Kyushu University Academic Staff Educational and Research Activities Database
List of Papers
Go Hirai Last modified date:2019.06.28

Professor / Department of Chemo-Pharmaceutical Sciences / Faculty of Pharmaceutical Sciences

1. Yu Mikame, Kazuko Yoshida, Daisuke Hashizume, Go Hirai, Kazuo Nagasawa, Hiroyuki Osada, Mikiko Sodeoka, Synthesis of All Stereoisomers of RK460 and Evaluation of Their Activity and Selectivity as Abscisic Acid Receptor Antagonists, Chemistry - A European Journal, 10.1002/chem.201806056, 25, 14, 3496-3500, 2019.03, The PYR/PYL/RCAR protein families have recently emerged as receptors of the phytohormone abscisic acid (ABA, 1), which regulates plant responses to environmental stress. These families have multiple members with different physiological actions, and so selective agonists or antagonists are needed both as tools to elucidate functional differences and as lead compounds for agrochemicals. We previously identified RK460 (rac-3 a) as a PYR1-selective antagonist, and showed that it possesses five stereocenters on a 6,5-cis-bicyclo skeleton. Here, we synthesized all the stereoisomers of RK460 and evaluated their activity towards a panel of receptors. Relative stereochemistry as well as absolute stereochemistry was important for selective action..
2. Kazuma Shimoda, Takahiro Mitsuoka, Kenta Ueda, Hiroshi Suemune, Go Hirai, Mariko Aso, Synthesis of dendritic bisphosphonates as bone targeting ligands, Tetrahedron Letters, 10.1016/j.tetlet.2018.11.028, 59, 51, 4528-4531, 2018.12, A dendritic bisphosphonate carrying three bisphosphonate (BP) units in close proximity was designed as a ligand to conjugate large therapeutic molecules for their bone selective delivery. The Bu
P-catalyzed conjugate addition of nitromethane to vinylidene bisphosphonate was effective to construct a quaternary carbon center carrying BP units. Owing to multivalent interactions, the dendritic bisphosphonate showed considerable affinity for the bone mineral hydroxyapatite even in the presence of a competitor, demonstrating potential as a bone targeting ligand..
3. Kazuteru Usui, Kosuke Yamamoto, Yuhei Ueno, Kazunobu Igawa, Ryusuke Hagihara, Toshinobu Masuda, Akio Ojida, Satoru Karasawa, Katsuhiko Tomooka, Go Hirai, Hiroshi Suemune, Internal-Edge-Substituted Coumarin-Fused [6]Helicenes
Asymmetric Synthesis, Structural Features, and Control of Self-Assembly, Chemistry - A European Journal, 10.1002/chem.201803270, 24, 55, 14617-14621, 2018.10, π-Conjugated helicenes containing heteroatoms have attracted significant attention due to their diverse chemical and electronic structures, as well as tunable physical properties. It was rationally anticipated that the self-assembly of coumarin-fused helicenes would be controlled by the effects of a substituent on the internal edge of the helix. Here, this work reports the efficient syntheses of coumarin-fused helicenes 1 a,b (R=Ph, Me), and the enantioselective synthesis of 1 a (R=Ph) by chiral AuI-catalyzed hydroarylation. The helical structure of 1 was unambiguously determined by X-ray crystallography. Of particular note, the enantiomerically pure crystal of 1 a adopted a one-dimensional columnar structure based on π–π stacking interactions, as expected. Furthermore, a significant difference between the fluorescence quantum yields of the enantiomerically pure form and racemate of 1 a was observed..
4. Eisuke Ota, Kazuteru Usui, Kana Oonuma, Hiroyuki Koshino, Shigeru Nishiyama, Go Hirai, Mikiko Sodeoka, Thienyl-Substituted α-Ketoamide
A Less Hydrophobic Reactive Group for Photo-Affinity Labeling, ACS Chemical Biology, 10.1021/acschembio.7b00988, 13, 4, 876-880, 2018.02, Photoaffinity labeling (PAL) is an important tool in chemical biology research, but application of α-ketoamides for PAL has been hampered by their photoinstability. Here, we show that 2-thienyl-substituted α-ketoamide is a superior photoreactive group for PAL. Studies with a series of synthetic mannose-conjugated α-ketoamides revealed that 2-thienyl substitution of α-ketoamide decreased the electrophilicity of the keto group and reduced the rate of photodegradation. Mannose-conjugated thienyl α-ketoamide showed greater concanavalin A labeling efficiency than other alkyl or phenyl-substituted α-ketoamides. In comparison with representative conventional photoreactive groups, 2-thienyl ketoamide showed reduced labeling of nontarget proteins, probably owing to its lower hydrophobicity..
5. Kosuke Morishita, Yuna Okamoto, Shuhei Murayama, Kazuteru Usui, Eriko Ohashi, Go Hirai, Ichio Aoki, Satoru Karasawa, Water-Proton Relaxivities of Radical Nanoparticles Self-Assembled via Hydration or Dehydration Processes, Langmuir, 10.1021/acs.langmuir.7b01126, 33, 31, 7810-7817, 2017.08, Nanoparticles capable of accumulating in tumor tissues are promising materials for tumor imaging and therapy. In this study, two radical nanoparticles (RNPs), denoted as 1 and 2, composed of self-assembled ureabenzene derivatives possessing one or two amphiphilic side chains were demonstrated to be candidates for metal-free functional magnetic resonance imaging (MRI) contrast agents (CAs). Because of the self-assembly behavior of 1 and 2 in a saline solution, spherical RNPs of sizes ∼50-90 and ∼30-100 nm were detected. In a highly concentrated solution, RNP 1 showed considerably small water-proton relaxivity values (r1 and r2), whereas RNP 2 showed an r1 value that was around 5 times larger than that of RNP 1. These distinct r1 values might be caused by differences in the self-assembly behavior by a hydration or dehydration process. In vivo studies with RNP 2 demonstrated a slightly enhanced T1-weighted image in mice, suggesting that the RNPs can potentially be used as metal-free functional MRI CAs for T1-weighted imaging..
6. Morita Masaki, Shuntaro Kojima, Megumi Ohkubo, Hiroyuki Koshino, Daisuke Hashizume, Go Hirai, Keiji Maruoka, Mikiko Sodeoka, Synthesis of the Right-Side Structure of Type B Physalins, ISRAEL JOURNAL OF CHEMISTRY, 10.1002/ijch.201600110, 57, 309-318, 2017.04.
7. Yusuke Kimuro, Kazuteru Usui, Satoru Karasawa, Go Hirai, Mariko Aso, 7-Hydroxy-3-methyleneisoindolin-1-one as a New ESIPT-Fluorescent Probe to Monitor Aqueous Environments, Chemical and Pharmaceutical Bulletin, 10.1248/cpb.c17-00306, 65, 8, 796-800, 2017.04, A 7-hydroxy derivative of 3-methyleneisoindolin-1-one 1 was synthesized and its properties as a new fluorophore undergoing excited-state intramolecular proton transfer (ESIPT) were investigated. In alcohols and dimethylsulfoxide, 1 exhibited dual emission at ca. 380 and 525-540 nm when excited at ca. 336 nm, which agreed well with the density functional theory (DFT) and time-dependent (TD)-DFT-calculated emission predictions of 1 and its ESIPT tautomer. In aqueous solutions at near neutral pH, 1 exhibited a broad emission band at ca. 497 nm, presumably caused by the overlap of emissions from 1 and the excited state phenolate species of 1. In binary mixtures of H2O and EtOH, the wavelength and intensity of fluorescence maxima were dependent on the dielectric constant of the solvent, suggesting that 1 could be applied as a fluorescent probe to monitor aqueous environments..
8. Qianqian Wang, Yuta Kuramoto, Yozo Okazaki, Eisuke Ota, Masaki Morita, Go Hirai, Kazuki Saito, Mikiko Sodeoka, Synthesis of polyunsaturated fatty acid-containing glucuronosyl-diacylglycerol through direct glycosylation, Tetrahedron Letters, 10.1016/j.tetlet.2017.06.034, 58, 30, 2915-2918, 2017.01, We describe a total synthesis of a polyunsaturated fatty acid (PUFA)-containing glucuronosyldiacylglycerol (GlcADG), which is a surrogate glycolipid whose synthesis is remarkably upregulated in plant membranes under phosphorus-depleted conditions. Glycosylation between the glucuronide donor bearing 3,4-dimethoxybenzyl (DMPM) protecting groups and di-acylglycerol acceptor proceeded smoothly in the presence of gold(I) catalyst to provide the protected α-isomer of GlcADG as the major product..
9. Atsushi Fukushima, Michimi Nakamura, Hideyuki Suzuki, Mami Yamazaki, Eva Knoch, Tetsuya Mori, Naoyuki Umemoto, Masaki Morita, Go Hirai, Mikiko Sodeoka, Kazuki Saito, Comparative Characterization of the Leaf Tissue of Physalis alkekengi and Physalis peruviana Using RNA-seq and Metabolite Profiling, FRONTIERS IN PLANT SCIENCE, 10.3389/fpls.2016.01883, 7, 1883, 2016.12.
10. Takayuki Ohyoshi, Yuki Tamura, Ichiro Hayakawa, Go Hirai, Yamato Miyazawa, Shota Funakubo, Mikiko Sodeoka, Hideo Kigoshi, Total synthesis of natural derivatives and artificial analogs of 13-oxyingenol and their biological evaluation, ORGANIC & BIOMOLECULAR CHEMISTRY, 10.1039/c6ob02268e, 14, 11426-11437, 2016.11, We have established an efficient synthetic methodology for the 13-oxyingenol natural derivative (13-oxyingenol-13-dodecanoate-20-hexanoate), featuring a ring-closing olefin metathesis reaction for the "direct" construction of a highly strained inside-outside framework and a Mislow-Evans-type [2,3]-sigmatropic rearrangement for the stereoselective introduction of the hydroxy group at C5. We also synthesized artificial analogs of 13-oxyingenol and ingenol by using our synthetic strategy. In vitro activation assays of protein kinase C (PKC) α and δ revealed that the dodecanoyl group at O13 on 13-oxyingenol analogs had a significant role in PKCδ activation. The PKCα- or PKCδ-activating 13-oxyingenol and ingenol analogs induced both distinct morphological changes and increases of CD11b expression in HL-60 cells, which would be typical signs of HL-60 cell differentiation to macrophage-like cells, as expected by previous reports. Intriguingly, however, similar differentiation phenotypes were observed with the use of 13-oxyingenol natural derivatives and 13-oxyingenol-13-dodecanoate showing a remarkably less potent PKCα or PKCδ activation ability, which the PKC inhibitor Gö6983 diminished. This indicated the involvement of other PKC isozymes or related kinase activities. 13-Oxyingenol analogs, which induced HL-60 cell differentiation, also induced HL-60 cell death, similar to the action of a phorbol ester, a strong PKC activator..
11. Kosuke Yamamoto, Takashi Shimizu, Kazunobu Igawa, Katsuhiko Tomooka, Go Hirai, Hiroshi Suemune, Kazuteru Usui, Rational Design and Synthesis of [5] Helicene-Derived Phosphine Ligands and Their Application in Pd-Catalyzed Asymmetric Reactions, SCIENTIFIC REPORTS, 10.1038/srep36211, 6, 36211, 2016.11.
12. Yuya Hikone, Go Hirai, Masaki Mishima, Kohsuke Inomata, Teppei Ikeya, Souichiro Arai, Masahiro Shirakawa, Mikiko Sodeoka, Yutaka Ito, A new carbamidemethyl-linked lanthanoid chelating tag for PCS NMR spectroscopy of proteins in living HeLa cells, JOURNAL OF BIOMOLECULAR NMR, 10.1007/s10858-016-0059-4, 66, 99-110, 2016.10.
13. Xiaoying Sun, Go Hirai, Masashi Ueki, Hiroshi Hirota, Qianqian Wang, Yayoi Hongo, Takemichi Nakamura, Yuki Hitora, Hidekazu Takahashi, Mikiko Sodeoka, Hiroyuki Osada, Makiko Hamamoto, Minoru Yoshida, Yoko Yashiroda, Identification of novel secreted fatty acids that regulate nitrogen catabolite repression in fission yeast, Scientific Reports, 10.1038/srep20856, 6, 20856, 2016.02.
14. Eisuke Ota, Yu Mikame, Go Hirai, Shigeru Nishiyama, Mikiko Sodeoka, Photochemical and Additive-Free Coupling Reaction of α-Cumyl α-Keto Esters via Intermolecular C–H Bond Activation, SYNLETT, 10.1055/s-0035-1561098, 27, 1128-1132, 2016.01.
15. Eisuke Ota, Yu Mikame, Go Hirai, Hiroyuki Koshino, Shigeru Nishiyama, Mikiko Sodeoka, Photo-induced formation of cyclopropanols from α-ketoamides via γ-C-H bond activation, Tetrahedron Lett., 10.1016/j.tetlet.2015.09.038, 56, 5991-5994, 2015.09.
16. Masaaki Ozawa, Masaki Morita, Go Hirai, Satoru Tamura, Masao Kawai, Ayako Tsuchiya, Kana Oonuma, Keiji Maruoka, and Mikiko Sodeoka, Contribution of Cage-Shaped Structure of Physalins to Their Mode of Action in Inhibition of NF-kB Action, ACS Med. Chem. Lett. , 10.1021/ml400144e, 4, 730-735, 2013.06.
17. Ayako Tsuchiya, Miwako Asanuma, Go Hirai, Kana Oonuma, Muhammad Muddassar, Eri Nishizawa, Yusuke Koyama, Yuko Otani, Kam Y. J. Zhang, and Mikiko Sodeoka, CDC25A-inhibitory RE Derivatives Bind to Pocket Adjacent to the Catalytic Site, Mol. BioSyst., 10.1039/C3MB00003F, 9, 1026-1034, 2013.02.
18. Ayako Tsuchiya, Go Hirai, Yusuke Koyama, Kana Oonuma, Yuko Otani, Hiroyuki Osada, and Mikiko Sodeoka, Dual-specificity Protein Phosphatase CDC25A/B Inhibitor Identified from a Focused Library with Non-electrophilic Enamine Core Structure, ACS Med. Chem. Lett. , 10.1021/ml2002778, 3, 264-298, 2012.02.
19. Go Hirai, Ayako Tsuchiya, Yusuke Koyama, Yuko Otani, Kana Oonuma, Kosuke Dodo, Siro Simizu, Hiroyuki Osada, and Mikiko Sodeoka, Development of a Vaccinia H1-Related (VHR) Phosphatase Inhibitor with NonAcidic Phosphate-Mimicking Core Structure, ChemMedChem, 10.1002/cmdc.201100107, 6, 617-622, 2011.03.
20. Megumi Ohkubo, Go Hirai, Mikiko Sodeoka, Synthesis of the DFGH ring system of Type B Physalins: Highly Oxygenated, Cage-Shaped Molecules, Angew. Chem. Int. Ed., 10.1002/anie.200900634, 48, 3862-3866, 2009.04.
21. Isao Fukuda, Akihiro Ito, Go Hirai, Shinichi Nishimura, Hisashi Kawasaki, Hisato Saitoh, Ken-ichi Kimura, Mikiko Sodeoka, Minoru Yoshida, Ginkgolic Acid Inhibits Protein SUMOylation by Blocking Formation of the E1-SUMO Intermediate, Chemistry & Biology, 10.1016/j.chembiol.2009.01.009, 16, 133-140, 2009.02.
22. Toru Watanabe, Go Hirai, Marie Kato, Daisuke Hashizume, Taeko Miyagi, and Mikiko Sodeoka, Synthesis of CH2-Linked α(2,3)Sialylgalactose Analogue: On the Stereoselectivity of the Key Ireland-Claisen Rearrangement, Org. Lett., 10.1021/ol801519j, 10, 4167-4170, 2008.09.
23. Go Hirai, Toru Watanabe, Kazunori Yamaguchi, Taeko Miyagi, and Mikiko Sodeoka, Stereocontrolled and Convergent Entry to CF2-Sialosides: Synthesis of CF2-Linked Ganglioside GM4, J. Am. Chem. Soc., 10.1021/ja075738w, 129, 15420-15421, 2007.11.
24. Go Hirai, Hiroki Oguri, Masahiro Hirama, Synthetic Study of Zoanthamine Alkaloids: The C-ring Model Possessing Three Consecutive Quaternary Carbons, Chem. Lett., 141-142.
25. Sameh M. Moharram, Go Hirai, Koji Koyama, Hiroki Oguri, Masahiro Hirama, Enatio-face Control by Molecular Sieves in the Asymmetric Diels-Alder Reaction, Tetrahedron Lett., 41, 6669-6673.
26. Go Hirai, Hiroki Oguri, Sameh M. Moharram, Koji Koyama, Masahiro Hirama, Convergent Synthesis of ABC-ring Moiety of Zoanthenol: Intramolecular Mizoroki-Heck Reaction, Tetrahedron Lett., 42, 5789-5787.
27. Go Hirai, Yuuki Koizumi, Sameh M. Moharram, Hiroki Oguri, Masahiro Hirama, Construction of Quaternary Carbon Center of Zoanthenol by Intramolecular Mizoroki-Heck Reaction of Enone, Org. Lett., 4, 1627-1630.
28. Yoshiyasu Baba, Yosuke Ogoshi, Go Hirai, Takeshi Yanagisawa, Kumiko Nagamatsu, Satoshi Mayumi, Yuichi Hashimoto, and Mikiko Sodeoka, Design, Synthesis, and Structure-Activity Relationship of New Isobenzofuranone Ligands of Protein Kinase C., Bioorg. Med. Chem. Lett., 14, 2963-2967.
29. Yoshiyasu Baba, Satoshi Mayumi, Go Hirai, Hidekazu Kawasaki, Yosuke Ogoshi, Takeshi Yanagisawa, Yuichi Hashimoto, and Mikiko Sodeoka, Evaluation of Series of Isobenzofuranone Dimers as PKCa Ligands: Implication for the Distance between the Two Ligand Binding Sites., Bioorg. Med. Chem. Lett., 14, 2696-2972.
30. Keisuke Ishida, Go Hirai, Koji Murakami, Takayuki Teruya, Siro Simizu, Mikiko Sodeoka, and Hiroyuki Osada, Structure-based Design of a Selective Heparanase Inhibitor as an Antimetastatic Agent., Mol. Cancer Therapeutics, 3, 1069-1077.
31. Go Hirai, Hiroki Oguri, Masahiko Hayashi, Koji Koyama, Yuuki Koizumi, Sameh M. Moharram, Masahiro Hirama*, Synthesis and preliminary biological evaluation of truncated zoanthenol analogues, 14, 2647-2651.
32. Go Hirai, Tadashi Shimizu, Toru Watanabe, Yosuke Ogoshi, Megumi Ohkubo, and Mikiko Sodeoka, Importance of interaction between C1 domain and lipids in protein kinase Cα activation: Hydrophobic side chain direction in isobenzofuranone ligands controls enzyme activation level., ChemMedChem, 2, 1006-1009.
33. Keiko Hata, Koichi Koseki, Kazunori Yamaguchi, Setsuko Moriya, Yasuo Suzuki, Sangchai Yingsakmongkon, Go Hirai, Mikiko Sodeoka, Mark von Itzstein, and Taeko Miyagi, Limited Inhibitory Effects of Oseltamivir and Zanamivir on Human Sialidases, Antimicrob. Agents Chemother., 52, 3484-3491.
34. Naoki Sugano, Yuuki. Koizumi, Go Hirai, Hiroki Oguri, Shoji Kobayashi, Shuji Yamashita, Masahiro Hirama, Enatioselective Synthesis of the Fully Functionalized ABC Ring of Zoanthenol, Chem. Asian J., 3, 1549-1557.
35. Go Hirai, Yosuke Ogoshi, Megumi Ohkubo, Yuki Tamura, Toru Watanabe, Tadashi Shimizu, Mikiko Sodeoka, Asymmetric synthesis of isobenzofuranone derivatives and their unique character as protein kinase Cα (PKCα) activators, Tetrahedron Lett., 50, 3609-3612.
36. Go Hirai, Megumi Ohkubo, Yuki Tamura, Mikiko Sodeoka, Design and Synthesis of Protein Kinase Cα activators based on 'out of pocket' interaction, Bioorg. Med. Chem. Lett. , 21, 3587-3590.
37. Marie Kato, Go Hirai, Mikiko Sodeoka, Studies on the Selectivity between Glycosylation and Intermolecular Aglycone Transfer of Thioglucoside in Synthesis of Lactose Derivatives, Chem. Lett., 40, 877-879.
38. Masaki Morita, Go Hirai, Meguni Ohkubo Hiroyuki koshino, Daisuke Hashizume, Keiji Maruoka, and Mikiko Sodeoka, Kinetically Controlled One-Pot Formation of DEFGH-Rings of Type B Physalins through Domino-Type Transformations, Org, Lett., 14, 3434-3437.
39. Katsunori Tanaka, Yuka Nakamoto, Eric R. O. Siwu, Ambara R. Pradipta, Koji Morimoto, Takeshi Fujiwara, Suguru Yoshida, Takamitsu Hosoya, Yuki Tamura, Go Hirai, Mikiko Sodeoka and Koichi Fukase, Development of bis-unsaturated ester aldehydes as amino-glue probes: sequential double azaelectrocyclization as a promising strategy for bioconjugation, Org. Biomol. Chem., 11, 7326-7333.
40. Takahiro Suzuki, Yuria Miyajima, Kaname Suzuki, Kanako Iwakiri, Masaki Koshimizu, Go Hirai, Mikiko Sodeoka, and Susumu Kobayashi, Unexpected Diels–Alder/Carbonyl-ene Cascade toward the Biomimetic Synthesis of Chloropupukeananin, Org, Lett., 15, 1748-1751.
41. Frédéric Thuaud, Shuntaro Kojima, Go Hirai, Kana Oonuma, Ayako Tsuchiya, Takako Uchida, Teruhisa Tsuchimoto, Mikiko Sodeoka, RE12 derivatives displaying Vaccinia H1-related phosphatase (VHR) inhibition in the presence of detergent and their anti-proliferative activity against HeLa cells, Bioorg. Med. Chem., 22, 2771-2782.
42. Shan Lu, Shinichi Nishimura, Go Hirai, Masashi Ito, Teppei Kawahara, Miho Izumikawa, Mikiko Sodeoka, Kazuo Shin-ya, Toshio Tsuchida and Hideaki Kakeya, Saccharothriolides A-C, novel phenyl-substituted 10-membered macrolides from a rare actinomycete Saccharothrix sp., Chem. Commun., 51, 8047-8077.
43. Go Hirai, Eri Nishizawa, Daiki Kakumoto, Masaki Morita, Mitsuaki Okada, Daisuke Hashizume, Sayoko Nagashima, Mikiko Sodeoka, Reactions of Carbonyl Compounds with Phosphorus Ylide Generated from Tribromofluoromethane and Tris(dimethylamino)phosphine, Chem. Lett., 44, 1389-1391.