2010年以降

Peer-Reviewed Papers

  1. Design, synthesis, and biological activity of synthetically-accessible analog of aplysiatoxin with (R)-(−)-carvone-based conformation-controlling unit.
    Yoshiyuki Suzuki, Keiichi Moritoki, Mizuki Kajiwara, Ryo C. Yanagita, Yasuhiro Kawanami, Yusuke Hanaki, Kazuhiro Irie
    Biosci. Biotechnol. Biochem. 2022, accepted. [DOI: 10.1093/bbb/zbac084] [Accepted Manuscript]
  2. AI and computational chemistry-accelerated development of an alotaketal analogue with conventional PKC selectivity.
    Jumpei Maki, Asami Oshimura, Chihiro Tsukano, Ryo C. Yanagita, Yutaka Saito, Yasubumi Sakakibara, Kazuhiro Irie
    Chem. Commun. 2022, 58, 6693–6696. [DOI: 10.1039/D2CC01759H]
  3. Analysis of binding mode of vibsanin A with protein kinase C C1 domains: An experimental and molecular dynamics simulation study.
    Ryo C. Yanagita, Mao Otani, Satoshi Hatanaka, Hiroto Nishi, Shota Miyake, Yusuke Hanaki, Masashi Sato, Yasuhiro Kawanami, Kazuhiro Irie
    J. Mol. Struct. 2022, 1260, 132866. [DOI: 10.1016/j.molstruc.2022.132866]  [Accepted Manuscript]
  4. Structure optimization of the toxic conformation model of amyloid β42 by intramolecular disulfide bond formation.
    Yuka Matsushima, Yumi Irie, Yusuke Kageyama, Jean-Pierre Bellier, Ikuo Tooyama, Takahito Maki, Toshiaki Kume, Ryo C. Yanagita, Kazuhiro Irie
    ChemBioChem 2022, in press. [DOI: 10.1002/cbic.202200029]
  5. Evaluation of the in vitro cytotoxicity of oscillatoxins E and F under nutrient-starvation culture conditions.
    Yusuke Hanaki, Yusuke Araki, Toshio Nishikawa, Ryo C. Yanagita.
    Fundam. Toxicol. Sci. 2021, 8, 69–73. [DOI: 10.2131/fts.8.69]
  6. Effects of side chain length of 10-methyl-aplog-1, a simplified analog of debromoaplysiatoxin, on PKC binding, anti-proliferative, and pro-inflammatory activities.
    Atsuko Gonda, Koji Takada, Ryo C. Yanagita, Shingo Dan, Kazuhiro Irie.
    Biosci. Biotechnol. Biochem. 2021, 85, 168–180. [DOI: 10.1093/bbb/zbaa024] [Pubmed: 33577665]
  7. Synthesis and biological activities of simplified aplysiatoxin analogs focused on the CH/π interaction.
    Takumi Kobayashi, Ryo C. Yanagita, Kazuhiro Irie.
    Bioorg. Med. Chem. Lett. 2021, 30, 127657. [DOI: 10.1016/j.bmcl.2020.127657] [Pubmed: 33130291]
  8. Evaluation of the Anti-Proliferative Activity of Rare Aldohexoses against MOLT-4F and DU-145 Human Cancer Cell Line and Structure-Activity Relationship of D-Idose.
    Hironobu Ishiyama, Ryo C. Yanagita, Kazune Takemoto, Natsumi Kitaguchi, Yuuki Uezato, Yasunori Sugiyama, Masashi Sato, Yasuhiro Kawanami.
    J. Appl. Glycosci. 2020, 67, 95–101. [DOI: 10.5458/jag.jag.JAG-2020_0006]
  9. Control of the toxic conformation of amyloid β42 by intramolecular disulfide bond formation.
    Yuka Matsushima, Ryo C. Yanagita, Kazuhiro Irie.
    Chem. Commun. 2020, 56, 4118–4121. [DOI: 10.1039/D0CC01053G] [Pubmed: 32163091]
  10. Nematocidal Activity of 6-O-octanoyl- And 6-O-octyl-D-allose Against Larvae of Caenorhabditis elegans.
    Hirofumi Sakoguchi, Tomoya Shintani, Hironobu Ishiyama, Ryo C. Yanagita, Yasuhiro Kawanami, Masashi Sato.
    Biosci. Biotechnol. Biochem. 2019, 83 (12), 2194–2197. [DOI: 10.1080/09168451.2019.1648206] [Pubmed: 31357905]
  11. Synthesis, Conformation, and Biological Activities of a Des-A-Ring Analog of 18-Deoxy-aplog-1, a Simplified Analog of Debromoaplysiatoxin.
    Yoshiki Ashida, Ryo C. Yanagita, Yasuhiro Kawanami, Mutsumi Okamura, Shingo Dan, Kazuhiro Irie.
    Heterocycles 2019, 99 (2), 942–957. [DOI: 10.3987/COM-18-S(F)60] [Accepted Manuscript]
  12. Synthesis and biochemical characterization of quasi-stable trimer models of full-length amyloid β40 with a toxic conformation.
    Yumi Irie, Mizuho Hanaki, Kazuma Murakami, Tsuneo Imamoto, Takumi Furuta, Takeo Kawabata, Taiji Kawase, Kenji Hirose, Yoko Monobe, Ken-ichi Akagi, Ryo C. Yanagita, Kazuhiro Irie.
    Chem. Commun. 2019, 55 (2), 182–185. [DOI: 10.1039/C8CC08618D] [Pubmed: 30519688]
  13. Synthesis and Biological Activities of Acetal Analogs at Position 3 of 10-Methyl-Aplog-1, a Potential Anti-Cancer Lead Derived from Debromoaplysiatoxin.
    Koutaro Hayakawa, Yusuke Hanaki, Harukuni Tokuda, Ryo C. Yanagita, Yu Nakagawa, Mutsumi Okamura, Shingo Dan, Kazuhiro Irie.
    Heterocycles 2018, 97 (1), 478–492. [DOI: 10.3987/COM-18-S(T)37]
  14. Synthesis and inhibitory activity of deoxy-D-allose amide derivative against plant growth.
    Md. Tazul Islam Chowdhury, Hikaru Ando, Ryo C. Yanagita, Yasuhiro Kawanami.
    Biosci. Biotechnol. Biochem. 2018, 82 (5), 775–779. [DOI: 10.1080/09168451.2018.1445521] [Pubmed: 29513080]
  15. Loss of the phenolic hydroxyl group and aromaticity from the side chain of anti-proliferative 10-methyl-aplog-1, a simplified analog of aplysiatoxin, enhances its tumor-promoting and proinflammatory activities.
    Yusuke Hanaki, Masayuki Kikumori, Harukuni Tokuda, Mutsumi Okamura, Shingo Dan, Naoko Adachi, Naoaki Saito, Ryo C. Yanagita, Kazuhiro Irie.
    Molecules 2017, 22 (4), E631. [DOI: 10.3390/molecules22040631] [Pubmed: 28406454]
  16. Binding mode prediction of aplysiatoxin, a potent agonist of protein kinase C, through molecular simulation and structure–activity study on simplified analogs of the receptor-recognition domain.
    Yoshiki Ashida, Ryo C. Yanagita, Chise Takahashi, Yasuhiro Kawanami, Kazuhiro Irie.
    Bioorg. Med. Chem. 2016, 24 (18), 4218-4227. [DOI: 10.1016/j.bmc.2016.07.011] [Pubmed: 27436807] [Accepted Manuscript] 1-s2-0-s096808961630503x-fx1
  17. Syntheses and biological activities of deoxy-D-allose fatty acid ester analogs.
    Md. Tazul Islam Chowdhury, Hikaru Ando, Ryo C. Yanagita, Yasuhiro Kawanami.
    Biosci. Biotechnol. Biochem. 2016, 80 (4), 676-681. [DOI: 10.1080/09168451.2015.1132151] [Pubmed: 26822163]
  18. Structural optimization of 10-methyl-aplog-1, a simplified analog of debromoaplysiatoxin, as an anticancer lead.
    Masayuki Kikumori, Ryo C. Yanagita, Harukuni Tokuda, Kiyotake Suenaga, Hiroshi Nagai, Kazuhiro Irie.
    Biosci. Biotechnol. Biochem. 2016, 80 (2) 221-231. [DOI: 10.1080/09168451.2015.1091718] [Pubmed: 26452398]
  19. Synthesis and biological activities of the amide derivative of aplog-1, a simplified analog of aplysiatoxin with anti-proliferative and cytotoxic activities.
    Yusuke Hanaki, Ryo C. Yanagita, Takahiro Sugahara, Misako Aida, Harukuni Tokuda, Nobutaka Suzuki, Kazuhiro Irie.
    Biosci. Biotechnol. Biochem. 2015, 79 (6) 888-895. [DOI: 10.1080/09168451.2014.1002452] [Pubmed: 25612633]
  20. Effect of BF3 on the enantioselective reduction of trifluoromethyl ketones using a chiral lactam alcohol with borane.
    Yuki Harauchi, Chihiro Takakura, Toshio Furumoto, Ryo C. Yanagita, Yasuhiro Kawanami.
    Tetrahedron: Asymmetry 2015, 26 (7) 333-337. [DOI: 10.1016/j.tetasy.2015.02.011]
  21. Synthesis of 6-O-decanoyl-D-altrose and 6-O-decanoyl-D-gulose and evaluation of their biological activity on plant growth.
    Md. Tazul Islam Chowdhury, Madoka Naito, Ryo C. Yanagita, Yaushiro Kawanami.
    Plant Growth Regul. 2015, 75 (3) 707-713. [DOI: 10.1007/s10725-014-9972-2]
  22. Improved and large-scale synthesis of 10-methyl-aplog-1, a potential lead for an anticancer drug.
    Masayuki Kikumori, Ryo C. Yanagita, Kazuhiro Irie.
    Tetrahedron 2014, 70 (52) 9776-9782. [DOI: 10.1016/j.tet.2014.11.026]
  23. Anti-proliferative activity of 6-O-acyl-D-allose against the human leukemia MOLT-4F cell line.
    Ryo C. Yanagita, Katsuya Kobashi, Chisa Ogawa, Yoshiki Ashida, Haruka Yamaashi, Yasuhiro Kawanami.
    Biosci. Biotechnol. Biochem. 201478 (2) 190-194. [DOI: 10.1080/09168451.2014.882747] [Pubmed: 25036670]
    allose1
  24. Effects of two sulfated triterpene saponins echinoside A and holothurin A on the inhibition of dietary fat absorption and obesity reduction.
    Yuming Wang, Jiahui Wang, Ryo C. Yanagita, Chunhua Liu, Xiaoqian Hu, Ping Dong, Changhu Xue, Yong Xue.
    Biosci. Biotechnol. Biochem. 2014, 78 (1) 139-146. [DOI: 10.1080/09168451.2014.877830] [Pubmed: 25036496]
  25. Effects of the methoxy group in the side chain of debromoaplysiatoxin on its tumor-promoting and anti-proliferative activities.
    Ryo C. Yanagita, Hiroaki Kamachi, Masayuki Kikumori, Harukuni Tokuda, Nobutaka Suzuki, Kiyotake Suenaga, Hiroshi Nagai, Kazuhiro Irie.
    Bioorg. Med. Chem. Lett. 2013, 23 (15) 4319-4323. [DOI: 10.1016/j.bmcl.2013.05.096] [Pubmed: 23803585]
    1-s2-0-s0960894x13007026-fx1
  26. Structure–activity studies on the side chain of a simplified analog of aplysiatoxin (aplog-1) with anti-proliferative activity.
    Hiroaki Kamachi, Keisuke Tanaka, Ryo C. Yanagita, Akira Murakami, Kazuma Murakami, Harukuni Tokuda, Nobutaka Suzuki, Yu Nakagawa, Kazuhiro Irie.
    Bioorg. Med. Chem. 2013, 21 (10) 2695-2702. [DOI: 10.1016/j.bmc.2013.03.013] [Pubmed: 23582444]
  27. Synthesis of antineoplastic analogs of aplysiatoxin with various side chain structures.
    Yuki Shu, Ryo C. Yanagita, Harukuni Tokuda, Nobutaka Suzuki, Kazuhiro Irie.
    Heterocycles 2012, 86 (1) 281-303. [DOI: 10.3987/COM-12-S(N)8]
  28. Identification and biolofical activities of bryostatins from Japanese bryozoan.
    Sayo Ueno. Ryo C. Yanagita, Kazuma Murakami, Akira Murakami, Harukuni Tokuda, Nobutaka Suzuki, Takeshi Fujiwara, Kazuhiro Irie.
    Biosci. Biotechnol. Biochem. 2012, 76 (5) 1041-1043. [DOI: 10.1271/bbb.120026] [Pubmed: 22738985]
  29. Structure–activity studies on the spiroketal moiety of a simplified analogue of debromoaplysiatoxin with antiproliferative activity.
    Masayuki Kikumori. Ryo C. Yanagita, Harukuni Tokuda, Nobutaka Suzuki, Hiroshi Nagai, Kiyotake Suenaga, Kazuhiro Irie.
    J. Med. Chem. 2012, 55 (11) 5614-5626. [DOI: 10.1021/jm300566h] [Pubmed: 22625994]
  30. Synthesis and structure–activity studies of simplified analogues of aplysiatoxin with antiproliferative activity like bryostatin-1.
    Kazuhiro Irie, Masayuki Kikumori, Hiroaki Kamachi, Keisuke Tanaka, Akira Murakami, Ryo C. Yanagita, Harukuni Tokuda, Nobutaka Suzuki, Hiroshi Nagai, Kiyotake Suenaga, Yu Nakagawa.
    Pure Appl. Chem. 2012, 84 (6) 1341-1351. [DOI: 10.1351/PAC-CON-11-08-22]
  31. Enantioselective reduction of α,β-enones using an oxazaborolidine catalyst generated in situ from a chiral lactam alcohol.
    Yasuhiro Kawanami, Yudai Mikami, Kazuya Kiguchi, Yuki Harauchi, Ryo C. Yanagita.
    Tetrahedron: Asymmetry 2011, 22 (20—22), 1891–1894. [DOI: 10.1016/j.tetasy.2011.10.018]
  32. Generation of ‘unnatural natural product’ library and identification of a small molecule inhibitor of XIAP.
    Tatsuro Kawamura, Kohei Matsubara, Hitomi Otaka, Etsu Tashiro, Kazutoshi Shindo, Ryo C. Yanagita, Kazuhiro Irie, Masaya Imoto.
    Bioorg. Med. Chem. 2011, 19 (14), 4377–4385. [DOI: 10.1016/j.bmc.2011.05.009]  [PubMed: 21696964]
  33. Synthesis and biological evaluation of the 12,12-dimethyl derivative of aplog-1, an anti-proliferative analog of tumor-promoting aplysiatoxin.
    Yu Nakagawa, Masayuki Kikumori, Ryo C. Yanagita, Akira Murakami, Harukuni Tokuda, Hiroshi Nagai, Kazuhiro Irie.
    Biosci. Biotechnol. Biochem. 2011, 75 (6),   1167–1173.   [DOI: 10.1271/bbb.110130] [PubMed: 21670518]
  34. Role of the phenolic hydroxyl Group in the biological activities of simplified analogue of aplysiatoxin with antiproliferative activity.
    Ryo C. Yanagita, Hiroaki Kamachi, Keisuke Tanaka, Akira Murakami, Yu Nakagawa, Harukuni Tokuda, Hiroshi Nagai, Kazuhiro Irie.
    Bioorg. Med. Chem. Lett. 2010, 20 (20), 6064–6066.   [DOI: 10.1016/j.bmcl.2010.08.051] [PubMed: 20817520]
    1-s2-0-s0960894x10011741-fx1

Book Chapters and Reviews

  1. Practical Enantioselective Reduction of Ketones Using Oxazaborolidine Catalysts Generated In Situ from Chiral Lactam Alcohols.
    Yasuhiro Kawanami, Ryo C. Yanagita.
    Molecules 2018, 23 (10), E2408. [DOI: 10.3390/molecules23102408] [Pubmed: 30241305]
  2. Synthesis and biological activities of simplified analogs of the natural PKC ligands, bryostatin-1 and aplysiatoxin.
    Kazuhiro Irie, Ryo C. Yanagita.
    Chem. Rec. 2014, 14 (2), 251–267.   [DOI: 10.1002/tcr.201300036] [PubMed: 24677503]
  3. Challenges to the development of bryostatin-type anticancer drugs based on the activation mechanism for protein kinase Cδ.
    Kazuhiro Irie, Ryo C. Yanagita, Yu Nakagawa.
    Med. Res. Rev. 2012, 32 (3), 518–535.  [DOI: 10.1002/med.20220] [PubMed: 21064191]