Bicyclic peptides as potent inhibitors of histone deacetylases: Optimization of alkyl loop length

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 3, 2010, Pages 997-999

  Islam, Nurul M ^a   Kato, Tamaki ^a   Nishino, Norikazu ^a   Kim, Hyun Jung ^b   Ito, Akihiro ^c   Yoshida, Minoru ^c  

^a KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

^b BioRunx Co Ltd   (South Korea)

^c RIKEN   (Japan)

Author keywords

Bicyclic peptide; Design and synthesis; HDAC inhibitor; Optimum loop length; Ring closing metathesis

Indexed keywords

ALIPHATIC COMPOUND; BICYCLIC TETRAPEPTIDE HYDROXAMIC ACID; BICYCLO COMPOUND; HISTONE DEACETYLASE 1; HISTONE DEACETYLASE 4; HISTONE DEACETYLASE 6; HISTONE DEACETYLASE INHIBITOR; PEPTIDE DERIVATIVE; UNCLASSIFIED DRUG; HISTONE DEACETYLASE; HYDROXAMIC ACID; OLIGOPEPTIDE;

ARTICLE; CONTROLLED STUDY; DRUG INHIBITION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VIVO STUDY; COMPARATIVE STUDY;

BICYCLO COMPOUNDS; HISTONE DEACETYLASE INHIBITORS; HISTONE DEACETYLASES; HYDROXAMIC ACIDS; OLIGOPEPTIDES;

EID: 74049094482     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.12.054     Document Type: Article

References (28)

1. Hassig C.A., and Schreiber S.L. Curr. Opin. Chem. Biol. 1 (1997) 300-308
2. Grozinger C.M., and Schreiber S.L. Chem. Biol. 9 (2002) 3-16
3. Yoshida M., Matsuayama A., Komatsu Y., and Nishino N. Curr. Med. Chem. 10 (2003) 2351-2358
4. Urnov F.D., and Wolffe A.P. Emerg. Ther. Targets 4 (2000) 665-685
5. Mahlknecht U., and Hoelzer D. Mol. Med. 6 (2000) 623-644
6. Timmermann S., Lehrmann H., Polesskaya A., and Harel-Bellan A. Cell Mol. Life Sci. 58 (2001) 728-736
7. Yoshida M., Kijima M., Akita M., and Beppu T. J. Biol. Chem. 265 (1990) 17174-17179
8. Ueda H., Nakajima H., Hori Y., Fujita T., Nishimura M., Goto T., and Okuhara M. J. Antibiot. 47 (1994) 301-310
9. Kijima M., Yoshida M., Sugita K., Horinouchi S., and Beppu T. J. Biol. Chem. 268 (1993) 22429-22435
10. De Schepper S., Bruwiere H., Verhulst T., Steller U., Andries L., Wouters W., Janicot M., Arts J., and Van Heusden J. J. Pharmacol. Exp. Ther. 304 (2003) 881-888
11. Pope M.R., Ciuffetti L.M., Knoche H.W., McCrery D., Daly J.M., and Dunkle L.D. Biochemistry 22 (1983) 3502-3506
12. Darkin-Rattray S.J., Gurnett A.M., Myers R.W., Dulski P.M., Crumley T.M., Allocco J.J., Cannova C., Meinke P.T., Colletti S.L., Bednarek M.A., Singh S.B., Goetz M.A., Dombrowski A.W., Polishook J.D., and Schmatz D.M. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 13143-13147
13. Richon V.M., Emiliani S., Verdin E., Webb Y., Breslow R., Rifkind R.A., and Marks P.A. Proc. Natl. Acad. Sci. U.S.A. 95 (1998) 3003-3007
14. Suzuki T., Ando T., Tsuchiya K., Fukazawa N., Saito A., Mariko Y., Yamanashi T., and Nakanishi O. J. Med. Chem. 42 (1999) 3001-3003
15. Komatsu Y., Tomizaki K., Tsukamoto M., Kato T., Nishino N., Sato S., Yamori T., Tsuruo T., Furumai R., Yoshida M., Horinouchi S., and Hayashi H. Cancer Res. 61 (2001) 4459-4466
16. Nishino N., Jose B., Okamura S., Ebisusaki S., Kato T., Sumida Y., and Yoshida M. Org. Lett. 5 (2003) 5079-5082
17. Bhuiyan M.P.I., Kato T., Okauchi T., Nishino N., Maeda S., Nishino T.G., and Yoshida M. Bioorg. Med. Chem. 14 (2006) 3438-3446
18. Kahnberg P., Lucke A.J., Glenn M.P., Boyle G.M., Tyndall J.D.A., Parsons P.G., and Fairlie D.P. J. Med. Chem. 49 (2006) 7611-7622
19. Nielsen T.K., Hildmann C., Dickmanns A., Schwienhorst A., and Ficner R. J. Mol. Biol. 354 (2005) 107-120
20. Shivashimpi G.M., Amagai S., Kato T., Nishino N., Maeda S., Nishino T.G., and Yoshida M. Bioorg. Med. Chem. 15 (2007) 7830-7839
21. Nishino N., Jose B., Shinta R., Kato T., Komatsu Y., and Yoshida M. Bioorg. Med. Chem. 12 (2004) 5777-5784
22. Nishino N., Yoshikawa D., Watanabe L.A., Kato T., Jose B., Komatsu Y., Sumida Y., and Yoshida M. Bioorg. Med. Chem. Lett. 14 (2004) 2427-2431
23. Wels B., Kruijtzer J.A.W., Nijenhuis W.A.J., Gispen W.H., Adan R.A.H., and Liskamp R.M.J. Bioorg. Med. Chem. 13 (2005) 4221-4227
24. Mollica A., Guardiani G., Davi P., Ma S., Prreca F., Lai J., Mannina L., Sobolev A.P., and Hruby V.J. J. Med. Chem. 50 (2007) 3138-3142
25. Deshmukh P.H., Schultz-Fademrecht C., Procopiou P.A., Vigushin D.A., Coombes C., and Barett A.G.M. Adv. Synth. Catal. 349 (2007) 175-183
26. Nishino N., Shivashimpi G.M., Soni P.B., Bhuiyan M.P.I., Kato T., Maeda S., Nishino T.G., and Yoshida M. Bioorg. Med. Chem. 16 (2008) 437-445
27. Han G., Tamaki M., and Hruby V.J. J. Peptide Res. 58 (2001) 338-341
28. 3CN with 0.1% TFA using a solvent gradient of A-B over 15 min with a flow rate of 2 mL/min, with detection at 220 nm.