Carbonyl- and sulfur-containing analogs of suberoylanilide hydroxamic acid: Potent inhibition of histone deacetylases

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 10, 2006, Pages 3320-3329

  Gu, Wenxin ^a   Nusinzon, Inna ^a,b   Smith Jr , Ronald D ^a   Horvath, Curt M ^a,b   Silverman, Richard B ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

^b Evanston Northwestern Healthcare ^*  (United States)

Author keywords

Mercaptoketone; Thioacetoxyketone; Histone deacetylase; Inhibitors; SAHA; Suberoylanilide hydroxamic acid

Indexed keywords

6 (2 HYDROXYACETYLAMINO) N PHENYLHEXANAMIDE; 6 (2 MERCAPTOACETYLAMINO) N PHENYLHEXANAMIDE; 6 [2 ACETYLTHIO(ACETYLAMINO)] N PHENYLHEXANAMIDE; 6 [2 MERCAPTO(THIOACETYLAMINO)] N PHENYLHEXANAMIDE; 7 OXIRANYL HEPTANOIC ACID PHENYLAMIDE; 8,9 DIHYDROXY N PHENYLNONANAMIDE; 9 ACETYLTHIO 8 OXO N PHENYLNONANAMIDE; 9 HYDROXY 8 OXO N PHENYLNONANAMIDE; 9 MERCAPTO 8 OXO N PHENYLNONANAMIDE; 9 METHYLTHIO 8 OXO N PHENYLNONANAMIDE; ALPHA MERCAPTOKETONE; ALPHA THIOACETOXYKETONE; CARBONYL DERIVATIVE; HISTONE DEACETYLASE; HISTONE DEACETYLASE INHIBITOR; INTERFERON; KETONE DERIVATIVE; N PHENYL 8 NONENAMIDE OXIDE; SULFUR DERIVATIVE; THIOSUBEROYLANILIDE HYDROXAMIC ACID; UNCLASSIFIED DRUG; VORINOSTAT;

ARTICLE; ASSAY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME ISOLATION; HUMAN; HUMAN CELL; IN VITRO STUDY;

CELLS, CULTURED; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; GENES, REPORTER; HELA CELLS; HISTONE DEACETYLASES; HUMANS; HYDROXAMIC ACIDS; KETONES; LIGANDS; MOLECULAR STRUCTURE; SULFHYDRYL COMPOUNDS; TRANSCRIPTION, GENETIC;

EID: 33645847864     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.12.047     Document Type: Article

References (46)

1. 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) 7816-7827
2. Grozinger C.M., and Schreiber S.L. Chem. Biol. 9 (2002) 3-16
3. Grunstein M. Nature 389 (1997) 349-352
4. Kouzarides T. Curr. Opin. Genet. Dev. 9 (1999) 40-48
5. Archer S.Y., and Hodin R.A. Curr. Opin. Genet. Dev. 9 (1999) 171-174
6. Yoshida M., Matsuayama A., Komatsu Y., and Nishino N. Curr. Med. Chem. 10 (2003) 2351-2358
7. Marks P.A., Richon V.M., Breslow R., and Rifkind R.A. Curr. Opin. Oncol. 13 (2001) 477-483
8. Marks P.A., Rifkind R.A., Richon V.M., and Breslow R. Clin. Cancer Res. 7 (2001) 759-760
9. Miller T.A., Witter D.J., and Belvedere S. J. Med. Chem. 46 (2003) 5097-5116
10. Moreira J.M.A. BMC Cancer 3 (2003) 30
11. Monneret C. Eur. J. Med. Chem. 40 (2005) 1-13
12. Breslow, R.; Marks, P. A.; Rifkind, R. A.; Jursic, B. Alkanedioic acid derivatives, novel potent inducers of terminal differentiation and methods of use thereof. PTC Int. Appl. WO 93/07148, April 15, 1993.
13. Yoshida M., Horinouchi S., and Beppu T. BioEssays 17 (1995) 423-430
14. 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) 5705-5708
15. 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
16. Cohen L.A., Amin S., Marks P.A., Rifkind R.A., Desai D., and Richon V.M. Anticancer Res. 19 (1999) 4999-5005
17. Kelly W.K., and Marks P.A. Nat. Clin. Prac. Oncol. 2 (2005) 150-157
18. 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) 188-193
19. Somoza J.R., Skene R.J., Katz B.A., et al. Structure 12 (2004) 1325-1334
20. Vannini A., Volpari C., Filocamo G., Casavola E.C., Brunetti M., Renzoni D., Chakravarty P., Paolini C., De Francesco R., Gallinari P., Stinkuhler C., and De Marco S. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 15064-15069
21. Mulder G.J., and Meerman J.H. Environ. Health Perspect. 49 (1983) 27-32
22. Michaelides M.R., Dellaria J.F., Gong J., Holms J.H., Bouska J.J., Stacey J., Wada C.K., Heyman H.R., Curtin M.L., Guo Y., Goodfellow C.L., Elmore I.B., Albert D.H., Magoc T.J., Marcotte P.K., Morgan D.W., and Davidsen S.K. Bioorg. Med. Chem. Lett. 11 (2001) 1553-1556
23. Frey R.R., Wada C.K., Garland R.B., Curtin M.L., Michaelides M.R., Li J., Pease L.J., Glaser K.B., Marcotte P.A., Bouska J.J., Murphy S.S., and Davidsen S.K. Bioorg. Med. Chem. Lett. 12 (2002) 3443-3447
24. Suzuki T., Kouketsu A., Matsuura A., Kohara A., Ninomiya S.-i., Kohda K., and Miyata N. Bioorg. Med. Chem. Lett. 14 (2004) 3313-3317
25. Jose B., Oniki Y., Kato T., Nishino N., Sumida Y., and Yoshida M. Bioorg. Med. Chem. Lett. 14 (2004) 5343-5346
26. Vassiliou S., Mucha A., Cuniasse P., Georgiadis D., Lucet-Levannier K., Beau F., Kannan R., Murphy G., Knaeuper V., Rio M.C., Basset P., Yiotakis A., and Dive V. J. Med. Chem. 42 (1999) 2610-2620
27. Syvertsen C., and McKinley-McKee J.S. Arch. Biochem. Biophys. 228 (1984) 159-169
28. Opie L.H., and Kowolik H. Cardiovascular Res. 30 (1995) 18-25
29. Suzuki T., Nagano Y., Kouketsu A., Matsuura A., Maruyama S., Kurotaki M., Nakagawa H., and Miyata N. J. Med. Chem. 48 (2005) 1019-1032
30. Suzuki T., Matsuura A., Kouketsu A., Nakagawa H., and Miyata N. Bioorg. Med. Chem. Lett. 15 (2005) 331-335
31. Chen B., Petukhov P.A., Jung M., Velena A., Eliseeva E., Dritschilo A., and Kozikowski A.P. Bioorg. Med. Chem. Lett. 15 (2005) 1389-1392
32. Stowell J.C., Huot R.I., and Voast L.V. J. Med. Chem. 38 (1995) 1411-1413
33. Chan T.H., and Stossel D. J. Org. Chem. 51 (1986) 2423-2428
34. Oh T., Wrobel Z., and Rubenstein S.M. Tetrahedron Lett. 32 (1982) 4647-4650
35. Bovicelli P., Lupattelli P., and Mincione A.S. Tetrahedron Lett. 38 (1994) 8477-8480
36. Menger F.M., and Lee C. J. Org. Chem. 44 (1979) 3446-3448
37. The assay of HDAC activity was performed using the HDAC fluorescent activity assay/drug discovery kit AK-500 (HDACs) and AK-518 (HDAC8) from BIOMOL Research Laboratories.
38. Lan-Hargest, H.-Y.; Kaufman, R. J. Histone deacetylase inhibitors based on alpha-chalcogenmethylcarbonyl compounds. U.S. Patent Appl. 2004/0023944 A1, 2004.
39. Wash, P. L.; Wiley, B. M.; Hassig, C.; Malecha, J. W.; Noble, S. A. Carbonyl compounds as inhibitors of histone deacetylase for the treatment of disease. WO 2004/110418 A2.
40. Delorme, D.; Woo, S. H.; Vaisburg, A., Inhibitors of histone deacetylase. WO 01/70675.
41. Brown S., Bernardo M.M., Li Z.-H., Kotra L.P., Tanaka Y., Fridman R., and Mobashery S. J. Am. Chem. Soc. 122 (2000) 6799-6800
42. Gu Z., Cui J., Brown S., Fridman R., Mobashery S., Strongin A.Y., and Lipton S.A.A. J. Neurosci. 25 (2005) 6401-6408
43. Nusinzon I., and Horvath C.M. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 14742-14747
44. Sakamoto S., Potla R., and Larner A.C. J. Biol. Chem. 279 (2004) 40362-40367
45. Chang H.M., Paulson M., Holko M., Rice C.M., Williams B.R., Marie I., and Levy D.E. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 9578-9583
46. Klampfer L., Huang J., Swaby L.A., and Augenlicht L. J. Biol. Chem. 279 (2004) 30358-30368