POLYMER CHEMISTRY: BIOCATALYSIS AND MATERIALS II   Vol. 1144   page: 223 - 233   2013

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  10. Peroxidase Activity of G-Quadruplex Hemin-Binding DNA Aptamers Determined by Electrochemical Measurement

    Kubo I., Eguchi T., Hoshino Y., Liu M., Abe H., Ito T.

    BIOENGINEERING BASED ON ELECTROCHEMISTRY   Vol. 50 ( 28 ) page: 1 - 7   2013

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    Publisher:ECS Transactions  

    Certain guanine-rich DNA oligomers that form a G-quadruplex structure and bind hemin inside are called hemin-binding DNA aptamers. A hemin-binding DNA aptamer with the 4c15 sequence forms a parallel G quadraplex and the PS2.M sequence folds and forms an anti-parallel structure. We propose a novel method to examine the peroxidase activity of hemin-binding DNA aptamers through electrochemical measurements. In this study, a polyA chain and thiol were introduced to the 5' terminal of each oligonucleotide. The peroxidase activity of hemin-binding DNA aptamers was determined after modifying a gold electrode with the aptamers. The distance to hemin from the surface of the electrode is most important to determine catalytic activity. Catalytic activity, shown as KM of the examined parallel DNA aptamers, was around 20 μM. 4c15 without a poly A linker showed the highest catalytic activity, and its KM was 19 μM. The KM of the anti-parallel aptamer was almost the same as that of the parallel aptamer. © The Electrochemical Society.

    DOI: 10.1149/05028.0001ecst

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  11. Development of new luminogenic probes for detection of glutathione s-transferase activity in living cells

    Ito Mika, Shibata Aya, Abe Hiroshi, Zhang Jie, Morgenstern Ralf, Shuto Satoshi, Ito Yoshihiro

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   Vol. 244   2012.8

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  12. Synthesis, structure, and biological activity of dumbbell-shaped nanocircular RNAs for RNA interference. Reviewed

    Abe N, Abe H, Nagai C, Harada M, Hatakeyama H, Harashima H, Ohshiro T, Nishihara M, Furukawa K, Maeda M, Tsuneda S, Ito Y

    Bioconjugate chemistry   Vol. 22 ( 10 ) page: 2082 - 92   2011.10

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    DOI: 10.1021/bc2003154

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  13. Creation of Polymer Catalysts by Molecular Evolutionary Engineering and Hybridization of Biocatalysts

    Liu Mingzhe, Abe Hiroshi, Ito Yoshihiro

    KOBUNSHI RONBUNSHU   Vol. 68 ( 7 ) page: 405 - 416   2011

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    Publisher:Kobunshi Ronbunshu  

    We developed a new type of oligonucleotide-based catalysts which can be called DNAzyme, ribozyme, or aptazyme. They were in vitro selected from a random sequence library of DNA or RNA for binding hemin. The selected oligonucleotides exhibited peroxidase activity by forming a complex with hemin. In addition, an azobenzene-containing oligonucleotide which bound to hemin was also selected. The binding and the catalytic activity was controlled by photo-irradiation. Subsequently, hybridized biocatalysts with synthetic polymers were synthesized. Polyethylene glycol-conjugated antibodies and oligonucleotides were synthesized and it was demonstrated that they were active in organic media. A photo-responsive polymer was also conjugated with an enzyme and its catalytic activity was controlled in organic media. © 2011, The Society of Polymer Science Japan.

    DOI: 10.1295/koron.68.405

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  14. Hemin-binding aptamers and aptazymes

    Liu M., Abe H., Ito Y.

    ACS Symposium Series   Vol. 1043   page: 111 - 123   2010.8

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    Aptamers are oligonucleotides that have been engineered through repeated rounds of in vitro selection or by the process of Systematic Evolution of Ligands by EXponential enrichment (SELEX) to bind to various molecular targets such as small molecules, proteins, nucleic acids, and even cells and tissues. Aptamers offer similar molecular recognition properties to the more commonly used antibodies. In addition to their ability to discriminate their target, aptamers offer some advantages over antibodies. For example, aptamers can be engineered completely in a test tube and are readily produced using chemical processes. On the other hand, some aptamers that have been developed exhibit enzyme activity after binding to their target molecule, and function as 'aptazymes'. Numerous aptamers and aptazymes have been used in biotechnology, diagnostics and therapy. In this study, we demonstrate that natural DNA/RNA aptamers produced by selection in vitro, not only bind to hemin, but also show peroxidase activity when in such complexes (i.e., they function as aptazymes). © 2010 American Chemical Society.

    DOI: 10.1021/bk-2010-1043.ch009

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  15. New fluorogenic probe for detection of glutathione s-transferase activity in living cells

    Ito Mika, Abe Hiroshi, Shibata Aya, Shimizu Shigeru, Alander Johan, Morgenstern Ralf, Ito Yoshihiro

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   Vol. 239   2010.3

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  16. Hemin-Binding Aptamers and Aptazymes

    Liu Mingzhe, Abe Hiroshi, Ito Yoshihiro

    GREEN POLYMER CHEMISTRY: BIOCATALYSIS AND BIOMATERIALS   Vol. 1043   page: 111 - 123   2010

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  17. Establishment of a deformable aorta model based on patient's chest CT data

    Tokuyasu T., Shuto T., Yufu K., Abe H., Marui A., Kanao S., Komeda M.

    2009 4th International Conference on Innovative Computing, Information and Control, ICICIC 2009     page: 1339 - 1342   2009.12

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    Publisher:2009 4th International Conference on Innovative Computing, Information and Control, ICICIC 2009  

    For arch aorta surgery, cardiac surgeons approach to the diseased area with median incision and stemotomy according to the operation plan based on patient's medical images. Even using latest medical diagnosis instruments, however, it is impossible to estimate the shape of aneurysm, so that operation planning plan based on medical images is hard to be perfect. As the mentioned above, cardiac surgeons can not recognize the statement of patient's aneurysm before operation. Because of difficulty to completely recognize the statement of aneurysm from patient's medical images, operation plan often has to be changed during the operation. Therefore the coauthor cardiac surgeons highly expect a diagnosis support system that enables them to observe the shape of aneurysm from any angle and to virtually palpate it in order to make more safety operation plan. Then this study aims to develop of a diagnosis assistant system by using virtual reality and haptic interface under considering realtime interaction between them. © 2009 IEEE.

    DOI: 10.1109/ICICIC.2009.194

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  18. Synthetic nanocircular RNA for controlling of gene expression. Reviewed

    Abe H, Abe N, Uda M, Tsuneda S, Ito Y

    Nucleic acids symposium series (2004)   ( 53 ) page: 65 - 6   2009

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    DOI: 10.1093/nass/nrp033

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  19. Protein detection using oligonucleotide probes. Reviewed

    Shibata A, Abe H, Furukawa K, Tsuneda S, Ito Y

    Nucleic acids symposium series (2004)   ( 53 ) page: 157 - 8   2009

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    DOI: 10.1093/nass/nrp079

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  20. In vitro selection of RNA aptamer to hemin.

    Liu M., Kagahara T., Abe H., Ito Y.

    Nucleic acids symposium series (2004)   ( 52 ) page: 513 - 514   2008.12

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    Publisher:Nucleic acids symposium series (2004)  

    A new RNA aptamer-binding hemin was synthesized by the in vitro selection (SELEX) method. A pool of 103 bases single strand DNAs containing a randomized sequence of 59 bases was synthesized. The pool was incubated with hemin on hemin-immobilized affinity column. Bound RNAs were eluted off with hemin solution and amplified by PCR. After 3 rounds of selection process, the selected RNAs were cloned and sequenced. Some RNA aptamers, which have affinity to hemin, was selected.

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  21. Nanocircular RNAs for RNA interference.

    Abe H., Abe N., Harada M., Tsuneda S., Ito Y.

    Nucleic acids symposium series (2004)   ( 52 ) page: 505 - 506   2008.12

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    Publisher:Nucleic acids symposium series (2004)  

    We designed and synthesized dumbbell-shaped nanocircular RNAs for RNA interference applications, which consist of a stem and two loops(1). RNA dumbbells are specifically recognized and cleaved by the human Dicer enzyme, and are thus transformed into double-stranded RNA in cells, although this RNA is resistant to degradation in serum. The structure was optimized to maximize its RNAi activity. The most potent activity was achieved when the stem length was 23 base pairs. The RNAi activity is prolonged by the shape of the molecule, an endless structure, compared with that of normal siRNA.

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  22. Fluorogenic probe triggered by reduction for nucleic acids sensing.

    Furukawa K., Abe H., Wang J., Oki K., Uda M., Tsuneda S., Ito Y.

    Nucleic acids symposium series (2004)   ( 52 ) page: 353 - 354   2008.12

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    A reduction-triggered fluorescence probe with a new fluorogenic compound derivatized from rhodamine 110 was developed for sensing oligonucleotides. The chemistry to activate the compound involves the reaction between the azide group of rhodamine derivatives and reducing reagents, with the fluorescence signal appearing after reduction of the azide group. The reaction proceeds under biological conditions to produce fluorescence signal within 10-20 min in the presence of target DNA or RNA. The probes were successfully applied to the detection of oligonucleotides in solution and endogenous RNA in bacterial cells.

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  23. MEDI 134-Multiple chemical ligation under thermal cycle

    Kondo Yuko, Abe Hiroshi, Jinmei Hiroshi, Abe Naoko, Aikawa Kyoko, Matsumoto Isamu, Ito Yoshihiro

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   Vol. 235   2008.4

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  24. Design and Synthesis of Biorelated Polymers by Combinatorial Bioengineering

    Ito Yoshihiro, Abe Hiroshi, Wada Akira, Liu Mingzhe

    POLYMER BIOCATALYSIS AND BIOMATERIALS II   Vol. 999   page: 194 - 215   2008

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  25. Nanocircular RNAs for RNA interference. Reviewed

    Abe H, Abe N, Harada M, Tsuneda S, Ito Y

    Nucleic acids symposium series (2004)   ( 52 ) page: 505 - 6   2008

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1093/nass/nrn256

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  26. In vitro selection of RNA aptamer to hemin. Reviewed

    Liu M, Kagahara T, Abe H, Ito Y

    Nucleic acids symposium series (2004)   ( 52 ) page: 513 - 4   2008

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    DOI: 10.1093/nass/nrn260

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  27. Multiple chemical ligation under thermal cycle. Reviewed

    Kondo Y, Abe H, Jinmei H, Abe N, Aikawa K, Matsumoto I, Ito Y

    Nucleic acids symposium series (2004)   ( 51 ) page: 353 - 4   2007

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    DOI: 10.1093/nass/nrm177

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  28. Intermolecular transfer of aminoacylated adenosine towards chemical aminoacylation of tRNA. Reviewed

    Liu M, Jinmei H, Fukuzono K, Abe H, Ito Y

    Nucleic acids symposium series (2004)   ( 51 ) page: 365 - 6   2007

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    DOI: 10.1093/nass/nrm183

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  29. Development and Comparison of 4-Thiouridine to Cytidine Base Conversion Reaction Invited Reviewed

    Sana Ohashi, Mayu Nakamura, Susit Acharyya, Masahito Inagaki, Naoko Abe, Yasuaki Kimura, Fumitaka Hashiya, Hiroshi Abe

    ACS Omegam   Vol. 9 ( 8 ) page: 9300 - 9308   2024.2

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    DOI: 10.1021/acsomega.3c08516

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  30. Development of PCR Primer Enabling the Design of Flexible Sticky Ends for Efficient Concatenation of Long DNA Fragments Reviewed

    Kohei Nomura, Kaoru Onda, Hirotaka Murase, Fumitaka Hashiya, Yukiteru Ono, Goro Terai, Natsuhisa Oka, Kiyoshi Asai, Daisuke Suzuki, Naho Takahashi, Haruka Hiraoka, Masahito Inagaki, Yasuaki Kimura, Yoshihiro Shimizu, Naoko Abe, Hiroshi Abe

    RSC Chemical Biology     2024

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry (RSC)  

    We developed chemically modified PCR primers that allow the design of flexible sticky ends by introducing a photo-cleavable group at the phosphate moiety. Nucleic acid derivatives containing o-nitrobenzyl photo-cleavable groups...

    DOI: 10.1039/d3cb00212h

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  31. Topological capture of mRNA for silencing gene expression. Reviewed International journal

    Fangjie Lyu, Takashi Tomita, Naoko Abe, Haruka Hiraoka, Fumitaka Hashiya, Yuko Nakashima, Shiryu Kajihara, Fumiaki Tomoike, Zhaoma Shu, Kazumitsu Onizuka, Yasuaki Kimura, Hiroshi Abe

    Chemical communications (Cambridge, England)   Vol. 59 ( 77 ) page: 11564 - 11567   2023.9

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    Authorship:Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:ROYAL SOC CHEMISTRY  

    We describe herein topological mRNA capture using branched oligodeoxynucleotides (ODNs) with multiple reactive functional groups. These fragmented ODNs efficiently formed topological complexes on template mRNA in vitro. In cell-based experiments targeting AcGFP mRNA, the bifurcated reactive ODNs showed a much larger gene silencing effect than the corresponding natural antisense ODN.

    DOI: 10.1039/d2cc06189a

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  32. The effect of γ phosphate modified deoxynucleotide substrates on PCR activity and fidelity. Reviewed International journal

    Fumitaka Hashiya, Hirotaka Murase, Akash Chandela, Haruka Hiraoka, Masahito Inagaki, Yuko Nakashima, Naoko Abe, Mayu Nakamura, Goro Terai, Yasuaki Kimura, Kaori Ando, Natsuhisa Oka, Kiyoshi Asai, Hiroshi Abe

    Chembiochem : a European journal of chemical biology   Vol. 24 ( 14 ) page: e202200572   2023.5

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    Controlling PCR fidelity is an important issue for molecular biology and high-fidelity PCR is essential for gene cloning. In general, fidelity control is achieved by protein engineering of polymerases. In contrast, only a few studies have reported controlling fidelity using chemically modified nucleotide substrates. In this report, we synthesized nucleotide substrates possessing a modification on Pγ and evaluated the effect of this modification on PCR fidelity. One of the substrates, nucleotide tetraphosphate, caused a modest decrease in Taq DNA polymerase activity and the effect on PCR fidelity was dependent on the type of mutation. The use of deoxyadenosine tetraphosphate enhanced the A:T→G:C mutation dramatically, which is common when using Taq polymerase. Conversely, deoxyguanosine tetraphosphate (dG4P) suppressed this mutation but increased the G:C→A:T mutation during PCR. Using an excess amount of dG4P suppressed both mutations successfully and total fidelity was improved.

    DOI: 10.1002/cbic.202200572

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  33. Synthesis of nucleoside oligophosphates by electrophilic activation of phosphorothioate. Reviewed International journal

    Shogo Hasegawa, Masahito Inagaki, Shunichi Kato, Zhenmin Li, Yasuaki Kimura, Hiroshi Abe

    Organic & biomolecular chemistry   Vol. 21 ( 19 ) page: 3997 - 4001   2023.5

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    We herein report a new synthetic method of nucleoside oligophosphates based on an electrophilic activation of 5'-phosphorothioate nucleotides. Treatment of the phosphorothioate with 2,4-dinitrochlorobenzene (DNCB) efficiently afforded the key activated...

    DOI: 10.1039/d2ob02260e

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  34. Cap analogs with a hydrophobic photocleavable tag enable facile purification of fully capped mRNA with various cap structures. Reviewed International journal

    Masahito Inagaki, Naoko Abe, Zhenmin Li, Yuko Nakashima, Susit Acharyya, Kazuya Ogawa, Daisuke Kawaguchi, Haruka Hiraoka, Ayaka Banno, Zheyu Meng, Mizuki Tada, Tatsuma Ishida, Pingxue Lyu, Kengo Kokubo, Hirotaka Murase, Fumitaka Hashiya, Yasuaki Kimura, Satoshi Uchida, Hiroshi Abe

    Nature communications   Vol. 14 ( 1 ) page: 2657 - 2657   2023.5

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    Removing immunogenic uncapped mRNA from in vitro transcribed mRNA is critical in mRNA research and clinical applications. Commonly used capping methods provide a maximum capping efficiency of around 80-90% for widely used Cap-0- and Cap-1-type mRNAs. However, uncapped and capped mRNA possesses almost identical physicochemical properties, posing challenges to their physical separation. Herein, we developed hydrophobic photocaged tag-modified cap analogs, which separated capped mRNA from uncapped mRNA by reversed-phase HPLC. Subsequent photo-irradiation recovers footprint-free native capped mRNA. This approach provided 100% capping efficiency even in Cap-2-type mRNA with versatility applicable to 650 nt and 4,247 nt mRNA. The Cap-2-type mRNA showed up to 3 to 4-fold higher translational activity in cultured cells and animals than mRNA prepared by the standard capping method. Notably, the purification process simultaneously removed immunogenic double-stranded mRNA, another major contaminant of in vitro transcribed mRNA, drastically reducing mRNA immunogenicity in cultured cells.

    DOI: 10.1038/s41467-023-38244-8

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  35. Creation of single molecular conjugates of metal-organic cages and DNA. International journal

    Toshinobu Nakajo, Shinpei Kusaka, Haruka Hiraoka, Kohei Nomura, Noriaki Matsubara, Rintaro Baba, Yuki Yoshida, Kosuke Nakamoto, Masakazu Honma, Hiroaki Iguchi, Takayuki Uchihashi, Hiroshi Abe, Ryotaro Matsuda

    Chemical communications (Cambridge, England)   Vol. 59 ( 33 ) page: 4974 - 4977   2023.4

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    Here we report the development of an equimolar conjugate of a metal-organic cage (MOC) and DNA (MOC-DNA). Several MOC-DNA conjugates were assembled into a programmed structure by coordinating with a template DNA having a complementary base sequence. Moreover, conjugation with the MOC drastically enhanced the permeability of DNA through the lipid bilayer, presenting great potential as a drug delivery system.

    DOI: 10.1039/d3cc00460k

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  36. Use of Iontophoresis Technology for Transdermal Delivery of a Minimal mRNA Vaccine as a Potential Melanoma Therapeutic. Reviewed

    Rabab A Husseini, Naoko Abe, Tomoaki Hara, Hiroshi Abe, Kentaro Kogure

    Biological & pharmaceutical bulletin   Vol. 46 ( 2 ) page: 301 - 308   2023

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    mRNA vaccines have attracted considerable attention as a result of the 2019 coronavirus pandemic; however, challenges remain regarding use of mRNA vaccines, including insufficient delivery owing to the high molecular weights and high negative charges associated with mRNA. These characteristics of mRNA vaccines impair intracellular uptake and subsequent protein translation. In the current study, we prepared a minimal mRNA vaccine encoding a tumor associated antigen human gp10025-33 peptide (KVPRNQDWL), as a potential treatment for melanoma. Minimal mRNA vaccines have recently shown promise at improving the translational process, and can be prepared via a simple production method. Moreover, we previously reported the successful use of iontophoresis (IP) technology in the delivery of hydrophilic macromolecules into skin layers, as well as intracellular delivery of small interfering RNA (siRNA). We hypothesized that combining IP technology with a newly synthesized minimal mRNA vaccine can improve both transdermal and intracellular delivery of mRNA. Following IP-induced delivery of a mRNA vaccine, an immune response is elicited resulting in activation of skin resident immune cells. As expected, combining both technologies led to potent stimulation of the immune system, which was observed via potent tumor inhibition in mice bearing melanoma. Additionally, there was an elevation in mRNA expression levels of various cytokines, mainly interferon (IFN)-γ, as well as infiltration of cytotoxic CD8+ T cells in the tumor tissue, which are responsible for tumor clearance. This is the first report demonstrating the application of IP for delivery of a minimal mRNA vaccine as a potential melanoma therapeutic.

    DOI: 10.1248/bpb.b22-00746

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  37. Chemical synthesis of super messenger RNA medicine Reviewed

    Tada Mizuki, Naoko Abe, Hiroshi Abe

    Drug Delivery System   Vol. 38 ( 1 ) page: 15 - 23   2023

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  38. Complete chemical synthesis of mRNA

    Kazuya Ogawa, Hiroshi Abe

        2022.10

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  39. Development of Fluorophosphoramidate as a Biocompatibly Transformable Functional Group and its Application as a Phosphate Prodrug for Nucleoside Analogs. International journal

    Yuki Yoshida, Ti Zheng, Wataru Tanabe, Fumiaki Tomoike, Fumitaka Hashiya, Tetsuro Suzuki, Shuto Hirota, Yuriko Saiki, Akira Horii, Akiyoshi Hirayama, Tomoyosi Soga, Yasuaki Kimura, Hiroshi Abe

    ChemMedChem   Vol. 17 ( 17 ) page: e202200188   2022.9

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    Synthetic phosphate-derived functional groups are important for controlling the function of bioactive molecules in vivo. Herein we describe the development of a new type of biocompatible phosphate analog, a fluorophosphoramidate (FPA) functional group that has characteristic P-F and P-N bonds. We found that FPA with a primary amino group was relatively unstable in aqueous solution and was converted to a monophosphate, while FPA with a secondary amino group was stable. Furthermore, by improving the molecular design of FPA, we developed a reaction in which a secondary amino group is converted to a primary amino group in the intracellular environment and clarified that the FPA group functions as a phosphate prodrug of nucleoside. Various FPA-gemcitabine derivatives were synthesized and their toxicity to cancer cells were evaluated. One of the FPA-gemcitabine derivatives showed superior toxicity compared with gemcitabine and its ProTide prodrug, which methodology is widely used in various nucleoside analogs, including anti-cancer and anti-virus drugs.

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  40. A 2'-modified uridine analog, 2'-O-(methylthiomethoxy)methyl uridine for siRNA applications Reviewed International journal

    Lyu Fangjie, Seongjin An, Yoshiaki Kobayashi, Kohei Nomura, Rintaro Baba, Naoko Abe, Haruka Hiraoka, Fumitaka Hashiya, Zhaoma Shu, Kumiko Ui-Tei, Yasuaki Kimura, Hiroshi Abe

    Bioorganic & Medicinal Chemistry Letters   Vol. 74   page: 128939 - 128939   2022.8

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    The medicinal applications of siRNAs have been intensively examined but are still hindered by their low molecular stability under biological conditions and off-target effects, etc. The introduction of chemical modifications to the nucleoside is a promising strategy for solving these limitations. Herein, we describe the development of a new uridine analog, U*, that has a (methylthiomethoxy)methoxy group at the 2' position. The phosphoramidite reagent corresponding to U* was easily synthesized and the RNA oligonucleotides containing U* were stably prepared using a standard protocol for oligonucleotide synthesis. The introduction of U* into the siRNA resulted in positive or negative effects on the targeted gene silencing in a position-dependent manner, and the positive effects were attributed to the improved stability under biological conditions. The thermodynamic analysis of the U*-modified RNAs revealed a slight destabilization of the dsRNA, based depending on which U was strategically utilized to restrain the off-target effects of the siRNA. This study describes a rare example of nucleoside analogs with a large substitution at the 2'-position in the context of an siRNA application and is informative for the development of other analogs to further improve the molecular properties of siRNAs for medicinal applications.

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  41. Design of Synthetic mRNAs for Highly Efficient Translation

    Masahito Inagaki, Mizuki Tada, Hiroshi Abe

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  42. Complete Chemical Synthesis of Minimal Messenger RNA by Efficient Chemical Capping Reaction. International journal

    Naoko Abe, Akihiro Imaeda, Masahito Inagaki, Zhenmin Li, Daisuke Kawaguchi, Kaoru Onda, Yuko Nakashima, Satoshi Uchida, Fumitaka Hashiya, Yasuaki Kimura, Hiroshi Abe

    ACS chemical biology   Vol. 17 ( 6 ) page: 1308 - 1314   2022.6

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    Site-specific chemical modification of mRNA can improve its translational efficiency and stability. For this purpose, it is desirable to develop a complete chemical synthesis method for chemically modified mRNA. The key is a chemical reaction that introduces a cap structure into the chemically synthesized RNA. In this study, we developed a fast and quantitative chemical capping reaction between 5'-phosphorylated RNA and N7-methylated GDP imidazolide in the presence of 1-methylimidazole in the organic solvent dimethyl sulfoxide. It enabled quantitative preparation of capping RNA within 3 h. We prepared chemically modified 107-nucleotide mRNAs, including N6-methyladenosine, insertion of non-nucleotide linkers, and 2'-O-methylated nucleotides at the 5' end and evaluated their effects on translational activity in cultured HeLa cells. The results showed that mRNAs with non-nucleotide linkers in the untranslated regions were sufficiently tolerant to translation and that mRNAs with the Cap_2 structure had higher translational activity than those with the Cap_0 structure.

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  43. Ligandability Assessment of Human Glutathione Transferase M1-1 Using Pesticides as Chemical Probes Reviewed

    Bodourian Charoutioun S., Poudel Nirmal, Papageorgiou Anastassios C., Antoniadi Mariana, Georgakis Nikolaos D., Abe Hiroshi, Labrou Nikolaos E.

    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES   Vol. 23 ( 7 )   2022.4

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    Glutathione transferases (GSTs; EC 2.5.1.18) form a group of multifunctional enzymes that are involved in phase II of the cellular detoxification mechanism and are associated with increased susceptibility to cancer development and resistance to anticancer drugs. The present study aims to evaluate the ligandability of the human GSTM1-1 isoenzyme (hGSTM1-1) using a broad range of struc-turally diverse pesticides as probes. The results revealed that hGSTM1-1, compared to other classes of GSTs, displays limited ligandability and ligand-binding promiscuity, as revealed by kinetic inhibition studies. Among all tested pesticides, the carbamate insecticide pirimicarb was identified as the strong-est inhibitor towards hGSTM1-1. Kinetic inhibition analysis showed that pirimicarb behaved as a mixed-type inhibitor toward glutathione (GSH) and 1-chloro-2,4-dinitrobenzene (CDNB). To shine a light on the restricted hGSTM1-1 ligand-binding promiscuity, the ligand-free crystal structure of hGSTM1-1 was determined by X-ray crystallography at 1.59 Å-resolution. Comparative analysis of ligand-free structure with the available ligand-bound structures allowed for the study of the enzyme’s plasticity and the induced-fit mechanism operated by hGSTM1-1. The results revealed important structural features of the H-site that contribute to xenobiotic-ligand binding and specificity. It was concluded that hGSTM1-1 interacts preferentially with one-ring aromatic compounds that bind at a discrete site which partially overlaps with the xenobiotic substrate binding site (H-site). The results of the study form a basis for the rational design of new drugs targeting hGSTM1-1.

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  44. Antisense Oligonucleotide Modified with Disulfide Units Induces Efficient Exon Skipping in mdx Myotubes through Enhanced Membrane Permeability and Nucleus Internalization

    Hiraoka, Haruka, Shu, Zhaoma, Tri Le, Bao, Masuda, Keiko, Nakamoto, Kosuke, Fangjie, Lyu, Abe, Naoko, Hashiya, Fumitaka, Kimura, Yasuaki, Shimizu, Yoshihiro, Veedu, Rakesh N., Abe, Hiroshi

    Chembiochem   Vol. 22 ( 24 ) page: 3437 - 3442   2021.12

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    DOI: 10.1002/cbic.202100413

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  45. Complete chemical synthesis of long DNA transcriptable in human cells

    Kazuki Yamaoka, Ryota Oikawa, Naoko Abe, Kosuke Nakamoto, Fumiaki Tomoike, Fumitaka Hashiya, Yasuaki Kimura, Hiroshi Abe

    ChemBioChem   Vol. 22 ( 23 ) page: 3273 - 3276   2021.12

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    DOI: 10.1002/cbic.202100312

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  46. Variety of nucleotide polymerase mutants aiming to synthesize modified RNA

    Sana Ohashi, Fumitaka Hashiya, Hiroshi Abe

    ChemBioChem   Vol. 22 ( 14 ) page: 2398 - 2406   2021.7

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    DOI: 10.1002/cbic.202100004

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  47. Structure, Synthesis and Inhibition Mechanism of Nucleoside Analogues as HIV‐1 Reverse Transcriptase Inhibitors (NRTIs)

    Yuki Yoshida, Masakazu Honma, Yasuaki Kimura, Hiroshi Abe

    ChemMedChem   Vol. 16 ( 5 ) page: 743 - 766   2021.3

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    DOI: 10.1002/cmdc.202000695

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  48. Chemical Synthesis of Circular RNAs with Phosphoramidate Linkages for Rolling‐Circle Translation

    Kosuke Nakamoto, Hiroshi Abe

    Current Protocols   Vol. 1 ( 3 ) page: e43   2021.3

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    DOI: 10.1002/cpz1.43

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  49. 化学修飾核酸の合成と核酸医薬への応用

    野村 浩平, 村瀬 裕貴, 中本 航介, 木村 康明, 阿部 奈保子, 安 成鎮, 小林 芳明, 程 久美子, 阿部 洋

    日本薬学会年会要旨集   Vol. 141年会   page: 27V05 - pm02S   2021.3

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  50. Phosphorothioate Modification of mRNA Accelerates Rate of Translation Initiation Providing More Efficient Protein Synthesis Reviewed

    Hiroshi Abe, Daisuke Kawaguchi, Ayumi Kodama, Naoko Abe, Kei Takebuchi, Fumitaka Hashiya, Fumiaki Tomoike, Kousuke Nakamoto, Yasuaki Kimura, Yoshihiro Shimizu

    Angewandte Chemie International Edition   Vol. 59 ( 40 ) page: 17403 - 17407   2020.9

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    DOI: 10.1002/anie.202007111

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  51. Free-Energy Calculation of Ribonucleic Inosines and Its Application to Nearest-Neighbor Parameters

    Shun Sakuraba, Junichi Iwakiri, Michiaki Hamada, Tomoshi Kameda, Genichiro Tsuji, Yasuaki Kimura, Hiroshi Abe, Kiyoshi Asai

    Journal of Chemical Theory and Computation   Vol. 16 ( 9 ) page: 5923 - 5935   2020.9

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  52. Developments in siRNA Modification and Ligand Conjugated Delivery To Enhance RNA Interference Ability. International journal

    Ander Maguregui, Hiroshi Abe

    Chembiochem : a European journal of chemical biology   Vol. 21 ( 13 ) page: 1808 - 1815   2020.7

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    There is great potential for siRNA in the treatment of diseases through the reduction of damaging protein translation by RNA interference. However, the delivery and cell uptake of siRNA pose a serious problem in its therapeutic application. Methods to overcome this issue include chemical modification of the siRNA duplex to improve pharmacokinetics, stability and efficacy, and conjugation to small ligand molecules to enable membrane penetration, targetability and potency. In this review, the most common modifications of siRNA will be discussed, along with ligand conjugates that are believed to be the most promising in advancing the field of targeted siRNA delivery.

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  53. Chemically synthesized circular RNAs with phosphoramidate linkages enable rolling circle translation Reviewed

    Kosuke Nakamoto, Naoko Abe, Genichiro Tsuji, Yasuaki Kimura, Fumiaki Tomoike, Yoshihiro Shimizu, Hiroshi Abe

    Chemical Communications   Vol. 56 ( 46 ) page: 6217 - 6220   2020.6

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    DOI: 10.1039/d0cc02140g

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  54. Quantification of native mRNA dynamics in living neurons using fluorescence correlation spectroscopy and reduction-triggered fluorescent probes Reviewed

    Fujita Hirotaka, Oikawa Ryota, Hayakawa Mayu, Tomoike Fumiaki, Kimura Yasuaki, Okuno Hiroyuki, Hatashita Yoshiki, Fiallos Oliveros Carolina, Bito Haruhiko, Ohshima Toshio, Tsuneda Satoshi, Abe Hiroshi, Inoue Takafumi

    JOURNAL OF BIOLOGICAL CHEMISTRY   Vol. 295 ( 23 ) page: 7923 - 7940   2020.6

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  55. Disulfide-unit Conjugation Enables Ultrafast Cytosolic Internalization of Antisense DNA and siRNA Reviewed

    Nakamoto Kosuke, Shu Zhaoma, Abe Hiroshi

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   Vol. 78 ( 5 ) page: 456 - 464   2020.5

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  56. Translational control by secondary-structure formation in mRNA in a eukaryotic system

    Kawaguchi Daisuke, Shimizu Saaya, Abe Naoko, Hashiya Fumitaka, Tomoike Fumiaki, Kimura Yasuaki, Abe Hiroshi

    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS   Vol. 39 ( 1-3 ) page: 195 - 203   2020.2

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  57. SYNTHESIS AND BIOLOGICAL EVALUATION OF NMDI14 DERIVATIVES AS ANTI-MESOTHELIOMA AGENTS Reviewed

    Hong Nhung Nguyen, Suzuki Koya, Kimura Yasuaki, Hirokawa Takatsugu, Murakami-Tonami Yuko, Abe Hiroshi

    HETEROCYCLES   Vol. 100 ( 2 ) page: 253 - 266   2020.2

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    DOI: 10.3987/COM-19-14191

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  58. A robust model for quantitative prediction of the silencing efficacy of wild-type and A-to-I edited miRNAs Reviewed

    Tian Shen, Terai Goro, Kobayashi Yoshiaki, Kimura Yasuaki, Abe Hiroshi, Asai Kiyoshi, Ui-Tei Kumiko

    RNA BIOLOGY   Vol. 17 ( 2 ) page: 264 - 280   2020.2

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  59. Intracellular Delivery of Antisense DNA and siRNA with Amino Groups Masked with Disulfide Units Reviewed

    Shu Zhaoma, Ota Azumi, Takayama Yukiya, Katsurada Yuri, Kusamori Kosuke, Abe Naoko, Nakamoto Kosuke, Tomoike Fumiaki, Tada Seiichi, Ito Yoshihiro, Nishikawa Makiya, Kimura Yasuaki, Abe Hiroshi

    CHEMICAL & PHARMACEUTICAL BULLETIN   Vol. 68 ( 2 ) page: 129 - 132   2020.2

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  60. Intracellular build-up RNAi with single-strand circular RNAs as siRNA precursors Reviewed

    Kimura Yasuaki, Shu Zhaoma, Ito Mika, Abe Naoko, Nakamoto Kosuke, Tomoike Fumiaki, Shuto Satoshi, Ito Yoshihiro, Abe Hiroshi

    CHEMICAL COMMUNICATIONS   Vol. 56 ( 3 ) page: 466 - 469   2020.1

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  61. SYNTHESIS AND BIOLOGICAL EVALUATION OF NMDI14 DERIVATIVES AS ANTI-MESOTHELIOMA AGENTS Reviewed

    Hong Nhung Nguyen, Suzuki Koya, Kimura Yasuaki, Hirokawa Takatsugu, Murakami-Tonami Yuko, Abe Hiroshi

    Heterocycles   Vol. 100 ( 2 ) page: 253 - 266   2020.1

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  62. Intracellular delivery of Antisense DNA and siRNA with amino groups masked with disulfide units Reviewed

    Zhaoma Shu, Azumi Ota, Yukiya Takayama, Yuri Katsurada, Kosuke Kusamori, Naoko Abe, Kosuke Nakamoto, Fumiaki Tomoike, Seiichi Tada, Yoshihiro Ito, Makiya Nishikawa, Yasuaki Kimura, Hiroshi Abe

    Chemical and Pharmaceutical Bulletins     2020

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  63. Intracellular Build-up RNAi with Single-Strand Circular RNAs as siRNA Precursors Reviewed

    Yasuaki Kimura, Zhaoma Shu, Mika Ito, Naoko Abe, Kosuke Nakamoto, Fumiaki Tomoike, Satoshi Shuto, Yoshihiro Ito, Hiroshi Abe

    Chemical Communications     2020

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  64. Quantification of native mRNA dynamics in living neurons using fluorescence correlation spectroscopy and reduction-triggered fluorescent probes Reviewed International journal

    Hirotaka Fujita, Ryota Oikawa, Mayu Hayakawa, Fumiaki Tomoike, Yasuaki Kimura, Hiroyuki Okuno, Yoshiki Hatashita, Carolina Fiallos Oliveros, Haruhiko Bito, Toshio Ohshima, Satoshi Tsuneda, Hiroshi Abe, Takafumi Inoue

    Journal of Biological Chemistry   Vol. in press   2020

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  65. Intracellular Delivery of Antisense DNA and siRNA with Amino Groups Masked with Disulfide Units. Reviewed

      Vol. 68 ( 2 ) page: 129 - 132   2020

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  66. Synthesis of 1,1,2-trisubstituted cyclopropane nucleosides in enantiomerically pure forms. Reviewed International journal

    Daichi Fushihara, Hayato Fukuda, Hiroshi Abe, Satoshi Shuto

    Nucleosides, nucleotides & nucleic acids   Vol. 38 ( 12 ) page: 921 - 941   2019.12

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    Due to the unique rigid and small steric feature of cyclopropane, cyclopropane nucleosides (CPNs) in which the ribose (deoxyribose) of nucleosides are replaced by a hydroxy-substituted cyclopropane, are of great biological interest. Novel 1,1,2-trisubstituted cyclopropane nucleosides were synthesized in enantiomerically pure forms as potential antiviral agents. In the synthesis, two cyclopropane tosylates, which were prepared from chiral cyclopropane lactones previously reported by us, were used effectively as common intermediates for the CPNs. These CPNs are also potentially useful as nucleoside units to incorporate into oligonucleotides in nucleic acids chemotherapy studies.

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  67. N-6-methyl adenosine in siRNA evades immune response without reducing RNAi activity Reviewed

    Imaeda Akihiro, Tomoike Fumiaki, Hayakawa Mayu, Nakamoto Kosuke, Kimura Yasuaki, Abe Naoko, Abe Hiroshi

      Vol. 38 ( 12 ) page: 972 - 979   2019.12

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  68. Translational contro by secondary-structure formation in mRNA in eukaryotic system Reviewed

    Daisuke Kawaguchi, Saaya Shimizu, Naoko Abe, Fumitaka Hashiya, Tomoike Fumiaki, Yasuaki Kimura, Hiroshi Abe

    Nucleosides, Nucleotides and Nucleic Acids     page: 1 - 9   2019.9

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  69. RNA imaging by chemical probes Invited Reviewed

    TOMOIKE Fumiaki, ABE Hiroshi

    Advanced Drug Delivery Reviews   Vol. 147   page: 44 - 58   2019.7

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    DOI: 10.1016/j.addr.2019.08.001

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  70. Disulfide-Unit Conjugation Enables Ultrafast Cytosolic Internalization of Antisense DNA and siRNA Reviewed

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   Vol. 58 ( 20 ) page: 6611 - 6615   2019.5

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    DOI: 10.1002/anie.201900993

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  71. Disulfide‐Unit Conjugation Enables Ultrafast Cytosolic Internalization of Antisense DNA and siRNA Reviewed

    Zhaoma Shu, Iku Tanaka, Azumi Ota, Daichi Fushihara, Naoko Abe, Saki Kawaguchi, Kosuke Nakamoto, Fumiaki Tomoike, Seiichi Tada, Yoshihiro Ito, Yasuaki Kimura, Hiroshi Abe

    Angewandte Chemie   Vol. 131 ( 20 ) page: 6683   2019.5

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    DOI: 10.1002/ange.201900993

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  72. A Covalent Inhibitor for Glutathione S-Transferase Pi (GSTP(1-1)) in Human Cells Reviewed

    Shishido Yuko, Tomoike Fumiaki, Kuwata Keiko, Fujikawa Haruka, Sekido Yoshitaka, Murakami-Tonami Yuko, Kameda Tomoshi, Abe Naoko, Kimura Yasuaki, Shuto Satoshi, Abe Hiroshi

    CHEMBIOCHEM   Vol. 20 ( 7 ) page: 900 - 905   2019.4

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    DOI: 10.1002/cbic.201800671

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  73. 膜透過性を有するGST共有結合性阻害剤の開発

    友池 史明, 宍戸 裕子, 藤川 遥加, 木村 康明, 桑田 啓子, 村上 優子, 福井 健二, 関戸 好孝, 矢野 貴人, 亀田 倫史, 周東 智, 阿部 洋

    日本薬学会年会要旨集   Vol. 139年会 ( 2 ) page: 80 - 80   2019.3

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  74. ウイルスタンパク質の活性をトリガーとした新規不可逆阻害剤の開発 Reviewed

    福井 竜介, 新美 結士, 片倉 秀雄, 鈴木 哲郎, 村上 努, 児玉 栄一, 木村 康明, 阿部 洋

    日本薬学会年会要旨集   Vol. 139年会 ( 2 ) page: 103 - 103   2019.3

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  75. Disulfide‐unit conjugation enables ultrafast cytosolic internalization of antisense DNA and siRNA Reviewed

    Zhaoma Shu, Iku Tanaka, Azumi Ota, Daichi Fushihara, Naoko Abe, Saki Kawaguchi, Kosuke Nakamoto, Fumiaki Tomoike, Seiichi Tada, Yoshihiro Ito, Yasuaki Kimura, Hiroshi Abe

    Angewandte Chemie International Edition   Vol. 58   page: 6611 - 6615   2019

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  76. A Covalent Inhibitor for Glutathione S‐Transferase Pi (GSTP1‐1) in Human Cells Reviewed

    Yuko Shishido, Fumiaki Tomoike, Keiko Kuwata, Haruka Fujikawa, Yoshitaka Sekido, Yuko Murakami-Tonami, Tomoshi Kameda, Naoko Abe, Yasuaki Kimura, Satoshi Shuto, Hiroshi Abe

    ChemBioChem   Vol. 20   page: 900 - 905   2019

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  77. N6-methyl adenosine in siRNA evades immune response without reducing RNAi activity Reviewed

    Akihiro Imaeda, Fumiaki Tomoike, Mayu Hayakawa, Kosuke Nakamoto, Yasuaki Kimura, Naoko Abe, Hiroshi Abe

    Nucleosides, Nucleotides and Nucleic Acids   Vol. 38   page: 6611 - 6615   2019

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  78. Nearest-neighbor parameter for inosine-cytosine pairs through a combined experimental and computational approach Reviewed

    Shun Sakuraba, Junichi Iwakiri, Michiaki Hamada, Tomoshi Kameda, Genichiro Tsuji, Yasuaki Kimura, Hiroshi Abe, Kiyoshi Asai

        2018.10

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    <title>Abstract</title>In RNA secondary structure prediction, nearest-neighbor parameters are used to determine the stability of a given structure. We derived the nearest-neighbor parameters for RNAs containing inosine-cytosine pairs. For parameter derivation, we developed a method that combines UV adsorption measurement experiments with free-energy calculations using molecular dynamics simulations. The method provides fast drop-in parameters for modified bases. Derived parameters were compared and found to be consistent with existing parameters for canonical RNAs. A duplex with an internal inosine-cytosine pair is 0.9 kcal/mol more unstable than the same duplex with an internal guanine-cytosine pair, and is as stable as the one with an internal adenine-uracil pair (only 0.1 kcal/mol more stable) on average.

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  79. Chemical ligation reaction for oligonucleotides based on electrophilic phosphorothioester Reviewed

    Kimura Yasuaki, Maruyama Hideto, Oikawa Ryota, Hayakawa Mayu, Abe Naoko, Tsuji Genichiro, Matsuda Akira, Shuto Satoshi, Ito Yoshihiro, Abe Hiroshi

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   Vol. 255   2018.3

  80. Development of glutathione S-transferase (GST) covalent inhibitor

    Shishido Yuko, Tomoike Fumiaki, Kimura Yasuaki, Kuwata Keiko, Yano Takato, Fukui Kenji, Fujikawa Haruka, Sekido Yoshitaka, Murakami-Tonami Yuko, Kameda Tomoshi, Shuto Satoshi, Abe Hiroshi

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   Vol. 255   page: .   2018.3

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  81. Nano structure design for RNA interference

    Shu Zhaoma, Abe Naoko, Tomoike Fumiaki, Kimura Yasuaki, Ito Yoshihiro, Abe Hiroshi

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   Vol. 255   page: .   2018.3

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  82. Chemical Ligation Reactions of Oligonucleotides for Biological and Medicinal Applications

    Abe Hiroshi, Kimura Yasuaki

    CHEMICAL & PHARMACEUTICAL BULLETIN   Vol. 66 ( 2 ) page: 117-122   2018.2

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  83. Development of GST (Glutathione S-transferase) covalent inhibitor

    Shishido Yuko, Sekido Yoshitaka, Murakami-Tonami Yuko, Abe Hiroshi

    CANCER SCIENCE   Vol. 109   page: 374-374   2018.1

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  84. MGST1, a GSH transferase/peroxidase essential for development and hematopoietic stem cell differentiation Reviewed

    Lars Bräutigam, Jie Zhang, Kristian Dreij, Linda Spahiu, Arne Holmgren, Hiroshi Abe, Kenneth D. Tew, Danyelle M. Townsend, Michael J. Kelner, Ralf Morgenstern, Katarina Johansson

    Redox Biology   Vol. 17   page: 171 - 179   2018

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  85. Preparation of circular RNA in vitro Reviewed

    Naoko Abe, Ayumi Kodama, Hiroshi Abe

    Methods in Molecular Biology   Vol. 1724   page: 181 - 192   2018

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    This chapter describes a simple and straightforward way to obtain single-stranded circular RNA sequences in vitro. Linear RNA that is phosphorylated at the 5′ end is first prepared by a chemical or enzymatic method, then circularized using ligase. The function of the prepared circular RNA molecule, such as an ability to induce translation, can then be investigated.

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  86. Chemical Ligation Reactions of Oligonucleotides for Biological and Medicinal Applications

    Hiroshi Abe, Yasuaki Kimura

    Chemical and Pharmaceutical Bulletin   Vol. 66 ( 2 ) page: 117 - 122   2018

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  87. Structural optimization of pseudorotaxane-forming oligonucleotides for efficient and stable complex formation Reviewed

    Kazumitsu Onizuka, Takuya Miyashita, Tomoko Chikuni, Mamiko Ozawa, Hiroshi Abe, Fumi Nagatsugi

    Nucleic Acids Research   Vol. 46   page: 8710 - 8719   2018

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  88. グルタチオン-S-トランスフェラーゼを標的とした共有結合性阻害剤の開発

    宍戸 裕子, 藤川 遥加, 友池 史明, 木村 康明, 桑田 啓子, 村上 優子, 福井 健二, 関戸 好孝, 矢野 貴人, 周東 智, 阿部 洋

    生命科学系学会合同年次大会   Vol. 2017年度   page: [3P - 0205]   2017.12

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  89. A covalent G-site inhibitor for glutathione S-transferase Pi (GSTP(1-1)) Reviewed

    Yuko Shishido, Fumiaki Tomoike, Yasuaki Kimura, Keiko Kuwata, Takato Yano, Kenji Fukui, Haruka Fujikawa, Yoshitaka Sekido, Yuko Murakami-Tonami, Tomoshi Kameda, Satoshi Shuto, Hiroshi Abe

    CHEMICAL COMMUNICATIONS   Vol. 53 ( 81 ) page: 11138 - 11141   2017.10

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    We herein report the first covalent G-site-binding inhibitor for GST, GS-ESF (1), which irreversibly inhibited the GSTP1-1 function. LC-MS/MS and X-ray structure analyses of the covalently linked GST-inhibitor complex suggested that 1 reacted with Tyr108 of GSTP1-1. The mechanism of covalent bond formation was discussed based on MD simulation results.

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  90. Tethered 1,2-Si-Group Migrations in Radical-Mediated Ring Enlargements of Cyclic Alkoxysilanes: An EPR Spectroscopic and Computational Investigation

    Walton John C., Kanada Ryutaro, Iwamoto Takeaki, Shuto Satoshi, Abe Hiroshi

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 82 ( 13 ) page: 6886-6894   2017.7

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    DOI: 10.1021/acs.joc.7b01011

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  91. Chemical ligation of oligonucleotides using an electrophilic phosphorothioester Reviewed

    Hideto Maruyama, Ryota Oikawa, Mayu Hayakawa, Shono Takamori, Yasuaki Kimura, Naoko Abe, Genichiro Tsuji, Akira Matsuda, Satoshi Shuto, Yoshihiro Ito, Hiroshi Abe

    Nucleic Acids Research   Vol. 45 ( 12 ) page: 7042-7048   2017.7

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  92. Enhancement of synergistic gene silencing by RNA interference using branched "3-in-1" trimer siRNA

    Nair Baiju G., Zhou Yue, Hagiwara Kyoji, Ueki Masashi, Isoshima Takashi, Abe Hiroshi, Ito Yoshihiro

    JOURNAL OF MATERIALS CHEMISTRY B   Vol. 5 ( 22 ) page: 4044-4051   2017.6

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  93. Pseudorotaxane formation via the slippage process with chemically cyclized oligonucleotides

    Onizuka Kazumitsu, Chikuni Tomoko, Amemiya Takuya, Miyashita Takuya, Onizuka Kyoko, Abe Hiroshi, Nagatsugi Fumi

    NUCLEIC ACIDS RESEARCH   Vol. 45 ( 9 ) page: 5036-5047   2017.5

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  94. Enhancement of synergistic gene silencing by RNA interference using branched “3-in-1” trimer siRNA Reviewed

      Vol. 5   page: 4044-4051   2017.5

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  95. Rolling Circle Translation of Circular RNA

    ABE Naoko, ABE Hiroshi

    Seibutsu Butsuri   Vol. 57 ( 1 ) page: 5 - 10   2017

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    <p>In an <i>E. coli</i> cell-free translation system, we found that a circular RNA containing an infinite open reading frame produced more translation product than its linear counterpart by two orders of magnitude, because a ribosome can work more effectively towards the elongation on circular RNA than it can on linear RNA. We then tested circular RNAs containing an infinite open reading frame could be translated in eukaryotic systems, in the absence of any particular element for internal ribosome entry, a poly-A tail, or a cap structure. We found that the circular RNAs also produced long peptides in eukaryotic translation systems, possibly owing to the rolling circle amplification mechanism.</p>

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  96. Design and Synthesis of Cyclopropane Congeners of Resolvin E2, an Endogenous Proresolving Lipid Mediator, as Its Stable Equivalents Reviewed

    Hayato Fukuda, Ryuta Muromoto, Yuuki Takakura, Kohei Ishimura, Ryutaro Kanada, Daichi Fushihara, Makoto Tanabe, Kotaro Matsubara, Toru Hirao, Koki Hirashima, Hiroshi Abe, Mitsuhiro Arisawa, Tadashi Matsuda, Satoshi Shuto

    Organic Letters   Vol. 18 ( 24 ) page: 6224 - 6227   2016.12

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    © 2016 American Chemical Society. Lipid chemical mediator resolvins with highly potent anti-inflammatory activity can be leads to develop novel anti-inflammatory drugs; however, they are unstable in oxygen due to their characteristic polyunsaturated structures. To solve the problem, CP-RvE2 has been designed and synthesized in which the cis-olefin of RvE2 was replaced with a cyclopropane. CP-RvE2s were much more stable than RvE2 against autoxidation and equipotent or more potent than RvE2. CP-RvE2s were successfully identified as stable equivalents of RvE2.

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  97. Catalytic Conversion of Lipophilic Substrates by Phase constrained Enzymes in the Aqueous or in the Membrane Phase Reviewed

    Marcus Cebula. Ilke Simek Turan, Birgitta Sjodin, Madhuranayaki Thulasingam, Joseph Brock, Volodymyr Chmyrov, Jerker Widengren, Hiroshi Abe, Bengt Mannervik, Jesper Haeggstrom, Agnes Rinaldo-Matthis, Engin Akkaya, Ralf Morgenstern

    Scientific Reports   Vol. 6   page: 38316   2016.12

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  98. Design and Synthesis of Cyclopropane Congeners of Resolvin E2, an Endogenous Proresolving Lipid Mediator, as Its Stable Equivalents Reviewed

    Hayato Fukuda, Ryuta Muromoto, Yuuki Takakura, Kohei Ishimura, Ryutaro Kanada, Daichi Fushihara, Makoto Tanabe, Kotaro Matsubara, Toru Hirao, Koki Hirashima, Hiroshi Abe, Mitsuhiro Arisawa, Tadashi Matsuda, Satoshi Shuto

    Organic Letters   Vol. 18   page: 6224-6227   2016.11

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  99. Chemical Reactivity Window Determines Prodrug Efficiency toward Glutathione Transferase Overexpressing Cancer Cells Reviewed

    Marike W. van Gisbergen, Marcus Cebula, Jie Zhang, Astrid Ottosson-Wadlund, Ludwig Dubois, Philippe Lambin, Kenneth D. Tew, Danyelle M. Townsend, Guido R. M. M. Haenen, Marie-Jose Drittij-Repders, Hisao Saneyoshi, Mika Araki, Yuko Shishido, Yoshihiro Ito, Elias S. J. Arner, Hiroshi Abe, Ralf Morgenstern, Katarina Johansson

    MOLECULAR PHARMACEUTICS   Vol. 13 ( 6 ) page: 2010 - 2025   2016.6

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    Glutathione transferases (GSTs) are often overexpressed in tumors and frequently correlated to bad prognosis and resistance against a number of different anticancer drugs. To selectively target these cells and to overcome this resistance we previously have developed prodrugs that are derivatives of existing anticancer drugs (e.g., doxorubicin) incorporating a sulfonamide moiety. When cleaved by GSTs, the prodrug releases the cytostatic moiety predominantly in GST overexpressing cells, thus sparing normal cells with moderate enzyme levels. By modifying the sulfonamide it is possible to control the rate of drug release and specifically target different GSTs. Here we show that the newly synthesized compounds, 4-acetyl-2-nitro-benzenesulfonyl etoposide (ANS-etoposide) and 4-acetyl-2-nitro-benzenesulfonyl doxorubicin (ANS-DOX), function as prodrugs for GSTA1 and MGST1 overexpressing cell lines. ANS-DOX, in particular, showed a desirable cytotoxic profile by inducing toxicity and DNA damage in a GST-dependent manner compared to control cells. Its moderate conversion of 500 nmol/min/mg, as catalyzed by GSTA1, seems hereby essential since the more reactive 2,4-dinitrobenzenesulfonyl doxorubicin (DNS-DOX) (14000 nmol/min/mg) did not display a preference for GSTA1 overexpressing cells. DNS-DOX, however, effectively killed GSTP1 (20 nmol/min/mg) and MGST1 (450 nmol/min/mg) overexpressing cells as did the less reactive 4-mononitrobenzenesulfonyl doxorubicin (MNS-DOX) in a MGST1-dependent manner (1.5 nmol/min/mg) as shown previously. Furthermore, we show that the mechanism of these prodrugs involves a reduction in GSH levels as well as inhibition of the redox regulatory enzyme thioredoxin reductase 1 (TrxR1) by virtue of their electrophilic sulfonamide moiety. TrxR1 is upregulated in many tumors and associated with resistance to chemotherapy and poor patient prognosis. Additionally, the prodrugs potentially acted as a general shuttle system for DOX, by overcoming resistance mechanisms in cells. Here we propose that GST-dependent prodrugs require a conversion rate "window" in order to selectively target GST overexpressing cells, while limiting their effects on normal cells. Prodrugs are furthermore a suitable system to specifically target GSTs and to overcome various drug resistance mechanisms that apply to the parental drug.

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  100. Chemical reactivity window determines prodrug efficiency towards glutathione transferase overexpressing cancer cells Reviewed

    Marie van Gisbergen, Marcus Cebula, Jie Zhang, Astrid Ottosson-Wadlund, Ludwig Dubois, Philippe Lambin, Kenneth D. Tew, Danyelle Townsend, Guido Haenen, Marie-Jose Drittij-Reijnders, Hisao Saneyoshi, Mika Araki, Yuko Shishido, Yoshihiro Ito, Elias Arner, Hiroshi Abe, Ralf Morgenstern, Katarina Johansson

    Molecular Pharmaceutics   Vol. 13   page: 2010-2025   2016.4

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  101. Diastereoselective Synthesis of 6″-(Z)- and 6″-(E)-Fluoro Analogues of Anti-hepatitis B Virus Agent Entecavir and Its Evaluation of the Activity and Toxicity Profile of the Diastereomers. Reviewed International journal

    Hiroki Kumamoto, Misato Fukano, Tomohiko Nakano, Keito Iwagami, Chiaki Takeyama, Satoru Kohgo, Shuhei Imoto, Masayuki Amano, Nobuyo Kuwata-Higashi, Manabu Aoki, Hiroshi Abe, Hiroaki Mitsuya, Kiyoshi Fukuhara, Kazuhiro Haraguchi

    The Journal of organic chemistry   Vol. 81 ( 7 ) page: 2827 - 2836   2016.4

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    A method for the diastereoselective synthesis of 6″-(Z)- and 6″-(E)-fluorinated analogues of the anti-HBV agent entecavir has been developed. Construction of the methylenecyclopentane skeleton of the target molecules has been accomplished by radical-mediated 5-exo-dig cyclization of the selenides 6 and 15 having the phenylsulfanylethynyl structure as a radical accepting moiety. In the radical reaction of the TBS-protected precursor 6, (Z)-anti-12 was formed as a major product. On the other hand, TIPS-protected 15 gave (E)-anti-12. The sulfur-extrusive stannylation of anti-12 furnished a mixture of geometric isomers of the respective vinylstannane, whereas benzoyl-protected 17 underwent the stannylation in the manner of retention of configuration. Following XeF2-mediated fluorination, introduction of the purine base and deoxygenation of the resulting carbocyclic guanosine gave the target (E)- and (Z)-3 after deprotection. Evaluation of the anti-HBV activity of 3 revealed that fluorine-substitution at the 6″-position of entecavir gave rise to a reduction in the cytotoxicity in HepG2 cells with retention of the antiviral activity.

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  102. Effect of sigma-pi conjugation between Si-Si bond and pyridine ring in tris(trimethylsilyl) silylpyridine on its spectroscopic property and SN2 reaction with methyl iodide Reviewed

    Ichinose Wataru, Abe Hiroshi, Shuto Satoshi

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   Vol. 251   2016.3

  103. Rolling Circle Translation of Circular RNA in Living Human Cells Reviewed

    Naoko Abe, Ken Matsumoto, Mizuki Nishihara, Yukiko Nakano, Aya Shibata, Hideto Maruyama, Satoshi Shuto, Akira Matsuda, Minoru Yoshida, Yoshihiro Ito, Hiroshi Abe

    SCIENTIFIC REPORTS   Vol. 5   page: 16435   2015.11

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    We recently reported that circular RNA is efficiently translated by a rolling circle amplification (RCA) mechanism in a cell-free Escherichia coli translation system. Recent studies have shown that circular RNAs composed of exonic sequences are abundant in human cells. However, whether these circular RNAs can be translated into proteins within cells remains unclear. In this study, we prepared circular RNAs with an infinite open reading frame and tested their translation in eukaryotic systems. Circular RNAs were translated into long proteins in rabbit reticulocyte lysate in the absence of any particular element for internal ribosome entry, a poly-A tail, or a cap structure. The translation systems in eukaryote can accept much simpler RNA as a template for protein synthesis by cyclisation. Here, we demonstrated that the circular RNA is efficiently translated in living human cells to produce abundant protein product by RCA mechanism. These findings suggest that translation of exonic circular RNAs present in human cells is more probable than previously thought.

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  104. Nickel-catalyzed Suzuki-Miyaura coupling of a tertiary iodocyclopropane with wide boronic acid substrate scope: Coupling reaction outcome depends on radical species stability Reviewed

    Keisuke Yotsuji, Naoyuki Hoshiya, Takaaki Kobayashi, Hayato Fukuda, Hiroshi Abe, Mitsuhiro Arisawa, Satoshi Shuto

    Advanced Synthesis and Catalysis   Vol. 357 ( 5 ) page: 1022 - 1028   2015.3

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    © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. We describe a nickel-catalyzed Suzuki-Miyaura arylation of a tertiary iodocyclopropane with arylboronic acids; this is an efficient and convergent strategy for providing various enantioenriched arylcyclopropanes with a quaternary stereogenic center. This is the first metal-catalyzed coupling between a tertiary alkyl electrophile and a wide range of aromatics, including heteroaromatics. We found that the outcome of the Ni-catalyzed coupling with halides as electrophiles was dependent on the stability of the radical species formed during the reaction. The use of tert-butyl alcohol (t-BuOH) as the reaction solvent was very effective, because of its stability under the radical-generating reaction conditions.

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  105. Nanostructured RNAs for RNA interference Reviewed

    Yuko Nakashima, Naoko Abe, Yoshihiro Ito, Hiroshi Abe

    RNA Interference: Challenges and Therapeutic Opportunities   Vol. 1218   page: 17 - 36   2015

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    We synthesized three types of nanostructured RNAs that induce RNA interference (RNAi): branched RNAs, dumbbell-shaped RNA, and circular double-stranded RNAs. All three nanostructured RNAs were transformed into double-stranded RNA of approximately 20 base pairs when they were treated with nuclease enzymes such as Dicer. These dsRNA species induced gene silencing when they are were introduced into mammalian cells.

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  106. Phosphorylated 5-ethynyl-2 '-deoxyuridine for advanced DNA labeling Reviewed

    Siyoong Seo, Kazumitsu Onizuka, Chieko Nishioka, Eiki Takahashi, Satoshi Tsuneda, Hiroshi Abe, Yoshihiro Ito

    ORGANIC & BIOMOLECULAR CHEMISTRY   Vol. 13 ( 15 ) page: 4589 - 4595   2015

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    The representative DNA-labeling agent 5-ethynyl-2'-deoxyuridine (EdU) was chemically modified to improve its function. Chemical monophosphorylation was expected to enhance the efficiency of the substrate in DNA polymerization by circumventing the enzymatic monophosphorylation step that consumes energy. In addition, to enhance cell permeability, the phosphates were protected with bis-pivaloyloxymethyl that is stable in buffer and plasma, and degradable inside various cell types. The phosphorylated EdU (PEdU) was less toxic than EdU, and had the same or a slightly higher DNA-labeling ability in vitro. PEdU was also successfully applied to DNA labeling in vivo. In conclusion, PEdU can be used as a less toxic DNA-labeling agent for studies that require long-term cell survival or very sensitive cell lines.

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  107. Synthesis of 3 ',4 '-difluoro-3 '-deoxyribonucleosides and its evaluation of the biological activities: Discovery of a novel type of anti-HCV agent 3 ',4 '-difluorocordycepin Reviewed

    Hisashi Shimada, Kazuhiro Haraguchi, Kumi Hotta, Tomoko Miyaike, Yasuyuki Kitagawa, Hiromichi Tanaka, Ryutaro Kaneda, Hiroshi Abe, Satoshi Shuto, Kyoko Mori, Youki Ueda, Nobuyuki Kato, Robert Snoeck, Graciela Andrei, Jan Balzarini

    BIOORGANIC & MEDICINAL CHEMISTRY   Vol. 22 ( 21 ) page: 6174 - 6182   2014.11

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    Upon reacting 3',4'-unsaturated cytosine (8 and 9) and adenine nucleosides (13 and 14) with XeF2/BF3 center dot OEt2, the respective novel 3',4'-difluoro-3'-deoxyribofuranosyl nucleosides (10-12 and 15-18) could be obtained. Formation of anti-adducts (11, 16 and 18) revealed that the fluorination involved oxonium ions as incipient intermediates. TBDMS-protected 3',4'-unsaturated adenosine provided the beta-face adducts as sole stereoisomers whereas a-face-selectivity was observed with the TBDPS-protected adenosine 14. The evaluation of the novel 3'-deoxy-3',4'-difluororibofuranosylcytosine-(19-21) and adenine nucleosides (22-25) against antitumor and antiviral activities revealed that 3',4'-difluorocordycepin (24) was found to possess anti-HCV activity. The SI of 24 was comparable to that of the anti-HCV drug ribavirin. However, sofosbuvir, FDA-approved novel anti-HCV drug, showed better SI value. Our finding revealed that the introduction of the fluoro-substituent into the 4'-position of cordycepin derivatives decreased the cytotoxicity to the host cell with retention of the antiviral activity. (C) 2014 Elsevier Ltd. All rights reserved.

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  108. Fluorogenic probes using 4-substituted-2-nitrobenzenesulfonyl derivatives as caging groups for the analysis of human glutathione transferase catalyzed reactions (vol 138, pg 7326, 2013) Reviewed

    Aya Shibata, Yukiko Nakano, Mika Ito, Mika Araki, Jie Zhang, Yasuhiko Yoshida, Satoshi Shuto, Bengt Mannervik, Ralf Morgenstern, Yoshihiro Ito, Hiroshi Abe

    ANALYST   Vol. 139 ( 17 ) page: 4382 - 4382   2014.9

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  109. Conformationally restricted GABA with bicyclo[3.1.0]hexane backbone as the first highly selective BGT-1 inhibitor Reviewed

    Takaaki Kobayashi, Akihiro Suemasa, Arisa Igawa, Soichiro Ide, Hayato Fukuda, Hiroshi Abe, Mitsuhiro Arisawa, Masabumi Minami, Satoshi Shuto

    ACS Medicinal Chemistry Letters   Vol. 5 ( 8 ) page: 889 - 893   2014.8

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    On the basis of the three-dimensional diversity-oriented conformational restriction strategy using key chiral cyclopropane units, we previously identified 3 ((2S,3R)-4-amino-3,4-methanobutyric acid) with a chiral trans-cyclopropane structure as a γ-aminobutyric acid (GABA) transporter inhibitor selective for GABA transporter (GAT) subtypes GAT-3 and BGT-1 (betaine/GABA transporter-1). Further conformational restriction of 3 with the rigid bicyclo[3.1.0]hexane backbone led to the successful development of the first highly potent and selective BGT-1 inhibitor 4 (IC50 = 0.59 μM). The bioactive conformation of 3 for BGT-1 was also identified. © 2014 American Chemical Society.

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  110. Development of Molecular Probe Targeting on Glutathion Transferase Reviewed

    Mika Ito, Satoshi Shuto, Yoshihiro Ito, Hiroshi Abe

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   Vol. 72 ( 7 ) page: 822 - 831   2014.7

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    Glutathione S-transferase (GST) are phase II enzymes that catalyze the nucleophilic attack of glutathione (GSH) to a wide range of hydrophobic and electrophilic compounds. GST is of high clinical interest in inflammation, pathophysiology and tumor drug resistance. In addition, GST is known to highly express in cancer cells. Therefore, we tried to develop new luminescent probes that can detect and image GST expression in living cells. Recently, we found that the electrophilic centre in the dinitrobenzenesulfonamide derivative is attacked by GSH and that this reaction is catalyzed by GST releasing the strong fluorophore. Based on this knowledge, we synthesized fluorescent probe, F-19 MRI probe, and bioluminogenic probe. The fluorescent probe and kinetic parameters for purified GST were giving a rate enhancement of 10(6) compared with the nonenzymatic reaction. In addition, fluorescent probe successfully image GST in living cells. The fluorescent probe is potentially useful reagent for detection of GST activity in living cells.
    F-19 MRI and bioluminogenic probes were synthesized using 4-acetyl-2-nitrobenzenesulfonyl group. F-19 MRI probe exhibited a peak shift of F-19 MRI signal and fluorescence enhancement in a bimodal way in response to GST activity. Bioluminogenic probe provided strong bioluminescence from GST activity. Moreover, both probes were successfully applied to the monitoring of GST expression in living E. coli cells. Successful detection of GST activity in living cells could be very useful for identifying tumor cells that overexpress GSTs.

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  111. Automatic Pseudorotaxane Formation Targeting on Nucleic Acids Using a Pair of Reactive Oligodeoxynucleotides Reviewed

    Kazumitsu Onizuka, Fumi Nagatsugi, Yoshihiro Ito, Hiroshi Abe

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 136 ( 20 ) page: 7201 - 7204   2014.5

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    Here we report a novel method to form a pseudorotaxane architecture using only a pair of reactive oligodeoxyribonucleotides (ODNs), which we designed and synthesized, and then performed the pseudorotaxane formation reaction with both DNA and RNA oligonucleotides. The reaction proceeded smoothly without any extra reagents at 37 degrees C and pH 7.2, leading to the formation of a stable complex on a denaturing polyacrylamide gel. Interestingly, the pseudorotaxane was formed with the cyclized ODN reversibly by the slipping process. This new pseudorotaxane formation represents a promising method for developing new DNA nanotechnologies and antisense oligonucleotides.

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  112. Development of rapid DNA templated reaction based on nucleophilic aromatic substitution reaction Reviewed

    Aya Shibata, Hiroshi Abe, Takanori Uzawa, Yukiko Nakano, Satoshi Shuto, Yoshihiro Ito

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   Vol. 247   2014.3

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  113. Synthesis of active siRNA species via chemical ligation Reviewed

    Hideto Maruyama, Akira Matsuda, Satoshi Shuto, Yoshihiro Ito, Hiroshi Abe

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   Vol. 247   2014.3

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  114. Triphenylphosphinecarboxamide: an effective reagent for the reduction of azides and its application to nucleic acid detection. Reviewed

    Saneyoshi H, Ochikubo T, Mashimo T, Hatano K, Ito Y, Abe H

    Organic letters   Vol. 16 ( 1 ) page: 30-3   2014.1

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  115. An intracellular buildup reaction of active siRNA species from short RNA fragments Reviewed

    Hideto Maruyama, Yuko Nakashima, Satoshi Shuto, Akira Matsuda, Yoshihiro Ito, Hiroshi Abe

    CHEMICAL COMMUNICATIONS   Vol. 50 ( 11 ) page: 1284 - 1287   2014

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    Here we report a new strategy for the buildup reaction of active siRNA species from short RNA fragments in living cells using a chemical ligation reaction. This strategy could decrease undesired immune responses and provide more latitude for RNAi technology in the design and concentration of introduced RNA compared to traditional siRNA methods.

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  116. Transmembrane molecular transport through nanopores formed by protein nanotubes Reviewed

    Baiju G. Nair, Yukiko Nakano, Yoshihiro Ito, Hiroshi Abe

    CHEMICAL COMMUNICATIONS   Vol. 50 ( 5 ) page: 602 - 604   2014

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    Protein nanotubes formed by layer-by-layer (LbL) assembly can penetrate cells and act as nanopores for direct transmembrane delivery of chemical compounds.

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  117. 非酵素的に高効率シグナル増幅を可能とする新規RNA検出法を開発

    柴田綾、鵜澤尊規、伊藤嘉浩、周東智、阿部洋

    化学と生物   Vol. 52 ( 11 ) page: 771-776   2014

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  118. 非酵素的に高効率シグナル増幅を可能とする新規RNA検出法を開発

    柴田 綾, 鵜澤 尊規, 伊藤 嘉浩, 周東 智, 阿部 洋

    化学と生物   Vol. 52 ( 11 ) page: 771 - 776   2014

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  119. Nanostructured RNAs for RNA interference

    Yuko Nakashima, Naoko Abe, Yoshihiro Ito, Hiroshi Abe

    Humana Press New York     page: 全   2014

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  120. グルタチオントランスフェラーゼを標的とした分子プローブの開発

    伊藤美香,周東智,伊藤嘉浩,阿部洋

    有機合成化学教会誌     page: 822   2014

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  121. Polycation-assisted DNA detection by reduction triggered fluorescence amplification probe Reviewed

    Hisao Saneyoshi, Naohiko Shimada, Atsushi Maruyama, Yoshihiro Ito, Hiroshi Abe

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   Vol. 23 ( 24 ) page: 6851 - 6853   2013.12

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    We have developed a fluorescence detection system for DNA, assisted by a comb-type cationic polymer (PLL-g-DX), for accelerating the reaction turnover. The combination of fluorogenic DNA probes with a comb-type cationic polymer has been demonstrated to be an effective means of signal amplification during the detection process. The method described herein represents a simple and enzyme-free detection. (C) 2013 Elsevier Ltd. All rights reserved.

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  122. Synthesis of novel 4′-C-methyl-1′,3′-dioxolane pyrimidine nucleosides and evaluation of its anti-HIV-1 activity Reviewed

    Yutaka Kubota, Yuri Kaneda, Kazuhiro Haraguchi, Mirei Mizuno, Hiroshi Abe, Satoshi Shuto, Takayuki Hamasaki, Masanori Baba, Hiromichi Tanaka

    Tetrahedron   Vol. 69 ( 51 ) page: 10884 - 10892   2013.12

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  123. An epidermal growth factor derivative with binding affinity for hydroxyapatite and titanium surfaces Reviewed

    Jeonghwa Kang, Seiichi Tada, Makoto Sakuragi, Hiroshi Abe, Reiko Ito, Junko Ishikawa, Shino Kurata, Takashi Kitajima, Tae Il Son, Toshiro Aigaki, Yoshihiro Ito

    BIOMATERIALS   Vol. 34 ( 38 ) page: 9747 - 9753   2013.12

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    An epidermal growth factor (EGF) derivative with affinity for apatite and titanium surfaces was designed using a peptide moiety derived from salivary statherin, a protein that adheres to hydroxyapatite. Since the active sequence has two phosphoserine residues, the EGF derivative was prepared by organic synthesis, and a 54 residue peptide was successfully prepared using this method. Circular dichroism spectra indicated that the conformation of EGF was not significantly altered by the addition of the affinity peptide sequence and the mitogenic activity was only slightly reduced when compared with the wild-type protein. However, the binding affinity of the modified EGF to hydroxyapatite and titanium was significantly higher than the unmodified EGF. The phosphate groups in the affinity sequence contributed to the affinity of modified EGF to both apatite and titanium. The modified EGF significantly enhanced the growth of cells on hydroxyapatite and titanium. It was also demonstrated that the bound EGF enhanced the signal transduction for longer periods than unbound EGF. In conclusion, the modified EGF had significantly higher binding affinity for apatite and titanium than soluble EGF, and the bound EGF significantly enhanced cell growth by long-lasting activation of intracellular signal transduction. (C) 2013 Elsevier Ltd. All rights reserved.

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  124. Very Rapid DNA-Templated Reaction for Efficient Signal Amplification and Its Steady-State Kinetic Analysis of the Turnover Cycle Reviewed

    Aya Shibata, Takanori Uzawa, Yuko Nakashima, Mika Ito, Yukiko Nakano, Satoshi Shuto, Yoshihiro Ito, Hiroshi Abe

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 135 ( 38 ) page: 14172 - 14178   2013.9

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    Oligonucleotide-templated reactions are powerful tools for the detection of nucleic acid sequences. One of the major scientific challenges associated with this technique is the rational design of non-enzyme-mediated catalytic templated reactions capable of multiple turnovers that provide high levels of signal amplification. Herein, we report the development of a nucleophilic aromatic substitution reaction-triggered fluorescent probe. The probe underwent a rapid templated reaction without any of the undesired background reactions. The fluorogenic reaction conducted in the presence of a template provided a 223-fold increase in fluorescence after 30 s compared with the nontemplated reaction. The probe provided an efficient level of signal amplification that ultimately enabled particularly sensitive levels of detection. Assuming a simple model for the templated reactions, it was possible to estimate the rate constants of the chemical reaction in the presence and in the absence of the template. From these kinetic analyses, it was possible to confirm that an efficient turnover cycle had been achieved, on the basis of the dramatic enhancement in the rate of the chemical reaction considered to be the rate-determining step. With maximized turnover efficiency, it was demonstrated that the probe could offer a high turnover number of 1500 times to enable sensitive levels of detection with a detection limit of 0.5 pM in the catalytic templated reactions.

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  125. Long-Lived Luminogenic Probe for Detection of RNA in a Crude Solution of Living Bacterial Cells Reviewed

    Hisao Saneyoshi, Yoshihiro Ito, Hiroshi Abe

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 135 ( 37 ) page: 13632 - 13635   2013.9

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    A pre-type sensitizer for a lanthanide complex on an oligonucleotide was successfully converted to a perfect final structure in a target DNA/RNA-templated reaction, without any chemical reagent or enzyme, under neutral conditions. The final form of the lanthanide oligonucleotide provided a long-lived luminescence signal, appropriate for time-gated luminescence analysis and signal amplification. Target DNA/RNA-assisted time-gated luminescence analysis is a powerful tool for elimination of autofluorescence and detection of target RNA in living bacterial cells.

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  126. Sustained delivery of siRNA from dopamine-coated stainless steel surfaces Reviewed

    Binata Joddar, Aydin Albayrak, Jeonghwa Kang, Mizuki Nishihara, Hiroshi Abe, Yoshihiro Ito

    ACTA BIOMATERIALIA   Vol. 9 ( 5 ) page: 6753 - 6761   2013.5

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    Dopamine, an adhesive protein can be covalently deposited onto biomaterials. In this study, we evaluated the ability of dopamine-coated surfaces for small interfering RNA (siRNA) immobilization and release. Dopamine was deposited onto 316L stainless steel discs either as a monolayer at acidic pH or as polydopamine at alkaline pH, following which siRNA was immobilized onto these discs. To investigate the RNA interference ability of immobilized siRNA, reduction of luciferase expression in HeLa, and reduction of Egr-1 expression and cell proliferation in human aortic smooth muscle cells (HAoSMCs) were determined. Dopamine treatment of 316L stainless steel discs under both the acidic and alkaline conditions resulted in the deposition of amino (NH2) groups, which enabled electrostatic immobilization of siRNA. The immobilized siRNA was released from both types of coatings, and enhanced the percent suppression of firefly luciferase activity of HeLa significantly up to similar to 96.5% compared to HeLa on non-dopamine controls (18%). Both the release of siRNA and the percent suppression of firefly luciferase activity were sustained for at least 7 days. In another set of experiments, siRNA sequences targeting to inhibit the activity of the transcription factor Egr-1 were eluted from dopamine-coated surfaces to HAoSMCs. Egr-1 siRNA eluted from dopamine-coated surfaces, significantly reduced the proliferation of HAoSMCs and their protein expression of Egr-1. Therefore, this method of surface immobilization of siRNA onto dopamine-coated surfaces might be effective for nucleic acid delivery from stents. (C) 2013 Acta Materialia Inc. Published by Elsevier Ltd. All rights reserved.

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  127. Nano-sized Molecule: New Approach for Diagnosis and Drug Discovery Reviewed

    Abe Hiroshi, Mizukami Shin

    YAKUGAKU ZASSHI   Vol. 133 ( 3 ) page: 349 - 349   2013.3

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  128. Nanostructured RNA for RNA Intereference Reviewed

    Hiroshi Abe

    Yakugaku Zasshi   Vol. 133 ( 3 ) page: 373 - 378   2013.3

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    RNA interference (RNAi) is a potent and highly specific gene-silencing phenomenon which is initiated or triggered by double-stranded RNAs (dsRNAs). Shortly after the development of RNAi, small interfering RNAs (siRNAs) that are 21 nucleotides in length with a 3′ nucleotide overhang were shown to be very effective in mammalian cells. Much effort has been dedicated to the application of siRNAs, both as biological tools and as therapeutic agents. Currently, synthetic siRNA would be the method of choice for clinical purposes. However, natural RNA strands are quickly degraded in biological fluids. Chemically synthesized unnatural nucleotides have been developed and introduced into the siRNA strand. For example, modification of the ribose moiety with a 2′-deoxy, 2′-O-methyl, or 2′-fluoro group, or modification of the phosphate backbone have been examined. Although these modifications improve the stability of siRNA in serum, they often cause a decrease in RNAi activity. There is also concern that unnatural RNA derivatives are toxic in the human body. A method to stabilize nontoxic natural RNA strands should be very useful for applications in RNAi technology. We came up with an idea that nano-structural design stabilizes natural RNA. We tested several new designs such as dumbbell RNA, double stranded circular RNA, or branched RNA in biological stability and RNA interference activity. Consequently, dumbbell or branched design offered prolonged RNAi effect due to high biological stability. © 2013 The Pharmaceutical Society of Japan.

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  129. Synthesis of a nucleoside phosphorodithioate analogue responsive to microenvironmental changes through chiral induction Reviewed

    Hisao Saneyoshi, Takushi Mashimo, Ken Hatano, Yoshihiro Ito, Hiroshi Abe

    TETRAHEDRON LETTERS   Vol. 54 ( 9 ) page: 1080 - 1083   2013.2

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    We have synthesized a 2'-aminomethyl branched-chain sugar nucleoside phosphorodithioate from 2,2'-anhydro uridine and subjected the material to a subsequent cyclization reaction under aqueous conditions using bi-functional linkers. The rate of the cyclization reaction was dependent on the leaving group on the bi-functional linkers. The generation of a chiral phosphorous peak from the achiral precursor, as indicated by P-31 NMR, was identified as a good indicator for potentially probing the local and global features of the DNA structure. (C) 2012 Elsevier Ltd. All rights reserved.

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  130. PEGylated Antibodies and DNA in Organic Media and Genetic PEGylation Reviewed

    Seiichi Tada, Hiroshi Abe, Yoshihiro Ito

    GREEN POLYMER CHEMISTRY: BIOCATALYSIS AND MATERIALS II   Vol. 1144   page: 223 - 233   2013

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    Polyethylene glycol (PEG) is an amphiphilic polymer that is soluble in both water and organic media and can add many functions to biopolymers by conjugation. Here, PEG was coupled to antibodies or oligonucleotides for solubilization into organic media. The former interacted with antigens and the latter formed specific structures and had catalytic activity in organic media. In addition, we attempted to incorporate PEG genetically into a polypeptide. Although the PEG incorporation ratio decreased as the molecular weight of PEG was increased, PEG with a molecular weight of &lt;= 1000 Da was incorporated successfully. The potential applications of PEGylated biopolymers and the methodology for gene PEGylation are discussed.

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  131. Fluorogenic probes using 4-substituted-2-nitrobenzenesulfonyl derivatives as caging groups for the analysis of human glutathione transferase catalyzed reactions Reviewed

    Aya Shibata, Yukiko Nakano, Mika Ito, Mika Araki, Jie Zhang, Yasuhiko Yoshida, Satoshi Shuto, Bengt Mannervik, Ralf Mogenstern, Yoshihiro Ito, Hiroshi Abe

    Analyst   Vol. 138 ( 24 ) page: 7326 - 7330   2013

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    We have synthesized a series of 4-substituted-2-nitrobenzene-sulfonyl compounds for caged fluorogenic probes and conducted a Hammett plot analysis using the steady-state kinetic parameters. The results revealed that the glutathione transferase (GST) alpha catalyzed reaction was dependent on the σ value in the same way as the non-enzymatic reaction, whereas the dependence of the σ value of the GST mu and pi was not as pronounced as that of GST alpha. © 2013 The Royal Society of Chemistry.

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  132. RNA-templated molecule release induced protein expression in bacterial cells Reviewed

    Aya Shibata, Yoshihiro Ito, Hiroshi Abe

    CHEMICAL COMMUNICATIONS   Vol. 49 ( 3 ) page: 270 - 272   2013

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    We have developed a system to release a biologically active molecule in response to the sequence of a target gene. The releasing system, which was triggered by the reduction of an azidomethyl group, was successfully applied to protein expression induced by the release of IPTG triggered by endogenous RNA in bacterial cells.

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  133. One-pot ring-closing metathesis/1,3-dipolar cycloaddition through assisted tandem ruthenium catalysis: Synthesis of a dye with isoindolo[2,1-a]quinoline structure Reviewed

    Mitsuhiro Arisawa, Yuki Fujii, Hiroshige Kato, Hayato Fukuda, Takashi Matsumoto, Mika Ito, Hiroshi Abe, Yoshihiro Ito, Satoshi Shuto

    Angewandte Chemie - International Edition   Vol. 52 ( 3 ) page: 1003 - 1007   2013

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    The one-pot tandem reaction of N-alkyl-N-allyl-2-vinylaniline derivatives with benzo- or naphthoquinones and a ruthenium-alkylidene catalyst leads to isoindolo[2,1-a]quinolines in a variety of colors, which can be altered by exchanging the substituent on the core heterocycle (see scheme). This reaction offers a new synthetic method for π-conjugated small molecules from simple aniline derivatives. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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  134. Cationic cholesterol-modified gelatin as an in vitro siRNA delivery vehicle Reviewed

    Pallavi Ananda Kadengodlu, Toshiro Aigaki, Hiroshi Abe, Yoshihiro Ito

    Molecular BioSystems   Vol. 9 ( 5 ) page: 965 - 968   2013

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    Polymeric micelle prepared through the self-assembly of cationic cholesterol-modified gelatin was tested for siRNA delivery. It exerted the desired effect of gene knockdown in HeLa cells stably expressing the luciferase gene and achieved a two-fold increase in the knockdown ability when compared to Lipofectamine® 2000. It was found that the polymeric micelle exhibited excellent stability and increased the biological stability of the siRNA in serum. © 2013 The Royal Society of Chemistry.

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  135. Rolling circle amplification in a prokaryotic translation system using small circular RNA Reviewed

    Naoko Abe, Michio Hiroshima, Hideto Maruyama, Yuko Nakashima, Yukiko Nakano, Akira Matsuda, Yasushi Sako, Yoshihiro Ito, Hiroshi Abe

    Angewandte Chemie - International Edition   Vol. 52 ( 27 ) page: 7004 - 7008   2013

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    Getting the runaround: Small circular RNA molecules containing an infinite open reading frame were synthesized and tested in an E. coli cell-free translation system. A circular RNA 126 nucleotides in length was found to produce more product than its linear counterpart by two orders of magnitude, because a ribosome can work more effectively towards the elongation on circular RNA than it can on linear RNA in this continuous peptide synthesis. Copyright © 2013 WILEY-VCH Verlag GmbH &amp
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  136. ナノ構造化RNAを用いたRNA干渉法

    阿部洋

    薬学雑誌   Vol. 133 ( 3 ) page: 373-378   2013

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  137. "PEGylated Antibodies and DNA in Organic Media and Genetic PEGylation" in "Green Polymer 2"

    Seiichi Tada, Horoshi Abe, and Yoshihiro Ito

    American Chemical Society     page: 223-233   2013

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  138. Immobilization of epidermal growth factor on titanium and stainless steel surfaces via dopamine treatment Reviewed

    Jeonghwa Kang, Makoto Sakuragi, Aya Shibata, Hiroshi Abe, Takashi Kitajima, Seiichi Tada, Masayoshi Mizutani, Hitoshi Ohmori, Hirohito Ayame, Tae Il Son, Toshiro Aigaki, Yoshihiro Ito

    MATERIALS SCIENCE & ENGINEERING C-MATERIALS FOR BIOLOGICAL APPLICATIONS   Vol. 32 ( 8 ) page: 2552 - 2561   2012.12

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    Titanium and stainless steel were modified with dopamine for the immobilization of biomolecules, epidermal growth factor (EGF). First, the treatment of metal surfaces with a dopamine solution under different pH conditions was investigated. At higher pH, the dopamine solution turned brown and formed precipitates. Treatment of the metals with dopamine at pH 8.5 also resulted in the development of brown color at the surface of the metals. The hydrophobicity of the surfaces increased after treatment with dopamine, independently of pH. X-ray photoelectron spectroscopy revealed the formation of a significant amount of an organic layer on both surfaces at pH 8.5. According to ellipsometry measurements, the organic layer formed at pH 8.5 was about 1000 times as thick as that formed at pH 4.5. The amount of amino groups in the layer formed at pH 8.5 was also higher than that observed in the layer formed at pH 4.5. EGF molecules were immobilized onto the dopamine-treated surfaces via a coupling reaction using carbodiimide. A greater amount of EGF was immobilized on surfaces treated at pH 8.5 compared with pH 4.5. Significantly higher growth of rat fibroblast cells was observed on the two EGF-immobilized surfaces compared with non-immobilized surfaces in the presence of EGF. The present study demonstrated that metals can become bioactive via the surface immobilization of a growth factor and that the effect of the immobilized growth factor on metals was greater than that of soluble growth factor. (C) 2012 Elsevier B.V. All rights reserved.

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  139. Detection of pre-mRNA splicing in vitro by an RNA-templated fluorogenic reaction Reviewed

    Yasutsugu Tamura, Kazuhiro Furukawa, Rei Yoshimoto, Yuto Kawai, Minoru Yoshida, Satoshi Tsuneda, Yoshihiro Ito, Hiroshi Abe

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   Vol. 22 ( 23 ) page: 7248 - 7251   2012.12

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    RNA splicing is an important target for basic research of disease mechanisms and for drug discovery. Here, we report a new method for analysis of the in vitro RNA splicing process that produces fluorescence using a reduction-triggered fluorescence (RETF) probe. The fluorescence signal is produced only when the two probes bind side-by-side with a specific RNA target. Precursor messenger RNA and mature messenger RNA originating from the chicken delta-crystallin (CDC) gene were successfully discriminated in solution using an RETF probe with the assistance of helper oligonucleotide strands. Also, we successfully applied RETF probes to the detection of emerging mature mRNA in an in vitro splicing process. (C) 2012 Elsevier Ltd. All rights reserved.

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  140. ナノ構造を制御したRNA干渉法

    阿部洋、阿部奈保子、柴田綾、伊藤嘉浩

    アンチセンスDNA/RNA研究会誌   Vol. 16 ( 2 ) page: 3   2012.11

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  141. Design and synthesis of indomethacin analogues that inhibit P-glycoprotein and/or multidrug resistant protein without Cox inhibitory activity Reviewed

    Mitsuhiro Arisawa, Yayoi Kasaya, Tohru Obata, Takuma Sasaki, Tomonori Nakamura, Takuya Araki, Koujirou Yamamoto, Akito Sasaki, Akihito Yamano, Mika Ito, Hiroshi Abe, Yoshihiro Ito, Satoshi Shuto

    Journal of Medicinal Chemistry   Vol. 55 ( 18 ) page: 8152 - 8163   2012.9

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    We designed and synthesized conformationally restricted analogues and regioisomers of the nonsteroidal anti-inflammatory drug indomethacin. Evaluation of the inhibitory effects of these compounds on COX, P-glycoprotein, and multidrug resistance indicated that NSAIDS modulation of multidrug-resistant P-glycoprotein and multidrug-resistant protein-1 is not associated with COX-1 and COX-2 inhibitory activities. © 2012 American Chemical Society.

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  142. Development of new luminogenic probes for detection of glutathione s-transferase activity in living cells Reviewed

    Mika Ito, Aya Shibata, Hiroshi Abe, Jie Zhang, Ralf Morgenstern, Satoshi Shuto, Yoshihiro Ito

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   Vol. 244   2012.8

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  143. Universal Caging Group for the in-Cell Detection of Glutathione Transferase Applied to 19F NMR and Bioluminogenic Probes Reviewed

    Mika Ito, Aya Shibata, Jie Zhang, Michio Hiroshima, Yasushi Sako, Yukiko Nakano, Kyoko Kojima-Aikawa, Bengt Mannervik, Satoshi Shuto, Yoshihiro Ito, Ralf Morgenstern, Hiroshi Abe

    CHEMBIOCHEM   Vol. 13 ( 10 ) page: 1428 - 1432   2012.7

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  144. 還元反応を引き金とする off/on 型蛍光プローブを用いたRNA検出法の開発

    阿部 洋, 柴田 綾, 古川 和寛, 常田 聡, 伊藤 嘉浩

    化学と生物   Vol. 50 ( 7 ) page: 540 - 544   2012.7

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  145. 環元反応を引き金とするoff/on 型蛍光プローブを用いたRNA検出法の開発

    阿部洋、柴田綾、古川和寛、常田聡、伊藤嘉浩

    化学と生物   Vol. 50 ( 7月 ) page: 540   2012.7

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  146. Oligonucleotide-Templated Reactions for Sensing Nucleic Acids Reviewed

    Aya Shibata, Hiroshi Abe, Yoshihiro Ito

    MOLECULES   Vol. 17 ( 3 ) page: 2446 - 2463   2012.3

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    Oligonucleotide-templated reactions are useful for applying nucleic acid sensing. Various chemistries for oligonucleotide-templated reaction have been reported so far. Major scientific interests are focused on the development of signal amplification systems and signal generation systems. We introduce the recent advances of oligonucleotide-templated reaction in consideration of the above two points.

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  147. Synthesis of Dumbbell-Shaped Cyclic RNAs for RNA Interference

    Naoko Abe, Hiroshi Abe, Yoshihiro Ito

    Current Protocol Nucleic Acid Chemistry     page: 1-16   2012

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  148. In vitro selection of a photo-responsive peptide aptamer using ribosome display Reviewed

    Mingzhe Liu, Seiichi Tada, Mika Ito, Hiroshi Abe, Yoshihiro Ito

    CHEMICAL COMMUNICATIONS   Vol. 48 ( 97 ) page: 11871 - 11873   2012

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    A photo-responsive peptide aptamer against microbeads immobilized streptavidin was isolated using in vitro selection combined with photo-manipulation. This is the first example of the introduction of a peptide aptamer in the photo-control of dynamic molecular recognition.

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  149. Tuning efficiency of the 4-exo-trig cyclization by the electronic effect: ring closure of 3,3-difluoro-4-pentenyl carbon radicals and synthesis of a gem-difluorocyclobutane nucleoside Reviewed

    Hiroki Kumamoto, Sachiko Kawahigashi, Hiromi Wakabayashi, Tomohiko Nakano, Tomoko Miyaike, Yasuyuki Kitagawa, Hiroshi Abe, Mika Ito, Kazuhiro Haraguchi, Jan Balzarini, Masanori Baba, Hiromichi Tanaka

    CHEMICAL COMMUNICATIONS   Vol. 48 ( 89 ) page: 10993 - 10995   2012

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    4-exo-trig Cyclization reaction of a 4-pentenyl carbon radical containing the gem-difluoromethylene moiety adjacent to a radical accepting alpha,beta-unsaturated ester was found to proceed efficiently to furnish a novel gem-difluorocyclobutane derivative. The cyclized product could be transformed into a gem-difluoromethylene analogue of oxetanocin T.

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  150. Synthesis of dumbbell-shaped cyclic RNAs for RNA interference Reviewed

    Naoko Abe, Hiroshi Abe, Yoshihiro Ito

    Current Protocols in Nucleic Acid Chemistry   Vol. 1 ( 48 ) page: 16.4.11 - 11   2012

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    RNA interference (RNAi) is a potent and highly specific gene-silencing phenomenon that was first reported for the nematode Caenorhabditis elegans. It has been discovered that genes could be silenced by introducing double-stranded RNAs (dsRNAs) complementary to the messenger RNA sequences. Since then, RNAi has been shown as an evolutionarily well-conserved process that plays an important role in host defense and in regulation of gene expression. Much effort has been dedicated to the application of the short dsRNA species (short interfering RNAs
    siRNAs) as therapeutic agents, as they were shown to be effective in mammalian cells. Recently, we altered the structure of a siRNA molecule and produced dumbbell-shaped nanocircular RNAs. RNA dumbbells were shown to be stabilized in serum compared with its siRNA counterpart, despite their natural RNA strand. It has also been found that RNA dumbbells containing a 23-bp stem and two 9-nt loops exhibit a prolonged RNAi effect in cultured mammalian cells. In this unit, we describe the synthesis of RNA dumbbells from the design, its enzymatic synthesis, and to the purification. © 2012 by John Wiley &amp
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  151. Structure Formation and Catalytic Activity of DNA Dissolved in Organic Solvents Reviewed

    Hiroshi Abe, Naoko Abe, Aya Shibata, Keiji Ito, Yoshiyuki Tanaka, Mika Ito, Hisao Saneyoshi, Satoshi Shuto, Yoshihiro Ito

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   Vol. 51 ( 26 ) page: 6475 - 6479   2012

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  152. Positively charged cholesterol-recombinant human gelatins foster the cellular uptake of proteins and murine immune reactions Reviewed

    Pallavi A. Kadengodlu, Takehisa Hebishima, Shin-Nosuke Takeshima, Mika Ito, Mingzhe Liu, Hiroshi Abe, Yoko Aida, Toshiro Aigaki, Yoshihiro Ito

    INTERNATIONAL JOURNAL OF NANOMEDICINE   Vol. 7   page: 5437 - 5450   2012

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    Purpose: Recombinant human gelatins with defined molecular weights were modified with cholesterol to make them amphiphilic in nature. We investigated the feasibility of these modified human gelatins acting as a carrier of antigenic proteins for inducing cellular immunity. The aim of this study was to synthesize novel and effective compounds for vaccine delivery in vivo.
    Methods: Two types of cholesterol-modified gelatin micelles, anionic cholesterol-modified gelatin (aCMG) and cationic-cholesterol modified gelatin (cCMG), were synthesized using different cholesterol derivatives such as the cholesterol-isocyanate (Ch-I) for aCMG and amino-modified cholesterol for cCMG. One was anionic and the other cationic, and therefore they differed in terms of their zeta potential. The aCMG and cCMG were characterized for their size, zeta potential, and in their ability to form micelles. Cytotoxicity was also evaluated. The modified human gelatins were then investigated as a carrier of antigenic proteins for inducing cellular immunity both in vitro in DC 2.4 cells, a murine dendritic cell line, as well as in vivo. The mechanism of entry of the polymeric micelles into the cells was also evaluated.
    Results: It was found that only cCMG successfully complexed with the model antigenic protein, fluorescein-isothiocyanate ovalbumin (OVA) and efficiently delivered and processed proteins in DC 2.4 cells. It was hypothesized that cCMG enter the cells predominantly by a caveolae-mediated pathway that required tyrosine kinase receptors on the cell surface. Animal testing using mice showed that the cationic cholesterol-modified gelatin complexed with OVA produced significantly high antibody titers against OVA: 2580-fold higher than in mice immunized with free OVA.
    Conclusion: Conclusively, cCMG has shown to be very effective in stimulating an immune response due to its high efficiency, stability, and negligible cytotoxicity.

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  153. Synthesis, Structure, and Biological Activity of Dumbbell-Shaped Nanocircular RNAs for RNA Interference Reviewed

    Naoko Abe, Hiroshi Abe, Chisato Nagai, Mitsuru Harada, Hiroto Hatakeyama, Hideyoshi Harashima, Takahito Ohshiro, Mizuki Nishihara, Kazuhiro Furukawa, Mizuo Maeda, Satoshi Tsuneda, Yoshihiro Ito

    BIOCONJUGATE CHEMISTRY   Vol. 22 ( 10 ) page: 2082 - 2092   2011.10

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    RNA interference (RNAi) is one of the most promising new approaches for disease therapy. The design of a dumbbell shaped nanocircular RNA allows it to act as a short interfering RNA (siRNA) precursor. To optimize the,design, we studied the relationship between the nanostructure and RNAi activity by synthesizing various RNA - dumbbells. An RNA dumbbell with a 23 bp stem and 9-nt loops was the most potent. Sequence analysis by mass spectrometry showed that Dicer could edit RNA dumbbells to siRNA species. The reaction offered the slow release of siRNA species, which conferred prolonged RNAi activity. Introduction of DNA into the loop position significantly stabilized the dumbbell in biological fluid without any loss of RNAi activity. In-depth pharmacological evaluation was performed by introducing dumbbells into HeLa cells that stably express : the target luciferase gene. The dumbbells provided a rapid silencing effect and retained this effect for a longer time even at a lower concentration than that at which standard siRNA completely lost RNAi activity. We conclude that an RNA dumbbell with DNA the most promising design for in vivo applications for RNA medicine.

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  154. Synthesis and Characterization of a Series of Highly Fluorogenic Substrates for Glutathione Transferases, a General Strategy Reviewed

    Jie Zhang, Aya Shibata, Mika Ito, Satoshi Shuto, Yoshihiro Ito, Bengt Mannervik, Hiroshi Abe, Ralf Morgenstern

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 133 ( 35 ) page: 14109 - 14119   2011.9

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    Glutathione transferases (GSTs) are used in biotechnology applications as fusion partners for facile purification and are also overexpressed in certain tumors. Consequently, there is a need for sensitive detection of the enzymes. Here we describe a general strategy for the synthesis and characterization of novel fluorogenic substrates for GSTs. The substrates were synthesized by introducing an electrophilic sulfonamide linkage to fluorescent molecules containing an amino group [e.g., 2,4-dinitrobenzenesulfonamide (DNs) derivatives of coumarin, cresyl violet, and rhodamine]. The derivatives were essentially nonfluorescent, and upon GST catalyzed cleavage of the dinitrobenzenesulfonamide, free fluorophore is released (and 1-glutathionyl-2,4-dinitrobenzene + SO(2)). All the coumarin-, cresyl violet- and rhodamine-based fluorogenic probes turned out to be good substrates for most GSTs, especially for GSTA(1-1), in terms of strong fluorescence increases (71-1200-fold), high k(cat)/K(m) values (10(4)-10(7) M(-1) s(-1)) and significant rate enhancements (10(6)-10(9)-fold). The substrates were successfully applied to quantitate very low levels of GST activity in cell extracts and DNs-cresyl violet was also successfully applied to the imaging of microsomal MGST(1) activity in living cells. The cresyl violet stained cells retained their fluorescence after fixation, which is a very useful property. In summary, we describe a general and versatile strategy to generate fluorogenic GST substrates, some of them providing the most sensitive assays so far described for GSTs.

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  155. Synthesis of 4 &apos;-Ethynyl-2 &apos;-deoxy-4 &apos;-thioribonucleosides and Discovery of a Highly Potent and Less Toxic NRTI Reviewed

    Kazuhiro Haraguchi, Hisashi Shimada, Keigo Kimura, Genta Akutsu, Hiromichi Tanaka, Hiroshi Abe, Takayuki Hamasaki, Masanori Baba, Elizabeth A. Gullen, Ginger E. Dutschman, Yung-Chi Cheng, Jan Balzarini

    ACS MEDICINAL CHEMISTRY LETTERS   Vol. 2 ( 9 ) page: 692 - 697   2011.9

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    The synthesis of 4&apos;-ethynyl-2&apos;-deoxy-4&apos;-thioribonucleosides was carried out utilizing an electrophilic glycosidation in which 4-ethynyl-4-thiofuranoid glycal 16 served as a glycosyl donor. Electrophilic glycosidation between 16 and the silylated nucleobases (N(4)-acetylcytosine, N(6)-benzoyladenine, and N(2)-acetyl-O(6)-diphenylcarbamoylguanine) was carried out in the presence of N-iodosuccinimide (NIS), leading to the exclusive formation of the desired beta-anomers 29, 33, and 36. Anti-HIV studies demonstrated that these 4&apos;-thio nucleosides were less cytotoxic to T-lymphocyte (i.e., MT-4 cells) than the corresponding 4&apos;-ethynyl derivatives of 2&apos;-deoxycytidine (44), 2&apos;-deoxyadenosine (45), and 2&apos;-deoxyguanosine (46). Comparison of the selectivity indices (SI) was made between 4&apos;-thionucleosides (32, 41, and 43) and the corresponding 4&apos;-oxygen analogues 44-46 by using the reported CC(50) and EC(50) values. In the case of cytosine and adenine nucleosides, comparable SI values were obtained as follows: 32 (545) and 44 (458); 41 (&gt;230) and 45 (1630). In contrast, 4&apos;-ethynyl-2&apos;-deoxy-4&apos;-thioguanosine 43 was found to possess a SI value of &gt;18200, which is 20 times better than that of 46 (933).

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  156. PEGylated antibody in organic media Reviewed

    Mingzhe Liu, Muye Xu, Xian Jun Loh, Hiroshi Abe, Takeshi Tsumuraya, Ikuo Fujii, Jun Li, Tae Il Son, Yoshihiro Ito

    JOURNAL OF BIOSCIENCE AND BIOENGINEERING   Vol. 111 ( 5 ) page: 564 - 568   2011.5

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    Antibodies were covalently conjugated with poly(ethylene glycol) (PEG) and the properties of the PEGylated antibodies in organic media were investigated. Two types of monoclonal antibody were used in this study. One was a monoclonal antibody (abzyme) that was prepared against a hapten mimicking a transition state of hydrolysis. Another was a monoclonal antibody against estrogen, which is not soluble in water. By electrophoresis and mass spectral analysis, the covalent conjugation with PEG chains was confirmed. The PEGylated antibodies bound to antigens and the PEGylated abzyme catalyzed a hydrolysis reaction in an aqueous solution. The PEGylated antibodies were soluble in dichloromethane and acetone and interacted with antigen either in dichloromethane or in acetone. In conclusion, PEGylated antibodies can be employed as analytical tools for water-insoluble analytes. (C) 2011, The Society for Biotechnology, Japan. All rights reserved.

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  157. Indomethacin analogues that enhance doxorubicin cytotoxicity in multidrug resistant cells without cox inhibitory activity Reviewed

    Mitsuhiro Arisawa, Yayoi Kasaya, Tohru Obata, Takuma Sasaki, Mika Ito, Hiroshi Abe, Yoshihiro Ito, Akihito Yamano, Satoshi Shuto

    ACS Medicinal Chemistry Letters   Vol. 2 ( 5 ) page: 353 - 357   2011.5

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    Conformationally restricted indomethacin analogues were designed and prepared from the corresponding 2-substituted indoles, which were synthesized by a one-pot isomerization/enamide-ene metathesis as the key reaction. Conformational analysis by calculations, NMR studies, and X-ray crystallography suggested that these analogues were conformationally restricted in the s-cis or the s-trans form due to the 2-substituent as expected. Their biological activities on cyclooxygenase-1 (COX-1) inhibition, cyclooxygenase-2 (COX-2) inhibition, and modulation of MRP-1-mediated multidrug resistance (MDR) are described. Some of these indomethacin analogues enhanced doxorubicin cytotoxicity, although they do not have any COX inhibitory activity, which suggests that the MDR-modulating effect of an NSAID can be unassociated with its COX-inhibitory activity. This may be an entry into the combination chemotherapy of doxorubicin with a MDR modulator. © 2011 American Chemical Society.

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  158. Creation of Polymer Catalysts by Molecular Evolutionary Engineering and Hybridization of Biocatalysts Reviewed

    Mingzhe Liu, Hiroshi Abe, Yoshihiro Ito

    KOBUNSHI RONBUNSHU   Vol. 68 ( 7 ) page: 405 - 416   2011

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    We developed a new type of oligonucleotide-based catalysts which can be called DNAzyme, ribozyme, or aptazyme. They were in vitro selected from a random sequence library of DNA or RNA for binding hemin. The selected oligonucleotides exhibited peroxidase activity by forming a complex with hemin. In addition, an azobenzene-containing oligonucleotide which bound to hemin was also selected. The binding and the catalytic activity was controlled by photo-irradiation. Subsequently, hybridized biocatalysts with synthetic polymers were synthesized. Polyethylene glycol-conjugated antibodies and oligonucleotides were synthesized and it was demonstrated that they were active in organic media. A photo-responsive polymer was also conjugated with an enzyme and its catalytic activity was controlled in organic media.

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  159. Branched RNA nanostructures for RNA interference Reviewed

    Yuko Nakashima, Hiroshi Abe, Naoko Abe, Kyoko Aikawa, Yoshihiro Ito

    CHEMICAL COMMUNICATIONS   Vol. 47 ( 29 ) page: 8367 - 8369   2011

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    Branched RNAs with three- or four-way junctions were designed by assembling single-stranded RNA for RNA interference. Human Dicer transformed branched RNAs into about 20 base pairs of double-stranded RNA, which is a standard siRNA species. Our tetramer design provides a potent silencing effect over a period of 5 days.

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  160. Characterization of New Potential Anticancer Drugs Designed To Overcome Glutathione Transferase Mediated Resistance Reviewed

    Katarina Johansson, Mika Ito, Carolien M. S. Schophuizen, Sherin Mathew Thengumtharayil, Vanina D. Heuser, Jie Zhang, Miyuki Shimoji, Marie Vahter, Wee Han Ang, Paul J. Dyson, Aya Shibata, Satoshi Shuto, Ito Yoshihiro, Hiroshi Abe, Ralf Morgenstern

    MOLECULAR PHARMACEUTICS   Vol. 8 ( 5 ) page: 1698 - 1708   2011

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    Resistance against anticancer drugs remains a serious obstacle in cancer treatment. Here we used novel strategies to target microsomal glutathione transferase 1 (MGST1) and glutathione transferase pi (GSTP) that are often overexpressed in tumors and confer resistance against a number of cytostatic drugs, including cisplatin and doxorubicin (DOX). By synthetically combining cisplatin with a GST inhibitor, ethacrynic add, to form ethacraplatin, it was previously shown that cytosolic GST inhibition was improved and that cells became more sensitive to cisplatin. Here we show that ethacraplatin is easily taken up by the cells and can reverse cisplatin resistance in MGST1 overexpressing MCF7 cells. A second and novel strategy to overcome GST mediated resistance involves using GST releasable cytostatic drugs. Here we synthesized two derivatives of DOX, 2,4-dinitrobenzenesulfonyl doxorubicin (DNS-DOX) and 4-mononitrobenzenesulfonyl doxorubicin (MNS-DOX) and showed that they are substrates for MGST1 and GSTP (releasing DOX). MGST1 overexpressing cells are resistant to DOX. The resistance is partially reversed by DNS-DOX Interestingly, the less reactive MNS-DOX was more cytotoxic to cells overexpressing MGST1 than control cells. It would appear that, by controlling the reactivity of the prodrug and thereby the DOX release rate, selective toxicity to MGST1 overexpressing cells can be achieved. In the case of V79 cells, DOX resistance proportional to GSTP expression levels was noted. In this case, not only was drug resistance eliminated by DNS-DOX but a striking GSTP-dependent increase in toxicity was observed in the clonogenic assay. In summary, MGST1 and GSTP resistance to cytostatic drugs can be overcome and cytotoxicity can be enhanced in GST overexpressing cells.

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  161. 進化分子工学による高分子触媒合成と生体高分子のハイブリット化

    劉明哲、阿部洋、伊藤嘉浩

    高分子論文集   Vol. 68 ( 7 ) page: 405-416   2011

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  162. Synthesis and characterization of small circular double-stranded RNAs Reviewed

    Naoko Abe, Hiroshi Abe, Takahito Ohshiro, Yuko Nakashima, Mizuo Maeda, Yoshihiro Ito

    CHEMICAL COMMUNICATIONS   Vol. 47 ( 7 ) page: 2125 - 2127   2011

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    Small circular double-stranded RNAs (dsRNAs) were synthesized. The structural analysis by atomic force microscopy gave direct images for the interpretation of the structural strain present in circular dsRNAs. Finally, we demonstrated that circular dsRNA caused RNAi effect in cells.

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  163. Fluorescence Detection of Intron Lariat RNA with Reduction-Triggered Fluorescent Probes Reviewed

    Kazuhiro Furukawa, Hiroshi Abe, Yasutsugu Tamura, Rei Yoshimoto, Minoru Yoshida, Satoshi Tsuneda, Yoshihiro Ito

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   Vol. 50 ( 50 ) page: 12020 - 12023   2011

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  164. Synthesis and properties of a novel nucleoside derivative possessing a 2,3,5,6-tetraazabenzo[cd]azulene skeleton Reviewed

    Yasuyuki Hirama, Hiroshi Abe, Noriaki Minakawa, Akira Matsuda

    TETRAHEDRON   Vol. 66 ( 43 ) page: 8402 - 8406   2010.10

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    We describe herein the synthesis and properties of the novel nucleoside derivative, 4,7-diamino-2-(2-deoxy-beta-D-erythro-pentofuranosyl)-2,6-dihydro-7H-2,3,5,6-tetraazabenzo[cd]azulene (1). The palladium catalyzed cross-coupling reaction of 2,4-diamino-5-iodo-7-(2-deoxy-beta-D-erythro-pentofuranosyl) pyrrolo[2,3-d]pyrimidine (9) with acrylonitrile afforded 2,4-diamino-5-[(E)-1-cyano-2-ethenyl]-7-(2-deoxy-beta-D-erythro-pentofuranosyl)pyrrolo[2,3-d]pyrimidine (10) in 77% yield, which was treated with NaOMe in MeOH in the presence of NaSPh to give the desired 1 in 64% yield. Whereas 1 was stable in concentrated ammonia at room temperature, it was gradually hydrolyzed in water to give 4-amino-2-(2deoxy-beta-D-erythro-pentofuranosyl)-2,6-dihydro-7H-2,3,5,6-tetraazabenzo[cd]azulen-7-one (12). Density functional calculations indicated that 12 was 20 kcal/mol more thermodynamically stable than 1 in a model study. (C) 2010 Elsevier Ltd. All rights reserved.

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  165. In vitro selection of a photoresponsive RNA aptamer to hemin Reviewed

    Mingzhe Liu, Hiroshi Jinmei, Hiroshi Abe, Yoshihiro Ito

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   Vol. 20 ( 9 ) page: 2964 - 2967   2010.5

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    A photoresponsive RNA aptamer to hemin was selected in vitro from a random sequence library of RNAs with azobenzene residues. The aptamer bound to hemin under visible light irradiation and was released by ultraviolet light. (C) 2010 Elsevier Ltd. All rights reserved.

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  166. Design and synthesis of indole derivatives of adenophostin A. A entry into subtype-selective IP<inf>3</inf> receptor ligands Reviewed

    Tetsuya Mochizuki, Akihiko Tanimura, Akihiro Nezu, Mika Ito, Hiroshi Abe, Yoshihiro Ito, Mitsuhiro Arisawa, Satoshi Shuto

    Tetrahedron Letters   Vol. 51 ( 6 ) page: 977 - 979   2010.2

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    Indole derivatives 3a and 3b of adenophostin A (2) in which the adenine of 2 was replaced with indole or 4-fluoroindole was designed as potential inositol trisphosphate receptor ligands. These target compounds were successfully synthesized from the key disaccharide unit 6. Biological evaluation showed that 3b selectively activates IP3R1, a subtype of IP3 receptors. © 2009 Elsevier Ltd. All rights reserved.

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  167. Synthesis and structural and pharmacological properties of cyclopropane-based conformationally restricted analogs of 4-methylhistamine as histamine H<inf>3</inf>/H<inf>4</inf> receptor ligands Reviewed

    Takaaki Kobayashi, Mizuki Watanabe, Akira Yoshida, Shizuo Yamada, Mika Ito, Hiroshi Abe, Yoshihiro Ito, Mituhiro Arisawa, Satoshi Shuto

    Bioorganic and Medicinal Chemistry   Vol. 18 ( 3 ) page: 1076 - 1082   2010.2

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    On the basis of the previous results on a histamine H4 receptor agonist 4-methylhistamine and a cyclopropane-based conformationally restricted analog CEIC (3) with potent H3/H4 receptor antagonistic effect, 4-methylhistamine analogs 4 and 5 of CEIC were designed and synthesized. Compound 4 showed strong affinity (Ki = 38.7 nM) for the H3 receptor, which was more potent than a well-known H3 antagonist thioperamide. Stable tautomer and conformation of 3 and 4, which can affect the pharmacological activity, were analyzed by ab initio calculations. © 2009 Elsevier Ltd. All rights reserved.

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  168. Hemin-Binding Aptamers and Aptazymes Reviewed

    Mingzhe Liu, Hiroshi Abe, Yoshihiro Ito

    GREEN POLYMER CHEMISTRY: BIOCATALYSIS AND BIOMATERIALS   Vol. 1043   page: 111 - 123   2010

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    Aptamers are oligonucleotides that have been engineered through repeated rounds of in vitro selection or by the process of Systematic Evolution of Ligands by EXponential enrichment (SELEX) to bind to various molecular targets such as small molecules, proteins, nucleic acids, and even cells and tissues. Aptamers offer similar molecular recognition properties to the more commonly used antibodies. In addition to their ability to discriminate their target, aptamers offer some advantages over antibodies. For example, aptamers can be engineered completely in a test tube and are readily produced using chemical processes. On the other hand, some aptamers that have been developed exhibit enzyme activity after binding to their target molecule, and function as 'aptazymes'. Numerous aptamers and aptazymes have been used in biotechnology, diagnostics and therapy. In this study, we demonstrate that natural DNA/RNA aptamers produced by selection in vitro, not only bind to hemin, but also show peroxidase activity when in such complexes (i.e., they function as aptazymes).

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  169. Photoactivatable fluorescein derivatives with azidomethyl caging groups for tracing oligonucleotides in living human cells Reviewed

    Kazuhiro Furukawa, Hiroshi Abe, Satoshi Tsuneda, Yoshihiro Ito

    ORGANIC & BIOMOLECULAR CHEMISTRY   Vol. 8 ( 10 ) page: 2309 - 2311   2010

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    A new photocaged fluorescent compound, azidomethyl fluorescein, was successfully utilized to monitor the dynamics of oligonucleotides in living human cells.

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  170. Hemin-Binding Aptamers and Aptazymes

    Mingahe Liu, Horoshi Abe, Yoshihiro Ito

    ACS Symposium Series 1043(Green Polymer Chemistry)     page: 111-123   2010

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  171. Reduction-Triggered Fluorescence Probe for Peptide-Templated Reactions Reviewed

    Aya Shibata, Hiroshi Abe, Kazuhiro Furukawa, Satoshi Tsuneda, Yoshihiro Ito

    CHEMICAL & PHARMACEUTICAL BULLETIN   Vol. 57 ( 11 ) page: 1223 - 1226   2009.11

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    We developed a new nucleic acid-based fluorescence probe for protein detection. The method is based on the scission of an aptamer into two probes, which are then attached with a chemically reactive fluorogenic compound. The protein-dependent association of the two probes accelerates a reduction-triggered fluorogenic reaction and indicates the presence of the target protein. which is detected using a fluorescence readout. The fluorescence signal is generated via the deprotection of the azidomethyl group of fluorescein. The arginine-rich motif peptide of the human immunodeficiency virus-1 Rev protein was targeted by this type of probe. Emission was detected at 522 nm and was enhanced by about 19.4-fold in the presence of the target peptide. An oligonucleotide-based reduction-1 triggered fluorescence probe was successfully applied to the defection of the Rev peptide ill solution.

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  172. Characterization of a new fluorogenic substrate for microsomal glutathione transferase 1 Reviewed

    Johan Alander, Katarina Johansson, Vanina Dahlstrom Heuser, Henny Farebo, Julia Jarvliden, Hiroshi Abe, Aya Shibata, Mika Ito, Yoshihiro Ito, Ralf Morgenstern

    ANALYTICAL BIOCHEMISTRY   Vol. 390 ( 1 ) page: 52 - 56   2009.7

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    A new thiol-reactive electrophilic, disubstituted rhodamine-based fluorogenic probe (bis-2,4-dinitrobenzenesulfonyl rhodamine [BDR]) with very high quantum yield was synthesized and described recently [A. Shibata et al., Bioorg. Med. Chem. Lett. 18 (2008) 2246-2249]. Because hydrophobic electrophiles are often conjugated by glutathione transferases, the BDR or monosubstituted rhodamine derivatives (2,4-dinitrobenzenesulfonyl rhodamine [DR]) were tested with microsomal glutathione transferase 1 (MGST1) and shown to function as substrates. The kinetic parameters for purified enzyme and DR were k(cat) = 0.075 +/- 0.005 s(-1) and K(m) = 21 +/- 3 mu M (k(cat)/K(m) = 3.6 x 10(3) +/- 5.6 x 10(2) M(-1) s(-1)), giving a rate enhancement of 10(6) compared with the nonenzymatic reaction. In cells overexpressing MGST1, the addition of BDR Caused a time-dependent increase of fluorescence compared with control cells. Preincubating the cells with a thiol reagent (N-ethylmaleimide) abolished the fluorescent signal. By using DR, we Could determine the MGST1 activity in whole cell extracts with high sensitivity. In addition, the activity could be increased by thiol reagents (a hallmark of MGST1). Thus, we have identified a new fluorogenic substrate for MGST1 that will be a useful tool in the study of this enzyme and related enzymes. (C) 2009 Elsevier Inc. All rights reserved.

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  173. Reduction-Triggered Fluorescent Amplification Probe for the Detection of Endogenous RNAs in Living Human Cells Reviewed

    Kazuhiro Furukawa, Hiroshi Abe, Kayo Hibino, Yasushi Sako, Satoshi Tsuneda, Yoshihiro Ito

    BIOCONJUGATE CHEMISTRY   Vol. 20 ( 5 ) page: 1026 - 1036   2009.5

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    Oligonucleotide-templated reactions are attracting attention as a method for RNA detection in living cells. Previously, a reduction-triggered fluorescence probe has been reported that is based on azide reduction to switch fluorescence on. In this article, we report a more advanced probe, a reduction-triggered fluorescent amplification probe that is capable of amplifying a target signal. Azidomethyl fluorescein was newly synthesized and introduced into a probe. Azido-masked fluorescein on the probe showed a strong turn-on fluorescence signal upon oligonucleotide-templated Staudinger reduction. The catalytic reaction of the probe offered a turnover number of 50 as fluorescence readout within 4 h. Finally, probes were introduced into human leukemia HL-60 cells by use of streptolysin O pore-forming peptide. We successfully detected and quantitated the 28S rRNA and P-Actin mRNA signal above the background by flow cytometry. In addition, the same RNA targets were imaged by fluorescence microscopy. The data suggest that a reduction-triggered amplification probe may be a powerful tool in analyzing the localization, transcription, or processing of RNA species in living eukaryotic cells.

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  174. In vitro selection of hemin-binding catalytic RNA Reviewed

    Mingzhe Liu, Takuma Kagahara, Hiroshi Abe, Yoshihiro Ito

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   Vol. 19 ( 5 ) page: 1484 - 1487   2009.3

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    Catalytic RNAs with peroxidase activity were obtained by the in vitro selection of RNA aptamer-binding hemin. One of the RNA aptamers selected showed binding affinity to hemin with a dissociation constant of 0.8 mu M and exhibited high peroxidase activity by forming a complex with hemin. The catalytic efficiency of the RNA-hemin complex was 10-fold higher than that of hemin alone. (C) 2009 Elsevier Ltd. All rights reserved.

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  175. 細胞機能制御高分子と再生医療高分子

    伊藤嘉浩、北嶋隆、阿部洋

    細胞機能制御高分子と再生医療高分子   Vol. 58 ( 3月 ) page: 全   2009.3

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  176. Direct In Vitro Selection of Hemin-Binding DNA Aptamer with Peroxidase Activity Reviewed

    Mingzhe Liu, Takuma Kagahara, Hiroshi Abe, Yoshihiro Ito

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   Vol. 82 ( 1 ) page: 99 - 104   2009.1

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    A novel hemin-binding DNA was synthesized using in vitro selection (SELEX) method. The selected DNA not only bound to the hemin. but also had peroxidase activity when complexed with hemin. A pool of 104-nt single-stranded DNA (ssDNA) molecules containing a randomized sequence of 60nt was synthesized. The DNA pool having random sequences was incubated with a hemin-immobilized affinity column. Bound DNAs were eluted with hemin solution and amplified by PCR with biotin-labeled primers. ssDNAs were isolated from the biotin-labeled double-stranded DNA (dsDNA) molecules after each selection process. After four rounds of selection process, the selected DNAs were cloned and sequenced. Four DNA aptamers were chemically synthesized from the sequenced clones. Two aptamers exhibited binding, affinity to hermin and peroxidase activity. A 21-nt oligonucleotide was designed from the aptamer sequence that formed a complex with hermin and exhibited high peroxidase activity.

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  177. Protein detection using oligonucleotide probes Reviewed

    Aya Shibata, Hiroshi Abe, Kazuhiro Furukawa, Satoshi Tsuneda, Yoshihiro Ito

    Nucleic Acids Symposium Series   Vol. 53   page: 157 - 158   2009

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  178. DNA templated nucleophilic aromatic substitution reactions for fluorogenic sensing of oligonucleotides Reviewed

    Aya Shibata, Hiroshi Abe, Mika Ito, Yuko Kondo, Shigeru Shimizu, Kyoko Aikawa, Yoshihiro Ito

    CHEMICAL COMMUNICATIONS   Vol. 43 ( 43 ) page: 6586 - 6588   2009

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    We have developed an SNAr reaction-triggered fluorescence probe using a new fluorogenic compound derivatized from 7-aminocoumarin for oligonucleotides detection.

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  179. Reduction-triggered red fluorescent probes for dual-color detection of oligonucleotide sequences Reviewed

    Kazuhiro Furukawa, Hiroshi Abe, Jin Wang, Miwako Uda, Hiroyuki Koshino, Satoshi Tsuneda, Yoshihiro Ito

    ORGANIC & BIOMOLECULAR CHEMISTRY   Vol. 7 ( 4 ) page: 671 - 677   2009

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    We have developed a new red fluorogenic compound derived from naphthorhodamine for a reduction-triggered fluorescence probe to sense oligonucleotides. The fluorogenic reaction between naphthorhodamine azide derivatives and reducing reagents such as triphenylphosphine (TPP) on the DNA target does not use any enzyme or reagent, and fluoresces at 650 nm. The probes were used for dual color detection of a single nucleotide difference on the leukemia-related bcr/abl gene.

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  180. Synthetic nanocircular RNA for controlling of gene expression Reviewed

    Hiroshi Abe, Naoko Abe, Miwako Uda, Satoshi Tsuneda, Yoshihiro Ito

    Nucleic Acids Symposium Series   Vol. 53   page: 65 - 66   2009

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  181. Fluorescence generation from tandem repeats of a malachite green RNA aptamer using rolling circle transcription Reviewed

    Kazuhiro Furukawa, Hiroshi Abe, Naoko Abe, Mitsuru Harada, Satoshi Tsuneda, Yoshihiro Ito

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   Vol. 18 ( 16 ) page: 4562 - 4565   2008.8

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    We demonstrate a generation of tandem repeats of a malachite green (MG) RNA aptamer using rolling circle transcription. To keep the higher-order structure of each aptamer on long RNA, we designed a sequence of circular DNA with a 14-base linker. T7 RNA polymerase was superior to Escherichia coli RNA polymerase in the specific transcription of the MG RNA aptamer. Finally. the generation of the fluorescence signal was confirmed from aptamer repeats with MG. (c) 2008 Elsevier Ltd. All rights reserved.

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  182. A reduction-triggered fluorescence probe for sensing nucleic acids Reviewed

    Hiroshi Abe, Jin Wang, Kazuhiro Furukawa, Kazuma Oki, Miwako Uda, Satoshi Tsuneda, Yoshihiro Ito

    BIOCONJUGATE CHEMISTRY   Vol. 19 ( 6 ) page: 1219 - 1226   2008.6

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    We have developed a reduction-triggered fluorescence probe with a new fluorogenic compound derivatized from Rhodamine for sensing oligonucleotides. The chemistry to activate the compound involves the reaction between the azide group of rhodamine derivatives and the reducing reagents, with the fluorescence signal appearing after reduction of the azide group. The signal/background ratio of this fluorogenic compound reached 2100-fold enhancement in fluorescence intensity. Dithio-1,4-threitol or triphenylphosphine as reducing reagents were successfully utilized for this chemistry to be introduced into the DNA probe. The genetic detection requires that two strands of DNA bind onto target oligonticleotides, one probe carrying a reducible fluorogenic compound while the other carries the reducing reagents. The reaction proceeds automatically without any enzymes or reagents under biological conditions to produce a fluorescence signal within 10-20 min in the presence of target DNA or RNA. In addition, the probe was very stable tinder biological conditions, even such extreme conditions as pH 5 solution, pH 10 solution, or high temperature (90 degrees C) with no undesirable background signal. The probes were successfully applied to the detection of oligonucleotides at the single nucleotide level in solution and endogenous RNA in bacterial cells.

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  183. Rhodamine-based fluorogenic probe for imaging biological thiol Reviewed

    Aya Shibata, Kazuhiro Furukawa, Hiroshi Abe, Satoshi Tsuneda, Yoshihiro Ito

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   Vol. 18 ( 7 ) page: 2246 - 2249   2008.4

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    We have developed a new fluorescent probe for biological thiol. The probe was synthesized by the modi. cation of the 2,4-dinitrobenzenesulfonyl group with rhodamine 110. The selective detection of thiol species such as cysteine or glutathione was achieved in biological conditions. Moreover, the probe was successfully applied to the imaging of thiol species in living human cells. (C) 2008 Elsevier Ltd. All rights reserved.

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  184. Synthesis of (+/-)-9-[c-4, t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine (BCA) derivatives branched at the 4 '-position based on intramolecular SH2 ' cyclization Reviewed

    Hiroki Kumamoto, Nonoko Takahashi, Tomomi Shimamura, Hiromichi Tanaka, Kazuo T. Nakamura, Takayuki Hamasaki, Masanori Baba, Hiroshi Abe, Masahiko Yano, Nobuyuki Kato

    TETRAHEDRON   Vol. 64 ( 7 ) page: 1494 - 1505   2008.2

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    Synthesis of W-branched BCA analogues (5) was carried out. Stereospecific construction of the cis-disposed 4'-carbon-substituents and 5'-hydroxymethyl group was secured by employing the bicyclo[3.3.0]lactone 16 as a key intermediate, which was prepared by radical-mediated intramolecular S(H)2' cyclization of the phenylselenomethyl ester 15. After manipulation of the double bond of 16, bis(Boc)adenine was introduced based on the Mitsunobu reaction of the allyl alcohol 24. Transformation of the lactone function of 27 allowed preparation of the 4'-hydroxymethyl (31). the 4'-vinyl (32), the 4'-cyano (34), and the 4'-ethynyl (35) derivatives. Anti-HIV and anti-HCV activities of the free nucleosides 36-38 were also examined. (c) 2007 Elsevier Ltd. All rights reserved.

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  185. Chemical aminoacylation of RNA by an intermolecular adenosine transfer reaction Reviewed

    Mingzhe Liu, Hiroshi Jinmei, Hiroshi Abe, Yoshihiro Ito

    CHEMISTRY LETTERS   Vol. 37 ( 1 ) page: 102 - 103   2008.1

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    RNA aminoacylation, based on an adenosine transfer mechanism, was achieved by the intermolecular transfer of phenylalaninyl adenosine from a donor probe to an acceptor RNA. This method can be applied to a wide variety of unnatural amino acids for tRNA aminoacylation.

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  186. Stereoselective glycosylation based on the conformational restriction of pyranoses Reviewed

    Satoshi Shuto, Satoshi Ichikawa, Hiroshi Abe, Akira Matsuda

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   Vol. 66 ( 1 ) page: 50 - 60   2008.1

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    Despite considerable progress and extensive effort, a general method for highly stereoselective glycosylation particularly for the 1,2-cis-glycosylation has not yet been developed and therefore is required. The alpha/beta-stereo selectivity in glycosylation can be affected by the steric and stereoelectronic (anomeric) effects around the anomeric center, which depend on the conformation of the glycosyl donor substrates. Therefore, we hypothesized that highly alpha- and beta-selective glycosylation can be realized by employing conformationally restricted substrates. We showed that the alpha/beta-stereoselectivity was significantly increased by the conformational restriction and was completely inverted by changing the substrate conformation from the C-4(1)-form into the C-1(4)-form in radical and nucleophilic C-glycosylation reactions as well as in O-glycosylation reactions. The conformational restriction of substrates also effectively facilitates the alpha- and beta-selective radical cyclization reaction at the anomeric position. Using the method, C-glucoside trisphosphates designed as Ca2+-mobilizing agents were successfully,synthesized.

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  187. Rapid DNA chemical ligation for amplification of RNA and DNA signal Reviewed

    Hiroshi Abe, Yuko Kondo, Hiroshi Jinmei, Naoko Abe, Kazuhiro Furukawa, Atsushi Uchiyama, Satoshi Tsuneda, Kyoko Aikawa, Isamu Matsumoto, Yoshihiro Ito

    BIOCONJUGATE CHEMISTRY   Vol. 19 ( 1 ) page: 327 - 333   2008.1

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    Enzymatic ligation methods are useful in the diagnostic detection of DNA sequences. Here, we describe the investigation of nonenzymatic phosphorothioate-iodoacetyl DNA chemical ligation as a method for the detection and identification of RNA and DNA. The specificity of ligation on the DNA target is shown to allow the discrimination of a single point mutation with a drop in the ligation yield of up to 16.1-fold. Although enzymatic ligation has very low activity for RNA targets, this reaction is very efficient for RNA targets. The speed of the chemical ligation with an RNA target achieves a 70% yield in 5 s, which is equal to or better than that of ligase-enzyme-mediated ligation with a DNA target. The reaction also exhibits a significant level of signal amplification under thermal cycling in periods as short as 100-120 min, with the RNA or DNA target acting in a catalytic way to ligate multiple pairs of probes.

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  188. In vitro selection of RNA aptamer to hemin. Reviewed

    Mingze Liu, Takuma Kagahara, Hiroshi Abe, Yoshihiro Ito

    Nucleic Acids Symposium Series   Vol. 52   page: 513 - 514   2008

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  189. Fluorogenic probe triggered by reduction for nucleic acids sensing. Reviewed

    Furukawa K, Abe H, Wang J, Oki K, Uda M, Tsuneda S, Ito Y

    Nucleic acids symposium series (2004)   ( 52 ) page: 353-4   2008

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  190. Quenched Autoligation Probes Reviewed

    Adam P. Silverman, Hiroshi Abe, Eric T. Kool

    Methods in Molecular Biology   Vol. 429   page: 161 - 170   2008

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  191. 細胞内遺伝子シグナルの解析

    阿部洋、古川和寛、常田聡、伊藤嘉浩

    生物工学、日本生物工学会   Vol. 86 ( 6 ) page: 268-270   2008

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  192. Quenched autoligation probes

    Adam P. Silverman, Hiroshi Abe, Eric T. Kool

    Methods in Molecular Biology     page: 161-170   2008

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  193. ピラノースの配座制御に基づく立体選択的グリコシル化反応

    周東智、市川聡、阿部洋、松田彰

    有機合成化学協会誌     page: 50-60   2008

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  194. ダンベル型ナノサークルRNAでRNA干渉を長期安定に

    阿部洋、阿部奈保子、原田充、常田聡、伊藤嘉浩

    バイオインダストリー協会   Vol. 66 ( 8 ) page: 全   2008

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  195. Design and synthesis of biorelated polymers by combinatorial bioengineering

    Yoshihiro Ito, Hiroshi Abe, Akira Wada, Mingahe Liu

    ACS Symposium Series999(Polymer Biocatalysis and Biomaterials 2 )     page: 194-215   2008

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  196. Nanocircular RNAs for RNA interference Reviewed

    Hiroshi Abe, Naoko Abe, Mitsuru Harada, Satoshi Tsuneda, Yoshihiro Ito

    Nucleic Acids Symposium Series   Vol. 52   page: 505 - 506   2008

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  197. Fluorogenic probe triggered by reduction for nucleic acids sensing Reviewed

    Kazuhiro Furukawa, Hiroshi Abe, Jin Wang, Kazuma Oki, Miwako Uda, Satoshi Tsuneda, Yoshihiro Ito

    Nucleic Acids Symposium Series   Vol. 52   page: 353 - 354   2008

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  198. Dumbbell-shaped nanocircular RNAs for RNA interference Reviewed

    Naoko Abe, Hiroshi Abe, Yoshihiro Ito

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 129 ( 49 ) page: 15108 - +   2007.12

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    We designed and synthesized dumbbell-shaped nanocircular RNAs for RNA interference applications, which consist of a stem and two loops. RNA dumbbells are specifically recognized and cleaved by the human Dicer enzyme and are thus transformed into double-stranded RNA in cells, although this RNA is resistant to degradation in serum. The structure was optimized to maximize its RNAi activity. The most potent activity was achieved when the stem length was 23 base pairs. The RNAi activity is prolonged by the shape of the molecule, an endless structure, compared with that of normal siRNA.

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  199. [Bioprobe for imaging RNA in living cells]. Reviewed

    Abe H, Furukawa K, Tsuneda S, Ito Y

    Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme   Vol. 52 ( 13 Suppl ) page: 1619-24   2007.10

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  200. Intermolecular transfer of aminoacylated adenosine towards chemical aminoacylation of tRNA Reviewed

    Mingze Liu, Hiroshi Jinmei, Koji Fukuzono, Hiroshi Abe, Yoshihiro Ito

    Nucleic Acids Symposium Series   Vol. 51   page: 353 - 354   2007

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  201. Multiple chemical ligation under thermal cycle. Reviewed

    Yuko Kondo, Hiroshi Abe, Hiroshi Jinmei, Naoko Abe, Kyoko Aikawa, Isamu Matsumoto, Yoshihiro Ito

    Nucleic Acids Symposium Series   Vol. 51   page: 365 - 366   2007

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  202. Synthesis of adenophostin A analogues conjugating an aromatic group at the 5 '-position as potent IP3 receptor ligands Reviewed

    Tetsuya Mochizuki, Yoshihiko Kondo, Hiroshi Abe, Stephen C. Tovey, Skarlatos G. Dedos, Colin W. Taylor, Michael Paul, Barry V. L. Potter, Akira Matsuda, Satoshi Shuto

    JOURNAL OF MEDICINAL CHEMISTRY   Vol. 49 ( 19 ) page: 5750 - 5758   2006.9

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    Previous structure-activity relationship studies of adenophostin A, a potent IP3 receptor agonist, led us to design the novel adenophostin A analogues 5a-c, conjugating an aromatic group at the 5'-position to develop useful IP3 receptor ligands. The common key intermediate, a D-ribosyl alpha-D-glucoside 10 alpha, was stereoselectively synthesized by a glycosidation with the 1-sulfinylglucoside donor 11, which was conformationally restricted by a 3,4-O-cyclic diketal protecting group. After introduction of an aromatic group at the 5-position of the ribose moiety, an adenine base was stereoselectively introduced at the anomeric beta-position to form 7a-c, where the tetra-O-i-butyryl donors 9a-c were significantly more effective than the corresponding O-acetyl donor. Thus, the target compounds 5a-c were synthesized via phosphorylation of the 2', 3", and 4"-hydroxyls. The potencies of compounds 5a-c for Ca2+ release were shown to be indistinguishable from that of adenophostin A, indicating that bulky substitutions at the 5'-position of adenophostin A are well-tolerated in the receptor binding. This biological activity of 5a-c can be rationalized by molecular modeling using the ligand binding domain of the IP3 receptor.

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  203. Design and synthesis of 5'-deoxy-5'-phenyladenophostin A, a highly potent IP3 receptor ligand. Reviewed

    Mochizuki T, Kondo Y, Abe H, Taylor CW, Potter BV, Matsuda A, Shuto S

    Organic letters   Vol. 8 ( 7 ) page: 1455-8   2006.3

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  204. Design and synthesis of 5 '-deoxy-5 '-phenyladenophostin A, a highly potent IP3 receptor ligand Reviewed

    T Mochizuki, Y Kondo, H Abe, CW Taylor, BVL Potter, A Matsuda, S Shuto

    ORGANIC LETTERS   Vol. 8 ( 7 ) page: 1455 - 1458   2006.3

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    5'-Deoxy-5'-phenyladenophostin A (5), designed as a useful IP3 receptor ligand based on the previous structure-activity relationship studies, was successfully synthesized via two key stereoselective glycosidation steps. This compound proved to be a highly potent IP3 receptor agonist.

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  205. A systematic study of C-glucoside trisphosphates as myo-inositol trisphosphate receptor ligands. Synthesis of beta-C-glucoside trisphosphates based on the conformational restriction strategy Reviewed

    M Terauchi, H Abe, SC Tovey, SG Dedos, CW Taylor, M Paul, M Trusselle, BVL Potter, A Matsuda, S Shuto

    JOURNAL OF MEDICINAL CHEMISTRY   Vol. 49 ( 6 ) page: 1900 - 1909   2006.3

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    beta-C-Glucoside trisphosphates having a C2 side chain (3,7-anhydro-2-deoxy-D-glycero-D-gulo-octitol 1,5,6-trisphosphate, 11) and a C3 side chain (4,8-anhydro-2,3-dideoxy-D-glycero-D-gulo-nonanitol 1,6,7-trisphosphate, 12) were designed as structurally simplified analogues of a potent D-myo-inositol 1,4,5-trisphosphate (IP3) receptor ligand, adenophostin A. Construction of the beta-C-glucosidic structure, which was the key to their synthesis, was achieved by two different methods based on the conformational restriction strategy: (1) radical cyclization with a temporary connecting silicon tether and (2) silane reduction of glyconolactols having an anomeric allyl substituent. Using these methods, the target beta-C-glycoside trisphosphates 11 and 12 were successfully synthesized. A structure-activity relationship was established on a series of C-glucoside trisphosphates, including the previously synthesized related compounds, which were a C-glycosidic analogue 3 of adenophostin A, its uracil congener 5, alpha-C-glucoside trisphosphates 7-9 having a C1, C2, or C3 side chain, and the beta-C-glucoside trisphosphates 10-12 having a C1, C2, or C3 side chain. The O-glycosidic linkage of adenophostin A and its analogues proved to be replaced by the chemically and biologically more stable C-glycosidic linkage. The alpha-C2-glucoside trisphosphate 8 stimulates Call release with a potency similar to that of IP3 in spite of its simplified structure, indicating a better fit to the receptor than the beta-C-glucoside trisphosphates and also the alpha-congeners having a shorter or longer C1 side chain, which was supported by molecular modeling using the ligand binding domain of the IP3 receptor.

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  206. Flow cytometric detection of specific RNAs in native human cells with quenched autoligating FRET probes. Reviewed

    Abe H, Kool ET

    Proceedings of the National Academy of Sciences of the United States of America   Vol. 103 ( 2 ) page: 263-8   2006.1

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  207. Structure analysis of oligonucleotide in organic solvent Reviewed

    Hiroshi Abe, Naoko Abe, Yoshihiro Ito

    Nucleic Acids Symposium Series   Vol. 50   page: 25 - 26   2006

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  208. Structure analysis of oligonucleotide in organic solvent. Reviewed

    Abe H, Abe N, Ito Y

    Nucleic acids symposium series (2004)   ( 50 ) page: 25 - 6   2006

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  209. 新機能性核酸・タンパク質を生み出すコンビナトリアル・バイオエンジニアリング

    阿部洋、和田章、伊藤嘉浩

    生物工学会誌   Vol. 84 ( 8 ) page: 309   2006

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  210. Synthesis of 4,8-anhydro-D-glycero-D-ido-nonanitol 1,6,7-trisphosphate as a novel IP3 receptor ligand using a stereoselective radical cyclization reaction based on a conformational restriction strategy Reviewed

    M Terauchi, Y Yahiro, H Abe, S Ichikawa, SC Tovey, SG Dedos, CW Taylor, BVL Potter, A Matsuda, S Shuto

    TETRAHEDRON   Vol. 61 ( 15 ) page: 3697 - 3707   2005.4

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    4,8-Anhydro-D-glycero-D-ido-nonanitol 1,6,7-trisphosphate (9), designed as a novel IP3 receptor ligand having an alpha-C-glycosidic\ structure, was synthesized via a radical cyclization reaction with a temporary connecting allylsilyl group as the key-step. Phenyl 2-O-allyldimethylsilyt-3,4-bis-O-TBS-1-seleno- beta-D-glucopyranoside (10a), conformationally restricted in the unusual C-1(4)-conformation, was treated with Bu3SnH/AIBN to form the desired alpha-cyclization product 16a almost quantitatively. On the other hand, when a conformationally unrestricted O-benzyl-protected 2-O-allyldimethylsilyl -l-selenoglucoside 15 was used as the substrate, the radical reaction was not stereoselective and gave a mixture of the alpha-and beta-products. From 16a, the target C-glucoside trisphosphate 9 was synthesized via phosphorylation of the hydroxyls by the phosphoramidite method. During the synthetic study, an efficient procedure for the oxidative C-Si bond cleavage, via a nucleophilic substitution at the silicon with p-MeOPhLi followed by Fleming oxidation, was developed. The C-glycoside 9 was found to be a full agonist for Ca2+ mobilization, although its activity was weaker than that of the natural ligand IP3. Thus, the alpha-C-glucosidic structure was shown to be a useful mimic of the myo-inositol backbone of IP3. (c) 2005 Elsevier Ltd. All rights reserved.

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  211. Universal linkers for signal amplification in auto-ligating probes Reviewed

    Hiroshi Abe, Eric T. Kool

    Nucleic Acids Symposium Series   Vol. 49   page: 37 - 38   2005

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  212. Universal linkers for signal amplification in auto-ligating probes. Reviewed

    Abe H, Kool ET

    Nucleic acids symposium series (2004)   ( 49 ) page: 37-8   2005

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  213. Highly stereoselective Grignard addition to cis-substituted C-cyclopropylaldonitrones. The bisected s-trans transition state can be stabilized effectively by the Lewis acid-coordination Reviewed

    Y Kazuta, H Abe, A Matsuda, S Shuto

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 69 ( 26 ) page: 9143 - 9150   2004.12

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    We previously found that Grignard addition to a C-cyclopropylaldonitrone, C-[cis-2-(N,N-diethyl-carbamoyl)-trans-2-phenylcyclopropyl]-N-benzylaldonitrone (1), stereoselectively gave the antiproduct 3, in which the stereoselectivity was particularly high when MgBr2 was the additive. In this study, the reaction pathway was investigated in detail. The stereoselective addition was initially thought to occur via either a 1,5-chelation-controlled or a bisected s-trans conformation-controlled pathway. However, Grignard addition to a nonchelating silyl ether-type substrate, C-[cis-2-(tert-butyldiphenylsilyloxymethyl)-trans-2-phenylcyclopropyl]-N-benzylaldonitrone (7), also gave the antiproduct 9 with high stereoselectivity suggesting that chelation is not important in the reaction. Theoretical calculations of C-cyclopropylaldonitrones showed that the coordination of Mg2+ at the nitrone oxygen significantly stabilizes the bisected s-trans conformer due to the effective hyper-conjugation between the,pi* of the nitrone C=N bond and the electron-donating cyclopropane orbitals. This kind of orbital interaction is able to stabilize the transition state of the nucleophilic addition and is maximized in the bisected conformation, in which the orbitals of the forming bond and the cyclopropane C-C bond are in an almost planar arrangement. Thus, the high stereoselectivity can be explained by nucleophilic attack on the less hindered side of the C=N bond of the substrates in the Mg2+-coordinated bisected s-trans conformation.

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  214. Destabilizing universal linkers for signal amplification in self-ligating probes for RNA. Reviewed

    Abe H, Kool ET

    Journal of the American Chemical Society   Vol. 126 ( 43 ) page: 13980-6   2004.11

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  215. An efficient synthesis of beta-C-glycosides based on the conformational restriction strategy: Lewis acid promoted silane reduction of the anomeric position with complete stereoselectivity Reviewed

    M Terauchi, H Abe, A Matsuda, S Shuto

    ORGANIC LETTERS   Vol. 6 ( 21 ) page: 3751 - 3754   2004.10

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    The reduction of glyconolactols having an anomeric carbon substituent by Et3SiH/TMSOTf proceeded with complete stereoselectivity to produce the corresponding beta-C-glycosides when the substrates were conformationally restricted in the C-4(1)-chair form by a 3,4-O-cyclic diketal or a 4,6-O-benzylidene protecting group. Thus, the efficient construction beta-C-glycosides was achieved on the basis of the conformation restriction strategy.

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  216. Stereoselective synthesis of alpha- and beta-C-glucosides via radical cyclization with an allylsilyl tether. Control of the stereoselectivity by changing the conformation of the pyranose ring (vol 41, pg 4151, 2000) Reviewed

    S Shuto, M Terauchi, Y Yahiro, H Abe, S Ichikawa, A Matsuda

    TETRAHEDRON LETTERS   Vol. 45 ( 36 ) page: 6819 - 6819   2004.8

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  217. The unusual 1,4-chelation-controlled nucleophilic addition to aldehydes with high stereoselectivity. A systematic study of stereoselectivity in the addition reaction of carbon nucleophiles to cis-substituted cyclopropanecarbaldehydes Reviewed

    Y Kazuta, H Abe, T Yamamoto, A Matsuda, S Shuto

    TETRAHEDRON   Vol. 60 ( 31 ) page: 6689 - 6703   2004.7

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    The addition reaction of carbon nucleophiles to cis-substituted cyclopropanecarbaldehydes was systematically investigated. Ab initio calculations of model cyclopropanecarbaldehydes suggested that the bisected s-cis and s-trans conformers are the only two minimum energy conformers, which are stabilized due to the pi-donating stereoelectronic effect of the cyclopropane ring. The experimental results of a series of substrates, that is, cyclopropanecarbaldehydes 1-5 bearing a cis-(tert-butyldiphenyisilyloxy)methyl group, a cis-benzyloxymethyl group, a cis-(p-methoxybenzyloxy)methyl group, cis-N,N-diethylcarbamoyl and trans-phenyl groups, and cis-(tert-butyldiphenylsilyloxy)methyl and trans-phenyl groups, respectively, showed that highly anti-selective Grignard additions could be realized. It turned out that it occurred via an unusual 7-membered 1,4-chelation-controlled pathway. Highly stereoselective Grignard addition via the chelation-controlled pathway occurred even in the reaction of the usually non-chelating silyl ether-type substrate 5. The results have great importance because the 1,4-chelation-controlled stereoselective addition reactions can indeed be realized. Under non-chelation conditions, the syn-products were produced with moderate stereoselectivity, which are likely to be formed via the bisected s-cis conformation-like transition state stabilized by the characteristic orbital interaction. These reactions, especially the chelation-controlled reaction, should be useful because of their t stereoselectivity and stereochemical predictability. (C) 2004 Elsevier Ltd. All rights reserved.

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  218. Quenched auto-ligating DNAs: Multicolor identification of nucleic acids at single nucleotide resolution Reviewed

    S Sando, H Abe, ET Kool

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 126 ( 4 ) page: 1081 - 1087   2004.2

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    We describe the synthesis and study of multicolor quenched autoligating (QUAL) probes for identification and discrimination of closely related RNA and DNA sequences in solution and in bacteria. In these probes, a dabsyl quencher doubles as an activator in the oligonucleotide-joining reaction. The oligonucleotides remain dark until they bind at adjacent sites, and "light up" on nucleophilic displacement of the dabsyl probe by the phosphorothioate probe. Four fluorescent dye conjugates were prepared and tested with probes and targets that differ by one nucleotide. Experiments on polymer beads show clear color-based discrimination of DNAs added in solution. Two-color quenched probe pairs were then tested in the discrimination of 16S rRNA sequences in Escherichia coli. Single nucleotide resolution was achieved in the cells with green/red QUAL probes, allowing identification of a one-base sequencing error in the 16S rRNA database. Finally, QUAL probes were successfully applied in live bacterial cells. The method requires only incubation followed by fluorescence imaging, and requires no enzymes, added reagents, cross-linking, fixing, or washes. Because probes must bind side-by-side to generate signal, there is little or no interference from unintended protein binding, which can occur with other probe types. The results suggest that QUAL probes may be of general use in the detection and identification of sequences in solution, on microarrays, and in microorganisms.

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  219. Construction of a cis-cyclopropane via reductive radical decarboxylation. Enantioselective synthesis of cis- and trans-1-arylpiperazyl-2-phenyleyclopropanes designed as antidopaminergic agents Reviewed

    K Yamaguchi, Y Kazuta, H Abe, A Matsuda, S Shuto

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 68 ( 24 ) page: 9255 - 9262   2003.11

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    (1S,2S)-, (1S,2R)-, and (1R,2S)-1-(2,4-Dimethylphenyl)piperazyl-2-phenylcyclopropane (2a, 3, and ent-3, respectively), which were designed as conformationally restricted analogues of haloperidol (1), a clinically effective antipsychotic agent, were synthesized from chiral epichlorohydrins using the Barton reductive radical decarboxylation as the key step. (1S,2R)-1-(tert-Butyldiphenylsilyloxy)methyl-2-carboxy-2-phenylcyclopropane (5), which was prepared from (S)-epichlorohydrin ((S)-7), was converted into its N-hydroxypyridine-2-thione ester 12, the substrate for the reductive radical decarboxylation. When 12 was treated with TMS(3)SiH in the presence of Et(3)B or AIBN, the decarboxylation and subsequent hydride attack on the cyclopropyl radical intermediate from the side opposite to the bulky silyloxymethyl moiety occurred, resulting in selective formation of the corresponding reductive decarboxylation product 4-cis with the cis-cyclopropane structure. From 4-cis, the cis-cyclopropane-type target compound 3 was readily synthesized. Starting from (R)epichlorohydrin ((R)-7), ent-3 was similarly synthesized. Epimerization of the cyclopropanecarboxamide ent-16-cis, a synthetic intermediate for ent-3, on treatment with a base prepared from Bu(2)Mg and i-Pr(2)NH in THF occurred effectively to give the corresponding trans isomer 16-trans, which was converted into 2a with the trans-cyclopropane structure.

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  220. A study on the conformation-anomeric effect-stereoselectivity relationship in anomeric radical reactions, using conformationally restricted glucose derivatives as substrates Reviewed

    H Abe, M Terauchi, A Matsuda, S Shuto

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 68 ( 19 ) page: 7439 - 7447   2003.9

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    We previously theorized that, since the stereoselectivity of anomeric radical reactions is significantly influenced by the kinetic anomeric effect, which can be controlled by restricting the conformation of the radical intermediate, the proper conformational restriction of the pyranose ring of the substrates would therefore make highly alpha- and beta-stereoselective anomeric radical reactions possible. This theory was based on our previous results of the anomeric radical reactions with D-xylose derivatives as the substrates. We herein report the anomeric radical deuteration reactions with the conformationally restricted 1-phenylseleno-D-glucose derivatives, 2g and 3g, restricted in a C-4(1)-conformation by an beta-cyclic diketal moiety, and 4g, 5g, 6g, 7g, and 8g, restricted in a C-1(4)-conformation by bulky O-silyl protecting groups. The radical deuterations with Bu3SnD, using the C-4(1)-restricted substrates 2g and 3g, afforded the corresponding alpha-products (alpha/beta = 98:2) highly stereoselectively, whereas the C-1(4)-restricted substrate 6g, having a trigonal (sp(2)) carbon substituent, i.e., -CHO, at the 5-position, selectively gave the beta-products (alpha/beta = 0: 100). Thus, the stereoselectivity was significantly increased by the conformational restriction and was completely inverted by changing the substrate conformation from the C-4(1)-form to the C-1(4)-form. On the other hand, the deuterations with the C-1(4)-restricted substrates 4g and 5g showed that the 1,5-steric effect due to the tetrahedral carbon substituent (-CH2OTIPS or -CH2OH) at the 5-axial position dominantly prevented the hydride transfer from the beta-face competing with the kinetic anomeric effect. This study suggests that, depending on the restricted conformation of the substrates to the C-4(1)- or the C-1(4)-form, the alpha- or beta-products would be obtained highly stereoselectively via anomeric radical reactions of hexopyranoses.

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  221. A systematic study of the hydride reduction of cyclopropyl ketones with structurally simplified substrates. Highly stereoselective reductions of trans-substituted cyclopropyl ketones via the bisected s-cis conformation Reviewed

    Y Kazuta, H Abe, T Yamamoto, A Matsuda, S Shuto

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 68 ( 9 ) page: 3511 - 3521   2003.5

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    The stereoselective hydride reduction of the cis- and trans-substituted cyclopropyl ketones was systematically investigated using a series of structurally simplified substrates, trans-[tert-butyldiphenylsilyloxymethyl]cyclopropyl ketones la-a and trans- (benzyloxymethyl)cyclopropyl methyl ketone (2), and the corresponding cis congeners 3a,b,e and 4. The results showed that, not only in the reduction of the cis-substituted cyclopropyl ketones but also in that of the trans-substituted ketones, high stereoselectivity can be realized when the substrate has a bulky substituent on the cyclopropane ring, even though it is attached to the position trans to the acyl moiety. Ab initio calculations based on the density functional theory (DFT) of cyclopropyl ketones showed that (1) the bisected s-cis and s-trans conformers were the only two minimum energy conformers; while the s-cis conformer was more stable than the s-trans and (2) a bulky alkyl group in the acyl moiety and a cis substituent on the cyclopropane ring made the bisected s-cis conformer much more stable. On the basis of these calculations and experimental results, it is likely that the more stable the bisected s-cis conformer of the substrate, the more stereoselective the hydride reduction. Thus, the stereochemistry can be explained by hydride attack on the bisected s-cis conformation of the substrate from the less-hindered face. The predictability of the stereochemical results is predicated on the bisected s-cis transition-state model, which is very important from the viewpoint of synthetic organic chemistry.

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  222. Control of alpha/beta stereoselectivity in Lewis acid promoted C-glycosidations using a controlling anomeric effect based on the conformational restriction strategy Reviewed

    S Tamura, H Abe, A Matsuda, S Shuto

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   Vol. 42 ( 9 ) page: 1021 - +   2003

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  223. Development of New Radical Reactions with a Vinylsilyl Group and Their Application to the Synthesis of Branched-Chain Sugar Nucleosides

    Satoshi Shuto, Makiko Kanazaki, Isamu Sugimoto, Satoshi Ichikawa, Yuki Nagasawa, Yoshihito Ueno, Hiroshi Abe, Noriaki Minakawa, Makoto Sukeda, Tetsuya Kodama, Makoto Nomura, Akira Matsuda

    Recent Advances in Nucleosides: Chemistry and Chemotherapy     page: 21 - 55   2002

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  224. Synthesis and biological activity of adenophostin derivatives as IP3 receptor ligands. Reviewed

    Shuto S, Mochizuki T, Abe H, Kondo Y, Matsuda A

    Nucleic acids research. Supplement (2001)   ( 2 ) page: 23-4   2002

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  225. Development of new radical reactions with a vinylsilyl group and their application to the synthesis of branched-chain sugar nucleosides

    Satoshi Shuto, Maki kanazaki, Isamu Sugimoto, Satoshi Ichikawa, Yuki Nagasawa, Yoshihito Ueno, Hiroshi Abe, Noriaki Minakawa, Makoto Sukeda, Tetsuya Kodama, Makoto Nomura, Akira matsuda

    Recent Advances in Nucleosides     page: 21-55   2002

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  226. Synthesis and biological activity of adenophostin derivatives as IP3 receptor ligands Reviewed

    Satoshi Shuto, Tetsuya Mochizuki, Hiroshi Abe, Yoshihiko Kondo, Akira Matsuda

    Nucleic Acids Symposium Series   Vol. 2   page: 23 - 24   2002

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  227. Highly alpha- and beta-selective radical C-glycosylation reactions using a controlling anomeric effect based on the conformational restriction strategy. A study on the conformation-anomeric effect-stereoselectivity relationship in anomeric radical reactions Reviewed

    H Abe, S Shuto, A Matsuda

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 123 ( 48 ) page: 11870 - 11882   2001.12

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    We hypothesized that, because the stereoselectivity of anomeric radical reactions was significantly influenced by the anomeric effect, which can be controlled by restricting the conformation of the radical intermediate, the proper conformational restriction of the pyranose ring of the substrates would therefore make highly alpha- and beta -stereoselective anomeric radical reactions possible. Thus, the conformationally restricted 1-phenylseleno-D-xylose derivatives 9 and 10, restricted in a C-4(1)-conformation, and 11 and 12, restricted in a C-1(4)-conformation, were designed and synthesized by introducing the proper protecting groups on the hydroxyl groups on the pyranose ring as model substrates for the anomeric radical reactions. The radical deuterations with Bu3SnD and the C-glycosylation with Bu3SnCH2CH=CH2 or CH2 CHCN, using the C-4(1)-restricted substrates 9 and 10, afforded the corresponding alpha -products (alpha/beta = 97:3-85:15) highly stereoselectively, whereas the C-1(4)-restricted substrates 11 and 12 selectively gave the fl-products (alpha/beta = 1:99-0:100). Thus, stereoselectivity was significantly increased by conformational restriction and was completely inverted by changing the substrate conformation from the C-4(1)-form into the C-1(4)-form. Ab initio, calculations suggested that the radical intermediates produced from these substrates possessed the typical C-4(1)- or C-1(4)-Conformation, which was similar to that of the substrates, and that the anomeric effect in these conformations would be the factor controlling the transition state of the reaction. Therefore, the highly alpha- and beta -selective reactions would occur because of the anomeric effect, which could be manipulated by conformational restriction of the substrates, as expected. This would be the first radical C-glycosylation reaction to provide both alpha- and beta -C-glycosides highly stereoselectively.

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  228. An efficient method for preparing fully O-silylated pyranoses conformationally restricted in the unusual C-1(4)-form Reviewed

    H Abe, S Shuto, S Tamura, A Matsuda

    TETRAHEDRON LETTERS   Vol. 42 ( 35 ) page: 6159 - 6161   2001.8

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    An efficient method for preparing fully O-silylated pyranoses, which are conformationally restricted in the unusual C-1(4)-form, was developed. Thus, successive treatment of pyranosides, such as xylose and glucose derivatives, with NaH and TIPSOTf or TBSOTf in THF at room temperature gave the corresponding fully O-silylated products. (C) 2001 Elsevier Science Ltd. All rights reserved.

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  229. Significance of substrate hydrophobicity for recognition by an oligopeptide transporter (PEPT1) Reviewed

    R Tateoka, H Abe, S Miyauchi, S Shuto, A Matsuda, M Kobayashi, K Miyazaki, N Kamo

    BIOCONJUGATE CHEMISTRY   Vol. 12 ( 4 ) page: 485 - 492   2001.7

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    Our previous paper [(1999) Bioconjugate Chem. 10, 24-31] pointed out that hydrophobicity of substrates/inhibitors plays an important role in the recognition by an oligopeptide transporter (PEPT1) expressed in the human intestinal epithelial cell line Caco-8. To determine the significance of that hydrophobicity, we have now synthesized dipeptide analogues conjugating the E-amino group of Lys in Val-Lys with aliphatic carboxylic acids: acetic acid (C2), propanoic acid (C3), pentanoic acid (C5), hexanoic acid (C6), and decanoic acid (C10). The affinities of these conjugates were estimated by their inhibition of the accumulation rate of Gly-Sar, a well-established substrate for PEPT1. With the increase in length of the hydrocarbon chain of the conjugates, i.e., in the hydrophobicity of the conjugates, the inhibition strengthened. Dixon-Webb plot analysis of the inhibition by the C10-conjugated dipeptide showed competitive inhibition. The trans-stimulation effect of Val-Lys conjugated to C10 or C5 on the uptake of Ceftibuten was observed using rat brush border membrane vesicles. This findings showed that these conjugates are transportable substrates. These results confirmed that the hydrophobicity of substrates/inhibitor is one of the factors in the recognition by PEPT1.

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  230. INTRACELLULAR Ca2+-MOBILIZING ADENINE NUCLEOTIDES. SYNTHESIS AND BIOLOGICAL ACTIVITY OF CYCLIC ADP-CARBOCYCLIC-RIBOSE ANDC-GLYCOSIDIC ANALOG OF ADENOPHOSTIN A

    Satoshi Shuto, Masayoshi Fukuoka, Hiroshi Abe, Akira Matsuda

    Nucleosides, Nucleotides and Nucleic Acids   Vol. 20 ( 4-7 ) page: 461 - 470   2001.3

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  231. The bisected s-trans conformation-controlled highly stereoselective addition of Grignard reagents to C-cyclopropylaldonitrone. An efficient synthesis of 1-phenyl-2-[(S)-1-aminoalkyl]-N,N-diethylcyclopropanecarboxamides, a new class of potent NMDA receptor antagonists Reviewed

    Y Kazuta, S Shuto, H Abe, A Matsuda

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   Vol. 1 ( 6 ) page: 599 - 604   2001

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    An efficient synthesis of 1-phenyl-2-[(S)-1-aminoethyl]- and 1-phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamides [1a (PEDC) and 1b (PPDC), respectively], potent NMDA receptor antagonists having a cyclopropane structure, was achieved. We have shown for the first time that C-cyclopropylaldonitrone preferentially exists in the bisected s-trans conformation, due to the characteristic stereoelectronic effects of the cyclopropane ring, by X-ray crystallographic analysis, NMR studies, and theoretical calculations. Based on these findings, the highly stereoselective addition reaction of Grignard reagents to C-cyclopropylaldonitrone 6 was developed, and the reaction was successfully used as the key step for the preparation of the NMDA receptor antagonists 1a and 1b as well as for a newly designed isopropyl-type congener 1c. The facial selectivity of the addition of Grignard reagents can be explained by the attack of the reagents from the less hindered side of the substrate in the predicted bisected s-trans conformation. This Grignard reaction is the first example of a highly stereoselective addition to a nitrone via a non-chelation controlled pathway.

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  232. Intracellular Ca2+-mobilizing adenine nucleotides. Synthesis and biological activity of cyclic ADP-carbocyclic-ribose and C-glycosidic analog of adenophostin A

        page: 461-470   2001

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  233. The stereoselective synthesis of 4 '-beta-thioribonucleosides via the Pummerer reaction Reviewed

    T Naka, N Minakawa, H Abe, D Kaga, A Matsuda

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 122 ( 30 ) page: 7233 - 7243   2000.8

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    An efficient stereoselective synthesis of 4'-beta-thioribonucleosides 14, 15, 27, and 30 using the Pummerer reaction as the key step is described. The Pummerer reaction of 1,4-anhydro-2-0-(2,4-dimethoxybenzoyl)-3,5-O-( 1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-3-sulfinyl-D-ribitol (R-10:S-10 = 2.7:1) in the presence of silylated uracil afforded the desired p-anomer of the 4'-thiouridine derivative 11 in 66% yield without formation of its a-anomer. The reaction with R-10 gave 11 in 87% yield, while the one with S-10 resulted in a 27% decrease of the desired product 11 along with a 22% yield of 3,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-3-hydroxy-2-hydroxymethylthiophene (12). A likely explanation for the observed difference in the reaction of R-10 and S-10 is that the reaction proceeds via an E2 type pathway, which prefers anti elimination. Thus, R-10 would preferentially afford the alpha-thiocarbocation intermediate 21 via an E2 anti elimination under the reaction conditions. The resulting 21 would be expected to react with silylated uracil stereoselectively to give 11 in good yield. However, formation of the more stable tertiary alpha-thiocarbocation intermediate 23, which would prefer to give 12 and/or to decompose, would compete with the formation of the desired 21 in the reaction with S-10. Consequently, this argument would explain the low yields of the desired product 11 and the poor mass balance in the reaction with S-10. When the sulfoxide 10 (R-10:S-10 = &gt;16:1) prepared by oxidation of 9 with ozone was used for the Pummerer reaction, the desired 11 was obtained in 80% yield. Compound 11 was converted to 4'-beta-thiouridine (14) by treatment of 11 with ammonium fluoride, followed by methanolic ammonia. Similarly, 4'-beta-thiocytidine (15) was prepared when silylated N-4-acetylcytosine was used in the Pummerer reaction. For the Pummerer reactions with purine bases, 6-chloropurine and 2-amino-6-chloropurine were found to be the most suitable. When the reactions were conducted in a mixture of acetonitrile and 1,2-dichloroethane at room temperature, followed by reflux, the desired products 25 and 28 were obtained in 65% and 56% yields, respectively. These compounds were then converted to 4'-beta-thioadenosine (27) and 4'-beta-thioguanosine (30) under the usual conditions. This is therefore the first time that the stereoselective synthesis of 4'-beta-thioribonucleosides has been performed using the neighboring group participation of the Pummerer reaction.

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  234. Synthesis of the C-glycosidic analogue of adenophostin A and its uracil congener as potential IP3 receptor ligands. Stereoselective construction of the C-glycosidic structure by a temporary silicon-tethered radical coupling reaction Reviewed

    H Abe, S Shuto, A Matsuda

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 65 ( 14 ) page: 4315 - 4325   2000.7

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    Synthesis of the C-glycosidic analogue 9 of adenophostin A, a very potent IP3 receptor agonist, and its uracil congener 10 was achieved via a temporary silicon-tethered radical coupling reaction as the key step. Phenyl 3,4,6-tri-O-(p-methoxybenzyl)-1-seleno-beta-D-glucopyranoside (27) and 3-deoxy3-methylene-1,2-O-isopropylidene-alpha-D-erythro (30) were connected by a dimethylsilyl tether to give the radical coupling reaction substrate 24, which was successively treated with Bu-3-SnH/AIBN in benzene and TBAF in THF to give the coupling product 25 with the desired (3a,1'a)-configuration as the major product. From 25, the targets 9 and 10 were synthesized via introduction of adenine or uracil base by Vorbruggen's method and phosphorylation of the hydroxyls by the phosphoramidite method.

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  235. Stereoselective synthesis of alpha and beta-C-glucosides via radical cyclization with an allylsilyl tether. Control of the stereoselectivity by changing the conformation of the pyranose ring Reviewed

    S Shuto, M Terauchi, Y Yahiro, H Abe, S Ichikawa, A Matsuda

    TETRAHEDRON LETTERS   Vol. 41 ( 21 ) page: 4151 - 4155   2000.5

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    An efficient method for preparing both 1 alpha- and 1 beta-C-glucosides having a 3-hydroxypropyl group at the anomeric position via a radical cyclization reaction with an allylsilyl tether was developed. The stereoselectivity of the radical cyclization can be controlled by the conformation of the pyranose ring, which is effectively manipulated by the hyroxyl protecting groups. (C) 2000 Elsevier Science Ltd. All rights reserved.

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  236. Synthesis of the C-glycosidic analog of adenophostin A, a potent IP3 receptor agonist, using a temporary silicon-tethered radical coupling reaction as the key step Reviewed

    H Abe, S Shuto, A Matsuda

    TETRAHEDRON LETTERS   Vol. 41 ( 14 ) page: 2391 - 2394   2000.4

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    Synthesis of the C-glycosidic analog (3) of adenophostin A, a very potent IP3 receptor agonist, was achieved using a temporary silicon-tethered reductive radical coupling reaction as the key step. Radical reaction of the silaketal substrate 6 with Bu3SnH/AIBN in benzene occurred stereoselectively, and subsequent desilylation gave the desired C-glycosidic disaccharide 7 with the (3 alpha,1'alpha)-configuration as the major product. Compound 7 was converted into the target 3 via the introduction of an adenine base by a Vorbruggen glycosylation reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

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  237. Mechanistic study of the ring-enlargement reaction of (3-oxa-2-silacyclopentyl)methyl radicals into 4-oxa-3-silacyclohexyl radicals. Evidence for a pentavalent silicon-bridging radical transition state in 1,2-rearrangement reactions of beta-silyl radicals Reviewed

    S Shuto, Sugimoto, I, H Abe, A Matsuda

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 122 ( 7 ) page: 1343 - 1351   2000.2

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    A mechanistic study was performed on a novel radical ring-enlargement reaction of (3-oxa-2-silacyclopentyl)methyl radicals into 4-oxa-3-silacyclohexyl radicals. Two pathways, one via a pentavalent silicon bridging radical transition state (or intermediate), the other via beta-elimination to give a ring-opened silyl radical, can be postulated. The radical reactions of 1 and 2, which are precursors for a (3-oxa-2-silacyclopentyl)methyl radical C' and a 4-oxa-3-silacyclohexyl radical D', respectively, showed that the ring-enlargement rearrangement of C' into D' is irreversible. H-1 NMR analysis of the radical reactions of 8a and 8b, which have an asymmetric center at silicon, indicated that the configuration at the silicon atom is retained via a pentavalent silicon-bridging radical transition state (or intermediate) during the ring-enlargement reaction. Furthermore, examination of the radical ring-enlargement reaction with a deuterium-labeled substrate 12D showed that the ring-enlargement reaction did not involve beta-elimination to give a ring-opened silyl radical. Based on these results, we conclude that the ring-enlargement reaction occurs via a pentavalent silicon-bridging radical transition state (or intermediate). This is the first experimental evidence for such a pentavalent silicon radical, which has been previously postulated to understand radical reactions of organic silicon compounds.

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  238. Conjugation of dipeptide to fluorescent dyes enhances its affinity for a dipeptide transporter (PEPT1) in human intestinal Caco-2 cells Reviewed

    H Abe, M Satoh, S Miyauchi, S Shuto, A Matsuda, N Kamo

    BIOCONJUGATE CHEMISTRY   Vol. 10 ( 1 ) page: 24 - 31   1999.1

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    Dipeptide transporters in small intestine have a very wide substrate specificity, so that the transporter sometimes serves as a carrier for peptide-like compounds. We have synthesized dipeptide analogues conjugated at an E-amino group of Lys in Val-Lys or Lys-Sar with fluorescent compounds such as fluorescein isothiocyanate and coumarin-3-carboxylic acid. Uptakes of these peptide analogues were examined by measuring intracellular accumulations into monolayers of the human intestinal epithelial cell line Caco-2 expressing the dipeptide transporter PEPT1. Kinetic analysis and effects of addition either of uncoupler (protonophore) or by Gly-Sar, one of the good substrates of PEPT1, revealed that fluorescent dipeptides were taken up by passive diffusion. In contrast, these analogues remarkably inhibited the Gly-Sar uptake by Caco-2 cells. Among the fluorescent analogues synthesized in this paper, Vaf-Lys(Flu) was the most potent competitive inhibitor against the Gly-Sar uptake with an inhibition constant of 5 mu M. This value is the smallest among those ever reported: Val-Lys(Flu) has the highest affinity for PEPT1 among chemicals ever reported. The importance of the hydrophobic part of the substrate was pointed out.

    DOI: 10.1021/bc980049i

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Books 28

  1. 高純度キャップ化mRNAの調製を可能とするPureCap法の開発

    石田竜真, 阿部洋

    生化学 96巻1号 2024年2月刊  2024.2 

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  2. 2023 年ノーベル生理学・医学賞解説「mRNA 医薬品の実用化に向けた化学の役割」

    稲垣雅仁, 阿部洋

    月刊化学(化学同人)Vol.78 No12 (2023)  2023.11 

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  3. Synthesis of highly purified capped mRNA

    2023.10 

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  4. 核酸医薬分野における硫黄のマジック

    Meng Zheyu, 稲垣 雅仁, 阿部 洋

    「硫酸と工業」硫酸協会  2023.6 

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  5. mRNAの完全化学合成を可能とする化学的キャップ化法の開発

    小川和哉, 阿部洋

    現代科学  2023.5 

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  6. mRNAの完全化学合成を可能とする化学的キャップ化法の開発

    阿部 洋, 小川 和哉, 阿部 奈保子, 木村 康明

    MEDCHEM NEWS 33 巻 2 号 p. 75-78  2023.5 

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  7. 遺伝子治療開発研究ハンドブック 第2版

    坂野文香, 阿部奈保子, 阿部洋

    株式会社エヌ・ティー・エス  2023.4 

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  8. 核酸医薬・mRNA医薬の製造分析の基礎と基盤技術開発

    乙竹真美, 平岡陽花, 阿部洋

    株式会社シーエムシー・リサーチ  2023.2 

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  9. -

    Ohashi Sana, Hashiya Fumitaka, Hiroshi Abe

    2023.2 

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  10. 翻訳効率最大化のためのmRNA分子設計

    乙竹真美, 平岡陽花, 阿部洋

    株式会社シーエムシー出版  2023.2 

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  11. mRNA医薬の現在と未来 総合診療2023年1月号

    平岡陽花, 阿部洋

    医学書院  2023.1 

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  12. mRNAの完全化学合成

    小川和哉, 阿部洋

    現代科学2022年11月号  2022.10 

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  13. RNA干渉医薬の実現に向けた新手法の開発

    阿部洋、木村康明( Role: Joint author)

    2017 

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    Language:Japanese

  14. RNA干渉医薬の実現に向けた新手法の開発

    Biophilia  2017 

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  15. 環状RNAの合成とその翻訳反応 – 大腸菌と動物細胞の翻訳系

    阿部洋、阿部奈保子( Role: Joint author)

    羊土社  2016 

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  16. Nanostructured RNAs for RNA interference”, in “RNA interference: challenges and therapeutic opportunities. Methods in molecular biology

    Yuko Nakashima, Naoko Abe, Yoshihiro Ito, Hiroshi Abe(P.17-36)

    Humana Press  2015 

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  17. 「有機溶媒に溶ける核酸―DNA触媒の新たな可能性」

    阿部洋( Role: Sole author)

    東京化学同人  2013.1 

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  18. 「生細胞内RNA検出のための化学反応プローブ」「難培養微生物研究の最新技術2〜ゲノム解析を中心とした最前線と将来展望〜」

    古川和寛,阿部洋,伊藤嘉浩,常田聡( Role: Joint author)

    シーエムシー出版  2010 

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  19. 「生細胞内RNA検出のための化学反応プローブ」「難培養微生物研究の最新技術II~ゲノム解析を中心とした最前線と将来展望~」

    2010 

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  20. 終わりのない核酸の話ケミカルバイオロジー入門

    阿部洋( Role: Sole author)

    オーム社  2008.9 

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  21. 終わりのない核酸の話 ケミカルバイオロジー入門

    Abe Hiroshi

    オーム社  2008.9 

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  22. 細胞内RNA可視化のためのバイオプローブ蛋白質 核酸 酵素

    阿部洋,古川和寛,常田聡,伊藤嘉浩( Role: Joint author)

    共立出版株式会社  2007 

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  23. 細胞内遺伝子発現検出用の蛍光バイオプロープの設計と合成「ー細胞内定量解析の最前線」

    阿部洋,古川和寛,常田聡,伊藤嘉浩( Role: Joint author)

    シーエムシー出版  2007 

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  24. 抗体医薬の最前線

    和田章,阿部洋,伊藤嘉浩( Role: Joint author)

    シーエムシー出版  2007 

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  25. 細胞内遺伝子発現検出用の蛍光バイオプローブの設計と合成 「一細胞内定量解析の最前線」

    阿部洋, 古川和寛, 常田聡, 伊藤嘉浩(p135)

    シーエムーシー出版  2007 

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  26. アプタマー医薬 「抗体医薬の最前線」

    和田章, 阿部洋, 伊藤嘉浩(p213)

    シーエムーシー出版  2007 

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  27. 細胞内RNA可視化のためのバイオプローブ 蛋白質 核酸 酵素

    共立出版株式会社  2007 

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  28. バイオプロープを用いたイメージング法とチップ解析法「ナノオプティクス・ナノフォトニクスのすべて」

    阿部洋,伊藤嘉浩( Role: Joint author)

    フロンティア出版  2006 

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MISC 36

  1. Synthesis of chemically modified nucleic acids and their application to nucleic acid drugs

    野村浩平, 村瀬裕貴, 中本航介, 木村康明, 阿部奈保子, AN Seongjin, 小林芳明, 程久美子, 程久美子, 阿部洋, 阿部洋, 阿部洋

    日本薬学会年会要旨集(Web)   Vol. 141st   2021

  2. 新規2′修飾核酸によるsiRNAの標的特異性の向上

    馬場麟太郎, 野村浩平, 阿部奈保子, 安成鎮, 小林芳明, 程久美子, 橋谷文貴, 木村康明, 阿部洋

    中部化学関係学協会支部連合秋季大会講演予稿集   Vol. 52nd (CD-ROM)   2021

  3. Synthesis of 1,1,2-Trisubstituted Cyclopropane Nucleosides in Enantiomerically Pure Forms (vol 38, pg 921, 2019)

    Daichi Fushihara, Hayato Fukuda, Hiroshi Abe, Satoshi Shuto

    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS   Vol. 39 ( 1-3 ) page: 471 - 471   2020.2

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    DOI: 10.1080/15257770.2020.1736777

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  4. Disulfide-unit Conjugation Enables Ultrafast Cytosolic Internalization of Antisense DNA and siRNA

    Nakamoto Kosuke, Shu Zhaoma, Abe Hiroshi

    Journal of Synthetic Organic Chemistry, Japan   Vol. 78 ( 5 ) page: 456 - 464   2020

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    <p>Oligonucleotide-based therapeutics are expected as novel therapeutic modalities, because they have a strong potential to cure the diseases which could not be targeted by conventional low-molecular-weight drugs. However, oligonucleotide has a polyanion structure derived from a phosphodiester backbone and thus, it cannot penetrate cell membranes. To develop the oligonucleotides-based therapeutics, this extremely low membrane permeability should be improved. In this study, we focused on the disulfide modification of oligonucleotides. Several disulfide derivatives are known to show efficient cellular uptake triggered by disulfide exchanging reaction with thiol group of membrane proteins. Therefore, we have synthesized the series of disulfide LD, CD or PD-conjugate oligonucleotides. All these disulfide modifications improved the membrane permeability of Antisense DNA and siRNA. Furthermore, several disulfide-conjugated oligonucleotides showed higher cellular uptake over lipofection method without any cytotoxicity. Surprisingly, the disulfide modified oligonucleotides are internalized directly into the cytoplasm with only 10 min. This ultrafast internalization of oligonucleotides is an advantage for the therapeutic application. Currently, we are trying to apply this novel disulfide-based membrane permeable oligonucleotide (MPON) for the development of oligonucleotide-based therapeutics.</p>

    DOI: 10.5059/yukigoseikyokaishi.78.456

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  5. ウイルスタンパク質の活性をトリガーとした新規不可逆阻害剤の開発

    福井竜介, 新美結士, 片倉秀雄, 鈴木哲郎, 村上努, 児玉栄一, 木村康明, 阿部洋

    日本薬学会年会要旨集(CD-ROM)   Vol. 139th ( 2 ) page: ROMBUNNO.23K‐pm11 - 103   2019.3

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  6. 膜透過性を有するGST共有結合性阻害剤の開発

    友池史明, 宍戸裕子, 宍戸裕子, 藤川遥加, 木村康明, 桑田啓子, 村上優子, 福井健二, 関戸好孝, 矢野貴人, 亀田倫史, 周東智, 阿部洋, 阿部洋

    日本薬学会年会要旨集(CD-ROM)   Vol. 139th   2019

  7. ウイルスポリメラーゼの不可逆阻害を目指した新規2′‐&βセレノ核酸アナログの創製

    村上努, 木村康明, 新美結士, 藤野真之, 片倉秀雄, 鈴木哲朗, 児玉栄一, 阿部洋

    日本エイズ学会誌   Vol. 20 ( 4 ) page: 468 - 468   2018.11

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  8. ウイルスポリメラーゼの不可逆阻害を目指した新規2'-&βセレノ核酸アナログの創製

    村上 努, 木村 康明, 新美 結士, 藤野 真之, 片倉 秀雄, 鈴木 哲朗, 児玉 栄一, 阿部 洋

    日本エイズ学会誌   Vol. 20 ( 4 ) page: 468 - 468   2018.11

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  9. Development of glutathione S-transferase (GST) covalent inhibitor

    Shishido Yuko, Tomoike Fumiaki, Kimura Yasuaki, Kuwata Keiko, Yano Takato, Fukui Kenji, Fujikawa Haruka, Sekido Yoshitaka, Murakami-Tonami Yuko, Kameda Tomoshi, Shuto Satoshi, Abe Hiroshi

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   Vol. 255   page: .   2018.3

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  10. RETFプローブを用いた生体内の核酸検出

    友池史明, 山岡和樹, 伊藤真央, 木村康明, 井上貴文, 阿部洋

    日本化学会春季年会講演予稿集(CD-ROM)   Vol. 98th   2018

  11. グルタチオン-S-トランスフェラーゼを標的とした共有結合性阻害剤の開発

    宍戸 裕子, 藤川 遥加, 友池 史明, 木村 康明, 桑田 啓子, 村上 優子, 福井 健二, 関戸 好孝, 矢野 貴人, 周東 智, 阿部 洋

    生命科学系学会合同年次大会   Vol. 2017年度   page: [3P - 0205]   2017.12

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    Language:Japanese   Publisher:生命科学系学会合同年次大会運営事務局  

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  12. グルタチオンS-トランスフェラーゼのプローブ開発

    藤川 遥加, 宍戸 裕子, 村上 優子, 関戸 好孝, 阿部 洋

    日本癌学会総会記事   Vol. 76回   page: P - 2323   2017.9

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  13. 共有結合型グルタチオンS-転移酵素阻害剤の創薬研究

    宍戸 裕子, 関戸 好孝, 村上 優子, 阿部 洋

    日本癌学会総会記事   Vol. 76回   page: P - 1411   2017.9

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  14. 共有結合型グルタチオンS-転移酵素阻害剤の創薬研究

    宍戸 裕子, 藤川 遥加, 木村 康明, 友池 史明, 桑田 啓子, 矢野 貴人, 福井 健二, 関戸 好孝, 村上 優子, 周東 智, 阿部 洋

    日本薬学会年会要旨集   Vol. 137年会 ( 2 ) page: 68 - 68   2017.3

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  15. 糖部三員環型ヌクレオシドアナログの創成

    伏原大地, 福田隼, 阿部洋, 周東智

    日本薬学会年会要旨集(CD-ROM)   Vol. 137th   page: ROMBUNNO.26S‐pm10S   2017

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  16. 炎症収束性脂質・レゾルビンE2の安定等価体の創製

    石村航平, 福田隼, 高倉夕季, 金田龍太郎, 平尾徹, 平島洸基, 室本竜太, 松田正, 阿部洋, 周東智

    メディシナルケミストリーシンポジウム講演要旨集   Vol. 33rd   page: 78   2015.11

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  17. 内因性炎症収束脂質レゾルビンE2安定等価体の創製

    福田隼, 高倉夕季, 石村航平, 金田龍太郎, 平尾徹, 平島洸基, 室本竜太, 松田正, 阿部洋, 有澤光弘, 周東智

    反応と合成の進歩シンポジウム講演要旨集   Vol. 41st   page: 37   2015.10

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  18. 細胞表面へのホスホセリン提示可能なホスファチジルセリン二量体の設計と合成

    佐藤耀, 川村周平, 平尾徹, 室本竜太, 福田隼, 阿部洋, 松田正, 周東智

    万有生命科学振興国際交流財団札幌シンポジウム   Vol. 27th   page: 42   2015.7

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  19. 5配位ケイ素ラジカルを経由するラジカル環拡大反応:実験と理論計算に基づく反応機構の解析

    KANEDA RYUTARO, SUGIMOTO ISAMU, IWAMOTO TAKEAKI, FUKUDA HAYATO, ABE HIROSHI, ABE HIROSHI, SHUTO SATOSHI

    日本薬学会年会要旨集(CD-ROM)   Vol. 135th   page: ROMBUNNO.26I-PM12S   2015

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  20. スピロシクロプロパン型βストランドミメティックの創製研究

    KUWAHARA TOMOKI, MIZUNO AKIRA, FUKUDA HAYATO, ABE HIROSHI, ABE HIROSHI, SHUTO SATOSHI

    日本薬学会年会要旨集(CD-ROM)   Vol. 135th   page: ROMBUNNO.28I-PM11S   2015

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  21. ファゴサイトーシス誘導性ホスファチジルセリン二量体類縁化合物の創製研究

    SATO YO, KAWAMURA SHUHEI, HIRAO TOORU, MUROMOTO RYUTA, FUKUDA HAYATO, ABE HIROSHI, ABE HIROSHI, MATSUDA TADASHI, SHUTO SATOSHI

    日本薬学会年会要旨集(CD-ROM)   Vol. 135th   page: ROMBUNNO.28T-AM12S   2015

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  22. 誘導体合成を指向したレゾルビンE1の全合成

    ISHIMURA KOHEI, FUKUDA HAYATO, TAKAKURA YUKI, ABE HIROSHI, ABE HIROSHI, SHUTO SATOSHI

    日本薬学会年会要旨集(CD-ROM)   Vol. 135th   page: ROMBUNNO.28H-PM05S   2015

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  23. PdおよびNi触媒によるシクロプロパン第三級炭素上への芳香環導入反応―効率的化学空間探索型創薬ライブラリーの構築を目指して―

    HOSHIYA NAOYUKI, YOTSUJI KEISUKE, KOBAYASHI TAKAAKI, FUKUDA HAYATO, ABE HIROSHI, ARISAWA MITSUHIRO, SHUTO SATOSHI

    反応と合成の進歩シンポジウム講演要旨集   Vol. 40th   page: 94   2014.10

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  24. ルテニウムカルベン錯体を用いたワンポット反応の開発と新規多環性複素環骨格の構築

    FUJII YUKI, KATO HIROSHIGE, FUKUDA HAYATO, ABE HIROSHI, FUJIOKA HIROMICHI, SHUTO SATOSHI, ARISAWA MITSUHIRO

    複素環化学討論会講演要旨集   Vol. 44th   page: 227 - 228   2014.8

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  25. Sustained delivery of siRNA from dopamine-coated stainless steel surfaces (vol 9, pg 6753, 2013)

    Binata Joddar, Aydin Albayrak, Jeonghwa Kang, Mizuki Nishihara, Hiroshi Abe, Yoshihiro Ito

    ACTA BIOMATERIALIA   Vol. 10 ( 8 ) page: 3811 - 3811   2014.8

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    DOI: 10.1016/j.actbio.2014.05.034

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  26. GABA配座制限に基づく初のGABAトランスポーターBGT‐1サブタイプ高選択的阻害剤の創製

    SUEMASA AKIHIRO, NAKADA KAZUAKI, KOBAYASHI TAKAAKI, IKAWA ARISA, FUKUDA HAYATO, ABE YO, ARISAWA MITSUHIRO, IDE SOICHIRO, MINAMI MASABUMI, SHUTO SATOSHI

    万有生命科学振興国際交流財団札幌シンポジウム   Vol. 26th   page: 64   2014.7

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  27. 疎水性相互作用による相補的塩基対に基づく機能性核酸の開発

    ENDO HIDEYUKI, MIZUNO AKIRA, ABE YO, FUKUDA HAYATO, KOMATSU YASUO, SHUTO SATOSHI

    日本薬学会年会要旨集(CD-ROM)   Vol. 134th   page: ROMBUNNO.28Y-PM07   2014

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  28. Pdナノ粒子触媒SAPdを用いたアリルエステルの脱アリル化反応の開発

    高木耕治, 福田隼, 阿部洋, 周東智, 大高章, 有澤光弘, 有澤光弘

    反応と合成の進歩シンポジウム講演要旨集   Vol. 40th   2014

  29. ルテニウム触媒を用いた閉環メタセシス(RCM)‐[3+2]環化付加ワンポット反応の開発

    FUJII YUKI, KATO HIROSHIGE, FUKUDA HAYATO, ITO MIKA, ABE YO, ITO YOSHIHIRO, ARISAWA MITSUHIRO, SHUTO SATOSHI

    日本薬学会年会要旨集(CD-ROM)   Vol. 133rd   page: ROMBUNNO.30N-PM43   2013

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  30. New fluorogenic probe for detection of glutathione s-transferase activity in living cells

    Mika Ito, Hiroshi Abe, Aya Shibata, Shigeru Shimizu, Johan Alander, Ralf Morgenstern, Yoshihiro Ito

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   Vol. 239   2010.3

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  31. Polymers to Regulate Cell Functions for Regenerative Medicine

    ITO Yoshihiro, KITAJIMA Takashi, ABE Hiroshi

      Vol. 58 ( 3 ) page: 129 - 132   2009.3

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  32. 2Cp15 Dumbbell-shaped nanocircular RNA for RNA interference

    Abe Hiroshi, Abe Naoko, Uda Miwako, Tsuneda Satoshi, Ito Yoshihiro

      Vol. 21   page: 34 - 34   2009

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    CiNii Books

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  33. MEDI 134-Multiple chemical ligation under thermal cycle

    Yuko Kondo, Hiroshi Abe, Hiroshi Jinmei, Naoko Abe, Kyoko Aikawa, Isamu Matsumoto, Yoshihiro Ito

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   Vol. 235   2008.4

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    Web of Science

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  34. Bioprobe for imaging RNA in living cells

    Protein, nucleic acid and enzyme   Vol. 52 ( 13 ) page: 1619 - 1624   2007.10

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  35. 2S1AM5 DNA-templated chemical reactions for RNA detection in living cells

    Abe Hiroshi

      Vol. 19   page: 8 - 8   2007

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  36. 2E16-5 Synthesis of novel fluorescent compound and its application for nucleic acid sensing

    FURUKAWA Kazuhiro, ABE hiroshi, WANG Jin, OKI Kazuma, UDA Miwako, TSUNEDA Satoshi, ITO Yoshihiro

      Vol. 19   page: 124 - 124   2007

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Presentations 186

  1. テーマ3:核酸・DDS・ワクチン Invited

    阿部洋

    日本薬学会第 143 年会 領域融合企画「つながる・つきぬける」  2023.3.28  日本薬学会

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    Event date: 2023.3

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Country:Japan  

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  2. "ゲノムから見る生命システム (JST戦略的創造研究推進事業「ゲノムスケールのDNA設計・合成による細胞制御技術の創出」領域共催)" Invited

    阿部洋

    「細胞を創る」研究会  2022.10.18  「細胞を創る」研究会

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    Event date: 2022.10

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:東工大蔵前会館   Country:Japan  

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  3. 化学的手法を用いたmRNAの合成と創薬研究 Invited

    阿部洋

    BioJapan 2022  2022.10.12  BioJapan

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    Event date: 2022.10

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:パシフィコ横浜  

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  4. 翻訳反応の制御を目的とした核酸分子の開発 Invited

    阿部洋

    大阪府 2022年度 ライフサイエンス海外ビジネス展開等支援事業 9月度セミナー  2022.9.9  大阪府

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    Event date: 2022.9

    Language:Japanese   Presentation type:Oral presentation (keynote)  

    Venue:online   Country:Japan  

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  5. 翻訳反応サイクルを加速するmRNAの分子デザインと創薬への展開 Invited

    阿部洋

    東工大化学生命科学研究所シンポジウム「 化学生命科学先駆研究のNew Horizon」  2022.8.19  東工大化学生命科学研究所

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    Event date: 2022.8

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:東工大化学生命科学研究所(横浜市)   Country:Japan  

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  6. Improvement of mRNA function based on chemical modification and structure design Invited

    2022.8.2 

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    Event date: 2022.7 - 2022.8

    Language:English   Presentation type:Oral presentation (invited, special)  

    Country:Japan  

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  7. LINK-J 共催 名古屋大学発!ON LINE セミナー(核酸医薬関連) Invited

    阿部洋

    LINK-J 共催 名古屋大学発!ON LINE セミナー(核酸医薬関連)  2022.7.13  LINK-J

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    Event date: 2022.7

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:online   Country:Japan  

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  8. RNA創薬を目的とした核酸分子の開発 Invited

    阿部 洋

    千里ライフサイエンス振興団  2021.10.20 

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    Event date: 2021.10

    Language:Japanese   Presentation type:Oral presentation (keynote)  

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  9. 有機化学を基盤とする核酸医薬へのアプローチ Invited

    阿部 洋

    有機合成化学協会「ニューモダリティと有機合成化学」第5回勉強会  2021.8.19 

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    Event date: 2021.8

    Presentation type:Oral presentation (invited, special)  

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  10. 核酸医薬のための化学的アプローチ 硫黄のマジック Invited

    阿部 洋

    日本薬学会 第141年会  2021.3.27 

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    Event date: 2021.3

    Presentation type:Oral presentation (invited, special)  

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  11. Development of nucleic acid drug for controlling protein expression Invited

    Hiroshi Abe

    ACBI 2024 Istanbul  2024.3.2 

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    Event date: 2024.3

    Language:English   Presentation type:Oral presentation (invited, special)  

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  12. Development of nucleic acid drug for controlling protein expression Invited

    Hiroshi Abe

    Istanbul Medipol University “Infocus:Meeting for a Purpose”  2024.3.1 

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    Event date: 2024.3

    Language:English   Presentation type:Oral presentation (invited, special)  

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  13. PureCap法を用いた高純度mRNAの製造と医療応用 Invited

    阿部 洋

    難治疾患共同研究拠点シンポジウム  2024.2.27 

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    Event date: 2024.2

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

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  14. 化学を基盤とするmRNA医薬の創薬研究 Invited

    阿部 洋

    第18回理研 「バイオものづくり」シンポジウム  2024.1.24 

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    Event date: 2024.1

    Language:Japanese  

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  15. Chemistry-based mRNA design for the efficient translation

    Hiroshi Abe

    IsBOC-13  2023.12.19 

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    Event date: 2023.12

    Language:English   Presentation type:Oral presentation (general)  

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  16. Chemistry-based mRNA design for the efficient translation Invited

    Hiroshi Abe

    ACBI2023  2023.12.16 

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    Event date: 2023.12

    Language:English   Presentation type:Oral presentation (invited, special)  

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  17. PureCap法を用いた次世代mRNAの開発 Invited

    阿部 洋

    みずほ医薬・バイオカンファレンス  2023.12.12 

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    Event date: 2023.12

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

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  18. 化学を基盤とするmRNA医薬製造技術の開発 Invited

    阿部 洋

    日本プロセス化学会2023ウィンターシンポジウム  2023.12.8 

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    Event date: 2023.12

    Language:Japanese  

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  19. Chemistry-based mRNA design for the efficient translation Invited

    Hiroshi Abe

    FNA Pearth 2023 Conference  2023.11.23 

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    Event date: 2023.11

    Language:English  

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  20. 化学を基盤とするmRNA医薬の設計 Invited

    阿部 洋

    第40回メディシナルケミストリーシンポジウム  2023.11.14 

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    Event date: 2023.11

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

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  21. Chemistry-based mRNA design for the efficient translation Invited

    Hiroshi Abe

    A3RONA 2023  2023.11.11 

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    Event date: 2023.11

    Language:English   Presentation type:Oral presentation (invited, special)  

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  22. PureCap 法を用いた高純度mRNA合成 Invited

    阿部 洋

    第14回日本RNAi研究会  2023.9.1 

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    Event date: 2023.8 - 2023.9

    Presentation type:Oral presentation (invited, special)  

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  23. Chemistry-based mRNA design for studying structure, translation, and stability relationship Invited

    Hiroshi Abe

    The 39th Annual Meeting of the Japan Society of Drug Delivery System  2023.7.27 

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    Event date: 2023.7

    Language:English   Presentation type:Oral presentation (invited, special)  

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  24. Complete chemical synthesis of mRNA Invited

    Hiroshi Abe

    <natsj8>the Nucleic Acid Drug Conference  2023.7.11 

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    Event date: 2023.7

    Language:English   Presentation type:Oral presentation (invited, special)  

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  25. Design and Synthesis of mRNA by Chemical Methods Invited

    Hiroshi Abe

    Nucleosides, Nucleotides and Oligonucleotides Gordon Research Conference(GRC)  2023.6.27 

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    Event date: 2023.6

    Language:English   Presentation type:Oral presentation (invited, special)  

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  26. 化学を基盤とするmRNAの分子設計と医薬応用 Invited

    Hiroshi Abe

    2023.6.9 

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    Event date: 2023.6

    Language:Japanese  

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  27. Design and synthesis of super mRNA for Drug discovery Invited

    Hiroshi Abe

    2023.5.18 

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    Event date: 2023.5

    Language:English  

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  28. Chemistry-based mRNA synthesis using efficient capping reaction Invited

    Hiroshi Abe

    Asia tides 2023  2023.3.8 

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    Event date: 2023.3

    Language:English   Presentation type:Oral presentation (invited, special)  

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  29. Design and Synthesis of Super mRNA Invited

    Hiroshi Abe

    Azadi Ka Amirit Mahotsav Award Seminar at IICT (Indian Institute Of Chemical Technology)  2023.1.23 

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    Event date: 2023.1

    Language:English   Presentation type:Oral presentation (invited, special)  

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  30. Design and Synthesis of Super mRNA Invited

    Hiroshi Abe

    IIT(Indian Institute of Technology)  2023.1.20 

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    Event date: 2023.1

    Language:English  

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  31. Design and Synthesis of RNA medicine Invited

    Hiroshi Abe

    Sapala meeting  2023.1.17 

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    Event date: 2023.1

    Language:English   Presentation type:Oral presentation (invited, special)  

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  32. Synthesis and Design of RNA medicine Invited

    Hiroshi Abe

    Invited Seminar at CheerLand meeting  2023.1.12 

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    Event date: 2023.1

    Language:English   Presentation type:Public lecture, seminar, tutorial, course, or other speech  

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  33. 化学を基盤とするmRNAの分子設計・製造法の革新とワクチンへの展開 Invited

    阿部洋

    Leap meeting  2022.12.21 

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    Event date: 2022.12

    Language:Japanese   Presentation type:Public lecture, seminar, tutorial, course, or other speech  

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  34. 「mRNA医薬のための分子設計」 Invited

    阿部洋

    富士フイルム株式会社有機合成化学研究所講演会  2022.12.7  富士フイルム株式会社有機合成化学研究所

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    Event date: 2022.12

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:online  

    アブストラクト:mRNA医薬は次世代医薬技術として注目されており、タンパク質補充療法やワクチン療法への利用が期待されている。我々は、高い翻訳効率と生物学的安定性を有するmRNA分子の設計・合成を目指して研究に取り組んできた。その分子設計戦略として、翻訳反応サイクルの律速段階である開始段階を制御できるmRNA分子を設計を基盤として、タンパク質合成効率を向上できるmRNA分子を開発してきた。それらの成果について報告する。

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  35. 「メッセンジャーRNA(mRNA)による未来の医療」 Invited

    阿部洋

    名古屋市科学館 古川為三郎サイエンス講演会  2022.12.3  名古屋市科学館

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    Event date: 2022.12

    Language:Japanese   Presentation type:Oral presentation (keynote)  

    Venue:名古屋市科学館 生命館 地下2階 サイエンスホール   Country:Japan  

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  36. Synthetic Biology of Circular RNA Invited

    Hiroshi Abe

    Laronde Research Seminar  2022.11.11 

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    Event date: 2022.11

    Language:English   Presentation type:Oral presentation (invited, special)  

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  37. Complete Chemical Synthesis of Messenger RNA and PureCap Technology Invited

    Hiroshi Abe

    10th international mRNA health conference  2022.11.8 

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    Event date: 2022.11

    Language:English   Presentation type:Oral presentation (invited, special)  

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  38. 「翻訳機能を向上するmRNAの分子設計」 Invited

    阿部洋

    第43回生体膜と薬物の相互作用シンポジウム(薬学会)  2022.10.7 

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    Event date: 2022.10

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:北大(札幌市)   Country:Japan  

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  39. mRNA医薬の新規創薬基盤技術 Invited

    阿部洋

    日経バイオテク オンラインセミナー  2022.9.27  日経バイオテク

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    Event date: 2022.9

    Language:Japanese   Presentation type:Oral presentation (keynote)  

    Venue:online   Country:Japan  

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  40. Chemical Synthesis of mRNA & The Structure Activity Relationship Invited International conference

    Abe Hiroshi

    mRNA Process Development & Manufacturing Summit  2022.9.22 

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    Event date: 2022.9

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:online, Boston, MA   Country:United States  

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  41. 特別講演「RNA医薬」 Invited

    阿部洋

    第23回日本RNA学会年会  2022.7.21  日本RNA学会

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    Event date: 2022.7

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:みやこめっせ(京都市)   Country:Japan  

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  42. mRNAの完全化学合成と構造活性相関 Invited

    阿部洋

    第38回DDS学会学術集会  2022.6.29  mRNAの完全化学合成と構造活性送還

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    Event date: 2022.6

    Language:Japanese  

    Venue:online  

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  43. RNA創薬を志向した核酸分子の開発 Invited

    阿部洋

    第63回日本神経学会  2022.5.19  日本神経学会

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    Event date: 2022.5

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:東京国際フォーラム(東京都)  

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  44. 新規抗ウイルス薬を志向した修飾2-5Aの合成 Invited

    伏原 大地, 太田 杏摘, 田中 育, 今枝 昭裕, 永井 貴広, 星野 真一, 木村 康明, 友池 史明, 阿部 洋

    日本薬学会第138年会 

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    Event date: 2018.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  45. 高分子核酸医薬の低分子化戦略:細胞内ビルドアップ法の開発

    木村 康明, 丸山 豪斗, 笈川 涼太, 吉永 静也, 辻 厳一郎, 阿部 奈保子, 松田 彰, 周東 智, 伊藤 嘉浩, 阿部 洋

    日本薬学会第138年会 

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    Event date: 2018.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  46. 抗ウイルス活性を指向した新規2'修飾ヌクレオシドの合成および評価

    新美 結士, 片倉 秀雄, 阿部 奈保子, 木村 康明, 阿部 洋

    日本薬学会第138年会 

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    Event date: 2018.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  47. カチオン性ポリマーを結合した核酸誘導体によるアンチセンス効果

    太田 杏摘, 伏原 大地, Zhaoma SHU, 阿部 奈保子, 木村 康明, 阿部 洋

    日本薬学会第138年会 

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    Event date: 2018.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  48. 膜透過性核酸の開発

    Zhaoma SHU, 太田 杏積, 田中 育, 伏原 大地, 阿 部 奈保子, 友池 史明, 木村 康明, 阿部 洋

    日本薬学会第138年会 

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    Event date: 2018.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  49. 真核生物翻訳系における終わりのない回転式翻訳現象

    清水 沙彩, 児玉 亜有実, 富田 貴志, 阿部 奈保子, 友池 史明, 木村 康明, 阿部 洋

    日本薬学会第138年会 

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    Event date: 2018.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  50. 抗ウイルス活性を指向したヌクレオシドの開発

    片倉秀雄, 新美結士, 木村康明, 鈴木哲郎, 村上優子, 阿部洋

    日本化学会 第98春季年会 

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    Event date: 2018.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  51. N6-アルキルアデノシン導入によるRNAの機能制御

    今枝昭裕, 笈川涼太, 浅井潔, 桜庭俊, 岩切淳一, 阿部奈保子, 友池史明, 木村康明, 阿部洋

    日本化学会 第98春季年会 

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    Event date: 2018.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  52. 膜透過性分子を結合したオリゴ核酸の合成

    田中育, 太田杏摘, 伏原大地, SHU Zhaoma, 阿部奈保子, 友池史明, 木村康明, 阿部洋

    日本化学会 第98春季年会 

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    Event date: 2018.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  53. RETFプローブを用いた生体内の核酸検出

    友池史明, 山岡和樹, 伊藤真央, 木村康明, 井上貴文, 阿部洋

    日本化学会 第98春季年会 

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    Event date: 2018.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  54. 蛍光オフ・オン型分子を導入した核酸プローブの開発

    山岡和樹, 伊藤真央, 阿部奈保子, 友池史明, 木村康明, 阿部洋

    日本化学会 第98春季年会 

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    Event date: 2018.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  55. 多分岐型DNAケミカルライゲーションによる標的核酸分子のトポロジカル固定

    富田貴志, 阿部奈保子, 木村康明, 鬼塚和光, 阿部洋

    日本化学会 第98春季年会 

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    Event date: 2018.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  56. 共有結合型GST阻害剤の開発

    富田貴志, 阿部奈保子, 木村康明, 鬼塚和光, 阿部洋

    日本化学会 第98春季年会 

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    Event date: 2018.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  57. グルタチオン-S-トランスフェラーゼを標的とした共有結合性阻害剤の開発

    宍戸裕子、藤川遥加、友池史明、木村康明、桑田啓子、村上優子、福井健二、関戸好孝、矢野貴人、周東智、阿部洋

    分子生物学会 

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    Event date: 2017.12

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  58. RNA Interference by Intracellar Buildup of siRNA International conference

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    Event date: 2017.11

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  59. Development of intracellular RNA detection probe enable chemical signal amplification International conference

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    Event date: 2017.11

    Language:English   Presentation type:Poster presentation  

    Country:Japan  

  60. Development of Anti-cancer Agents based on Synthetic Lethality by LATS Mutation.

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    Event date: 2017.10

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  61. 抗ウイルス活性を指向した2'-β-チオ核酸の開発

    片倉秀雄, 木村康明, 阿部洋

    統合物質創製化学研究推進機構 第3回 国内シンポジウム 

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    Event date: 2017.10

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  62. ロタキサン構造形成による新規アンチセンス法の開発

    富田貴志, 阿部奈保子, 木村康明, 阿部洋

    統合物質創製化学研究推進機構 第3回 国内シンポジウム 

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    Event date: 2017.10

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  63. 細胞内グルタチオン-S-トンランスフェラーゼ活性を検出するためのプローブ開発

    友池史明、宍戸裕子、藤川遥加、木村康明、柴田綾、周東智、阿部洋

    日本分析化学会第66年会 

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    Event date: 2017.9

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  64. 高分子核酸医薬の低分子戦略:細胞内ビルドアップ法の開発

    木村康明、丸山豪斗、伊藤美香、笈川涼太、早川真由、辻厳一郎、阿部奈保子、松田彰、周東智、伊藤嘉浩、阿部洋

    第11回バイオ関連化学シンポジウム 

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    Event date: 2017.9

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  65. 高分子核酸医薬の低分子戦略:細胞内ビルドアップ法の開発

    木村康明、丸山豪斗、笈川涼太、早川真由、吉永静也、辻厳一郎、阿部奈保子、松田彰、周東智、伊藤嘉浩、阿部洋

    日本核酸医薬学会第3回年会 

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    Event date: 2017.7

    Language:Japanese   Presentation type:Poster presentation  

    Country:Japan  

  66. 高分子核酸医薬の低分子戦略:細胞内ビルドアップ法の開発

    木村康明、丸山豪斗、伊藤美香、笈川涼太、早川真由、辻厳一郎、阿部奈保子、松田彰、周東智、伊藤嘉浩、阿部洋

    ケミカルバイオロジー学会 

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    Event date: 2017.6

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  67. 高効率な核酸検出を可能にする核酸鋳型反応の開発

    伊藤真央、柴田綾、阿部奈保子、木村康明、阿部洋

    日本薬学会第137年会 

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    Event date: 2017.3

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  68. 共有結合型グルタチオンS-転移酵素阻害剤の創薬研究

    宍戸裕子、藤川遙加、木村康明、友池史明、桑田啓子、矢野貴人、福井健二、関戸好孝、村上優子、周東智、阿部洋

    日本薬学会137年会 

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    Event date: 2017.3

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  69. 糖部三員環型ヌクレオシドアナログの創成

    伏原大地、福田隼、阿部洋、周東智

    日本薬学会第137年会 

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    Event date: 2017.3

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  70. ビルドアップ型核酸分子の開発

    吉永静也、辻厳一郎、阿部奈保子、友池史明、木村康明、阿部洋

    統合物質創製化学研究推進機構第2回国内シンポジウム 

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    Event date: 2017.1

    Language:English   Presentation type:Poster presentation  

    Country:Japan  

  71. 光解除性保護基を有するヌクレオチドを利用した長鎖RNAのケミカルライゲーション

    辻厳一郎、笈川涼太、早川真由、木村康明、阿部洋

    統合物質創製化学研究推進機構第2回国内シンポジウム 

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    Event date: 2017.1

    Language:English   Presentation type:Poster presentation  

    Country:Japan  

  72. 共有結合型グルタチオンS-転移酵素阻害剤の創薬研究

    宍戸裕子、藤川遙加、木村康明、友池史明、桑田啓子、矢野貴人、福井健二、関戸好孝、村上優子、周東智、阿部洋

    第34回メディシナルケミストリーシンポジウム 

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    Event date: 2016.11 - 2016.12

    Language:English   Presentation type:Poster presentation  

    Country:Japan  

  73. 合成環状RNAからのタンパク質発現

    児玉亜有実、阿部奈保子、友池史明、伊藤嘉浩、松本健、吉田稔、清水義宏、亀田倫史、阿部洋

    第39回分子生物学会 

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    Event date: 2016.11 - 2016.12

    Language:English   Presentation type:Poster presentation  

    Country:Japan  

  74. 細胞内ビルドアップ型SiRNAを志向した新規核酸連結反応

    早川真由、笈川涼太、丸山豪斗、阿部奈保子、木村康明、周東智、松田彰、阿部洋

    日本核酸医薬学会第二会年会 

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    Event date: 2016.11

    Language:English   Presentation type:Poster presentation  

    Country:Japan  

  75. Development of novel chemical ligation reaction for RNA strands International conference

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    Event date: 2016.9

    Language:English   Presentation type:Poster presentation  

    Country:Japan  

  76. 求電子的ホスホロチオエステルによる核酸の化学的連結反応

    木村康明、丸山豪斗、笈川涼太、早川真由、阿部奈保子、松田彰、周東智、伊藤嘉浩、阿部洋

    第10回バイオ関連化学シンポジウム 

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    Event date: 2016.9

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  77. Nile Blueを基本骨格とした脂肪滴検出プローブの創製

    戸田直宏、伊藤美香、石田綾乃、鬼頭宏任、横川大輔、阿部洋

    第10回バイオ関連化学シンポジウム 

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    Event date: 2016.9

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  78. Rolling circle translation of Circular RNA

    Naoko Abe, Yasuaki Kimura, Fumiaki Tomoike, Ken Matsumoto, Minoru Yoshida, Yoshihiro Ito, Hiroshi Abe

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    Event date: 2016.6 - 2016.7

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  79. 核酸のケミカルバイオロジー

    阿部 洋

    総合物質創製化学研究推進機構キックオフシンポジウム 

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    Event date: 2016.6

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  80. Rolling circle translation using small circular RNA International conference

    Pacifichem 2015 

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    Event date: 2015.12

    Language:English   Presentation type:Poster presentation  

    Country:United States  

  81. 合成環状RNAからのタンパク質発現

    阿部洋、阿部奈保子、伊藤嘉浩、松本健、吉田稔

    日本核酸医薬学会第1回年会 

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    Event date: 2015.11 - 2015.12

    Language:Japanese   Presentation type:Poster presentation  

    Country:Japan  

  82. 細胞内RNAの解析と機能制御

    阿部洋

    特別招待セミナー(愛知がんセンター) 

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    Event date: 2015.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  83. DNA templated reaction for efficient signal amplification and its steady-state kinetic analysis of the turnover cycle International conference

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    Event date: 2015.9

    Language:Japanese   Presentation type:Poster presentation  

    Country:Japan  

  84. Synthetic biology of Circular Oligonucleotide International conference

    Hiroshi Abe

    The 3rd International Symposium on Transformative Bio-Molecules, Nagoya Univaersity 

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    Event date: 2015.5

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  85. 人工核酸を用いた細胞内RNAの解析及び機能制御

    阿部洋

    第1回新しい原子分子組織化物質・材料創出に向けた光・量子ビーム応用技術ン調査専門委員会 

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    Event date: 2015.5

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  86. 標的を触媒として利用する遺伝子検出のための化学反応プロ−ブの開発

    阿部洋

    若手研究者のための有機化学札幌セミナー 

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    Event date: 2014.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  87. DNA templated reaction for efficient signal amplication and its steady-state kinetic analysis of the turmover cycle

    The 41st International Symposium on Nucleic Acids Chemistry 

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    Event date: 2014.11

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  88. 細胞内RNAの機能制御と解析

    阿部洋

    名古屋大学、野依記念物質科学研究館講演室 

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    Event date: 2014.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  89. ROLLING CIRCLE AMPLIFICATION OF PEPTIDE IN TRANSLATION SYSTEM USING SMALL CIRCULAR RNA

    51st Japanese Peptide Symposium, Tokushima  

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    Event date: 2014.10

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  90. Synthetic bioligy of Circular RNA

    RIKEN SYMPOSIUM & 15th Tokyo RNA club 

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    Event date: 2014.10

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  91. DNA templated chemical reaction for detection of nucleic acids International conference

    Hiroshi Abe

    China/Japan Young Chemists Forum (Molecular Imgaing for Chemical Biology), 29th Chinese Chemical Society congress 

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    Event date: 2014.9

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  92. RNAのナノ構造化に基づく機能創発

    阿部洋

    RNAインフォマティクス道場 in 札幌 

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    Event date: 2014.8

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  93. 環状RNAの機能探索

    「阿部洋」「阿部奈保子」「中野佑妃子、伊藤嘉浩」「周東智」

    第51回日本生化学会北海道支部例会 

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    Event date: 2014.7

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  94. RNAナノ構造化による医薬機能創発

    阿部洋

    第25回未来創薬・医療イノベーションセミナー 

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    Event date: 2014.7

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  95. ナノ構造化による医薬機能創発

    阿部洋

    東京リサーチパークセミナー 

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    Event date: 2014.5

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  96. Synthetic Biology of Circular RNA

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    Event date: 2014.2

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  97. 環状RNAによる終わりのない回転式タンパク質翻訳

    「阿部洋」「阿部奈保子」「丸山豪斗」「中野佑妃子」「周東智」「松田彰」「伊藤嘉浩」

    第23回アンチセンスシンポジウム 

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    Event date: 2013.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  98. RNAを植物から考えるー植物を支えるRNA機能ー「化学反応プロープを用いたRNAイメージング法の開発」

    阿部洋

    第3回植物RNA研究ネットワークシンポジウム 

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    Event date: 2013.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  99. Rolling Circle Amplification in Translation System using small Circular RNA

    Hiroshi Abe, Naoko Abe, Michio Hiroshima, Hideto Maruyama, Yuko Nakashima, Yukiko Nakno,Akira Matsuda, SAtoshi Shuto, Yasushi Sako, Yoshihiro Ito

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    Event date: 2013.11

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  100. ナノ構造化したRNA分子の機能創発

    阿部洋

    日本農芸化学会中部支部第169回例会「核酸科学の新潮流」 

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    Event date: 2013.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  101. Nano-structured RNA for RNA interference International conference

    Hiroshi Abe

    ISAJ(Inadian Scientist, Association in Japan) symposium 

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    Event date: 2013.10

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  102. ナノ構造化RNAの機能創発

    阿部洋

    スパイバー社、鶴岡 

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    Event date: 2013.7

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  103. まるい核酸の研究

    阿部洋

    北海道大学大学院講義 

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    Event date: 2013.7

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  104. Synthetic biology of Nano-structured Nucleic Acids

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    Event date: 2013.5

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  105. 細胞内遺伝子発現の解析と制御法開発

    阿部洋

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    Event date: 2013.5

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  106. バイオイメージングに基づく診断法の開発

    阿部洋

    JST推薦シーズ新技術説明会 第2回ライフイノベーションの分野(創薬、医療技術) 

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    Event date: 2013.2

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  107. RNAイメージング法の開発(代表者 常田聡)

    阿部洋

    大学院講義 

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    Event date: 2012.12

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  108. 有機溶媒に溶けるDNAの構造と触媒機能

    「阿部洋」「阿部奈保子」「柴田綾」「伊藤圭司」「伊藤美香」「實吉尚郎」「田中好幸」「周東智」「伊藤嘉浩」

    第6回バイオ関連化学合同シンポジウム 

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    Event date: 2012.9

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  109. 「核酸高分子のナノ構造化や鋳型反応による機能創出」

    阿部洋

    第58回高分子研究発表会(代表者 西野孝) 

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    Event date: 2012.7

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  110. ナノ構造を制御したRNAを用いたRNA干渉法

    「阿部洋」【阿部奈保子」「西原みづき」「永井千里」「畠山浩人」「原島秀吉」「大城敬人」「前田瑞夫」「中嶋裕子」「伊藤嘉浩」

    日本DDS学会第28回学術集会 

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    Event date: 2012.7

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  111. 遺伝子シグナルの化学増幅

    阿部洋

    北海道大学薬学部講演会(代表者 周東智) 

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    Event date: 2012.7

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  112. 化学反応プローブを用いた細胞内遺伝子診断法の開発

    阿部洋

    Pharmaco-Hematology シンポジウム「血液からの創薬を考える」(代表者 宮崎洋)シンポジウム2「”眼に見える”分子機能研究へ向けた新展開」 

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    Event date: 2012.6

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  113. ナノ構造化RNAを用いるRNA干渉法

    阿部洋

    日本薬学会シンポジウム「ナノサイズの分子設計:診断・創薬へのアプローチ」(代表者 阿部洋) 

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    Event date: 2012.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  114. 生細胞内遺伝子の解析と制御を目的とした機能性核酸分子の創製

    阿部洋

    次代を担う若手大学人育成イニシアティブセミナー 

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    Event date: 2012.1

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  115. 遺伝子シグナルの化学的増幅

    阿部洋

    トクシマ・ファルマ・トライアングル(TPT)構築事業 特別講演会 

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    Event date: 2011.12

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  116. 「核酸工学・核酸医薬の新展開」「ナノ構造化RNAを用いるRNA干渉会」

    阿部洋

    第17回創剤フォーラム若手研究会 

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    Event date: 2011.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  117. Artificial Nucleic Acid probe for analysis and regulation of RNA expression in living cells International conference

    Hiroshi Abe

    Division of Biochemical Toxicology, Karolinska Institut 

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    Event date: 2011.9

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  118. Detection and Control of gene expression using artificial nucleic acids International conference

    Hiroshi Abe

    Division of Biochemical Toxicology, Karolinska Institut 

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    Event date: 2011.9

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  119. 医療応用を目指した人工核酸分子の創製

    阿部洋

    高分子学会関東支部 第22回埼玉地区談話会 

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    Event date: 2011.2

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  120. 人工核酸分子を用いた遺伝子発現の解析と制御

    阿部洋

    大阪大学 免疫学フロンティア研究センターセミナー 

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    Event date: 2010.7

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  121. 細胞内遺伝子発現の解析と制御を目的とした機能性核酸分子の創製

    阿部洋

    薬学会奨励賞受賞講演 

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    Event date: 2010.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  122. 細胞内現象を解析・制御する分子の創製

    阿部洋

    群馬大学 光化学研究会合同研究発表会 

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    Event date: 2009.12

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  123. Chemical reaction triggered fluorogenic probe for RNA detection in living cells International conference

    Hiroshi Abe

    BIT's 3rd world congress of Gene-2009 

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    Event date: 2009.12

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  124. Nanocircular RNA for RNA interference International conference

    Hiroshi Abe

    The 6th International symposium on Nucleic Acid Chemistry (6ISNAC2009) 

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    Event date: 2009.9

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  125. ダンベル型ナノサークルRNAを用いるRNA干渉法

    「阿部洋」「阿部奈保子」「原田充」「常田聡」「伊藤嘉浩」

    日本薬学会第129年会 

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    Event date: 2009.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  126. 細胞内RNA検出プローブの開発

    「阿部洋」「古川和寛」「王瑾」「鳥田美和子」「常田聡」「伊藤嘉浩」

    第18回アンチセンスシンポジウム 

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    Event date: 2008.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  127. ダンベル型ナノサークルRNAを用いるRNA干渉法

    「阿部洋」「阿部奈保子」「原田充」「常田聡」「伊藤嘉浩」

    第27回メディシナルケミストリーシンポジウム 

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    Event date: 2008.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  128. 新規蛍光化合物を導入したプロ−ブによる遺伝子シグナルの化学増幅

    「阿部洋」「古川和寛」「王瑾」「鳥田美和子」「常田聡」「伊藤嘉浩」

    第34回反応と合成の進歩シンポジウム 

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    Event date: 2008.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  129. 機能性人工核酸の創製

    阿部洋

    東京大学薬学部 

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    Event date: 2008.10

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  130. RNAのシンセティックバイオロジー

    阿部洋

    東京薬科大学 

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    Event date: 2008.10

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  131. 人工核酸を用いる細胞内遺伝子発現の解析と制御

    阿部洋

    日本化学会関東支部 シンポジウム 

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    Event date: 2008.9

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  132. 新規蛍光化合物を導入した化学反応プローブによる遺伝子シグナルの増幅

    「阿部洋」「古川和寛」「王瑾」「鳥田美和子」「常田聡」「伊藤嘉浩」

    第3回バイオ関連化学合同シンポジウム 

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    Event date: 2008.9

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  133. Nanocircular RNAs for RNA interference International conference

    Hiroshi Abe, Naoko Abe, Mitsuru harada, Satoshi Tsuneda, Yoshihiro Ito

    Joint Stmposium of the 18th International Round table on Nucleoside, Nucleotides and Nucleic Acids and the 35th International Symposium on Nucleic Acids Chemistry  

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    Event date: 2008.9

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  134. 機能性人工核酸の創製

    阿部洋

    分子研究会ー物質系と生体系での自己組織化ー 

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    Event date: 2008.8

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  135. 人工核酸を用いる細胞内遺伝子発現の解析と制御

    阿部洋

    第6回ライフサーベイヤシンポジウム 

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    Event date: 2008.6

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  136. ダンベル型なのサークルRNAを用いるRNA干渉法

    「阿部洋」「阿部奈保子」「原田充」「常田聡」「伊藤嘉浩」

    第24回DDS学会 

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    Event date: 2008.6

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  137. ダンベル型ナノサークルRNAを用いるRNA干渉法

    「阿部洋」「阿部奈保子」「原田充」「常田聡」「伊藤嘉浩」

    第3回ケミカルバイオロジー研究会年会 

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    Event date: 2008.5

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  138. 化学反応プローブを用いた細胞内遺伝子検出

    阿部洋

    第59回日本生物工学会大会 

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    Event date: 2007.9

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  139. 有機溶液に溶ける核酸の構造解析:有機溶媒中のGカルテット構造

    「阿部洋」「阿部奈保子」「伊藤嘉浩」

    第56回高分子討論会 

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    Event date: 2007.9

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  140. 新規蛍光化合物の合成と遺伝子検出への応用

    「阿部洋」「王瑾」「古川和寛」「島田美和子」「戸田雅也」「常田聡」「伊藤嘉浩」

    第22回生体機能関連化学シンポジウム 

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    Event date: 2007.9

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  141. 核酸の有機溶媒可視化と構造解析

    「阿部洋」「阿部奈保子」「神明博」「伊藤嘉浩」

    第56回高分子学会年次大会 

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    Event date: 2007.5

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  142. 化学的DNA連結反応を用いるヒト生細胞内RNAの可視化と定量

    阿部洋

    第22回ケミカルバイオロジー研究会 

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    Event date: 2006.12

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  143. Structure analysis of oligonucleotide in organic solvent International conference

    Hiroshi Abe, Naoko Abe, Yoshihiro Ito

    33rd Symposium on Nucleic Acids Chemistry 

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    Event date: 2006.11

    Language:English   Presentation type:Oral presentation (general)  

    Country:Japan  

  144. 化学的DNA連結反応を持ちいるヒト生細胞内mRNAの検出

    「阿部洋」「Kool Eric T」

    第16回アンチセンスシンポジウム 

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    Event date: 2006.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  145. 有機溶媒中の核酸の構造

    「阿部洋」『阿部奈保子」「神明博」「伊藤嘉浩」

    第21回生体機能関連化学シンポジウム(バイオテクノロジー部会9回)・生命化学研究会(9回)合同シンポジウム 

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    Event date: 2006.9

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  146. 細胞内分子遺伝子診断

    阿部洋

    第1回バイオ医工学シンポジウムーマイクロアレイ・バイオチップ最前線ー 

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    Event date: 2006.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  147. 化学的DNA連結反応を用いる細胞内遺伝子診断

    「阿部洋」「Kool Eric T」

    日本薬学会126年会 

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    Event date: 2006.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  148. Nile Blueを基本骨格とした脂肪滴検出プローブの創製

    戸田 直宏, 伊藤 美香, 石田 綾乃, 鬼頭 宏任, 横川 大輔, Stephan Irle, 木村 康明, 友池 史明, 西村 智, 阿部 洋

    第31回生体機能関連化学シンポジウム  2016.9 

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  149. グルタチオン-S-トランスフェラーゼのプローブ開発

    宍戸裕子, 村上優子, 関戸好孝, 阿部洋

    日本癌学会  2017.9 

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  150. カチオン性ポリマーを結合した核酸誘導体によるアンチセンス効果

    太田 杏摘, 伏原 大地, Zhaoma SHU, 阿部 奈保子, 木村 康明, 阿部 洋

    日本薬学会第138年会  2018.3 

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  151. Si-Si結合の特性を利用した光分解性保護基の開発

    伊藤 真央, 金田 龍太郎, 木村 康明, 周東 智, 阿部 洋

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  152. RNA干渉のためのナノ構造デザイン

    Shu Zhaoma, 阿部奈保子, 友池史明, 木村康明, 伊藤嘉浩, 阿部洋

    日本核酸医薬学会第3回年会  2017.7 

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  153. RNA Interference by Intracellar Buildup of siRNA

    木村康明, 丸山豪斗, 笈川涼太, 辻厳一郎, 吉永静也, 阿部奈保子, 周東智, 松田彰, 伊藤嘉浩, 阿部洋

    日本核酸化学会年会  2017.11 

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  154. RETFプローブを用いた生体内の核酸検出

    友池史明, 山岡和樹, 伊藤真央, 木村康明, 井上貴文, 阿部洋

    日本化学会 第98春季年会  2018.3 

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  155. N6-アルキルアデノシン導入によるRNAの機能制御

    今枝昭裕, 笈川涼太, 浅井潔, 桜庭俊, 岩切淳一, 阿部奈保子, 友池史明, 木村康明, 阿部洋

    日本化学会 第98春季年会  2018.3 

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  156. Development of intracellular RNA detection probe enable chemical signal amplification

    阿部洋, 伊藤真央, 友池史明, 木村康明, 阿部奈保子

    日本核酸化学会年会  2017.11 

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  157. Development of Anti-cancer Agents based on Synthetic Lethality by LATS Mutation.

    Nguyen Hong Nhung, 木村康明, 村上優子, 阿部洋

    統合物質創製化学研究推進機構 第3回 国内シンポジウム  2017.10 

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  158. グルタチオン-S-トランスフェラーゼを標的とした共有結合性阻害剤の開発

    宍戸裕子, 藤川遥加, 友池史明, 木村康明, 桑田啓子, 村上優子, 福井健二, 関戸好孝, 矢野貴人, 周東智, 阿部洋

    ConBio2017  2017.12 

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  159. 高分子核酸医薬の低分子戦略:細胞内ビルドアップ法の開発

    木村康明, 丸山豪斗, 伊藤美香, 笈川涼太, 早川真由, 辻厳一郎, 阿部奈保子, 松田彰, 周東智, 伊藤嘉浩, 阿部洋

    第11回バイオ関連化学シンポジウム  2017.9 

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  160. 高分子核酸医薬の低分子化戦略:細胞内ビルドアップ法の開発

    木村 康明, 丸山 豪斗, 笈川 涼太, 吉永 静也, 辻 厳一郎, 阿部 奈保子, 松田 彰, 周東 智, 伊藤 嘉浩, 阿部 洋

    日本薬学会第138年会  2018.3 

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  161. 遺伝子発現制御のためのRNA分子の形状デザイン

    阿部洋, 阿部奈保子, 木村康明, 友池史明

    ConBio2017  2017.12 

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  162. 蛍光オフ・オン型分子を導入した核酸プローブの開発

    山岡和樹, 伊藤真央, 阿部奈保子, 友池史明, 木村康明, 阿部洋

    日本化学会 第98春季年会  2018.3 

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  163. 膜透過性核酸の開発

    Zhaoma SHU, 太田 杏積, 田中 育, 伏原 大地, 阿 部 奈保子, 友池 史明, 木村 康明, 阿部 洋

    日本薬学会第138年会  2018.3 

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  164. 膜透過性分子を結合したオリゴ核酸の合成

    田中育, 太田杏摘, 伏原大地, SHU Zhaoma, 阿部奈保子, 友池史明, 木村康明, 阿部洋

    日本化学会 第98春季年会  2018.3 

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  165. 細胞内グルタチオン-S-トンランスフェラーゼ活性を検出するためのプローブ開発

    友池史明, 宍戸裕子, 藤川遥加, 木村康明, 柴田綾, 周東智, 阿部洋

    日本分析化学会第66年会  2017.9 

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  166. 真核生物翻訳系における終わりのない回転式翻訳現象

    清水 沙彩, 児玉 亜有実, 富田 貴志, 阿部 奈保子, 友池 史明, 木村 康明, 阿部 洋

    日本薬学会第138年会  2018.3 

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  167. 環状RNAを用いた終わりのない回転式翻訳によるタンパク質合成の効率化

    児玉亜有実, 阿部奈保子, 友池史明, 伊藤嘉浩, 松本健, 吉田稔, 清水義宏, 亀田倫史, 阿部洋

    ConBio2017  2017.12 

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  168. 環状RNAを用いた回転式翻訳によるタンパク質合成効率化

    児玉亜有実, 阿部奈保子, 友池史明, 木村康明, 伊藤嘉浩, 松本健, 吉田稔, 清水義宏, 亀田倫史, 阿部洋

    日本RNA学会  2017.7 

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  169. 環境応答性環状オリゴ核酸による遺伝子発現制御

    吉永静也, 阿部奈保子, 木村康明, 友池史明, 阿部洋

    第48回中化連秋季大会  2017.11 

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  170. 求電子的リン酸基を用いた核酸ケミカルライゲーション反応

    笈川涼太, 早川真由, 丸山豪斗, 阿部奈保子, 友池史明, 木村康明, 周東智, 松田彰, 南川典昭, 阿部洋

    第48回中化連秋季大会  2017.11 

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  171. 機能性核酸合成を志向した化学的核酸連結反応

    笈川涼太, 早川真由, 丸山豪斗, 阿部奈保子, 木村康明, 周東智, 松田彰, 南川典昭, 阿部洋

    日本核酸医薬学会第3回年会  2017.7 

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  172. 新規抗ウイルス薬を志向した修飾2-5Aの合成

    伏原 大地, 太田 杏摘, 田中 育, 今枝 昭裕, 永井 貴広, 星野 真一, 木村 康明, 友池 史明, 阿部 洋

    日本薬学会第138年会  2018.3 

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  173. 擬ロタキサン構造形成による翻訳制御

    富田貴志, 阿部奈保子, 木村康明, 阿部洋

    第48回中化連秋季大会  2017.11 

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  174. 抗ウイルス活性を指向した新規2'修飾ヌクレオシドの合成および評価

    新美 結士, 片倉 秀雄, 阿部 奈保子, 木村 康明, 阿部 洋

    日本薬学会第138年会  2018.3 

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  175. 抗ウイルス活性を指向したヌクレオシドの開発

    片倉秀雄, 新美結士, 木村康明, 鈴木哲郎, 村上優子, 阿部洋

    日本化学会 第98春季年会  2018.3 

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  176. 抗ウイルス活性を指向した2'-β-チオ核酸の開発

    片倉秀雄, 木村康明, 阿部洋

    統合物質創製化学研究推進機構 第3回 国内シンポジウム  2017.10 

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  177. 多分岐型DNAケミカルライゲーションによる標的核酸分子のトポロジカル固定

    富田貴志, 阿部奈保子, 木村康明, 鬼塚和光, 阿部洋

    日本化学会 第98春季年会  2018.3 

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  178. 化学的シグナル増幅を可能とするプローブによる細胞内RNA検出法

    伊藤真央, 柴田綾, 阿部奈保子, 友池史明, 木村康明, 阿部洋

    日本RNA学会  2017.7 

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  179. 共有結合性GST阻害剤の開発

    藤川遥加, 宍戸裕子, 木村康明, 友池史明, 村上優子, 青木正博, 福井健二, 矢野貴人, 阿部洋

    第48回中化連秋季大会  2017.11 

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  180. 共有結合型グルタチオンS-転移酵素阻害剤の開発

    宍戸裕子, 藤川遥加, 木村康明, 友池史明, 桑田啓子, 福井健二, 村上優子, 亀田倫史, 周東智, 阿部洋

    第11回バイオ関連化学シンポジウム  2017.9 

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  181. 共有結合型グルタチオンS-転移酵素阻害剤の創薬研究

    宍戸裕子, 関戸好孝, 村上優子, 阿部洋

    日本癌学会  2017.9 

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  182. 共有結合型GST阻害剤の開発

    藤川遥加, 宍戸裕子, 木村康明, 友池史明, 村上優子, 青木正博, 阿部洋

    日本化学会 第98春季年会  2018.3 

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  183. ロタキサン構造形成による新規アンチセンス法の開発

    富田貴志, 阿部奈保子, 木村康明, 阿部洋

    統合物質創製化学研究推進機構 第3回 国内シンポジウム  2017.10 

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  184. 高分子核酸医薬の低分子戦略:細胞内ビルドアップ法の開発

    木村康明, 丸山豪斗, 伊藤美香, 笈川涼太, 早川真由, 辻厳一郎, 阿部奈保子, 松田彰, 周東智, 伊藤嘉浩, 阿部洋

    ケミカルバイオロジー学会  2016.6 

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  185. Rolling Circle Translation of Circular RNA

    阿部奈保子, 木村 康明, 友池 史明, 松本 健, 吉田 稔, 伊藤 嘉浩, 阿部洋

    第18回日本RNA学会  2016.6 

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  186. Chemical ligation reaction for RNA strand

    木村 康明, 笈川涼太, 丸山豪斗, 早川真由, 阿部奈保子, 阿部洋

    第18回日本RNA学会  2016.6 

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Works 10

  1. Protein detection using oligonucleotide probes

    2009

  2. Synthetic nanocircular RNA for controlling of gene expression

    2009

  3. In vitro selection of RNA aptamer to hemin

    2008

  4. Fluorogenic trobe triggered by reduction for nucleic acids sensing

    2008

  5. Nanocircular RNAs fopr RNA interference

    2008

  6. Multiple chemical ligation under thermal cycle

    2007

  7. Intermolecular transfer of aminoacylated adenosine towards chemical aminoacylation of tRNA

    2007

  8. Structure analysis of oligonucleotide in organic solvent

    2006

  9. Universal linkers for signal amplification in auto-ligating probes

    2005

  10. Synthesis and biological activity of adenophostin derivativesas IP3 receptor ligands

    2002

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Research Project for Joint Research, Competitive Funding, etc. 11

  1. ポスト切断PCRプライマーを用いた新規DNAアセンブリ法の開発

    2018.10 - 2019.3

  2. 化学を基盤とするゲノムスケールDNA合成技術の開発

    2018 - 2025

  3. 長鎖DNAの細胞内ビルドアップ法の開発

    2018 - 2019

  4. 合成致死表現型を指標とした新規悪性中皮腫革新的がん医療実用化研究事業

    2017.11 - 2018.3

  5. 人工mRNA・非コードRNA分解機構の解明とRNA医薬安定化技術の開発

    2017.4 - 2020.3

    国内共同研究 

  6. 新規精神・発達障害治療薬の探索

    2017.4 - 2020.3

  7. RNAケミカルライゲーション法による翻訳可能な長鎖mRNAの全合成

    2016.1 - 2019.7

    国内共同研究 

  8. 環状RNAを用いたタンパク質翻訳現象の理解と利用

    2015.4

    国内共同研究 

  9. 蛋白質の高効率生産法の開発

    2015.4 - 2018.3

    国内共同研究 

  10. 脳神経回路の形成・動作と制御「シナプス可塑性に関わるRNA群の革新的イメージング法の開発

    2011

    科学技術振興機構 

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    Grant type:Competitive

  11. 単一分子レベルの酵素反応解析から癌治療法開発までの複合領域研究

    2011

    科学技術振興機構 

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    Grant type:Competitive

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KAKENHI (Grants-in-Aid for Scientific Research) 31

  1. 修飾塩基を持つRNAの情報解析基盤技術の開発

    Grant number:21H04912  2021.4 - 2024.3

    日本学術振興会  科学研究費助成事業 基盤研究(A)  基盤研究(A)

    浅井 潔, 阿部 洋, 櫻庭 俊, 阿部 洋, 櫻庭 俊

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    Authorship:Coinvestigator(s) 

    既に開発した様々なRNA2次構造情報解析ソフトウェアを基盤として、修飾塩基のエネルギーパラメー
    タを組み込むことで、修飾塩基を含むRNAの2次構造情報解析を実現するソフトウェアを開
    発する。さらに、機械学習を取り入れたエネルギーパラメータ推定法を開発する。また、RNA配列中の修
    飾の種類・位置を同定するため、1分子シークエンサの測定信号から修飾塩基を含む塩基配
    列を同定する手法を開発する。これらの技術の有用性を実証するため、塩基修飾がmRNAの
    翻訳効率に及ぼす影響を予測する手法の開発を行う。
    生体内に存在する膨大な種類のRNAは、転写後に様々な修飾を受けることで機能・活性が変化している。修飾塩基の含むRNAの2次構造エネルギーパラメータの同定とそのソフトウェアへの組み込み、1分子シークエンサー による修飾塩基検出技術の開発、およびmRNAの修飾塩基による翻訳効率変化の予測を行うことにより、全転写産物規模でのRNA修飾(エピトランスクリプトーム)に対応したRNAの情報解析基盤を構築することを目指して研究を行なった。既に開発した様々なRNA2次構造情報解析ソフトウェアを基盤として、修飾塩基を含むRNAの2次構造情報解析を実現するため、塩基対測定実験の結果から、2次構造エネルギーパラメータを推定する手法のプロトタイプを開発した。また、機械学習を取り入れたエネルギーパラメータ推定の理論的検討を行なった。
    さらに、RNA配列中の修飾の種類・位置を同定するため、1分子シークエンサによる修飾塩基検出技術の開発: 修飾塩基に対応した1分子シークエンサーのベースコールを行うための確率モデルを構築した。
    RNA 2次構造は細胞の中で揺らぎ、確率的な振る舞いをする。機能的に重要なRNA2次構造を抽出する有力な方法の1つは、多数の相同RNA配列の構造アラインメントから共通構造を探索することである。そこで、2次構造の熱力学的な確率分布と、アラインメントの確率分布を同時分布として扱うソフトウェアを開発した。さらに、2次構造と機能の関係を正確に分析するために、この確率的な揺らぎを考慮して機能を重要な関係をもつ2次構造特徴を抽出する手法を開発した。
    新型コロナ感染症の影響で博士研究員の来日が難しくなったため、研究計画の変更・延期が必要となった。
    大量の公開データを活用した機械学習により重点を置いたモデルを構築し、ソフトウェアの開発にも反映させていく。

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  2. 高分子RNA医薬の中分子化戦略

    2018.4 - 2020.3

    科学研究費補助金  新学術領域研究

  3. Medium molecularization strategy of high molecular weight RNA medicine

    Grant number:18H04398  2018.4 - 2020.3

    Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)

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    Authorship:Principal investigator 

    Grant amount:\5200000 ( Direct Cost: \4000000 、 Indirect Cost:\1200000 )

  4. 高分子RNA医薬の中分子化戦略

    2018.4 - 2020.3

    阿部 洋

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    Authorship:Principal investigator  Grant type:Competitive

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  5. 化学を基盤とするゲノムスケールDNA合成技術の開発

    2018 - 2023

    科学技術振興機構  戦略的な研究開発の推進 戦略的創造研究推進事業 CREST 

    阿部 洋

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    Authorship:Principal investigator 

    1正確性の高いPCR法、2新規DNAアセンブリ技術、3反復配列を構築可能なケミカルライゲーション、4合成効率・正確性が高いアミダイト化学、5本技術を利用するためのDNA配列設計アルゴリズム開発。以上の要素技術を開発することで、正確でかつ自動化可能なゲノムスケールでのDNA合成技術を確立します。

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  6. 核酸鋳型化学反応の遷移状態制御に基づく触媒回転数の向上

    2016.7 - 2019.3

    科学研究費補助金  基盤研究(B)

  7. Improvement of catalytic turnover based on transition state control of oligonucleotide template chemical reaction

    Grant number:16KT0052  2016.7 - 2019.3

    Abe Hiroshi

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    Authorship:Principal investigator 

    Grant amount:\18590000 ( Direct Cost: \14300000 、 Indirect Cost:\4290000 )

    The fluorescence reaction based on the oligonucleotide (ON) template reaction is one of the most basic working principles of the RNA detection probe. In this method, an ON probe having a reactive functional group and an ON probe having a fluorescent precursor whose fluorescence is suppressed by a protecting group are associated on the target RNA, and then the protective group is removed and fluorescence signal is generated. Since this fluorescence reaction specifically occurs in the presence of target RNA, it can be the working principle RNA detection probe. In order to detect intracellular RNA highly sensitively, we worked on (1) accelerating ON template reaction and (2) development of a new method of intracellular administration of ON probe without lipofection. Prospective results were obtained in (1) by appropriately selecting the nucleophile for the reaction, and in (2) by use of phosphorothioate in the ON probe.

  8. 核酸鋳型化学反応の遷移状態制御に基づく触媒回転数の向上

    2016.7 - 2019.3

    阿部 洋

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  9. エピトランスクリプトーム解析のためのRNAインフォマティクス基盤技術

    2016.4 - 2019.3

    科学研究費補助金  基盤研究(A)

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    Authorship:Principal investigator 

  10. 環状RNAを用いたタンパク質合成法

    2016.4 - 2019.3

    科学研究費補助金  基盤研究(B)

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    Authorship:Principal investigator 

  11. RNA informatics for epi-transcriptome analysis

    Grant number:16H02484  2016.4 - 2019.3

    Asai Kiyoshi

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    Authorship:Coinvestigator(s) 

    The energy parameters of the important modified bases, inosine and N6 methyladenosine were identified by a combination of thermometric experiments and molecular simulations. The effect of estimation error on structure prediction was evaluated and presented by theoretical analysis and computer experiments. A model of the effect of A-to-I editing on translational repression efficiency by miRNA was constructed and presented in a joint study using the identified inosine parameters.
    We have improved RintD, an analysis tool for secondary structure probability distribution, by developing RintW, which calculates the distribution of base pair probability, and RintC, which speeds up the calculation with maximum base pair constraint. At that time, the effect of the Fourier transform on the numerical error was analyzed using the accuracy guarantee calculation, and it was shown that the large probability was reliable.

  12. Protein synthesis using circular RNA

    Grant number:16H04178  2016.4 - 2019.3

    Abe Hiroshi

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    Authorship:Principal investigator 

    Grant amount:\17810000 ( Direct Cost: \13700000 、 Indirect Cost:\4110000 )

    Protein having a repetitive sequence is generated in a translation reaction on circular RNA template which contains a continuous open reading frame, because the ribosome performs translation rotating many times on the RNA. Optimization of the reaction condition in a E. coli cell-free translation system was performed. Development of efficient functional protein expression method in mammalian translation systems were carried out.

  13. 環状RNAを用いたタンパク質合成法

    2016.4 - 2019.3

    阿部 洋

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    Authorship:Principal investigator  Grant type:Competitive

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  14. エピトランスクリプトーム解析のためのRNAインフォマティクス基盤技術

    2016.4 - 2019.3

    浅井潔

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    Grant type:Competitive

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  15. iRed/iPedの完全化学合成を基軸とした実践的がん創薬基盤研究

    2015.4 - 2018.3

    科学研究費補助金  基盤研究(B)

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  16. Investigation of practical anticancer strategy based on chemically synthesized iRed/iPed

    Grant number:15H04656  2015.4 - 2018.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    MINAKAWA Noriaki

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    In this study, research was conducted to further enhance the function of a DNA device (iRed) capable of expressing functional RNA in cells. As a result, (1) cyclization aimed at stabilizing iRed, (2) complete chemical synthesis of iRed, (3) searching for new cancer therapeutic drugs by combination with innovative delivery method, and (4) possibility to evolve this device to iPed expressing functional peptide peptide/protein were demonstrated.

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  17. Development of molecular probe for GST

    Grant number:15K12751  2015.4 - 2017.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Challenging Exploratory Research

    Abe Hiroshi

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\3640000 ( Direct Cost: \2800000 、 Indirect Cost:\840000 )

    Glutathione S transferase (GST) is one of highly expressed enzymes in cancer cells. The subtype of this enzyme depends on the cancer species. Tough the determination of the cancer species by detecting GST subtype is thought to contribute to cancer therapy, the GST probe with subtype specificity remains to be developed. As fundamental step for developing the subtype-specific probe, glutathione derivatives were designed and synthesized and those subtype specificities were evaluated.
    We synthesize glutathione derivatives with fluorescent group or the functional group forming covalent bond with amino-acid residue. Using this derivative, we discovered the structure for the subtype-specificity. In addition, we succeeded in a synthesis of derivatives with several chemical groups at glycine residue in glutathione without reduction of GST binding ability. These results are thought to promote the development of probes with GST substrate specificity.

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  18. GSTを標的とする分子プローブの開発

    2015 - 2017.3

    科学研究費補助金  挑戦的萌芽研究

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    Authorship:Principal investigator 

  19. Development of RNA medicine based on nano-structured design and templated reaction

    Grant number:25282240  2013 - 2016.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (B)  Grant-in-Aid for Scientific Research (B)

    ABE HIROSHI

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    Authorship:Principal investigator  Grant type:Competitive

    We developed a new strategy for the buildup reaction of active siRNA species from short RNA fragments in living cells using a chemical ligation reaction. This strategy could decrease undesired immune responses and provide more latitude for RNAi technology in the design and concentration of introduced RNA compared to traditional siRNA methods.

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  20. ナノ構造化と鋳型反応に基づくRNAの医薬機能創発

    2013

    科学研究費補助金  基盤研究(B)

  21. Screening of peptide catalyst by chemically extended molecular evlutionary engineering

    Grant number:24656510  2012.4 - 2013.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Challenging Exploratory Research

    ITO Yoshihiro, WANG Wei, TADA Seiichi, UZAWA Takanori, ABE Hiroshi

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    Peptide which catalyzes a reaction in organic solvents was screened by chemically extended molecular evolutionary engineering. The target reaction was Aldol condensation which is important for biochemical industry. We prepared two substrates ; one is conjugated with tRNA and another conjugated with biotin molecule for recovery. Peptide catalyst was screened by molecular evolutionary engineering using mRNA display which is tough even in organic solvent due to covalent linking between peptide (phonotype) and mRNA (genotype)

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  22. Analysis and application of new translation system

    Grant number:24656511  2012

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Challenging Exploratory Research

    ABE Hiroshi

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    Authorship:Principal investigator 

    Grant amount:\4030000 ( Direct Cost: \3100000 、 Indirect Cost:\930000 )

    Small circular RNA molecules containing an infinite open reading frame were synthesized and tested in an E. coli cell-free translation system. A circular RNA 126 nucleotides in length was found to produce more product than its linear counterpart by two orders of magnitude, because a ribosome can work more effectively towards the elongation on circular RNA than it can on linear RNA in this continuous peptide synthesis.

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  23. シナプス可塑性に関わるRNA群の革新的イメージング法の開発

    2011 - 2014

    科学技術振興機構  戦略的な研究開発の推進 戦略的創造研究推進事業 さきがけ 

    阿部 洋

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    神経細胞内のmRNAをイメージングするための革新的なプローブを開発します。微量RNAを検出するためにプローブの高感度化、及び複数RNAの同時観察を可能とするために多色プローブの開発を進めます。さらに、シナプスの可塑性に関わる複数のmRNA群を標的にしたプローブを作成し、神経細胞における内在性mRNAの動態を直接イメージングし、その輸送と局所での翻訳過程との相関を解析することを目指します。

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  24. 単一分子レベルの酵素反応解析からがん治療法開発までの複合領域研究

    2011 - 2013

    国際的な科学技術共同研究などの推進 戦略的国際科学技術協力推進事業 SICP スウェーデン 

    阿部 洋

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    Authorship:Principal investigator 

    本研究交流は、がん細胞で過剰に発現していることが知られるグルタチオンSトランスフェラーゼ(GST)の新規基質となる新規化合物を設計し、1分子レベルでの酵素反応メカニズムを解析することを目的とする。具体的には、日本側はGSTと反応する蛍光化合物、化学発光化合物、核磁気共鳴プローブ、低分子薬剤の設計を担当し、スウェーデン側はその生物活性解析、速度論解析、細胞イメージングや薬効評価を担当する。両国の研究チームが有機合成化学および酵素学・生物物理化学の観点から相互補完的に取り組むことで、1分子酵素解析技術に基づき、体内における代謝によりはじめて薬効が現れるように工夫した薬(プロドラッグ)の設計法やがん細胞イメージング技術の開発が期待される。

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  25. 化学反応プローブとフローサイトメーターを用いた細菌の検出法の検討

    2011 - 2012

    産学が連携した研究開発成果の展開 研究成果展開事業 研究成果最適展開支援プログラム(A-STEP) 探索タイプ 

    阿部 洋

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    細菌同定に必要な高感度プローブを、複数の細菌について開発する。感度改良のためのプローブの鎖長、多色染色を可能とする蛍光発生型蛍光色素群の創製、プローブの細菌類への効率的な導入法を機軸とした研究を推進する。開発期間が短期間であることを考慮して、最適なプローブ鎖長の検討、新規蛍光発生化合物の開発にしぼり、最適な鎖長(15量体)並びに現在利用している緑色蛍光化合物から大きく波長を離した赤色蛍光剤の候補化合物を合成できた。今後は、一塩基変異を定量的かつ多色で検出できるプローブを創製し遺伝情報に立脚した細菌定量法へ展開する予定である。

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  26. Cell selection based on genetic signal

    Grant number:22686077  2010 - 2011

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Young Scientists (A)

    ABE Hiroshi

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    Authorship:Principal investigator 

    Grant amount:\26000000 ( Direct Cost: \20000000 、 Indirect Cost:\6000000 )

    Our aim is to develop new RNA detection probe which is capable of cell selection based on genetic signal. First, we synthesized red fluorescent probe to offer very high signal and background ratio. Next, the probe was designed to target miRNA which is expressed in stem cells. As a result, we confirmed specific miRNA signal in model cells. Now, we are trying to isolate cells with specific miRNA signal.

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  27. Chemical probe for amplification of genetic signal

    Grant number:20750146  2008 - 2009

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Young Scientists (B)

    ABE Hiroshi

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    Authorship:Principal investigator 

    Grant amount:\4420000 ( Direct Cost: \3400000 、 Indirect Cost:\1020000 )

    Our aim is to develop a new method for genetic detection which can amplify signal through multiple chemical reactions. The method will be applied for gene diagnosis in living cells.

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  28. Creation of growth factors binding to metal or ceramic for and their medical applications

    Grant number:19200041  2007 - 2009

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (A)

    ITO Yoshihiro, ABE Hiroshi, WADA Akira, YOSHIDA Yasuhiro, KITAJIMA Takashi

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    Authorship:Coinvestigator(s) 

    Design and synthesis for metal-or ceramic-binding growth factor proteins were performed. First, organic molecular coating was performed on titan or stainless steel for growth factor immobilization. Secondly, titan-or apatite-binding growth factor proteins were designed by molecular evolutionary engineering and chemical ligation using peptide carrying non-natural amino acid.

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  29. 有機溶媒中での試験管内進化法による触媒探索

    Grant number:19651098  2007 - 2008

    日本学術振興会  科学研究費助成事業  萌芽研究

    伊藤 嘉浩, 阿部 洋

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    前年度までに、我々は有機溶媒中で機能する核酸触媒を試験管内進化法により創製する研究の手始めに有機溶媒可溶化核酸の調製に成功した。すなわち、オリゴ核酸15塩基にPEG(分子量1万)を修飾し、種々の有機溶媒に100μMまで問題なく溶解することが明らかになった。また、TTAGGGの6塩基からなるDNAをPEG修飾し、これが各種有機溶媒中で、4量体を形成しGカルテット構造を形成することをCDスペクトルにより確認した。
    本年度は、この構造体とヘミンが水中で複合体を形成しルミノール反応を起こすことが報告されていたので、有機溶媒中でもこの現象が同様に起こるか検証した。その結果、メタノール中で、ルミノール反応が効率よく起こることを確認した。この結果により、核酸の構造体とヘミンが水中と同様に複合体を形成する能力をもち、さらに、触媒能力を維持できることを明らかにした。また、試験管内進化法で得られたディールズ・アルダー反応を触媒するDNAzymeについても、PEG修飾を行った。得られたハイブリッド体は、様々な有機溶媒に可溶化でき、水中と同じような触媒活性が観察できた。このようにPEG修飾により試験管内進化法で得られたオリゴ核酸が有機溶媒に可溶化され触媒活性をもつことがわかった。
    さらにPEG修飾DNAプライマーを用いてDNAをPCR増幅できることが明らかとなった。触媒探索のための試験管内進化法ではDNAをPCR法で増幅して、触媒反応を行うDNAを選別する必要があるため、この方法の確立により有機溶媒中での試験管内進化法による触媒探索が可能であることが明らかとなった。

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  30. 細胞内蛋白質を可視化できるバイオプローブの開発

    Grant number:18750159  2006 - 2007

    日本学術振興会  科学研究費助成事業  若手研究(B)

    阿部 洋

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    Authorship:Principal investigator 

    Grant amount:\3700000 ( Direct Cost: \3700000 )

    前回まで、蛋白質と化学反応することで蛍光発生する分子プローブの開発を目指していたが、蛋白質との化学反応性が低いプローブしか得られず、その開発は難しかった。一方、我々は遺伝子検出プローブとして、最近開発した分子は1分子内での蛍光のon/offが可能であり、蛋白質検出にも応用可能であることが期待された。この分子はアジドメチル基を持ち、トリフェニルボスフィン等の還元剤によってアジド基が還元されることにより構造変化が起こり蛍光を発することが可能となる。
    今回、アジドメチル基を有する蛍光分子をもちいた化学反応を引金とする蛍光発光システムによるタンパク質およびペプチド検出を試みた。標的として17merからなるヒトHIV-1 Revタンパク質のarginine-rich motif(ARM)を選択した。ヒトHIV-1 Rev ARMペプチドには35merからなるRNAアプタマーが結合することがこれまでに報告されている。そこでこのRNAアプタマー配列を2分割し、ペプチド検出用プローブとすることにした。配列の異なる2種類のプローブのうち、一方にはアジドメチル基を有する蛍光分子を結合させ、もう一方のプローブには還元剤であるトリフェニルホスフィン基を導入した。この2種類のプローブを用いることで溶液中のRev ARMペプチドの検出を試みた。50mM Tris-HC1溶液中37℃で30分間反応させた結果、Rev ARMペプチド存在下の場合、非存在下の場合と比較してその蛍光強度が約25倍に増強することが示された。

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  31. アノマー効果を利用する立体選択的ラジカルC-グリコシル化とIP3リガンドの創製

    Grant number:01J10599  2001 - 2002

    日本学術振興会  科学研究費助成事業 特別研究員奨励費  特別研究員奨励費

    阿部 洋

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    C-グリコシドは対応するO-グリコシドの生物学的安定等価体として機能することから注目されている。そのため、C-グリコシドの立体選択的構築法の開発が望まれている。筆者らは、^4C_1型あるいは^1C_4型配座に制御されたピラノース基質を用いたラジカルC-グリコシル化反応がαおよびβ高立体選択的にC-グリコシル体を与えることを発見した。これは、従来認識されていなかったラジカル反応における速度論的アノマー効果を立体選択制発現に積極的に利用した初めての例となった(J.Am.Chem. Soc.2001,123,11870-11882)。
    今回、さらに、このピラノース配座制御によるアノマー効果に基づく立体制御法をオキソカルベニウムイオン中間体をへるS_N1型C-グリコシル化反応に適用し検討した。^4C_1型あるいは^1C_4型に配座制御されアノマー位に脱離基としてフッ素を有するキシロシル糖基質をアリルトリメチルシランおよびBF_3/Et_2O存在下撹拌したところ、^4C_1型基質はα高選択的(85%,α/β=50:1)に、^1C_4型基質はβ高選択的(73%,βonly)にアリルC-グリコシド体を与えた(Angew.Chem.Int.Ed.2003,in press)。
    この結果から、本C-グリコシル化反応立体制御法がラジカル反応のみでなくカチオン中間体を経るS_N1型反応にも適用可能であることが確認できた。このことは、高立体選択的C-グリコシル化が種々の反応条件で可能になることを意味し、他の様々なC-グリコシド型化合物合成への応用が期待できる。

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Industrial property rights 16

  1. プロドラッグ化合物

    阿部 洋, 木村 康明

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    Applicant:国立大学法人東海国立大学機構

    Application no:特願2021-013946  Date applied:2021.1

    Announcement no:特開2022-117326  Date announced:2022.8

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  2. 核酸モノマー

    阿部 洋, 阿部 奈保子, 木村 康明, 野村 浩平, 程 久美子, 小林 芳明, 安 成鎮

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    Applicant:国立大学法人東海国立大学機構

    Application no:特願2020-159793  Date applied:2020.9

    Announcement no:特開2022-053148  Date announced:2022.4

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  3. β修飾リン酸化合物前駆体、β修飾リン酸化合物、反応阻害剤及びこれを含む医薬並びに反応阻害方法

    阿部 洋, 木村 康明

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    Applicant:国立研究開発法人科学技術振興機構

    Application no:JP2019009213  Date applied:2019.3

    Publication no:WO2019-172394  Date published:2019.9

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  4. 修飾ポリヌクレオチド

    阿部 洋, シュー ジャオマー

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    Applicant:国立大学法人東海国立大学機構

    Application no:JP2018030549  Date applied:2018.8

    Publication no:WO2019-039403  Date published:2019.2

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  5. グルタチオンS-トランスフェラーゼ阻害剤

    阿部 洋, 宍戸 裕子

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    Applicant:国立大学法人名古屋大学

    Application no:特願2016-133272  Date applied:2016.7

    Announcement no:特開2018-002669  Date announced:2018.1

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  6. グルタチオンS-トランスフェラーゼ阻害剤

    阿部 洋, 宍戸 裕子

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    Applicant:国立大学法人東海国立大学機構

    Application no:特願2016-133272  Date applied:2016.7

    Announcement no:特開2018-002669  Date announced:2018.1

    Patent/Registration no:特許第6787564号  Date registered:2020.11 

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  7. 非酵素的核酸鎖結合方法

    阿部 洋, 丸山 豪斗

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    Applicant:国立研究開発法人科学技術振興機構

    Application no:特願2016-544965  Date applied:2015.8

    Patent/Registration no:特許第6703948号  Date registered:2020.5 

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  8. 非酵素的核酸鎖結合方法

    阿部 洋, 丸山 豪斗

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    Application no:JP2015004294  Date applied:2015.8

    Publication no:WO2016-031247  Date published:2016.3

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  9. 新規化合物及び該化合物を含む脂肪滴及び/又は脂肪組織検出用試薬

    阿部 洋, 伊藤 美香, 伊藤 嘉浩, 西村 智

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    Applicant:国立研究開発法人理化学研究所

    Application no:特願2015-505607  Date applied:2014.3

    Patent/Registration no:特許第6241014号  Date registered:2017.11 

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  10. 新規化合物及び該化合物を含む脂肪滴及び/又は脂肪組織検出用試薬

    阿部 洋, 伊藤 美香, 伊藤 嘉浩, 西村 智

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    Applicant:国立研究開発法人理化学研究所

    Application no:JP2014056973  Date applied:2014.3

    Publication no:WO2014-142320  Date published:2014.9

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  11. 機能性核酸分子の構築法、および当該方法に用いる核酸組合せ物

    阿部 洋, 伊藤 嘉浩, 丸山 豪斗

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    Applicant:国立研究開発法人科学技術振興機構

    Application no:特願2014-502415  Date applied:2013.3

    Patent/Registration no:特許第6126075号  Date registered:2017.4 

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  12. 機能性核酸分子の構築法、および当該方法に用いる核酸組合せ物

    阿部 洋, 伊藤 嘉浩, 丸山 豪斗

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    Applicant:独立行政法人科学技術振興機構

    Application no:JP2013055732  Date applied:2013.3

    Publication no:WO2013-129663  Date published:2013.9

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  13. 環状RNA及びタンパク質の製造方法

    阿部 洋, 阿部 奈保子, 伊藤 嘉浩, 西原 みづき

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    Applicant:国立研究開発法人理化学研究所

    Application no:特願2013-557601  Date applied:2013.2

    Patent/Registration no:特許第6284181号  Date registered:2018.2 

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  14. 環状RNA及びタンパク質の製造方法

    阿部 洋, 阿部 奈保子, 伊藤 嘉浩, 西原 みづき

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    Applicant:独立行政法人理化学研究所

    Application no:JP2013053095  Date applied:2013.2

    Publication no:WO2013-118878  Date published:2013.8

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  15. 機能性核酸分子の構築法

    阿部 洋, 伊藤 美香, 伊藤 嘉浩

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    Applicant:国立研究開発法人理化学研究所

    Application no:特願2013-012686  Date applied:2013.1

    Announcement no:特開2014-143923  Date announced:2014.8

    Patent/Registration no:特許第6296434号  Date registered:2018.3 

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  16. 蛍光発生分子および標的核酸検出方法

    阿部 洋, 伊藤 嘉浩, 柴田 綾, 伊藤 美香

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    Applicant:国立研究開発法人理化学研究所

    Application no:特願2011-534352  Date applied:2010.10

    Patent/Registration no:特許第5733760号  Date registered:2015.4 

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Media Coverage 3

  1. mRNAワクチン国産化目指す 名古屋大など Newspaper, magazine

    中日新聞  朝刊  2022.3

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  2. mRNAワクチン国産化へ 大学発ベンチャー設立 Newspaper, magazine

    産経新聞  2022.3

  3. スタートアップのCrafton Biotechnology、日本発の技術でmRNA医薬を開発へ Internet

    日経バイオテク  2020.3

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Academic Activities 1

  1. 日本核酸医薬学会

    Role(s):Planning, management, etc.

    幹事  2021.2

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