Novel isatin-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents

European Journal of Medicinal Chemistry

Volumn 70, Issue , 2013, Pages 477-486

  Nam, Nguyen Hai ^a   Huong, Tran Lan ^a   Mai Dung, Do Thi ^a   Phuong Dung, Phan Thi ^a   Kim Oanh, Dao Thi ^a   Quyen, Do ^a   Thao, Le Thi ^a   Park, Sang Ho ^b   Kim, Kyung Rok ^b   Han, Byung Woo ^b   Yun, Jieun ^c   Kang, Jong Soon ^c   Kim, Youngsoo ^d   Han, Sang Bae ^d  

^a HANOI UNIVERSITY OF PHARMACY   (Viet Nam)

^b Seoul National University   (South Korea)

^c Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

^d Chungbuk National University   (South Korea)

Author keywords

Heterocycle; Histone deacetylase (HDAC) inhibitors; Hydroxamic acids; Isatin

Indexed keywords

7 (5 BROMO 3 (HYDROXYIMINO) 2 OXOINDOLIN 1 YL) N HYDROXYHEPTANAMIDE; 7 (5 BROMO 3 (METHOXYIMINO) 2 OXOINDOLIN 1 YL) N HYDROXYHEPTANAMIDE; 7 (5 CHLORO 3 (HYDROXYIMINO) 2 OXOINDOLIN 1 YL) N HYDROXYHEPTANAMIDE; 7 (5 CHLORO 3 (METHOXYMINO) 2 OXOINDOLIN 1 YL) N HYDROXYHEPTANAMIDE; 7 (5 FLUORO 3 (HYDROXYIMINO) 2 OXOINDOLIN 1 YL) N HYDROXYHEPTANAMIDE; 7 (5 FLUORO 3 (METHOXYIMINO) 2 OXOINDOLIN 1 YL) N HYDROXYHEPTANAMIDE; 7 (7 CHLORO 3 (HYDROXYIMINO) 2 OXOINDOLIN 1 YL) N HYDROXYHEPTANAMIDE; 7 (7 CHLORO 3 (METHOXYIMINO) 2 OXOINDOLIN 1 YL) N HYDROXYHEPTANAMIDE; ANTINEOPLASTIC AGENT; HISTONE DEACETYLASE 2; HISTONE DEACETYLASE 8; HISTONE DEACETYLASE INHIBITOR; HISTONE H3; HISTONE H4; HYDROXAMIC ACID; ISATIN; N HYDROXY 7 (3 (HYDROXYIMINO) 5 METHYL 2 OXOINDOLIN 1 YL)HEPTANAMIDE; N HYDROXY 7 (3 (HYDROXYIMINO) 5 NITRO 2 OXOINDOLIN 1 YL)HEPTANAMIDE; N HYDROXY 7 (3 (METHOXYIMINO) 2 OXOINDOLIN 1 YL)HEPTANAMIDE; N HYDROXY 7 (3 (METHOXYIMINO) 5 METHYL 2 OXOINDOLIN 1 YL)HEPTANAMIDE; N HYDROXY 7 (3 (METHOXYIMINO) 5 NITRO 2 OXOINDOLIN 1 YL)HEPTANAMIDE; N HYDROXY 7 (3 HYDROXYIMINO 2 OXOINDOLIN 1 YL)HEPTANAMIDE; OXIME DERIVATIVE; UNCLASSIFIED DRUG; VORINOSTAT;

ARTICLE; BINDING AFFINITY; BINDING SITE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DEACETYLATION; DRUG BINDING; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; TUMOR CELL LINE; WESTERN BLOTTING;

HETEROCYCLE; HISTONE DEACETYLASE (HDAC) INHIBITORS; HYDROXAMIC ACIDS; ISATIN;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; HUMANS; HYDROXAMIC ACIDS; ISATIN; MOLECULAR STRUCTURE; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 1; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84886742463     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.10.045     Document Type: Article

References (31)

1. O. Witt, H.E. Deubzer, T. Milde, and I. Oehme HDAC family: what are the cancer relevant targets? Cancer Lett. 277 2009 8 21
2. A.J.M. De Ruijter, A.H.V. Gennip, H.N. Caron, S. Kemp, and A.B.P.V. Kuilenburg Histone deacetylases (HDACs): characterization of the classical HDAC family Biochem. J. 370 2003 737 739
3. J. Li, G. Li, and W. Xu Histone deacetylase inhibitors: an attractive strategy for cancer therapy Curr. Med. Chem. 20 2013 1858 1886
4. M. Dokmanovic, and P.A. Marks Histone deacetylase inhibitors: discovery and development as anticancer agents Expert Opin. Investig. Drugs 14 2005 1497 1511 (Pubitemid 41749195)
5. K.B. Glaser HDAC inhibitors: clinical update and mechanism-based potential Biochem. Pharmacol. 74 2007 659 671 (Pubitemid 47096639)
6. R.W. Johnstone Histone-deacetylase inhibitors: novel drugs for the treatment of cancer Nat. Rev. Drug Discovery 1 2002 287 299 (Pubitemid 37361445)
7. K. Ververis, A. Hiong, T.C. Karagiannis, and P.V. Licciardi Histone deacetylase inhibitors (HDACIs): multitargeted anticancer agents Biologics. 7 2013 47 60
8. J.L. Hubbs, H. Zhou, A.M. Kral, J.C. Fleming, W.K. Dahlberg, B.L. Hughes, R.E. Middleton, A.A. Szewczak, J.P. Secrist, and T.A. Miller Amino acid derivatives as histone deacetylase inhibitors Bioorg. Med. Chem. Lett. 18 2008 34 38
9. T. Qiu, L. Zhou, W. Zhu, T. Wang, J. Wang, Y. Shu, and P. Liu Effects of treatment with histone deacetylase inhibitors in solid tumors: a review based on 30 clinical trials Future Oncol. 9 2013 255 269
10. S. Dallavalle, R. Cincinelli, R. Nannei, L. Merlini, G. Morini, S. Penco, C. Pisano, L. Vesci, M. Barbarino, V. Zuco, M. De Cesare, and F. Zunino Design, synthesis, and evaluation of biphenyl-4-yl-acrylohydroxamic acid derivatives as histone deacetylase (HDAC) inhibitors Eur. J. Med. Chem. 44 2009 1900 1912
11. T.U. Bracker, A. Sommer, I. Fichtner, H. Faus, B. Haendler, and H. Hess-Stumpp Efficacy of MS-275, a selective inhibitor of class I histone deacetylases, in human colon cancer models Int. J. Oncol. 35 2009 909 920
12. P. Jones, S. Altamura, P.K. Chakravarty, O. Cecchetti, R. De Francesco, P. Gallinari, R. Ingenito, P.T. Meinke, A. Petrocchi, M. Rowley, R. Scarpelli, S. Serafini, and C. Steinkühler A series of novel, potent, and selective histone deacetylase inhibitors Bioorg. Med. Chem. Lett. 16 2006 5948 5952 (Pubitemid 44755303)
13. M.S. Finnin, J.R. Donigian, A. Cohen, V.M. Richon, R.A. Rifkind, P.A. Marks, R. Breslow, and N.P. Pavietich Structures of a histone deacetylase homologue bound to the TSA and SAHA inhibitors Nature 401 1999 188 193 (Pubitemid 29436325)
14. D.T.K. Oanh, H.V. Hai, V.T.M. Hue, S.H. Park, H.J. Kim, B.W. Han, H.S. Kim, J.T. Hong, S.B. Han, and N.H. Nam Benzothiazole-containing hydroxamic acids as histone deacetylase inhibitors and antitumor agents Bioorg. Med. Chem. Lett. 21 2011 7509 7512
15. T.T. Tung, D.T.K. Oanh, V.T.M. Hue, S.H. Park, B.W. Han, Y.S. Kim, J.T. Hong, S.B. Han, and N.H. Nam New benzothiazole/thiazole-containing hydroxamic acid as potent histone deacetylase inhibitors and antitumor agents Med Chem. 8 2013 1051 1057
16. N.H. Nam, D.T.M. Dung, D.T.K. Oanh, T.L. Huong, P.T.P. Dung, K.R. Kim, B.W. Han, Y.S. Kim, J.T. Hong, and S.B. Han Synthesis, bioevaluation and docking study of 5-substitutedphenyl-1,3,4-thiadiazole-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents J. Enzyme Inhib. Med. Chem. 2013 Sep 11 http://informahealthcare.com/doi/abs/10.3109/14756366.2013.832238 (Epub ahead of print)
17. A. Beauchard, Y. Ferandin, S. Frère, O. Lozach, M. Blairvacq, L. Meijer, V. Thiery, and T. Besson Synthesis of novel 5-substituted indirubins as protein kinases inhibitors Bioorg. Med. Chem. 14 2006 6434 6474
18. M.J. Moon, S.K. Lee, J.W. Lee, W.K. Song, S.W. Kim, J.I. Kim, C. Cho, S.J. Choi, and Y.C. Kim Synthesis and structure-activity relationships of novel indirubin derivatives as potent anti-proliferative agents with CDK2 inhibitory activities Bioorg. Med. Chem. 14 2006 237 246 (Pubitemid 41635486)
19. R. Hoessel, S. Leclerc, J.A. Endicott, M.E. Nobel, A. Lawrie, P. Tunnah, M. Leost, E. Damiens, D. Marie, D. Marko, E. Niederberger, W. Tang, G. Eisenbrand, and L. Meijer Indirubin, the active constituent of a Chinese antileukaemia medicine, inhibits cyclin-dependent kinases Nat. Cell Biol. 1 1999 60 67 (Pubitemid 129495012)
20. M.N. Tam, N.H. Nam, G.J. Jin, and B.Z. Ahn 2-(1-Hydroxyiminoalkyl)-1,4- dimethoxy-9,10-anthraquinones: synthesis and evaluation of cytotoxicity Arch. Pharm. Res. 23 2000 283 287
21. M.D. Hall, K.R. Brimacombe, M.S. Varonka, K.M. Pluchino, J.K. Monda, J.Y. Li, M.J. Walsh, M.B. Boxer, T.H. Warren, H.M. Fales, and M.M. Gottesman Synthesis and structure-activity evaluation of isatin-β-thiosemicarbazones with improved selective activity toward multidrug-resistant cells expressing P-glycoprotein J. Med. Chem. 54 2011 5878 5889
22. M.D. Hall, N.K. Salam, J.L. Hellawell, H.M. Fales, C.B. Kensler, J.A. Ludwig, G. Szakacs, D.E. Hibbs, and M.M. Gottesman Synthesis, activity, and pharmacophore development for isatin-beta-thiosemicarbazones with selective activity toward multidrug-resistant cells J. Med. Chem. 52 2009 3191 3204
23. J.F.M. da Silva, S.J. Garden, and A.C. Pinto Chemistry of isatins: a review from 1975 to 1999 J. Braz. Chem. Soc. 12 2001 273 324
24. N.N. Sin, B.L. Venables, K.D. Combrink, H.G. Gulgeze, K.L. Yu, R.L. Civiello, J. Thuring, X.A. Wang, Z. Yang, L. Zadjura, A. Marino, K.F. Kadow, C.W. Cianci, J. Clarke, E.V. Genovesi, I. Medina, L. Lamb, K. Krystal, and N.A. Meanwell Respiratory syncytial virus fusion inhibitors. Part 7: structure-activity relationships associated with a series of isatin oximes that demonstrate antiviral activity in vivo Bioorg. Med. Chem. Lett. 19 2009 4857 4862
25. Y. Liu, H.A. Lashuel, S. Choi, X. Xing, A. Case, J. Ni, L.A. Yeh, G.D. Cuny, R.L. Stein, and P.T. Lansbury Jr. Discovery of inhibitors that elucidate the role of UCH-L1 activity in the H1299 lung cancer cell line Chem. Biol. 10 2003 837 846 (Pubitemid 37171901)
26. J.R. Somoza, R.J. Skene, B.A. Katz, C. Mol, J.D. Ho, A.J. Jennings, C. Luong, A. Arvai, J.J. Buggy, E. Chi, J. Tang, B.C. Sang, E. Verner, R. Wynands, E.M. Leahy, D.R. Dougan, G. Snell, M. Navre, M.W. Knuth, R.V. Swanson, D.E. McRee, and L.W. Tari Structural snapshots of human HDAC8 provide insights into the class I histone deacetylases Structure 12 2004 1325 1334 (Pubitemid 38900774)
27. O. Trott, and A.J. Olson AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading J. Comput. Chem. 31 2010 455 461
28. B.E. Lauffer, R. Mintzer, R. Fong, S. Mukund, C. Tam, I. Zilberleyb, B. Flicke, A. Ritscher, G. Fedorowicz, R. Vallero, D.F. Ortwine, J. Gunzner, Z. Modrusan, L. Neumann, C.M. Koth, P.J. Lupardus, J.S. Kaminker, C.E. Heise, and P. Steiner Histone deacetylase (HDAC) inhibitor kinetic rate constants correlate with cellular histone acetylation but not transcription and cell viability J. Biol. Chem. 2013 10.1074/jbc.M113.490706 (Epub ahead of print)
29. P. Skehan, R. Storeng, D. Scudiero, A. Monk, J. MacMahon, D. Vistica, J. Warren, H. Bokesch, S. Kenney, and M.R. Boyd New colorimetric cytotoxicity assay for anticancer drug screening J. Natl. Cancer Inst. 82 1990 1107 1112 (Pubitemid 20213250)
30. L. Wu, A.M. Smythe, S.F. Stinson, L.A. Mullendore, A. Monks, D.A. Scudiero, K.D. Paull, A.D. Koutsoukos, L.V. Rubinstein, M.R. Boyd, and R.H. Shoemaker Multidrug-resistant phenotype of disease-oriented panels of human tumor cell lines used for anticancer drug screening Cancer Res. 52 1992 3029 3034
31. A.W. Schuttelkopf, and D.M. van Aalten PRODRG: a tool for high-throughput crystallography of protein-ligand complexes Acta Crystallogr. D 60 2004 1355 1363 (Pubitemid 41079731)