Design and synthesis of novel hybrid benzamide-peptide histone deacetylase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 14, 2009, Pages 3928-3931

  Hu, Fang ^a   Chou, C James ^a   Gottesfeld, Joel M ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Cyclic tetrapeptide; HDAC; Solid phase peptide synthesis

Indexed keywords

BENZAMIDE DERIVATIVE; CYCLOPEPTIDE; HEPTANEDIAMIDE PEPTIDE CONJUGATE; HISTONE DEACETYLASE 1; HISTONE DEACETYLASE 3; HISTONE DEACETYLASE INHIBITOR; TETRAPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONJUGATION; DRUG DESIGN; DRUG SELECTIVITY; DRUG SYNTHESIS; IC 50; PEPTIDE SYNTHESIS; REACTION ANALYSIS; SOLID PHASE SYNTHESIS;

BENZAMIDES; CYCLIZATION; DRUG DESIGN; ENZYME INHIBITORS; HISTONE DEACETYLASES; HUMANS; NEUROPROTECTIVE AGENTS; PEPTIDES;

EID: 67649646671     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.03.085     Document Type: Article

References (33)

1. Hildmann C., Riester D., and Schwienhorst A. Appl. Microbiol. Biotechnol. 75 (2007) 487
2. Marks P.A., and Breslow R. Nat. Biotechnol. 25 (2007) 84
3. Outeiro T.F., Marques O., and Kazantsev A. Biochim. Biophys. Acta 1782 (2008) 363
4. Taunton J., Hassig C.A., and Schreiber S.L. Science 272 (1996) 408
5. Laherty C.D., Yang W.M., Sun J.M., Davie J.R., Seto E., and Eisenman R.N. Cell 89 (1997) 349
6. Emiliani S., Fischle W., Van Lint C., Al-Abed Y., and Verdin E. Proc. Natl. Acad Sci. U.S.A. 95 (1998) 2795
7. Hu E., Chen Z., Fredrickson T., Zhu Y., Kirkpatrick R., Zhang G.F., Johanson K., Sung C.M., Liu R., and Winkler J. J. Biol. Chem. 275 (2000) 15254
8. Grozinger C.M., Hassig C.A., and Schreiber S.L. Pro.c Natl. Acad. Sci. U.S.A. 96 (1999) 4868
9. Wang A.H., Bertos N.R., Vezmar M., Pelletier N., Crosato M., Heng H.H., Th'ng J., Han J., and Yang X.J. Mol. Cell Biol. 19 (1999) 7816
10. Verdel A., and Khochbin S. J. Biol. Chem. 274 (1999) 2440
11. Kao H.Y., Downes M., Ordentlich P., and Evans R.M. Gene Dev. 14 (2000) 55
12. Vaquero A., Sternglanz R., and Reinberg D. Oncogene 26 (2007) 5505
13. Gao L., Cueto M.A., Asselbergs F., and Atadja P. J. Biol. Chem. 277 (2002) 25748
14. Vannini A., Volpari C., Filocamo G., Casavola E.C., Brunetti M., Renzoni D., Chakravarty P., Paolini C., De Francesco R., Gallinari P., Steinkuhler C., and Di Marco S. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 15064
15. Marks P., Rifkind R.A., Richon V.M., Breslow R., Miller T., and Kelly W.K. Nat. Rev. Cancer 1 (2001) 194
16. Johnstone R.W., and Licht J.D. Cancer Cell 4 (2003) 13
17. Gottlicher M., Minucci S., Zhu P., Kramer O.H., Schimpf A., Giavara S., Sleeman J.P., Lo Coco F., Nervi C., Pelicci P.G., and Heinzel T. EMBO J. 20 (2001) 6969
18. Phiel C.J., Zhang F., Huang E.Y., Guenther M.G., Lazar M.A., and Klein P.S. J. Biol. Chem. 276 (2001) 36734
19. 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
20. Herman D., Jenssen K., Burnett R., Soragni E., Perlman S.L., and Gottesfeld J.M. Nat. Chem. Biol. 2 (2006) 551
21. Kijima M., Yoshida M., Sugita K., Horinouchi S., and Beppu T. J. Biol. Chem. 268 (1993) 22429
22. Thomas E.A., Coppola G., Desplats P.A., Tang B., Soragni E., Burnett R., Gao F., Fitzgerald K.M., Borok J.F., Herman D., Geschwind D.H., and Gottesfeld J.M. Proc. Natl. Acad. Sci. U.S.A. 105 (2008) 15564
23. Chou C.J., Herman D., and Gottesfeld J.M. J. Biol. Chem. 283 (2008) 35402
24. Revero P. In: Kates S.A., and Albericio F. (Eds). Solid-Phase Synthesis (2000), Dekker, New York 331
25. Lambert J.N., Mitchell J.P., and Roberts K.D. J. Chem. Soc., Perkin Trans. 1 (2001) 471
26. Tang Y.C., Xie H.B., Tian G.L., and Ye Y.H. J. Pept. Res. 60 (2002) 95
27. Alcaro M.C., Sabatino G., Uziel J., Chelli M., Ginanneschi M., Rovero P., and Papini A.M. J. Pept. Sci. 10 (2004) 218
28. Mazur S., and Jayalekshmy P. J. Am. Chem. Soc. 101 (1979) 677
29. Trzeciak A., and Bannwarth W. Tetrahedron Lett. 33 (1992) 4557
30. Abbenante G., Leung D., Bond T., and Fairlie D.P. Lett. Pept. Sci. 7 (2001) 347
31. Royo M., Nestn V.D.W., Fresno D.M., Frieden A., Yahalom D., Rosenblatt M., Chorev M., and Albericio F. Tetrahedron Lett. 42 (2001) 7387
32. 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
33. Furumai R., Komatsu Y., Nishino N., Khochbin S., Yoshida M., and Horinouchi S. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 87