Faculty Profiles - ABE Hiroshi

Papers - ABE Hiroshi

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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

Publishing type：Research paper (scientific journal)

© 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.

DOI： 10.1021/acs.orglett.6b02612

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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

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

Organic Letters Vol. 18 page： 6224-6227 2016.11

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

Language：English Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

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.

DOI： 10.1021/acs.molpharmaceut.6b00140

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

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

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

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.

DOI： 10.1021/acs.joc.6b00105

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

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

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

Language：English Publishing type：Research paper (scientific journal) Publisher：NATURE PUBLISHING GROUP

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.

DOI： 10.1038/srep16435

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

Publishing type：Research paper (scientific journal)

© 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.

DOI： 10.1002/adsc.201401000

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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

Language：English Publishing type：Part of collection (book) Publisher：Springer New York

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.

DOI： 10.1007/978-1-4939-1538-5_2

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

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

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.

DOI： 10.1039/c5ob00199d

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

Language：English Publishing type：Research paper (scientific journal) Publisher：PERGAMON-ELSEVIER SCIENCE LTD

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.

DOI： 10.1016/j.bmc.2014.08.024

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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

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

Publishing type：Research paper (scientific journal)

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.

DOI： 10.1021/ml500134k

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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

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

Language：Japanese Publisher：SOC SYNTHETIC ORGANIC CHEM JPN

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.

DOI： 10.5059/yukigoseikyokaishi.72.822

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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

Language：English Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

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.

DOI： 10.1021/ja5018283

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

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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Papers - ABE Hiroshi