Interaction of aliphatic cap group in inhibition of histone deacetylases by cyclic tetrapeptides

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 1, 2008, Pages 437-445

  Nishino, Norikazu ^a   Shivashimpi, Gururaj M ^a   Soni, Preeti B ^a   Bhuiyan, Mohammed P I ^a   Kato, Tamaki ^a   Maeda, Satoko ^b   Nishino, Tomonori G ^b   Yoshida, Minoru ^b  

^a KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

^b RIKEN   (Japan)

Author keywords

Bicyclic tetrapeptide; Chlamydocin; Grubb's alkene metathesis; Histone deacetylases; Inhibitors

Indexed keywords

AMINO ACID; ANTINEOPLASTIC AGENT; AROMATIC COMPOUND; BENZENE; BICYCLO COMPOUND; CHLAMYDOCIN; CYCLOPEPTIDE; DISULFIDE; HISTONE DEACETYLASE; HISTONE DEACETYLASE 1; HISTONE DEACETYLASE 4; HISTONE DEACETYLASE 6; HISTONE DEACETYLASE INHIBITOR; MACROCYCLIC COMPOUND; PHENYLALANINE; PROTEIN P21; TETRAPEPTIDE; TRICHOSTATIN A; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; GENE CONTROL; HUMAN; HUMAN CELL; HYBRID; IC 50; RING CLOSING METATHESIS; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL LINE; ENZYME INHIBITORS; HISTONE DEACETYLASES; HUMANS; INHIBITORY CONCENTRATION 50; PEPTIDES, CYCLIC; REPRESSOR PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 38049001966     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.09.021     Document Type: Article

References (53)

1. Hassig C.A., and Schrieber S.L. Curr. Opin. Chem. Biol. 1 (1997) 300-308
2. Kouzarides T. Curr. Opin. Gen. Dev. 9 (1999) 40-48
3. Grozinger C.M., and Schrieber S.L. Chem. Biol. 9 (2002) 3-16
4. Yoshida M., Matsuayama A., Komatsu Y., and Nishino N. Curr. Med. Chem. 10 (2003) 2351-2358
5. Yang X.J. Bioessays 26 (2004) 1076-1081
6. Urnov F.D., and Wolffe A.P. Emerging Ther. Targets 4 (2000) 665-685
7. Mahlknecht U., and Hoelzer D. Mol. Med. 6 (2000) 623-644
8. Timmerman S., et al. Cell. Mol. Life Sci. 58 (2001) 728-736
9. Crsee W.D., and Seto E.J. Cell. Physiol. 184 (2000) 1-16
10. Yoshida M., Kijima M., Akita M., and Beppu T. J. Biol. Chem. 265 (1990) 17174-17179
11. Ueda H., Nakajima H., Hori Y., Fujita T., Nishimura M., Goto T., and Okuhara M. J. Antibiot. 47 (1994) 301-310
12. Ueda H., Manda T., Matsumoto S., Mukumoto S., Nishigaki F., Kawamura I., and Shimomura K. J. Antibiot. 47 (1994) 315-323
13. Furumai R., Matsuyama A., Kobashi M., Lee K.-H., Nishiyama M., Nakajima H., Tanaka A., Komatsu Y., Nishino N., Yoshida M., and Horinouchi S. Cancer Res. 62 (2002) 4916-4921
14. Kijima M., Yoshida M., Suguta K., Horinouchi S., and Beppu T. J. Biol. Chem. 268 (1993) 22429-22435
15. Closse A., and Huguenin R. Helv. Chim. Acta 57 (1974) 545-553
16. Yoshimura, K.; Tsubotani, S.; Okazaki, K. JP 7196686, 1995.
17. Xie W., Zou B., Pei D., and Ma D. Org. Lett. 7 (2005) 2775-2777
18. Gupta S., Peiser G., Nakajima T., and Hwang Y.-S. Tetrahedron Lett. 35 (1994) 6009-6012
19. Liesch J.M., Sweeley C.C., Staffeld G.D., Anderson M.S., Weber D.J., and Scheffer R.P. Tetrahedron 38 (1982) 45-48
20. Pope M.R., Ciuffetti L.M., Knoche H.W., McCrery D., Daly J.M., and Dunkle L.D. Biochemistry 22 (1983) 3502-3506
21. Gross M.L., McCrery D., Crow F., Tomer K.B., Pope M.R., Ciuffetti L.M., Knoche H.W., Daly J.M., and Dunkle L.D. Tetrahedron Lett. 23 (1982) 5381-5384
22. Tanis S.P., Horenstein B.A., Scheffer R.P., and Rasmussen J.B. Heterocycles 24 (1986) 3423-3431
23. Kim S.-D., Knoche H.W., Dunkle L.D., McCrery D.A., and Tomer K.B. Tetrahedron Lett. 26 (1985) 969-972
24. Hirota A., Suzuki A., Suzuki H., and Tamura S. Agr. Biol. Chem. 37 (1973) 643-647
25. Hirota A., Suzuki A., Aizawa K., and Tamura S. Agr. Biol. Chem. 37 (1973) 955-956
26. Hirota A., Suzuki A., and Tamura S. Agr. Biol. Chem. 37 (1973) 1185-1189
27. Umehara K., Nakahara K., Kiyoto S., Iwami M., Okamoto M., Tanaka H., Kohsaka M., Aoki H., and Imanaka H. J. Antibiot. 36 (1983) 478-483
28. 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
29. Singh S.B., Zink D.L., Liesch J.M., Mosley R.T., Dombrowski A.W., Bills G.F., Darkin-Rattray S.J., Schmatz D.M., and Goetz M.A. J. Org. Chem. 67 (2002) 815-825
30. Han J.W., Ahn S.H., Park S.H., Wang S.Y., Bae G.U., Seo D.W., Known H.K., Hong S., Lee Y.W., and Lee H.W. Cancer Res. 60 (2000) 6068-6074
31. Meinke P.T., Colletti S.L., Ayer M.B., Darkin-Rattray S.J., Myers R.W., Schmatz D.M., Wyvratt M.J., and Fisher M.H. Tetrahedron Lett. 41 (2000) 7831-7835
32. Abe, F.; Hino, M.; Mori, H.; Yoshimura, S.; Takase, S. WO200008048-A2, 2000.
33. 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
34. Jung M., Brosch G., Kölle D., Scherf H., Gerhäuser C., and Loidl P. J. Med. Chem. 42 (1999) 4669-4679
35. Remiszewski S.W., Sambucetti L.C., Atadja P., Bair K.W., Cornell W.D., Green M.A., Howell K.L., Jung M., Known P., Trogani N., and Walker H. J. Med. Chem. 45 (2002) 753-757
36. Woo S.H., Frechette S., Khalil E.A., Bouchain G., Vaisburg A., Bernstein N., Moradei O., Leit S., Allan M., Fournel M., Trachy-Bourget M.-C., Li Z., Besterman J.M., and Delorme D. J. Med. Chem. 45 (2002) 2877-2885
37. Su G.H., Sohn T.A., Ryu B., and Kern S.E. Cancer Res. 60 (2000) 3137-3142
38. Suzuki T., Ando T., Tsuchiya K., Fukazawa N., Saito A., Mariko Y., Yamanashi T., and Nakanishi O. J. Med. Chem. 42 (1999) 3001-3003
39. Saito A., Yamashita T., Mariko Y., Nosaka Y., Tsuchiya K., Ando T., Suzuki T., Tsuruo T., and Nakanishi O. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 4592-4597
40. De Shepper S., Bruwiere H., Steller U., Andries L., Wouters W., Janicot M., Arts J., and Van Heusden J. J. Pharmacol. Exp. Ther. 304 (2003) 881-888
41. Furumai R., Komatsu Y., Nishino N., Kochbin S., Yoshida M., and Horinuchi S. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 87-92
42. 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
43. Nishino N., Jose B., Okamura S., Ebisusaki S., Kato T., Sumida Y., and Yoshida M. Org. Lett. 5 (2003) 5079-5082
44. Rutjes F.P.J.T., Wolf L.B., and Schoemaker H.E. J. Chem. Soc., Perkin Trans. 1 (2000) 4197-4212
45. Fink B.E., Kym P.R., and Katzenellenbogen J.A. J. Am. Chem. Soc. 120 (1998) 4334-4344
46. Miller S.J., Blackwell H.E., and Grubbs R.H. J. Am. Chem. Soc. 118 (1996) 9606-9614
47. Then K.C.M.F., Kinderman S.S., Schoemaker H.E., Hiemstra H., and Rutjes F.P.J.T. Chem. Commun. (2000) 699-700
48. Mollica A., Guardiani G., Davis P., Ma S., Prreca F., Lai J., Mannina L., Sobolev A.P., and Hruby V.J. J. Med. Chem. 50 (2007) 3138-3142
49. 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
50. Hirashima, Y.; Kato, T.; Nishino, N.; Maeda, S.; Nishino, T. G.; Yoshida, M. In Proceedings of 29th European Peptide Symposium (Peptides), 2006; pp 758-759.
51. Watanabe L.A., Jose B., Kato T., Nishino N., and Yoshida M. Tetrahedron Lett. 45 (2004) 491-494
52. 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
53. 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