Modified cap group suberoylanilide hydroxamic acid histone deacetylase inhibitor derivatives reveal improved selective antileukemic activity

Journal of Medicinal Chemistry

Volumn 53, Issue 8, 2010, Pages 3038-3047

  Salmi Smail, Chanaz ^a   Fabre, Aurélie ^a   Dequiedt, Franck ^b   Restouin, Audrey ^a   Castellano, Rémy ^a   Garbit, Slaveia ^a   Roche, Philippe ^c   Morelli, Xavier ^c   Brunel, Jean Michel ^d   Collette, Yves ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

^b FNRS   (Belgium)

^c CNRS and Aix Marseille University   (France)

^d AIX MARSEILLE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

HISTONE DEACETYLASE 8; HISTONE DEACETYLASE INHIBITOR; UNCLASSIFIED DRUG; VORINOSTAT; VORINOSTAT DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG PROTEIN BINDING; HUMAN; HUMAN CELL; MOLECULAR MODEL; MOUSE; NONHUMAN;

EID: 77951103831     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm901358y     Document Type: Article

References (39)

1. Kuo, M. H.; Allis, C. D. Roles of histone acetyltransferases and deacetylases in gene regulation BioEssays 1998, 20, 615-626
2. Minucci, S.; Pelicci, P. G. Histone deacetylase inhibitors and the promise of epigenetic (and more) treatments for cancer Nat. Rev. Cancer 2006, 6, 38-51
3. Freiman, R. N.; Tjian, R. Regulating the regulators: lysine modifications make their mark Cell 2003, 112, 11-17
4. Polevoda, B.; Sherman, F. The diversity of acetylated proteins. GenomeBiology 2002, 3, Reviews0006.1-0006
5. Sambucetti, L. C.; Fischer, D. D.; Zabludoff, S.; Kwon, P. O.; Chamberlin, H.; Trogan, N.; Xu, H.; Cohen, D. Histone deacetylase inhibition selectively alters the activity and expression of cell cycle proteins leading to specific chromatin acetylation and antiproliferative effects J. Biol. Chem. 1999, 274, 34940-34947
6. Dokmanovic, M.; Clarke, C.; Marks, P. A. Histone deacetylase inhibitors: overview and perspectives Mol. Cancer Res. 2007, 5, 981-989 (Pubitemid 350080267)
7. Ropero, S.; Esteller, M. The role of histone deacetylases (HDACs) in human cancer Mol. Oncol. 2007, 1, 19-15
8. de Ruijter, A. J.; van Gennip, A. H.; Caron, H. N.; Kemp, S.; van Kuilenburg, A. B. Histone deacetylases (HDACs): characterization of the classical HDAC family Biochem. J. 2003, 370, 737-749
9. Blander, G.; Guarente, L. The Sir2 family of protein deacetylases Annu. Rev. Biochem. 2004, 73, 417-435
10. Marks, P.; Rifkind, R. A.; Richon, V. M.; Breslow, R.; Miller, T.; Kelly, W. K. Histone deacetylases and cancer: causes and therapies Nat. Rev. Cancer 2001, 1, 194-202
11. Richon, V. M.; Webb, Y.; Merger, R.; Sheppard, T.; Jursic, B.; Ngo, L.; Civoli, F.; Breslow, R.; Rifkind, R. A.; Marks, P. A. Second generation hybrid polar compounds are potent inducers of transformed cell differentiation Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 5705-5708
12. Al-Janadi, A.; Chandana., S. R.; Cloney, B. A. Histone deacetylase: an attractive target for cancer therapy Drugs R&D. 2008, 9, 369-383
13. Lane, A. A.; Chabner, B. A. Histone deacetylase inhibitors in cancer therapy J. Clin Oncol. 2009, 27, 5459-5468
14. Liu, T.; Kuljaca, S.; Tee, A.; Marshall, G. M. Histone deacetylase inhibitors: multifunctional anticancer agents Cancer. Treat. Rev. 2006, 32, 157-165
15. Grant, S.; Easley, C.; Kirkpatrick, P. Vorinostat Nat. Rev. Drug Discovery 2007, 6, 21-22
16. Finnin, M. S.; Donigian, J. R.; Cohen, A.; Richon, V. M.; Rifkind, R. A.; Marks, P. A.; Breslow, R.; Pavletich, N. P. Structures of a histone deacetylase homologue bound to the TSA and SAHA inhibitors Nature 1999, 401, 188-193
17. Nielsen, T. K.; Hildmann, C.; Dickmanns, A.; Schwienhorst, A.; Ficner, R. Crystal structure of a bacterial class 2 histone deacetylase homologue J. Mol. Biol. 2005, 354, 107-120
18. 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.; Tari, L. W. Structural snapshots of human HDAC8 provide insights into the class I histone deacetylases Structure 2004, 12, 1325-1334
19. Bouchain, G.; Delorme, D. Novel hydroxamate and anilide derivatives as potent histone deacetylase inhibitors: synthesis and antiproliferative evaluation Curr. Med. Chem. 2003, 10, 2359-2372 (Pubitemid 37236393)
20. Nagaoka, Y.; Maeda, T.; Kawai, Y.; Nakashima, D.; Oikawa, T.; Shimoke, K.; Ikeuchi, T.; Kuwajima, H.; Uesato, S. Synthesis and cancer antiproliferative activity of new histone deacetylase inhibitors: hydrophilic hydroxamates and 2-aminobenzamide-containing derivatives Eur. J. Med. Chem. 2006, 41, 697-708
21. Uesato, S.; Kitagawa, M.; Nagaoka, Y.; Maeda, T.; Kuwajima, H.; Yamori, T. Novel histone deacetylase inhibitors: N -hydroxycarboxamides possessing a terminal bicyclic aryl group Bioorg. Med. Chem. Lett. 2002, 12, 1347-1349
22. Jung, M.; Brosch, G.; Kolle, D.; Scherf, H.; Gerhauser, C.; Loidl, P. Amide analogues of trichostatin A as inhibitors of histone deacetylase and inducers of terminal cell differentiation J. Med. Chem. 1999, 42, 4669-4679
23. Breslow, R.; Marks, P. A.; Rifkind, R. A.; Jursic, B. Novel Potent Inducers of Terminal Differentiation and Methods Thereof. PTC Int. Appl. WO 93/07148, April 15, 1993.
24. Stowell, J. C.; Hout, R. I.; Van Voast, L. The synthesis of N -hydroxy- N 1-phenyloctanediamide and its inhibitory effect on proliferation of AXC rat prostate cancer cells J. Med. Chem. 1995, 38, 1411-1413
25. Mai, A.; Esposito, M.; Sbardella, G.; Massa, S. A new facile and expeditious synthesis of N -hydroxy- N 1-phenyloctanediamide, a potent inducer of terminal cytodifferentiation OPPI Briefs 2001, 33, 391-394
26. Gediya, L. K.; Chopra, P.; Purushottamachar, P.; Maheshwari, N.; Njar, V. C. O. A new simple and high-yield synthesis of suberoyl anilide hydroxamic acid and its inhibitory effect alone or in combination with retinoids on proliferation of human prostate cancer cells J. Med. Chem. 2005, 48, 5047-5051
27. Marks, P. A.; Breslow, R. Dimethyl sulfoxide to vorinostat: development of this histone deacetylase inhibitor as an anticancer drug Nat. Biotechnol. 2007, 25, 84-90
28. Meinke, P. T.; Liberator, P. Histone deacetylase: a target for antiproliferative and antiprotozoal agents Curr. Med. Chem. 2001, 8, 211-235
29. Kozikowski, A. P.; Tapadar, S.; Luchini, D. N.; Hwan, K. K.; Billadeau, D. D. Use of the nitrile oxide cycloaddition (NOC) reaction for molecular probe generation: a new class of enzyme selective histone deacetylase inhibitors (HDACIs) showing picomolar activity at HDAC6 J. Med. Chem. 2008, 51, 4370-4373
30. Chen, Y.; Lopez-Sanchez, M.; Savoy, D. N.; Billadeau, D. D.; Dow, G. S.; Kozikowski, A. P. A series of potent and selective, triazolylphenyl-based histone deacetylases inhibitors with activity against pancreatic cancer cells and Plasmodium falciparum J. Med. Chem. 2008, 51, 3437-3448
31. Kozikowski, A. P.; Chen, Y.; Gaysin, A. M.; Savoy, D. N.; Billadeau, D. D.; Kim, K. H. Chemistry, biology, and QSAR studies of substituted biaryl hydroxamates and mercaptoacetamides as HDAC inhibitors - nanomolar potency inhibitors of pancreatic cancer cell growth ChemMedChem. 2008, 3, 487-501
32. Brunel, J. M.; Salmi, C.; Letourneux, Y. Efficient peptide coupling method of conjugated carboxylic acids with methyl ester amino acids hydrochloride. Application to the synthesis of Fa-Met, an important enzymatic substrate Tetrahedron Lett. 2005, 46, 217-220
33. Vannini, A.; Volpari, C.; Filocamo, G.; Casavola, E. C.; Brunetti, M.; Renzoni, D.; Chakravarty, P.; Paolini, C.; De Francesco, R.; Gallinari, P.; Steinkuhler, C.; Di Marco, S. Crystal structure of a eukaryotic zinc-dependent histone deacetylase, human HDAC8, complexed with a hydroxamic acid inhibitor Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 15064-15069
34. Clark, R. D.; Strizhev, A.; Leonard, J. M.; Blake, J. F.; Matthew, J. B. Consensus scoring for ligand/protein interactions J. Mol. Graphics Modell. 2002, 20, 281-282
35. Kramer, B.; Rarey, M.; Lengauer, T. Evaluation of the FLEXX incremental construction algorithm for protein-ligand docking Proteins 1999, 37, 228-241
36. Betzi, S.; Suhre, K.; Chetrit, B.; Guerlesquin, F.; Morelli, X. GFscore: a general nonlinear consensus scoring function for high-throughput docking J. Chem. Inf. Model. 2006, 46, 1704
37. Rarey, M.; Kramer, B.; Lengauer, T.; Klebe, G. A fast flexible docking method using an incremental construction algorithm J. Mol. Biol. 1996, 261, 470-489
38. Rarey, M.; Kramer, B.; Lengauer, T. The particle concept: placing discrete water molecules during protein-ligand docking predictions Proteins 1999, 34, 17-28
39. Fischle, W.; Dequiedt, F.; Hendzel, M. J.; Guenther, M. G.; Lazar, M. A.; Voelter, W.; Verdin, E. Enzymatic activity associated with class II HDACs is dependent on a multiprotein complex containing HDAC3 and SMRT/N-CoR Mol. Cell 2002, 9, 45-57