Correlation of hydrogen-bonding propensity and anticancer profile of tetrazole-tethered combretastatin analogues

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 16, 2013, Pages 4680-4684

  Jedhe, Ganesh S ^a   Paul, Debasish ^b   Gonnade, Rajesh G ^a   Santra, Manas K ^b   Hamel, Ernest ^c   Nguyen, Tam Luong ^d   Sanjayan, Gangadhar J ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b NATIONAL CENTRE FOR CELL SCIENCE   (India)

^c NATIONAL CANCER INSTITUTE   (United States)

^d SAIC FREDERICK INC   (United States)

Author keywords

Colchicine; Combretastatin; Crystal; Tetrazole; Tubulin

Indexed keywords

COLCHICINE; COMBRETASTATIN A1 PHOSPHATE; COMBRETASTATIN A4 PHOSPHATE; TETRAZOLE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CORRELATIONAL STUDY; CRYSTAL STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROGEN BOND; IC 50; MICROTUBULE ASSEMBLY; SUBSTITUTION REACTION;

COLCHICINE; COMBRETASTATIN; CRYSTAL; TETRAZOLE; TUBULIN;

ANTINEOPLASTIC AGENTS; BIBENZYLS; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HYDROGEN BONDING; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; TETRAZOLES; TUBULIN MODULATORS;

EID: 84880622103     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2013.06.004     Document Type: Article

References (37)

1. G.R. Pettit, S.B. Singh, M.L. Niven, E. Hamel, and J.M. Schmidt J. Nat. Prod. 50 1987 119
2. G.R. Pettit, S.B. Singh, E. Hamel, C.M. Lin, D.S. Alberts, and D. Garcia-Kendall Experientia 45 1989 209
3. G.M. Tozer, C. Kanthou, C.S. Parkins, and S.A. Hill Int. J. Exp. Pathol. 83 2002 21
4. J.A. Woods, J.A. Hadfield, G.R. Pettit, B.W. Fox, and A.T. McGown Br. J. Cancer 71 1995 705
5. D.M. Patterson, G.J.S. Rustin, N. Serradell, E. Rosa, and J. Bolos Drugs Future 1025 2007 32
6. I. Petit, M.A. Karajannis, L. Vincent, L. Young, J. Butler, A.T. Hooper, K. Shido, H. Steller, D.J. Chaplin, E. Feldman, and S. Rafii Blood 111 2008 1951
7. D.W. Siemann, D.J. Chaplin, and P.A. Walicke Expert Opin. Investig. Drugs 18 2009 189
8. I.G. Kirwan, P.M. Loadman, D.J. Swaine, D.A. Anthoney, G.R. Pettit, J.W. Lippert 3rd, S.D. Shnyder, P.A. Cooper, and M.C. Bibby Clin. Cancer Res. 10 2004 1446
9. L.K. Folkes, M. Christlieb, E. Madej, M.R. Stratford, and P. Wardman Chem. Res. Toxicol. 20 2007 1885
10. G.R. Pettit, A.J. Thornhill, B.R. Moser, and F. Hogan J. Nat. Prod. 71 2008 1561
11. H.P. Hsieh, J.P. Liou, and N. Mahindroo Curr. Pharm. Des. 11 2005 1655
12. G.C. Tron, T. Pirali, G. Sorba, F. Pagliai, S. Busacca, and A.A. Genazzani J. Med. Chem. 49 2006 3033
13. A. Chaudhary, S.N. Pandeya, P. Kumar, P.P. Sharma, S. Gupta, N. Soni, K.K. Verma, and G. Bhardwaj Mini-Rev. Med. Chem. 7 2007 1186
14. S. Aprile, E.D. Grosso, G.C. Tron, and G. Grosa Drug Metab. Dispos. 35 2007 2252
15. S. Theeramunkong, A. Caldarelli, A. Massarotti, S. Aprile, D. Caprioglio, R. Zaninetti, A. Teruggi, T. Pirali, G. Grosa, G.C. Tron, and A.A. Genazzani J. Med. Chem. 54 2011 4977
16. K. Ohsumi, T. Hatanaka, K. Fujita, R. Nakagawa, Y. Fukuda, Y. Nihei, Y. Suga, Y. Morinaga, Y. Akiyama, and T. Tsuji Bioorg. Med. Chem. Lett. 8 1998 3153
17. K. Bonezzi, G. Taraboletti, P. Borsotti, F. Bellina, R. Rossi, and R. Giavazzi J. Med. Chem. 52 2009 7906
18. J. Kaffy, R. Pontikis, D. Carrez, A. Croisy, C. Monneret, and J.C. Florent Bioorg. Med. Chem. 14 2006 4067
19. S. Lee, J.N. Kim, H.K. Lee, K.S. Yoon, K.D. Shin, B.M. Kwon, and D.C. Han Bioorg. Med. Chem. Lett. 21 2011 977
20. M. Wu, Q. Sun, C. Yang, D. Chen, J. Ding, Y. Chen, L. Lin, and Y. Xie Bioorg. Med. Chem. Lett. 17 2007 869
21. R. Romagnoli, P.G. Baraldi, O. Cruz-Lopez, C. Lopez Cara, M.D. Carrion, A. Brancale, E. Hamel, L. Chen, R. Bortolozzi, G. Basso, and G. Viola J. Med. Chem. 53 2010 4248
22. K. Odlo, J. Hentzen, J. Fournier, S. Ducki, O.A. Gani, I. Sylte, M. Skrede, V.A. Florenes, and T.V. Hansen Bioorg. Med. Chem. 16 2008 4829
23. ø.W. Akselsen, K. Odlo, J.J. Cheng, G. Maccari, M. Botta, and T.V. Hansen Bioorg. Med. Chem. 20 2012 234
24. T.M. Beale, D.M. Allwood, A. Bender, P.J. Bond, J.D. Brenton, D.S. Charnock-Jones, D.V. Ley, R.M. Myers, J.W. Shearman, J. Temple, J. Unger, C.A. Watts, and J. Xian ACS Med. Chem. Lett. 3 2012 177
25. R. Romagnoli, P.G. Baraldi, M.K. Salvador, D. Preti, M. Aghazadeh Tabrizi, A. Brancale, X.H. Fu, J. Li, S.Z. Zhang, E. Hamel, R. Bortolozzi, G. Basso, and G. Viola J. Med. Chem. 55 2012 475
26. G.R. Pettit, B.R. Moser, M.R. Boyd, J.M. Schmidt, R.K. Pettit, and J.C. Chapuis Anticancer Drug Des. 16 2001 185
27. N.H. Nam, Y. Kim, Y.J. You, D.H. Hong, H.M. Kim, and B.Z. Ahn Arch. Pharm. Res. 25 2002 600
28. M. Sriram, J.J. Hall, N.C. Grohmann, T.E. Strecker, T. Wootton, A. Franken, M.L. Trawick, and K.G. Pinney Bioorg. Med. Chem. 16 2008 8161
29. R.F. Cunico, and R.K. Pandey J. Org. Chem. 70 2005 5344
30. L. Kaisalo, A. Latvala, and T. Hase Synth. Commun. 16 1986 645
31. B. Cheng, S.Q. Zhang, L. Zhu, J. Zhang, Q. Li, A.L. Shan, and L. He Synthesis 15 2009 2501
32. B. Shen, D. Loffler, G. Reischl, H.J. Machulla, and K.P. Zeller J. Fluorine Chem. 130 2009 216
33. T.L. Su, B. Kohler, T.C. Chou, M.W. Chun, and K.A. Watanabe J. Med. Chem. 35 1992 2703
34. E.J. Corey, and J.P. Dittami J. Am. Chem. Soc. 107 1985 256
35. L.M. Varley, and C.J. Moody Synthesis 22 2008 3601
36. R.B. Ravelli, B. Gigant, P.A. Curmi, I. Jourdain, S. Lachkar, A. Sobel, and M. Knossow Nature 428 2004 198
37. T.L. Nguyen, C. McGrath, A.R. Hermone, J.C. Burnett, D.W. Zaharevitz, B.W. Day, P. Wipf, E. Hamel, and R. Gussio J. Med. Chem. 48 2005 6107