Azaindolylsulfonamides, with a more selective inhibitory effect on histone deacetylase 6 activity, exhibit antitumor activity in colorectal cancer HCT116 cells

Journal of Medicinal Chemistry

Volumn 57, Issue 10, 2014, Pages 4009-4022

  Lee, Hsueh Yun ^a   Tsai, An Chi ^a   Chen, Mei Chuan ^a   Shen, Po Jung ^a   Cheng, Yun Ching ^b   Kuo, Ching Chuan ^b   Pan, Shiow Lin ^a   Liu, Yi Min ^a   Liu, Jin Fen ^b   Yeh, Teng Kuang ^b   Wang, Jing Chi ^a   Chang, Chi Yen ^b   Chang, Jang Yang ^b,c   Liou, Jing Ping ^a  

^a TAIPEI MEDICAL UNIVERSITY   (Taiwan)

^b NATIONAL HEALTH RESEARCH INSTITUTES   (Taiwan)

^c NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

3 (3 ((1H PYRROLO[2,3 B]PYRIDIN 1 YLSULFONYL)PHENYL) N HYDROXYACRYLAMIDE; 3 (3 (1H INDAZOL 1 YLSULFONYL)PHENYL) HYDROXYACRYLAMIDE; 3 (3 (1H INDOL 1 YLSULFONYL)PHENYL) HYDROXYACRYLAMIDE; 3 (3 (1H PYRROLO[2,3 B]PYRIDIN 1 YLSULFONYL)PHENYL) N HYDROXYACRYLAMIDE; 3 (3 (2,3 DIHYDRO 1H PYRROLO[2,3 B]PYRIDIN 1 YLSULFONYL) PHENYL) N HYDROXYACRYLAMIDE; 3 (3 (3 (1H PYRROLO[2,3 C]PYRIDIN 1 YLSULFONYL)PHENYL) N HYDROXYACRYLAMIDE; 3 (3 (4 (1H INDAZOL 1 YLSULFONYL)PHENYL) HYDROXYACRYLAMIDE; 3 (4 (1H PYRROLO[2,3 B]PYRIDIN 1 YLSULFONYL)PHENYL) N HYDROXYACRYLAMIDE; 3 (4 (1H PYRROLO[2,3 C]PYRIDIN 1 YLSULFONYL)PHENYL) N HYDROXYACRYLAMIDE; 3 (4 (2,3 DIHYDRO 1H PYRROLO[2,3 B]PYRIDIN 1 YLSULFONYL)PHENYL) N HYDROXYACRYLAMIDE; ALPHA TUBULIN; ANTINEOPLASTIC AGENT; CASPASE 3; HISTONE DEACETYLASE 1; HISTONE DEACETYLASE 2; HISTONE DEACETYLASE 4; HISTONE DEACETYLASE 5; HISTONE DEACETYLASE 6; HISTONE DEACETYLASE 7; HISTONE DEACETYLASE 8; HISTONE DEACETYLASE INHIBITOR; HISTONE H3; HYDROXAMIC ACID DERIVATIVE; INDOLE DERIVATIVE; SULFONAMIDE; UNCLASSIFIED DRUG; VORINOSTAT;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; AREA UNDER THE CURVE; ARTICLE; BLOOD SAMPLING; CANCER CELL LINE; CANCER INHIBITION; CELL CYCLE PROGRESSION; CELL PROLIFERATION; CELL VIABILITY; COLORECTAL CANCER; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG BIOAVAILABILITY; DRUG CLEARANCE; DRUG EFFICACY; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; FEMALE; HCT116 CELL LINE; HT 29 CELL LINE; HUMAN; HUMAN CELL; IN VIVO STUDY; MAXIMUM TOLERATED DOSE; MCF 7 CELL LINE; MOUSE; NONHUMAN; PLASMA HALF LIFE; PROTEIN EXPRESSION; PROTON NUCLEAR MAGNETIC RESONANCE; TUMOR XENOGRAFT; UPREGULATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL CYCLE; FEMALE; HCT116 CELLS; HEK293 CELLS; HISTONE DEACETYLASE INHIBITORS; HISTONE DEACETYLASES; HUMANS; MICE; MICE, INBRED ICR; SULFONAMIDES; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84901263366     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm401899x     Document Type: Article

References (29)

1. Bolden, J. E.; Peart, M. J.; Johnstone, R. W. Anticancer activities of histone deacetylase inhibitors Nat. Rev. Drug Discovery 2006, 5, 769-784
2. O'Connor, O. A.; Heaney, M. L.; Schwartz, L.; Richardson, S.; Willim, R.; MacGregor-Cortelli, B.; Curly, T.; Moskowitz, C.; Portlock, C.; Horwitz, S.; Zelenetz, A. D.; Frankel, S.; Richon, V.; Marks, P.; Kelly, W. K. Clinical experience with intravenous and oral formulations of the novel histone deacetylase inhibitor suberoylanilide hydroxamic acid in patients with advanced hematologic malignancies J. Clin. Oncol. 2006, 24, 166-173
3. 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
4. Yoshida, M.; Kijima, M.; Akita, M.; Beppu, T. Potent and specific inhibition of mammalian histone deacetylase both in vivo and in vitro by trichostatin A J. Biol. Chem. 1990, 265, 17174-17179
5. Yoshida, M.; Horinouchi, S.; Beppu, T. Trichostatin A and trapoxin: novel chemical probes for the role of histone acetylation in chromatin structure and function BioEssays 1995, 17, 423-430
6. Marks, P. A.; Richon, V. M.; Breslow, R.; Rifkind, R. A. Histone deacetylase inhibitors as new cancer drugs Curr. Opin. Oncol. 2001, 13, 477-483
7. Duvic, M.; Talpur, R.; Ni, X.; Zhang, C.; Hazarika, P.; Kelly, C.; Chiao, J. H.; Reilly, J. F.; Ricker, J. L.; Richon, V. M.; Frankel, S. R. Phase 2 trial of oral vorinostat (suberoylanilide hydroxamic acid, SAHA) for refractory cutaneous T-cell lymphoma (CTCL) Blood 2007, 109, 31-39
8. Giles, F.; Fischer, T.; Cortes, J.; Garcia-Manero, G.; Beck, J.; Ravandi, F.; Masson, E.; Rae, P.; Laird, G.; Sharma, S.; Kantarjian, H.; Dugan, M.; Albitar, M.; Bhalla, K. A phase I study of intravenous LBH589, a novel cinammic hydroxamid acid analogue histone deacetylase inhibitor, in patients with refractory hematologic malignancies Clin. Cancer Res. 2006, 12, 4628-4635
9. Atadja, P. Development of the pan-HDAC inhibitor panobinostat (LBH589): success and challenges Cancer Lett. 2009, 280, 233-241
10. Steele, N. L.; Plumb, J. A.; Vidal, L.; Tjørnelund, J.; Knoblauch, P.; Rasmussen, A.; Ooi, C. E.; Buhl-Jensen, P.; Brown, R.; Evans, T. R.; Debono, J. S. A phase 1 pharmacokinetic and pharmacodynamic study of the histone deacetylase inhibitor belinostat in patients with advanced solid tumors Clin. Cancer Res. 2008, 14, 804-810
11. Plumb, J. A.; Finn, P. W.; Williams, R. J.; Bandara, M. J.; Romero, M. R.; Watkins, C. J.; Thangue, N. B. L.; Brown, R. Pharmacodynamic response and inhibition of growth of human tumor xenografts by the novel histone deacetylase inhibitor PXD101 Mol. Cancer Ther. 2003, 2, 721-728
12. Wagner, J. M.; Hackanson, B.; Lübbert, M.; Jung, M. Histone deacetylase (HDAC) inhibitors in recent clinical trials for cancer therapy Clin. Epigenet. 2010, 1, 117-136
13. Santo, L.; Hideshima, T.; Kung, A. L.; Tseng, J. C.; Tamang, D.; Yang, M.; Jarpe, M.; Duzer, J. H. V.; Mazitschek, R.; Ogier, W. C.; Cirstea, D.; Rodig, S.; Eda, H.; Scullen, T.; Canavese, M.; Bradner, J.; Anderson, K. C.; Jones, S. S.; Raje, N. Preclinical activity, pharmacodynamic, and pharmacokinetic properties of a selective HDAC6 inhibitor, ACY-1215, in combination with bortezomib in multiple myeloma Blood 2012, 119, 2579-2589
14. Kalin, J. H.; Butler, K. V.; Akimova, T.; Hancock, W. W.; Kozikowski, A. P. Second-generation histone deacetylase 6 inhibitors enhance the immunosuppressive effects of Foxp3+ T-regulatory cells J. Med. Chem. 2012, 55, 639-651
15. Lai, M. J.; Huang, H. L.; Pan, S. L.; Liu, Y. M.; Peng, C. Y.; Lee, H. Y.; Yeh, T. K.; Huang, P. H.; Teng, C. M.; Chen, C. S.; Chuang, H. Y.; Liou, J. P. Synthesis and biological evaluation of 1-arylsulfonyl-5-(N -hydroxyacrylamide)indoles as potent histone deacetylase inhibitors with antitumor activity in vivo J. Med. Chem. 2012, 55, 3777-3791
16. Lee, H. Y.; Yang, C. R.; Lai, M. J.; Huang, H. L.; Hsieh, Y. L.; Liu, Y. M.; Yeh, T. K.; Li, Y. H.; Mehndiratta, S.; Teng, C. M.; Liou, J. P. 1-Arylsulfonyl-5-(N -hydroxyacrylamide)indolines histone deacetylase inhibitors are potent cytokine release suppressors ChemBioChem 2013, 14, 1248-1254
17. Zhang, Y.; Yang, P.; Xu, W.; Chou, C. J.; Liu, C.; Wang, X. Development of N -hydroxycinnamamide-based histone deacetylase inhibitors with an indole-containing cap group ACS Med. Chem. Lett. 2013, 4, 235-238
18. Giannini, G.; Marzi, M.; Di Marzo, M.; Battistuzzi, G.; Pezzi, R.; Brunetti, T.; Cabri, W.; Vesci, L.; Pisano, C. Exploring bis-(indolyl)methane moiety as an alternative and innovative CAP group in the design of histone deacetylase (HDAC) inhibitors Bioorg. Med. Chem. Lett. 2009, 19, 2840-2843
19. Attenni, B.; Ontoria, J. M.; Cruz, J. C.; Rowley, M.; Schultz-Fademrecht, C.; Steinkuhler, C.; Jones, P. Histone deacetylase inhibitors with a primary amide zinc binding group display antitumor activity in xenograft model Bioorg. Med. Chem. Lett. 2009, 19, 3081-3084
20. Zhang, Z.; Yang, Z.; Meanwell, N. A.; Kadow, J. F.; Wang, T. A general method for the preparation of 4- and 6-azaindoles J. Org. Chem. 2002, 67, 2345-2347
21. Chen, W. S.; Lee, Y. J.; Yu, Y. C.; Hsaio, C. H.; Yen, J. H.; Yu, S. H.; Tsai, Y. J.; Chiu, S. J. Enhancement of p53-mutant human colorectal cancer cells radiosensitivity by flavonoid fisetin Int. J. Radiat. Oncol., Biol., Phys. 2010, 77, 1527-1535
22. Namdar, M.; Perez, G.; Ngo, L.; Marks, P. A. Selective inhibition of histone deacetylase 6 (HDAC6) induces DNA damage and sensitizes transformed cells to anticancer agents Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20003-20008
23. Kaliszczak, M.; Trousil, S.; Åberg, O.; Perumal, M.; Nguyen, Q. D.; Aboagye, E. O. A novel small molecule hydroxamate preferentially inhibits HDAC6 activity and tumour growth Br. J. Cancer. 2013, 108, 342-350
24. Chen, C. S.; Weng, S. C.; Tseng, P. H.; Lin, H. P.; Chen, C. S. Histone acetylation-independent effect of histone deacetylase inhibitors on Akt through the reshuffling of protein phosphatase 1 complexes J. Biol. Chem. 2005, 280, 38879-38887
25. Hong, S.; Lee, S.; Kim, B.; Lee, H.; Hong, S. S.; Hong, S. Discovery of new azaindole-based PI3Kα inhibitors: apoptotic and antiangiogenic effect on cancer cells Bioorg. Med. Chem. Lett. 2010, 20, 7212-7215
26. Hong, S.; Kim, J.; Seo, J. H.; Jung, K. H.; Hong, S. S.; Hong, S. Design, synthesis, and evaluation of 3,5-disubstituted 7-azaindoles as Trk inhibitors with anticancer and antiangiogenic activities J. Med. Chem. 2012, 55, 5337-5349
27. Horning, J. L.; Sahoo, S. K.; Vijayaraghavalu, S.; Dimitrijevic, S.; Vasir, J. K.; Jain, T. K.; Panda, A. K.; Labhasetwar, V. 3-D tumor model for in vitro evaluation of anticancer drugs Mol. Pharmaceutics 2008, 5, 849-862
28. Yeo, P.; Xin, L.; Goh, E.; New, L. S.; Zeng, P.; Wu, X.; Venkatesh, P.; Kantharaj, E. Development and validation of high-performance liquid chromatography-tandem mass spectrometry assay for 6-(3-benzoyl-ureido)-hexanoic acid hydroxyamide, a novel HDAC inhibitor, in mouse plasma for pharmacokinetic studies Biomed. Chromatogr. 2007, 21, 184-189
29. 3H]Dofetilide binding to HERG transfected membranes: a potential high throughput preclinical screen Eur. J. Pharmacol. 2001, 430, 147-148