Antiproliferative activities of a library of hybrids between indanones and HDAC inhibitor SAHA and MS-275 analogues

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 22, 2007, Pages 6142-6146

  Charrier, Cédric ^a   Roche, Joëlle ^a   Gesson, Jean Pierre ^a   Bertrand, Philippe ^a  

^a UNIVERSITÉ DE POITIERS   (France)

Author keywords

Cancer; Epigenetic; Histone deacetylase; Hybrid; Indanones; MS 275; SAHA; Trichostatin A

Indexed keywords

4 [N (2 HYDROXYETHYL) N [2 (3 INDOLYL)ETHYL]AMINOMETHYL]CINNAMOHYDROXAMIC ACID; BENZAMIDE DERIVATIVE; CRA 19156; HISTONE DEACETYLASE INHIBITOR; HYDROXAMIC ACID DERIVATIVE; INDANONE DERIVATIVE; MS 344; N (2 AMINOPHENYL) 4 (3 PYRIDINYLMETHOXYCARBONYLAMINOMETHYL)BENZAMIDE; UNCLASSIFIED DRUG; VORINOSTAT;

ALKYLATION; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LUNG SMALL CELL CANCER;

ANTINEOPLASTIC AGENTS; BENZAMIDES; BINDING SITES; CARCINOMA, NON-SMALL-CELL LUNG; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HISTONE DEACETYLASES; HUMANS; HYDROXAMIC ACIDS; INDANS; MOLECULAR STRUCTURE; PYRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 35148834194     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.09.041     Document Type: Article

References (35)

1. Chakraborty S., Senyuk V., and Nucifora G. J. Cell. Biochem. 82 (2001) 310
2. Kouzarides T. Cell 128 (2007) 693
3. Li B., Carey M., and Workman J.L. Cell 128 (2007) 707
4. Cairns B.R. Trends Cell Biol. 11 (2001) 15
5. Lund A.H., and van Lohuizen M. Genes Dev. 18 (2004) 2315
6. Jones P.A., and Baylin S.B. Cell 128 (2007) 683
7. Yang X.-J., and Seto E. Curr. Opin. Genet. Dev. 13 (2003) 143
8. Marks P.A., Rifkind R.A., Richon V.M., Breslow R., Miller T., and Kelly W.K. Nat. Rev. Cancer 1 (2001) 194
9. Xu W.S., Parmigiani R.B., and Marks P.A. Oncogene 26 (2007) 5541
10. Xang X.J., and Seto E. Oncogene 26 (2007) 5310
11. Minucci S., and Pelicci P.G. Nat. Rev. Cancer. 6 (2006) 38
12. Lin H.-Y., Chen C.-S., Lin S.-P., Weng J.-R., and Chen C.-S. Med. Res. Rev. 26 (2006) 397
13. Johnstone R.W. Nat. Rev. Drug Disc. 1 (2002) 287
14. Somech R., Izraeli S., and Simon A.J. Cancer Treat. Rev. 30 (2004) 461
15. Mai A., Massa S., Rotili D., Cerbara I., Valente S., Pezzi R., Simeoni S., and Ragno R. Med. Res. Rev. 25 (2005) 261
16. Monneret C. Eur. J. Med. Chem. 40 (2005) 1
17. Tsuji N., Kobayashi M., Nagashima K., Wakisaka Y., and Koizumi K. J. Antibiot. 29 (1976) 1
18. Yoshida M., Kijima M., Akita M., and Beppu T. J. Biol. Chem. 265 (1990) 17174
19. Richon V.M., Webb Y., Merger R., Sheppard T., Jursic B., Ngo L., Civoli F., Breslow R., Rifkind R.A., and Marks P.A. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 5705
20. Marks P.A. Oncogene 26 (2007) 1351
21. Miller T.A., Witter D.J., and Belvedere S. J. Med. Chem. 46 (2003) 5097
22. Cheson B.D. Br. J. Cancer 95 (2006) S1
23. Finnin M.S., Donigian J.R., Cohen A., Richon V.M., Rifkind R.A., Marks P.A., Breslow R., and Pavletich N.P. Nature 401 (1999) 188
24. Somoza J.R., Skene R.J., Katz B.A., Mol C., Ho J.D., Jennings A.J., Luong C., Arvai A., Buggy J.J., Chi E., Tang J., Sang B.C., Verner E., Wynands R., Leahy E.M., Dougan D.R., Snell G., Navre M., Knuth M.W., Swanson R.V., McRee D.E., and Tari L.W. Structure 12 (2004) 1325
25. 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
26. Charrier C., Bertrand P., Gesson J.-P., and Roche J. Bioorg. Med. Chem. Lett. 16 (2006) 5339
27. Anandan, S. K.; Xiao, Z.-Y.; Patel, D. V.; Ward, J. S. US Patent 2005234033 A1 20051020.
28. Delorme, D.; Woo, S. H.; Vaisburg, A.; Moradel, O.; Leit, S.; Raeppel, S.; Frechette, S.; Bouchan, G.; WO 03/024443 A3.
29. Maguire A.R., Papot S., Ford A., Touhey S., O'Connor S., and Clynes M. Synthesis 1 (2001) 41
30. Ludwig T., Ermert J., and Coenen H. Nucl. Med. Biol. 29 (2002) 255
31. Lucet D., Heyse P., Gissot A., Le Gall T., and Mioskowski C. Eur. J. Org. Chem. (2000) 3575
32. Liu P., Chen Y., Deng Jingen., and Tu Y. Synthesis 14 (2001) 2078
33. Johnson G.D., Lindsey W.B., and Jones B.R. J. Am. Chem. Soc. 78 (1956) 461
34. Kahnberg P., Lucke A.J., Glenn M.P., Boyle G.M., Tyndall J.A.D., Parsons P.G., and Fairlie D.P. J. Med. Chem. 49 (2006) 7611
35. Protein surfaces of HDAC8 were obtained from corresponding pdb files, using internet Chime pluggin from MDL. Theoritical calculations were realized at the AM1 level, using the closed shell (restricted) wave function from Chem3D facilities.