Discovery of Carboranes as Inducers of 20S Proteasome Activity
2010; Wiley; Volume: 5; Issue: 8 Linguagem: Inglês
10.1002/cmdc.201000112
ISSN1860-7187
AutoresHyun Seung Ban, Hidemitsu Minegishi, Kazuki Shimizu, Minako Maruyama, Yuka Yasui, Hiroyuki Nakamura,
Tópico(s)RNA modifications and cancer
ResumoChemMedChemVolume 5, Issue 8 p. 1236-1241 Communication Discovery of Carboranes as Inducers of 20S Proteasome Activity Hyun Seung Ban Dr., Hyun Seung Ban Dr. Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo, 171-8588 (Japan), Fax: (+81) 3-5992-1029Search for more papers by this authorHidemitsu Minegishi, Hidemitsu Minegishi Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo, 171-8588 (Japan), Fax: (+81) 3-5992-1029Search for more papers by this authorKazuki Shimizu, Kazuki Shimizu Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo, 171-8588 (Japan), Fax: (+81) 3-5992-1029Search for more papers by this authorMinako Maruyama, Minako Maruyama Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo, 171-8588 (Japan), Fax: (+81) 3-5992-1029Search for more papers by this authorYuka Yasui, Yuka Yasui Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo, 171-8588 (Japan), Fax: (+81) 3-5992-1029Search for more papers by this authorHiroyuki Nakamura Prof. Dr., Hiroyuki Nakamura Prof. Dr. [email protected] Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo, 171-8588 (Japan), Fax: (+81) 3-5992-1029Search for more papers by this author Hyun Seung Ban Dr., Hyun Seung Ban Dr. Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo, 171-8588 (Japan), Fax: (+81) 3-5992-1029Search for more papers by this authorHidemitsu Minegishi, Hidemitsu Minegishi Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo, 171-8588 (Japan), Fax: (+81) 3-5992-1029Search for more papers by this authorKazuki Shimizu, Kazuki Shimizu Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo, 171-8588 (Japan), Fax: (+81) 3-5992-1029Search for more papers by this authorMinako Maruyama, Minako Maruyama Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo, 171-8588 (Japan), Fax: (+81) 3-5992-1029Search for more papers by this authorYuka Yasui, Yuka Yasui Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo, 171-8588 (Japan), Fax: (+81) 3-5992-1029Search for more papers by this authorHiroyuki Nakamura Prof. Dr., Hiroyuki Nakamura Prof. Dr. [email protected] Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo, 171-8588 (Japan), Fax: (+81) 3-5992-1029Search for more papers by this author First published: 23 July 2010 https://doi.org/10.1002/cmdc.201000112Citations: 17Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract The carborane framework gives analogues able to induce 20S proteasome activities. A series of ortho-carboranylphenoxy derivatives were synthesized as 20S proteasome agonists, and carborane derivatives 11 a and 11 b were found to be potent inducers of the β1 and β2 activities of the 20S proteasome. Since small-molecule proteasome activators have not been developed, the carboranes described here have potential as chemical probes for the investigation of proteasome-dependent degradation pathways. Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description cmdc_201000112_sm_miscellaneous_information.pdf128.7 KB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1K. L. Rock, C. Gramm, L. Rothstein, K. Clark, R. Stein, L. Dick, D. Hwang, A. L. Goldberg, Cell 1994, 78, 761–771. 2A. Hershko, A. Ciechanover, Annu. Rev. Biochem. 1998, 67, 425–479. 3G. Nalepa, M. Rolfe, J. W. Harper, Nat. Rev. Drug Discovery 2006, 5, 596–613. 4C. M. Pickart, Cell 2004, 116, 181–190. 5A. Ciechanover, Angew. Chem. 2005, 117, 6095–6119; Angew. Chem. Int. Ed. 2005, 44, 5944–5967. 6M. Groll, C. R. Berkers, H. L. Ploegh, H. Ovaa, Structure 2006, 14, 451–456. 7M. Chu-Ping, C. A. Slaughter, G. N. DeMartino, J. Biol. Chem. 1992, 267, 10515–10523. 8V. Ustrell, L. Hoffman, G. Pratt, M. Rechsteiner, EMBO J. 2002, 21, 3516–3525. 9L. Borissenko, M. Groll, Chem. Rev. 2007, 107, 687–717. 10T. Watanabe, I. Momose, M. Abe, H. Abe, R. Sawa, Y. Umezawa, D. Ikeda, Y. Takahashi, Y. Akamatsu, Bioorg. Med. Chem. Lett. 2009, 19, 2343–2345. 11H. Nakamura, M. Watanabe, H. S. Ban, W. Nabeyama, A. Asai, Bioorg. Med. Chem. Lett. 2009, 19, 3220–3224. 12J. Adams, M. Behnke, S. Chen, A. A. Cruickshank, L. R. Dick, L. Grenier, J. M. Klunder, Y.-T. Ma, L. Plamondon, R. L. Stein, Bioorg. Med. Chem. Lett. 1998, 8, 333–338. 13R. Z. Orlowski, E. L. Zeger, Expet. Opin. Investig. Drugs 2006, 15, 117–130. 14R. C. Kane, P. F. Bross, A. T. Farrell, R. Pazdur, Oncologist 2003, 8, 508–513. 15N. Orlowski, S. Wilk, Biochem. Biophys. Res. Commun. 1981, 101, 814–822. 16B. Dahlmann, M. Rutschmann, L. Kuehn, H. Reinauer, Biochem. J. 1985, 228, 171–177. 17I. Ohkubo, S. Gasa, C. Namikawa, A. Makita, M. Sasaki, Biochem. Biophys. Res. Commun. 1991, 174, 1133–1140. 18K. Matsumura, K. Aketa, Development 1991, 33, 259–266. 19I. Ruiz de Mena, E. Mahillo, J. Arribas, J. G. Castaño, Biochem. J. 1993, 296, 93–97. 20S. Wilk, W.-E. Chen, Mol. Biol. Rep. 1997, 24, 119–124. 21S. Fulda, Mol. Nutr. Food Res. 2009, 53, 140–146. 22L. Huang, P. Ho, C.-H. Chen, FEBS Lett. 2007, 581, 4955–4959. 23Y. Endo, T. Iijima, Y. Yamakoshi, M. Yamaguchi, H. Fukasawa, K. Shudo, J. Med. Chem. 1999, 42, 1501–1504. 24Y. Endo, T. Iijima, Y. Yamakoshi, H. Fukasawa, C. Miyaura, M. Inada, A. Kubo, A. Itai, Chem. Biol. 2001, 8, 341–355. 25R. L. Julius, O. K. Farha, J. Chiang, L. J. Perry, M. F. Hawthorne, Proc. Natl. Acad. Sci. USA 2007, 104, 4808–4813. 26A. Asai, T. Tsujita, S. V. Sharma, Y. Yamashita, S. Akinaga, M. Funakoshi, H. Kobayashi, T. Mizukami, Biochem. Pharmacol. 2004, 67, 227–234. Citing Literature Volume5, Issue8August 2, 2010Pages 1236-1241 ReferencesRelatedInformation
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