研究業績

¹¹C-Labeling of 20(S)-protopanaxadiol, an aglycon of ginsenoside, based on the use of Pd(0)-mediated rapid C-[¹¹C]methylation of boronic precursors. Y. Ooshima, H. Koyama, Aya Ogata, Hiroshi Ikenuma, Takashi Yamada, Hiroyuki Kojima, Takashi Kato, Y. Kimura, M. Suzuki, Bioorg. Med. Chem. Lett. 128, 130356 (2025).

A novel PET probe to selectively image heat shock protein 90α/β isoforms in the brain. Takayuki Sakai, Aya Ogata, Hiroshi Ikenuma, Takashi Yamada, Saori Hattori, Junichiro Abe, Shinichi Imamura, Masanori Ichise, Mari Tada, Akiyoshi Kakita, Hiroko Koyama, Masaaki Suzuki, Takashi Kato, Kengo Ito, Yasuyuki Kimura* EJNMMI Radiopharm. Chem. 9, 19 (2024).
DOI: 10.1186/s41181-024-00248-0

Simple methods for measuring milk exosomes using fluorescent compound GIF-2250/2276. Saho Furukawa, Kyoka Kawaguchi, Kotomi Chikama, Ryohei Yamada, Yuji O. Kamatari,Lim Lee Wah, Hiroko Koyama, Yasuo Inoshima, Mitsushi J. Ikemoto, Saishi Yoshida, Yoko Hirata, Kyoji Furuta, Hiroshi Takemori*, Biochem. Biophys. Res. Commun. 696, 149505 (2024).
http://purl.org/coar/access_right/c_14cb

Synthesis and evaluation of a novel PET ligand, a GSK’963 analog, aiming at autoradiography and imaging of the receptor interacting protein kinase 1 in the brain. Hiroshi Ikenuma, Aya Ogata, Hiroko Koyama, Bin Ji, Hideki Ishii, Takashi Yamada, Junichiro Abe, Chie Seki, Yuji Nagai, Masanori Ichise, Takafumi Minamimoto, Makoto Higuchi, Ming-Rong Zhang, Takashi Kato, Kengo Ito, Masaaki Suzuki, Yasuyuki Kimura, EJNMMI Radiopharm. Chem. 8, 31 (2023).
DOI: 10.1186/s41181-023-00217-z

ARL-17477 is a dual inhibitor of NOS1 and the autophagic-lysosomal system that prevents tumor growth in vitro and in vivo, Teiko Komori Nomura, Satoshi Endo, Takuma Kuwano, Kazuya Fukasawa, Shigeo Takashima, Tomoki Todo, Kyoji Furuta, Takuhei Yamamoto, Eiichi Hinoi, Hiroko Koyama, and Ryo Honda, Sci. Rep. 13, 10757(2023).
DOI: 10.1038/s41598-023-37797-4

Acyclic retinoid peretinoin reduces hemorrhage-associated brain injury in vitro and in vivo, Sakino Nakanishi, Keita Kinoshita, Yuki Kurauchi, Takahiro Seki, Yasuyuki Kimura, Masaaki Suzuki, Keiichi Suzuki, Hiroko Koyama, Hiroyuki Kagechika, Hiroshi Katsuki,Eurp. J. Pharmacol. 954, 175899 (2023).
DOI: 10.1016/j.ejphar.2023.175899

¹¹C-labeling of Acyclic Retinoid Peretinoin by Rapid C-[¹¹C]Methylation to Disclose Novel Brain Permeability and Central Nervous System Activities Hidden in Antitumor Agent, Keiichi Suzuki, Hiroko Koyama, Narumasa Nakamura, Yasuyuki Kimura, Aya Ogata, Hiroshi Ikenuma, Hideki Ishii, Ming-Rong Zhang, Kazunori Kawamura, Takafumi Minamimoto, Yuji Nagai, Hiroshi Katsuki, Tetsuya Kimura, Nobuyuki Kimura, Masanori Ichise, Takasi Kato, Kengo Ito, and Masaaki Suzuki, Bioorg. Med. Chem. Lett. (2023) 85, 129212.
DOI: 10.1016/j.bmcl.2023.129212

[¹¹C]NCGG401, a novel PET ligand for imaging of colony-stimulating factor 1 receptors, Aya Ogata, Bin Ji, Takashi Yamada, Saori Hattori, Junichiro Abe, Hiroshi Ikenuma, Masanori Ichise, Hiroko Koyama, Masaaki Suzuki, Takashi Kato, Kengo Ito, Yasuyuki Kimura*, Bioorg. Med. Chem. Lett. 65, 128704 (2022).
https://doi.org/10.1016/j.bmcl.2022.128704

Thioxothiazolidin Derivative, 4-OST, Inhibits Melanogenesis by Enhancing the Specific Recruitment of Tyrosinase-containing Vesicles to Lysosome, Kenta Isogawa*, Masataka Asano*, Masumi Hyazaki, Kenichi Koga, Miyu Watanabe, Keiichi Suzuki, Takahiro Kobayashi, Kyoka Kawaguchi, Akane Ishizuka, Shinya Kato, Hironari Ito, Akie Hamamoto, Hiroko Koyama, Kyoji Furuta, Hiroshi Takemori. J. Cell. Biochem. 122, 667-678 (2021).
DOI: 10.1002/jcb.29895

Brain pharmacokinetics and biodistribution of ¹¹C-labeled isoproterenol in rodents, Aya Ogata, Yasuyuk Kimura, Hiroshi Ikenuma, Takashi Yamada, Junichiro Abe, Hiroko Koyama, Masaaki Suzuki, Masanori Ichise, Takashi Kato, Kengo Ito, Nucl. Med. Biol. 86-87, 52-58 (2020).
DOI: 10.1016/j.nucmedbio.2020.06.002

Synthesis of (R,S)-isoproterenol, an inhibitor of tau aggregation, as an ¹¹C-labeled PET tracer via reductive alkylation of (R,S)-norepinephrine with [2-¹¹C]acetone, Hiroshi Ikenuma, Hiroko Koyama, Naoya Kajino, Yasuyuki Kimura, Aya Ogata, Junichiro Abe, Yasuhiro Kawasumi, Takashi Kato, Akihiko Takashima, Kengo Ito, Masaaki Suzuki, Bioorg. Med. Chem. Lett. 29, 2107-2111 (2019).
DOI: 10.1016/j.bmcl.2019.07.005

Organozinc-aided, HMPA-free, stoichiometric three-component coupling for the general synthesis of prostaglandins and stable prostacyclin analogs with biological significance, Hiroko Koyama, Atsuto Izumiseki, Masaaki Suzuki, Tetrahedron Lett. 60, 1467-1470 (2019).
DOI: 10.1016/j.tetlet.2019.04.037

Synthesis of 3-arylmethyl-2-oxindole derivatives and their effects on neuronal cell death, Kyoji Furuta, Yosuke Mizuno, Masahide Maeda, Hiroko Koyama, Yoko Hirata, Chem. Pharm. Bull. 65, 1093-1097 (2017).
DOI: 10.1248/cpb.c17-00627

Synthesis of 3-[4-(dimethylamino)phenyl]alkyl-2-oxindole derivatives and their effects on neuronal cell death, Kyoji Furuta, Yu Kawai, Yosuke Mizuno, Yorika Hattori, Hiroko Koyama, Yoko Hirata, Bioorg. Med. Chem. Lett. 27, 4457-4461 (2017).
DOI: 10.1016/j.bmcl.2017.08.005

Remote ischemic preconditioning protects human neural stem cells from oxidative stress, Ayako Motomura, Mikiko Shimizu, Kazuya Motomura, Hiroko Koyama, Fumiharu Ohka, Yusuke Nishimura, Masahito Hara, Tetsuya Fukuda, Sayaka Mikami, Yasuhiko Bando, Toshihide Nishimura, Toshihiko Wakabayashi and Atsushi Natsume, Apoptosis 22, 1353-1361 (2017).
DOI: 10.1007/s10495-017-1425-8

Synthesis of PET probe O⁶-[(3-[¹¹C]methyl)benzyl]guanine by Pd⁰-mediated rapid C-[¹¹C]methylation toward imaging DNA repair protein O⁶-methylguanine-DNA methyltransferase in glioblastoma, Hiroko Koyama, Hiroshi Ikenuma, Hiroshi Toda, Goro Kondo, Masaki Hirano, Masaya Kato, Junichiro Abe, Takashi Yamada, Toshihiko Wakabayashi, Kengo Ito, Atsushi Natsume, Masaaki Suzuki, Bioorg. Med. Chem. Lett. 27, 1892-1896 (2017).
DOI: 10.1016/j.bmcl.2017.03.045

Blood-brain barrier permeability of ginkgolide: Comparison of the behavior of PET Probes 7α-[¹⁸F]fluoro- and 10-O-p-[¹¹C]methylbenzyl ginkgolide B in monkey and rat brains, Hisashi Doi, Kengo Sato, Hideo Shindou, Kengo Sumi, Hiroko Koyama, Takamitsu Hosoya, Yasuyoshi Watanabe, Satoshi Ishii, Hideo Tsukada, Koji Nakanishi, and Masaaki Suzuki, Bioorg. Med. Chem. 24, 5148-5157 (2016).
DOI: 10.1016/j.bmc.2016.08.032

Toxic tau oligomer formation blocked by capping of cysteine residues with 1,2-dihydroxybenzene groups; Yoshiyuki Soeda, Misato Yoshikawa, Osborne F. X. Almeida, Akio Sumioka, Sumihiro Maeda, Hiroyuki Osada, Yasumitsu Kondoh, Akiko Saito, Tomohiro Miyasaka, Tetsuya Kimura, Masaaki Suzuki, Hiroko Koyama, Yuji Yoshiike, Hachiro Sugimoto, Yasuo Ihara, and Akihiko Takashima, Nat. Commun. 6, 10216 (2015),
DOI: 10.1038/ncomms10216

Synthesis of ¹¹C-labeled retinoic acid, [¹¹C]ATRA, via an alkenylboron precursor by Pd(0)-mediated rapid C-[¹¹C]methylation; M. Suzuki, M.Takashima-Hirano, H. Ishii, C. Watanabe, K. Sumi, H. Koyama, H. Doi, Bioorg. Med. Chem. Lett. 24, 3622-3625 (2014).
10.1016/j.bmcl.2023.129212

Efficient syntheses of [¹¹C]zidovudine and its analogs by convenient one-pot palladium(0)-copper(I) co-mediated rapid C-[¹¹C]methylation; Z. Zhang, H. Doi, H. Koyama, Y. Watanabe, M. Suzuki, J. Labelled Compd. Radiopharm. 57, 540-549 (2014).

Evaluation of TlOH effect for Pd⁰-mediated cross-coupling of methyl iodide and excess boronic acid ester toward fabrication of [¹¹C]CH₃-incorporated PET tracer; H. Koyama, H. Doi, M. Suzuki, Int. J. Org. Chem. 3, 220-223 (2013).
DOI: 10.4236/ijoc.2013.33030

Pd⁰-mediated rapid coupling of methyl iodide with excess amounts of benzyl- and cinnamylboronic acid estsers: Efficient method for incorporation of positron-emitting ¹¹C radionuclide into organic frameworks by coupling between two sp³-hybridized carbons; H. Koyama, Z. Zhang, R. Ijuin, Siqin, J. Son, Y. Hatta, M. Ohta, M. Wakao, T. Hosoya, H. Doi, M. Suzuki, RSC Advances 3(24), 9391-9401 (2013).
DOI: 10.1039/c3ra40815a

Identification of a novel compound with antiviral activity against influenza A virus depending on PA subunit of viral RNA polymerase; K. Yamada, H. Koyama, K. Hagiwara, A. Ueda, Y. Sasaki, S. Kanesashi, R. Ueno, H. K. Nakamura, K. Kuwata, K.Shimizu, M.Suzuki, Y. Aida, Microbes Infect. 14, 740-747 (2012).
DOI: 10.1016/j.micinf.2012.02.012

Efficient synthesis of [¹¹C]H-1152, a PET probe specific for Rho-kinases, highly potential targets in diagnostic medicine and drug development; M. Suzuki, M. Takashima-Hirano, H. Koyama, T. Yamaoka, K. Sumi, H. Nagata, H. Hidaka, H. Doi, Tetrahedron 68, 2336-2341 (2012).
https://doi.org/10.1016/j.tet.2012.01.033

Correlation between quantified promoter methylation and enzymatic activity of O(6)-methylguanine-DNA methyltransferase in glioblastomas; Y. Kishida, A. Natsume, H. Toda, Y. Toi, K. Motomura, H. Koyama, K. Matsuda, O. Nakayama, M. Sato, M. Suzuki, Y. Kondo, T. Wakabayashi, Tumour Biol. 33, 373-381 (2012).

Synthesis and biological evaluation of deoxy-hematoxylin derivatives as a novel class of anti-HIV-1 agents; H. Ishii, H. Koyama, K. Hagiwara, T. Miura, G. Xue, Y. Hashimoto, G. Kitahara, Y. Aida, M. Suzuki, Bioorg. Med. Chem. Lett. 22, 1469-1474 (2012).
https://doi.org/10.1016/j.bmcl.2011.06.066

The kinase inhibitor SFV785 dislocates dengue virus envelope protein from the replication complex and blocks virus assembly; A. Anwar, T. Hosoya, K. Leong, H. Onogi, Y. Okuno, T. Hiramatsu, H. Koyama, M. Suzuki, M. Hagiwara, M. A. Garcia-Blanco, Plos One 6 (8), e23246, 1-12 (2011).
DOI: 10.1371/journal.pone.0023246

Highly efficient syntheses of [methyl-¹¹C]thymidine and its analogue 4’-[methyl-¹¹C]thiothymidine as nucleoside PET probes for cancer cell proliferation by Pd⁰-mediated rapid C-[¹¹C]methylation; H. Koyama, Siqin, Z. Zhang, K. Sumi, Y. Hatta, H. Nagata, H. Doi, M. Suzuki, Org. Biomol. Chem. 9 (11), 4287-4294 (2011).
DOI: 10.1039/c0ob01249a

1-Benzyl-1,2,3,4-tetrahydroisoquinoline binds with tublin β, a substrate of parkin, and reduces its polyubiquitination; R. Kohta, Y. Kotake, T. Hosoya, T. Hiramatsu, Y. Otsubo, H. Koyama, Y. Hirokane, Y. Yokoyama, H. Ikeshoji, K. Oofune, M. Suzuki, S. Ohta, J. Neurochem. 114, 1291-1301 (2010).
DOI: 10.1111/j.1471-4159.2010.06576.x

Pd⁰-mediated rapid coupling between methyl iodide and heteroarylstannanes: an efficient and general method for the incorporation of a positron-emitting ¹¹C radionuclide into heteroaromatic frameworks; M. Suzuki, K. Sumi, H. Koyama, Siqin, T. Hosoya, M. Takashima-Hirano, H. Doi, Chem. Eur. J. 15, 12489-12495 (2009).
DOI: 10.1002/chem.200901145

⁷Li- and ³¹P-NMR spectra of cyclopentanone lithium enolate in ethereal solvents: identification of the HMPA- coordinated aggregate structures; M. Suzuki, H. Koyama, R. Noyori, Tetrahedron 60, 1571-1579 (2004).
https://doi.org/10.1016/j.tet.2003.12.011

Effects of HMPA on the structure and reactivity of the lithium enolate of cyclopentanone in THF: the dimer is responsible for alkylation and proton exchange reactions; M. Suzuki, H. Koyama, R. Noyori, Bull. Chem. Soc. Jpn. 77, 259-268 (2004).（BCSJ賞受賞）
https://doi.org/10.1246/bcsj.77.259

古山浩子、脳移行性を有する機能性PETプローブの開発研究、豊田研究報告、72、202-203 (2019)；Hiroko Koyama, Development of functional probes for PET with brain penetration, Reports of Toyota Physical and Chemical Research Institute, 72, 202-203 (2019).

Pd⁰-mediated rapid cross-coupling reactions, the rapid C-[¹¹C]methylations, revolutionarily advancing the syntheses of short-lived PET molecular probes; M. Suzuki, H. Doi, H. Koyama, Z. Zhang, T. Hosoya, H. Onoe, Y. Watanabe, Chem. Rec. 14, 516-541 (2014).