Synthesis, biological evaluation and molecular docking studies of resveratrol derivatives possessing curcumin moiety as potent antitubulin agents

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 2, 2012, Pages 1113-1121

  Ruan, Ban Feng ^a,b   Lu, Xiang ^b   Li, Ting Ting ^a   Tang, Jian Feng ^b   Wei, Yao ^b   Wang, Xiao Liang ^b   Zheng, Shi Li ^a   Yao, Ri Sheng ^a   Zhu, Hai Liang ^b  

^a HEFEI UNIVERSITY OF TECHNOLOGY   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

Antiproliferative activity; Antitubulin polymerization activity; Curcumin; Molecular docking; Resveratrol

Indexed keywords

1 (2 BROMOPHENYL) 5 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL]PENTA 1,4 DIEN 3 ONE; 1 (2 CHLOROPHENYL) 5 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL]PENTA 1,4 DIEN 3 ONE; 1 (2,4 DICHLOROPHENYL) 5 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL]PENTA 1,4 DIEN 3 ONE; 1 (2,6 DICHLOROPHENYL) 5 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL]PENTA 1,4 DIEN 3 ONE; 1 (3 BROMOPHENYL) 5 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL]PENTA 1,4 DIEN 3 ONE; 1 (3 CHLORO 4 FLUOROPHENYL) 5 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL]PENTA 1,4 DIEN 3 ONE; 1 (3 CHLOROPHENYL) 5 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL]PENTA 1,4 DIEN 3 ONE; 1 (3,4 DICHLOROPHENYL) 5 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL]PENTA 1,4 DIEN 3 ONE; 1 (3,5 DICHLOROPHENYL) 5 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL]PENTA 1,4 DIEN 3 ONE; 1 (4 BROMOPHENYL) 5 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL]PENTA 1,4 DIEN 3 ONE; 1 (4 CHLOROPHENYL) 5 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL]PENTA 1,4 DIEN 3 ONE; 1 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL] 5 (2 FLUOROPHENYL)PENTA 1,4 DIEN 3 ONE; 1 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL] 5 (2 METHOXYPHENYL)PENTA 1,4 DIEN 3 ONE; 1 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL] 5 (2,5 DIMETHOXYPHENYL)PENTA 1,4 DIEN 3 ONE; 1 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL] 5 (3 FLUOROPHENYL)PENTA 1,4 DIEN 3 ONE; 1 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL] 5 (3 METHOXYPHENYL)PENTA 1,4 DIEN 3 ONE; 1 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL] 5 (3 TOLYL)PENTA 1,4 DIEN 3 ONE; 1 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL] 5 (3,4 DIMETHOXYPHENYL)PENTA 1,4 DIEN 3 ONE; 1 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL] 5 (3,5 DIMETHOXYPHENYL)PENTA 1,4 DIEN 3 ONE; 1 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL] 5 (4 FLUOROPHENYL)PENTA 1,4 DIEN 3 ONE; 1 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL] 5 (4 METHOXYPHENYL)PENTA 1,4 DIEN 3 ONE; 1 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL] 5 (4 TOLYL)PENTA 1,4 DIEN 3 ONE; 1 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL] 5 PHENYLPENTA 1,4 DIEN 3 ONE; 4 [2,4 DIMETHOXY 6 (4 METHOXYSTYRYL)PHENYL]BUT 3 EN 2 ONE; ANTIMITOTIC AGENT; COLCHICINE; CURCUMIN; RESVERATROL; TUBULIN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BINDING SITE; CANCER CELL; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CONTROLLED STUDY; CYTOTOXICITY; DRUG MECHANISM; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; LIVER CELL CARCINOMA; LUNG CARCINOMA; MELANOMA; MICROTUBULE ASSEMBLY; MOLECULAR DOCKING; NONHUMAN; PROTEIN INTERACTION; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; BINDING SITES; CELL CYCLE CHECKPOINTS; CELL LINE, TUMOR; CELL PROLIFERATION; COMPUTER SIMULATION; CURCUMIN; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MICE; PROTEIN STRUCTURE, TERTIARY; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN; TUBULIN MODULATORS;

MURINAE;

EID: 84855760125     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.11.017     Document Type: Article

References (43)

1. J.W. Hammond, D. Cai, and K.J. Verhey Curr. Opin. Cell Biol. 20 2008 71
2. E. Nogales, and H.W. Wang Curr. Opin. Cell Biol. 18 2006 179
3. G.M. Cragg, S.A. Schepartz, M. Suffness, and M.R. Grever J. Nat. Prod. 56 1993 1657
4. M. Suffness, and M.E. Wall Taxol: Science, Applications 1995 CRC Press, Inc. Boca Raton, FL pp 3-25
5. C.J. Bode Jr., M.L. Gupta, E.A. Reiff, K.A. Suprenant, G.I. Georg, and R.H. Himes Biochemistry 41 2002 3870
6. J.M. Pezzuto Biochem. Pharmacol. 53 1997 121
7. J.-X. Duan, X.-H. Cai, F.-Y. Meng, L. Lan, C. Hart, and M. Matteucci J. Med. Chem. 50 2007 1001
8. S. Gupta, L. Das, A.B. Datta, A. Poddar, M.E. Janik, and B. Bhattacharyya Biochemistry 45 2006 6467
9. M. Sridhare, M. Manuel, G. Sanjay, V.-D. Dominik, F. Tito, R. Mace, and C. Dimitrios Anticancer Drugs 15 2004 553
10. M. Jang, L.N. Cai, G.O. Udeani, K.V. Slowing, C.F. Thomas, C.W.W. Beecher, H.H.S. Fong, N.R.A. Farnsworth, D. Kinghorn, R.G. Mehta, R.C. Moon, and J.M. Pezzuto Science 275 1997 218
11. S. Mukherjee, B.R. Acharya, B. Bhattacharyya, and G. Chakrabarti Biochemistry 49 2010 1702
12. R.H. Thomson Naturally Occurring Quinones IV: Recent Advances 4th ed. 1997 Blackie London
13. B.R. Acharya, B. Bhattacharyya, and G. Chakrabarti Biochemistry 47 2008 7838
14. D.K. Agrawal, and P.K. Misbra Med. Res. Rev. 30 2010 818
15. F.H. Sarkar, and Y. Li Cancer Treat. Rev. 35 2009 597
16. H. Hatcher, R. Planalp, J. Cho, F.M. Torti, and S.V. Torti Cell. Mol. Life Sci. 65 2008 1631
17. B.B. Aggarwal, and B. Sung Trends Pharmacol. Sci. 30 2009 85
18. T. Kálai, M.L. Kuppusamy, M. Balog, K. Selvendiran, B.K. Rivera, P. Kuppusamy, and K. Hideg J. Med. Chem. 54 2011 5414
19. D.K. Agrawal, and K. Misbra Med. Res. Rev. 30 2010 818
20. E. Simoni, C. Bergamini, R. Fato, A. Tarozzi, S. Bains, R. Motterlini, A. Cavalli, M.L. Bolognesi, A. Minarini, P. Hrelia, G. Lenaz, M. Rosini, and C. Melchiorre J. Med. Chem. 53 2010 7264
21. P. Anand, A.B. Kunnumakkara, R.A. Newman, and B.B. Aggarwal Mol. Pharmaceutics 4 2007 807
22. A. Safavy, K.P. Raisch, S. Mantena, L.L. Sanford, S.W. Sham, N.R. Krishna, and J.A. Bonner J. Med. Chem. 50 2007 6284
23. S. Chakraborti, L. Das, N. Kapoor, A. Das, V. Dwivedi, A. Poddar, G. Chakraborti, M. Janik, G. Basu, D. Panda, P. Chakrabarti, A. Surolia, and B. Bhattacharyya J. Med. Chem. 54 2011 6183
24. N. Dhillon, B.B. Aggarwal, R.A. Newman, R.A. Wolff, A.B. Kunnumakkara, J.L. Abbruzzese, C.S. Ng, V. Badmaev, and R. Kurzrock Clin. Cancer Res. 14 2008 4491
25. K.K. Gupta, S.S. Bharne, K. Rathinasamy, N.R. Naik, and D. Panda FEBS J. 273 2006 5320
26. M. Banerjee, P. Singh, and D. Panda FEBS J. 277 2010 3437
27. P. Anand, A.B. Kunnumakkara, R.A. Newman, and B.B. Aggarwal Mol. Pharm. 4 2007 807
28. J.R. Dimmock, M.P. Padmanilayam, R.N. Puthucode, A.J. Nazarali, N.L. Motaganahalli, G.A. Zello, J.W. Quail, E.O. Oloo, H.B. Kraatz, J.S. Prisciak, T.M. Allen, C.L. Santos, J. Balzarini, E. De Clercq, and E.K. Manavathu J. Med. Chem. 44 2001 586
29. V.M. Makarov, I.L. Odinets, K.A. Lyssenko, Y.E. Rybalkina, M.J. Antipin, and T.V. Timofeeva J. Heterocycl. Chem. 45 2008 729
30. H. Ohtsu, Z. Xiao, J. Ishida, M. Nagai, H. Wang, H. Itokawa, C. Su, C. Shih, T. Chiang, and E. Chang J. Med. Chem. 45 2002 5037
31. A. Zambre, V. Kulkarni, S. Padhye, S. Sandur, and B. Aggarwal Bioorg. Med. Chem. 14 2006 7196
32. W. Weber, L. Hunsaker, C. Roybal, E. Bobrovnikova-Marjon, S. Abcouwer, R. Royer, L. Deck, and D. Vander Jagt Bioorg. Med. Chem. 14 2006 2450
33. S. Padhye, D. Chavan, S. Pandey, J. Deshpande, K.V. Swamy, and F.H. Sarkar Mini-Rev. Med. Chem. 10 2010 372
34. B.F. Ruan, X. Lu, J.F. Tang, Y. Wei, X.L. Wang, Y.B. Zhang, L.S. Wang, and H.L. Zhu Bioorg. Med. Chem. 19 2011 2688
35. P. Signorelli, and R. Ghidoni J. Nutr. Biochem. 16 2005 449
36. X.F. Huang, B.F. Ruan, X.T. Wang, C. Xu, H.M. Ge, H.L. Zhu, and R.X. Tan Eur. J. Med. Chem. 42 2007 263
37. M.C. Cui, M. Ono, H. Kimura, B.L. Liu, and H. Saji J. Med. Chem. 54 2011 2225
38. A. Boumendjel, J. Boccard, P.-A. Carrupt, E. Nicolle, M. Blanc, A. Geze, L. Choisnard, D. Wouessidjewe, E.-L. Matera, and C. Dumontet J. Med. Chem. 51 2008 2307
39. E. Hamel, and C.M. Lin Biochemistry 23 1984 4173
40. E. Hamel Cell Biochem. Biophys. 38 2003 1
41. H.D. Guthrie, G.R. Welch, B.S. Cooper, A.D. Zakaria, and L.A. Johnson Biol. Reprod. 50 1994 1303
42. R. Huey, G.M. Morris, A.J. Olson, and D.S. Goodsell J. Comput. Chem. 28 2007 1145
43. F. Musiani, E. Arnofi, R. Casadio, and S. Ciurli J. Biol. Inorg. Chem. 6 2001 300