The three dimensional quantitative structure activity relationships (3D-QSAR) and docking studies of curcumin derivatives as androgen receptor antagonists

International Journal of Molecular Sciences

Volumn 13, Issue 5, 2012, Pages 6138-6155

  Xu, Guanhong ^a   Chu, Yanyan ^a   Jiang, Nan ^a   Yang, Jing ^a,b   Li, Fei ^a  

^a NANJING MEDICAL UNIVERSITY   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

Androgen receptor antagonists; CoMFA; CoMSIA; Curcumin derivatives; Docking

Indexed keywords

ANDROGEN RECEPTOR ANTAGONIST; CURCUMIN DERIVATIVE; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; CURCUMIN;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING SITE; CANCER CELL; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DETERMINATION; DRUG EFFECT; DRUG STRUCTURE; HUMAN; HUMAN CELL; HYDROGEN BOND; MALE; MOLECULAR DOCKING; MOLECULAR MODEL; PREDICTION; PROSTATE CANCER; QUANTITATIVE STRUCTURE ACTIVITY RELATION; VALIDATION PROCESS; ANALOGS AND DERIVATIVES; CELL PROLIFERATION; CHEMISTRY; DRUG DESIGN; DRUG EFFECTS; PATHOLOGY; PROSTATE TUMOR; TUMOR CELL LINE;

ANDROGEN RECEPTOR ANTAGONISTS; ANTINEOPLASTIC AGENTS; BINDING SITES; CELL LINE, TUMOR; CELL PROLIFERATION; CURCUMIN; DRUG DESIGN; HUMANS; MALE; MOLECULAR DOCKING SIMULATION; PROSTATIC NEOPLASMS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84861553068     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms13056138     Document Type: Article

References (20)

1. Siegel, R.; Ward, E.; Brawley, O.; Jemal, A. Cancer statistics. CA Cancer J. Clin. 2011, 61, 212-236.
2. Lin, L.; Shi, Q.; Nyarko, A.K.; Bastow, K.F.; Wu, C.; Su, C.; Shih, C.C.Y.; Lee, K. Antitumor agents. 250. Design and synthesis of new curcumin analogues as potential anti-prostate cancer agents. J. Med. Chem. 2006, 49, 3963-3972.
3. Henderson, L.C.; Altimari, J.M.; Dyson, G.; Servinis, L.; Niranjan, B.; Risbridger, G.P. A comparative assessment of α-lipoic acid N-phenylamides as non-steroidal androgen receptor antagonists both on and off gold nanoparticles. Bioorg. Chem. 2012, 40, 1-5.
4. Kirby, M.; Hirst, C.; Crawford, E.D. Characterising the castration-resistant prostate cancer population: A systematic review. Int. J. Clin. Pract. 2011, 65, 1180-1192.
5. Chen, Y.; Sawyers, C.L.; Scher, H.I. Targeting the androgen receptor pathway in prostate cancer. Curr. Opin. Pharmacol. 2008, 8, 440-448.
6. Zhou, J.; Geng, G.; Shi, Q.; Sauriol, F.; Wu, J.H. Design and synthesis of androgen receptor antagonists with bulky side chains for overcoming antiandrogen resistance. J. Med. Chem. 2009, 52, 5546-5550.
7. Estebanez-Perpina, E.; Moore, J.M.R.; Mar, E.; Delgado-Rodrigues, E.; Nguyen, P.; Baxter, J.D.; Buehrer, B.M.; Webb, P.; Fletterick, R.J.; Guy, R.K. The molecular mechanisms of coactivator utilization in ligand-dependent transactivation by the androgen receptor. J. Biol. Chem. 2005, 280, 8060-8068.
8. Markus, A.L. Multi-dimensional QSAR in drug discovery. Drug Discov. Today 2007, 12, 1013-1017.
9. Cramer, R.D.; Patterson, D.E.; Bunce, J.D. Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J. Am. Chem. Soc. 1988, 110, 5959-5967.
10. Klebe, G.; Abraham, U.; Mietzner, T. Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J. Med. Chem. 1994, 37, 4130-4146.
11. Yi, P.; Qiu, M. 3D-QSAR and docking studies of aminopyridine carboxamide inhibitors of c-Jun N-terminal kinase-1. Eur. J. Med. Chem. 2008, 43, 604-613.
12. Liao, S.Y.; Qian, L.; Miao, T.F.; Lu, H.L.; Zheng, K.C. CoMFA and docking studies of 2-phenylindole derivatives with anticancer activity. Eur. J. Med. Chem. 2009, 44, 2822-2827.
13. Clark, M.; Cramer, R.D.; van Opdenbosch, N. Validation of the general purpose tripos 5.2 force field. J. Comput. Chem. 1989, 10, 982-1012.
14. Cho, S.J.; Tropsha, A. Cross-validated r2-guided region selection for comparative molecular field analysis: A simple method to achieve consistent results. J. Med. Chem. 1995, 38, 1060-1066.
15. Zhao, X.; Chen, M.; Huang, B.; Ji, H.; Yuan, M. Comparative Molecular Field Analysis (CoMFA) and Comparative Molecular Similarity Indices Analysis (CoMSIA) studies on alpha(1A)-adrenergic receptor antagonists based on pharmacophore molecular alignment. Int. J. Mol. Sci. 2011, 12, 7022-7237.
16. Pirhadi, S.; Ghasemi, J.B. 3D-QSAR analysis of human immunodeficiency virus entry-1 inhibitors by CoMFA and CoMSIA. Eur. J. Med. Chem. 2010, 45, 4897-4903.
17. Vong, R.; Geladi, P.; Wold, S.; Esbensen, K. Source contributions to ambient aerosol calculated by discriminat partial least squares regression (PLS). J. Chemometrics 1988, 2, 281-296.
18. Srivastava, V.; Gupta, S.P.; Siddiqi, M.I.; Mishra, B.N. 3D-QSAR studies on quinazoline antifolate thymidylate synthase inhibitors by CoMFA and CoMSIA models. Eur. J. Med. Chem. 2010, 45, 1560-1571.
19. Ai, Y.; Wang, S.T.; Sun, P.H.; Song, F.J. Combined 3D-QSAR modeling and molecular docking studies on pyrrole-indolin-2-ones as aurora a kinase inhibitors. Int. J. Mol. Sci. 2011, 12, 1605-1624.
20. Ping, L.; Chen, W.N.; Chen, W.M. Molecular modeling studies on imidazo[4,5-b]pyridine derivatives as Aurora A kinase inhibitors using 3D-QSAR and docking approaches. Eur. J. Med. Chem. 2011, 46, 77-94.