Chlamydocin analogs bearing carbonyl group as possible ligand toward zinc atom in histone deacetylases

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 10, 2006, Pages 3438-3446

  Bhuiyan, Mohammed P I ^a   Kato, Tamaki ^a   Okauchi, Tatsuo ^a   Nishino, Norikazu ^a   Maeda, Satoko ^b   Nishino, Tomonori G ^b   Yoshida, Minoru ^b  

^a KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

^b RIKEN   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; APICIDIN; CARBONYL DERIVATIVE; CHLAMYDOCIN DERIVATIVE; HISTONE DEACETYLASE; HISTONE DEACETYLASE INHIBITOR; KETONE DERIVATIVE; LIGAND; TETRAPEPTIDE; UNCLASSIFIED DRUG; ZINC;

ARTICLE; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS;

ALDEHYDES; CELL LINE; CELLS, CULTURED; ENZYME INHIBITORS; HISTONE DEACETYLASES; HUMANS; KETONES; LIGANDS; MOLECULAR STRUCTURE; PEPTIDES, CYCLIC; STRUCTURE-ACTIVITY RELATIONSHIP; ZINC;

EID: 33645892015     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.12.063     Document Type: Article

References (46)

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. Urnov F.D., and Wolfeffe. Emerging Ther. Targets 4 (2000) 665-685
6. Mahlknecht U., and Hoelzer D. Mol. Med. 6 (2000) 623-644
7. Timmerman S., et al. Cell Mol. Life Sci. 58 (2001) 728-736
8. Crsee W.D., and Seto E. J. Cell Physiol. 184 (2000) 1-16
9. Yoshida M., Kijima M., Akita M., and Beppu T. J. Biol. Chem. 265 (1990) 17174-17179
10. Ueda H., Nakajima H., Hori Y., Fujita T., Nishimura M., Goto T., and Okuhara M. J. Antibiot. 47 (1994) 301-310
11. Ueda H., Manda T., Matsumoto S., Mukumoto S., Nishigaki F., Kawamura I., and Shimomura K. J. Antibiot. 47 (1994) 315-323
12. 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
13. Kijima M., Yoshida M., Suguta K., Horinouchi S., and Beppu T. J. Biol. Chem. 268 (1993) 22429-22435
14. Closse A., and Huguenin R. Helv. Chim. Acta 57 (1974) 545-553
15. Yoshimura, K.; Tsubotani, S.; Okazaki, K. JP 7196686, 1995.
16. Xie W., Zou B., Pei D., and Ma D. Org. Lett. 7 (2005) 2775-2777
17. Gupta S., Peiser G., Nakajima T., and Hwang Y.-S. Tetrahedron Lett. 35 (1994) 6009-6012
18. Liesch J.M., Sweeley C.C., Staffeld G.D., Anderson M.S., Weber D.J., and Scheffer R.P. Tetrahedron 38 (1982) 45-48
19. Pope M.R., Ciuffetti L.M., Knoche H.W., McCrery D., Daly J.M., and Dunkle L.D. Biochemistry 22 (1983) 3502-3506
20. 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
21. Tanis S.P., Horenstein B.A., Scheffer R.P., and Rasmussen J.B. Heterocycles 24 (1986) 3423-3431
22. Kim S.-D., Knoche H.W., Dunkle L.D., McCrery D.A., and Tomer K.B. Tetrahedron Lett. 26 (1985) 969-972
23. Hirota A., Suzuki A., Suzuki H., and Tamura S. Agric. Biol. Chem. 37 (1973) 643-647
24. Hirota A., Suzuki A., Aizawa K., and Tamura S. Agric. Biol. Chem. 37 (1973) 955-956
25. Hirota A., Suzuki A., and Tamura S. Agric. Biol. Chem. 37 (1973) 1185-1189
26. Umehara K., Nakahara K., Kiyoto S., Iwami M., Okamoto M., Tanaka H., Kohsaka M., Aoki H., and Imanaka H. J. Antiobiot. 36 (1983) 478-483
27. 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
28. 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
29. 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
30. 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
31. Abe, F.; Hino, M.; Mori, H.; Yoshimura, S.; Takase, S. WO200008048-A2, 2000.
32. 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
33. Jung M., Brosch G., Kölle D., Scherf H., Gerhäuser C., and Loidl P. J. Med. Chem. 42 (1999) 4669-4679
34. 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
35. 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
36. Su G.H., Sohn T.A., Ryu B., and Kern S.E. Cancer Res. 60 (2000) 3137-3142
37. Suzuki T., Ando T., Tsuchiya K., Fukazawa N., Saito A., Mariko Y., Yamanashi T., and Nakanishi O. J. Med. Chem. 42 (1999) 3001-3003
38. 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
39. 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
40. Kim S.-D. J. Biochem. Mol. Biol. 28 (1995) 227-231
41. Furumai R., Komatsu Y., Nishino N., Kochbin S., Yoshida M., and Horinouchi 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. The synthesis of 2-amino-8-nonenoic acid (Ae9) will be reported elsewhere.
45. Nagayama S., Endo M., and Kobayashi S. J. Am. Chem. Soc. 63 (1998) 6094-6095
46. 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