Synthesis and biological evaluation of podophyllotoxin congeners as tubulin polymerization inhibitors

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 19, 2014, Pages 5466-5475

  Kamal, Ahmed ^a,b   Srinivasa Reddy, T ^a   Polepalli, Sowjanya ^a   Shalini, Nekkanti ^b   Reddy, V Ganga ^a   Subba Rao, A V ^a   Jain, Nishant ^a   Shankaraiah, Nagula ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

Benzimidazole; Cytotoxicity; Molecular docking; Podophyllotoxin; Tubulin polymerization

Indexed keywords

ETOPOSIDE; METHYL 7 (1H BENZO[D]IMIDAZOL 2 YL) 5 (3,4,5 TRIMETHOXYPHENYL) 5,6 DIHYDRONAPHTHO[2,3 D][1,3]DIOXOLE 6 CARBOXYLATE; METHYL 7 (1H NAPHTHO[2,3 D]IMIDAZOL 2 YL) 5 (3,4,5 TRIMETHOXYPHENYL) 5,6 DIHYDRONAPHTHO[2,3 D][1,3]DIOXOLE 6 CARBOXYLATE; METHYL 7 (5 CHLORO 6 FLUORO 1H BENZO[D]IMIDAZOL 2 YL) 5 (3,4,5 TRIMETHOXYPHENYL) 5,6 DIHYDRONAPHTHO[2,3 D][1,3]DIOXOLE 6 CARBOXYLATE; METHYL 7 (5,6 DICHLORO 1H BENZO[D]IMIDAZOL 2 YL) 5 (3,4,5 TRIMETHOXYPHENYL) 5,6 DIHYDRONAPHTHO[2,3 D][1,3]DIOXOLE 6 CARBOXYLATE; METHYL 7 (5,6 DIMETHYL 1H BENZO[D]IMIDAZOL 2 YL) 5 (3,4,5 TRIMETHOXYPHENYL) 5,6 DIHYDRONAPHTHO[2,3 D][1,3]DIOXOLE 6 CARBOXYLATE; METHYL 7 (6 BROMO 1H BENZO[D]IMIDAZOL 2 YL) 5 (3,4,5 TRIMETHOXYPHENYL) 5,6 DIHYDRONAPHTHO[2,3 D][1,3]DIOXOLE 6 CARBOXYLATE; METHYL 7 (6 CHLORO 1H BENZO[D]IMIDAZOL 2 YL) 5 (3,4,5 TRIMETHOXYPHENYL) 5,6 DIHYDRONAPHTHO[2,3 D][1,3]DIOXOLE 6 CARBOXYLATE; METHYL 7 (6 FLUORO 1H BENZO[D]IMIDAZOL 2 YL) 5 (3,4,5 TRIMETHOXYPHENYL) 5,6 DIHYDRONAPHTHO[2,3 D][1,3]DIOXOLE 6 CARBOXYLATE; METHYL 7 (6 METHOXY 1H BENZO[D]IMIDAZOL 2 YL) 5 (3,4,5 TRIMETHOXYPHENYL) 5,6 DIHYDRONAPHTHO[2,3 D][1,3]DIOXOLE 6 CARBOXYLATE; METHYL 7 (6 METHYL 1H BENZO[D]IMIDAZOL 2 YL) 5 (3,4,5 TRIMETHOXYPHENYL) 5,6 DIHYDRONAPHTHO[2,3 D][1,3]DIOXOLE 6 CARBOXYLATE; METHYL 7 FORMYL 5 (3,4,5 TRIMETHOXYPHENYL) 5,6 DIHYDRONAPHTHO[2,3 D][1,3]DIOXOLE 6 CARBOXYLATE; METHYL 7 [6 (TRIFLUOROMETHYL) 1H BENZO[D]IMIDAZOL 2 YL] 5 (3,4,5 TRIMETHOXYPHENYL) 5,6 DIHYDRONAPHTHO[2,3 D][1,3]DIOXOLE 6 CARBOXYLATE; METHYL 7 [7 BROMO 5 (TRIFLUOROMETHYL) 1H BENZO[D]IMIDAZOL 2 YL] 5 (3,4,5 TRIMETHOXYPHENYL) 5,6 DIHYDRONAPHTHO[2,3 D][1,3]DIOXOLE 6 CARBOXYLATE; NOCODAZOLE; PODOPHYLLOTOXIN; PODOPHYLLOTOXIN DERIVATIVE; TUBULIN; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; TUBULIN MODULATOR;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BINDING SITE; BIOACCUMULATION; BIOLOGICAL ACTIVITY; CANCER CELL LINE; CANCER INHIBITION; CONTROLLED STUDY; DRUG BINDING; DRUG CYTOTOXICITY; DRUG MECHANISM; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; G2 PHASE CELL CYCLE CHECKPOINT; HELA CELL LINE; HUMAN; HUMAN CELL; IN VITRO STUDY; M PHASE CELL CYCLE CHECKPOINT; MCF 7 CELL LINE; MICROTUBULE; MOLECULAR DOCKING; POLYMERIZATION; STRUCTURE ACTIVITY RELATION; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; METABOLISM; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HELA CELLS; HUMANS; MCF-7 CELLS; MOLECULAR DOCKING SIMULATION; MOLECULAR STRUCTURE; PODOPHYLLOTOXIN; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN; TUBULIN MODULATORS;

EID: 84907519177     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.07.031     Document Type: Article

References (40)

1. Y.Q. Liu, L. Yang, and X. Tian Curr. Bioact. Compd. 3 2007 37
2. T.F. Imbert Biochimie 80 1998 207
3. T.W. Doyle Etoposide (VP-16) Current Status and New Developments 1984 Academic New York
4. Z.Q. Wang, Y.H. Kuo, D. Schnur, J.P. Bowen, S.Y. Liu, F.S. Han, Y.C. Cheng, and K.H. Lee J. Med. Chem. 33 1990 2660
5. S.J. Fields, L.N. Igwemezie, S. Kaul, L.P. Schacter, R.J. Schilder, P.P. Litam, B.S. Himpler, C. Mcaleer, J. Wright, R.H. Barbhaiya, C.J. Langer, and P. Odwyer Clin. Cancer Res. 1 1995 105
6. L.P. Schacter, L.N. Igwemezie, and M. Seyedsadr Cancer Chemother. Pharmacol. 34 1994 s58
7. D.R. Budman Semin. Oncol. 23 1996 8
8. X.K. Zhu, J. Guan, Y. Tachibana, K.F. Bastow, S.J. Cho, H.H. Cheng, Y.C. Cheng, M. Gurwith, and K.H. Lee J. Med. Chem. 42 1999 2441
9. Z. Xiao, K.F. Bastow, J.R. Vance, R.S. Sidwell, H.K. Wang, M.S. Chen, Q. Shi, and K.H. Lee J. Med. Chem. 47 2004 5140
10. F. Cortese, B. Bhattacharyya, and B. Wolf J. Biol. Chem. 252 1977 1134
11. E. Haar, H.S. Rosenkranz, E. Hamel, and B.W. Day Bioorg. Med. Chem. 4 1996 1659
12. M.N. Islam, and M.N. Iskander Mini-Rev. Med. Chem. 4 2004 1077
13. W. Ross, T. Rowe, B. Glisson, J. Yalowich, and L. Liu Cancer Res. 44 1984 5857
14. B.H. Long, and A. Minocha Proc. Am. Assoc. Cancer Res. 24 1983 1271
15. B.H. Long, S.T. Musial, and M.G. Brattain Biochemistry 23 1984 1183
16. Y. Damayanthi, and J.W. Lown Curr. Med. Chem. 5 1998 205
17. M. Gordaliza, M.A. Castro, J.M. Miguel del Corral, and A. San Feliciano Curr. Pharm. Des. 2000 1811 6
18. M. Gordaliza, M.A. Castro, J.M. Miguel del Corral, M.L. Lopez-Vazquez, P.A. Garcia, A. San Feliciano, M.D. Garcia-Gravalos, and H. Broughton Tetrahedron 53 1997 15743
19. J. Li, H.M. Hua, Y.B. Tang, S. Zhang, E. Ohkoshi, K.H. Lee, and Z. Xiao Bioorg. Med. Chem. Lett. 22 2012 4293
20. M.A. Castro, J.M. Miguel del Corral, M. Gordaliza, P.A. Garcia, M.A. Gomez- Zurita, M.D. Garcia-Gravalos, J. de la Iglesia-Vicente, C. Gajate, F. An, F. Mollinedo, and A. San Feliciano J. Med. Chem. 47 2004 1214
21. M.A. Castro, J.M. Miguel del Corral, P.A. Garcia, M.V. Rojo, J. de la Iglesia-Vicente, F. Mollinedo, C. Cuevas, A. San Feliciano, M.A. Castro, and M.A. Castro J. Med. Chem. 53 2010 983
22. R.V. Shingalapur, K.M. Hosamani, and R.S. Keri Eur. J. Med. Chem. 44 2009 4244
23. J.F. Miller, E.M. Turner, K.S. Gudmundsson, S. Jenkinson, A. Splatenstein, M. Thomson, and P. Wheelan Bioorg. Med. Chem. Lett. 20 2010 2125
24. K.C.S. Achar, K.M. Hosamani, and H.R. Seetharamareddy Eur. J. Med. Chem. 45 2010 2048
25. A.O. El-Nezhawy, A.R. Biuomy, F.S. Hassan, A.K. Ismaiel, and H.A. Omar Bioorg. Med. Chem. 21 2013 1661
26. K. Nagata, H. Satoh, T. Iwahi, T. Shimoyama, and T. Tamura Antimicrob. Agents Chemother. 37 1993 769
27. J.Y. Xu, Y. Zeng, Q. Ran, Z. Wei, Y. Bi, Q.H. He, Q.J. Wang, S. Hu, J. Zhang, M.Y. Tang, W.Y. Hua, and X.M. Wu Bioorg. Med. Chem. Lett. 17 2007 2921
28. Y. Luo, F. Xiao, S. Qian, W. Lu, and B. Yang Eur. J. Med. Chem. 46 2011 417
29. M. Hranjec, G. Pavlovi, M. Marjanovi, M. Kralj, and G.K. Zamola Eur. J. Med. Chem. 45 2010 2405
30. T.D. Penning, G.D. Zhu, J. Gong, S. Thomas, V.B. Gandhi, X. Liu, Y. Shi, V. Klinghofer, E.F. Johnson, C. Park, E. Fry, C. Donawho, D. Frost, G. Buchanan, G. Bukofzer, L. Rodriguez, V. Bontcheva-Diaz, J. Bouska, D.J. Osterling, A. Olson, K.C. Marsh, Y. Luo, and V. Giranda J. Med. Chem. 53 2010 3142
31. C. Duanmu, L.K. Shahrik, H.H. Holly, and E. Hamel Cancer Res. 49 1989 1344
32. R.J. Vasquez, B. Howell, A.M. Yvon, P. Wadsworth, and L. Cassimeris Mol. Biol. Cell 8 1997 973
33. A. Kamal, P. Suresh, M.J. Ramaiah, T. Srinivasareddy, R.K. Kapavarapu, B.N. Rao, S. Imthiajali, T. Lakshminarayanreddy, S.N.C.V.L. Pushpavalli, N. Shankaraiah, and M. Pal-Bhadra Bioorg. Med. Chem. 21 2013 5198
34. A. Kamal, J.R. Tamboli, V.L. Nayak, S.F. Adil, M.V.P.S. Vishnuvardhan, and S. Ramakrishna Bioorg. Med. Chem. 22 2014 2714
35. A. Kamal, J.R. Tamboli, V.L. Nayak, S.F. Adil, M.V.P.S. Vishnuvardhan, and S. Ramakrishna Bioorg. Med. Chem. Lett. 23 2013 273
36. S. Kasibhatla, H. Gourdeau, K. Meerovitch, J. Drewe, S. Reddy, L. Qiu, H. Zhang, F. Bergeron, D. Bouffard, Q. Yang, J. Herich, S. Lamothe, S.X. Cai, and B. Tseng Mol. Cancer Ther. 3 2004 1365
37. S.B. Hastie Pharmacol. Ther. 51 1991 377
38. M.A. Reddy, N. Jain, D. Yada, C. Kishore, J.R. Vangala, P.S. Reddy, A. Addlagatta, S.V. Kalivendi, and B. Sreedhar J. Med. Chem. 54 2011 6751
39. Schrödinger; LLC: New York, NY, 2012.
40. J.M. Miguel del Corral, M. Gordaliza, J.L. López, E. del Olmo, M.A. Castro, L. Morales, and M.L. López Helv. Chim. Acta 78 1995 1793