Synthesis and biological evaluation of colchicine C-ring analogues tethered with aliphatic linkers suitable for prodrug derivatisation

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 24, 2012, Pages 7693-7696

  Fournier Dit Chabert, Jérémie ^a   Vinader, Victoria ^a   Santos, Ana Rita ^a   Redondo Horcajo, Mariano ^b   Dreneau, Aurore ^a   Basak, Ramkrishna ^a   Cosentino, Laura ^a   Marston, Gemma ^a   Abdel Rahman, Hamdy ^a   Loadman, Paul M ^a   Shnyder, Steven D ^a   Díaz, José Fernando ^b   Barasoain, Isabel ^b   Falconer, Robert A ^a   Pors, Klaus ^a  

^a UNIVERSITY OF BRADFORD   (United Kingdom)

^b CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

Author keywords

Class III tubulin resistance; Colchicine; Matrix metalloproteinases (MMPs); MDR (ABCB1, P glycoprotein); Prodrug

Indexed keywords

ANTINEOPLASTIC AGENT; BETA TUBULIN; COLCHICINE; COLCHICINE DERIVATIVE; HETEROCYCLIC AMINE; MUTANT PROTEIN; PACLITAXEL; PRODRUG;

AMINATION; ARTICLE; BINDING AFFINITY; CANCER CELL CULTURE; CHEMICAL REACTION; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYTOTOXICITY; DERIVATIZATION; DRUG SYNTHESIS; ENTROPY; HELA CELL; HUMAN; HUMAN CELL; IC 50; MOLECULAR LIBRARY; MOLECULAR MODEL; PHYSICAL CHEMISTRY;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; CELL PROLIFERATION; COLCHICINE; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HELA CELLS; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PRODRUGS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84870248825     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.09.104     Document Type: Article

References (33)

1. C. Cerquaglia, M. Diaco, G. Nucera, M. La Regina, M. Montalto, and R. Manna Curr. Drug Targets Inflamm. Allergy 4 2005 117
2. E. Ben-Chetrit, and M. Levy Semin. Arthritis Rheum. 28 1998 48
3. E. Pasquier, N. Andre, and D. Braguer Curr. Cancer Drug Targets 7 2007 566
4. B.C. Baguley, K.M. Holdaway, L.L. Thomsen, L. Zhuang, and L.J. Zwi Eur. J. Cancer 27 1991 482
5. G.M. Tozer, C. Kanthou, and B.C. Baguley Nat. Rev. Cancer 5 2005 423
6. E.L. Schwartz Clin. Cancer Res. 15 2009 2594
7. C. Kanthou, and G.M. Tozer Int. J. Exp. Pathol. 90 2009 284
8. Y. Zhao, W.S. Fang, and K. Pors Expert Opin. Ther. Pat. 19 2009 607
9. P. Hinnen, and F.A. Eskens Br. J. Cancer 96 2007 1159
10. W.J. van Heeckeren, S. Bhakta, J. Ortiz, J. Duerk, M.M. Cooney, A. Dowlati, K. McCrae, and S.C. Remick J. Clin. Oncol. 24 2006 1485
11. E.I. Deryugina, and J.P. Quigley Cancer Metastasis Rev. 25 2006 9
12. M. Egeblad, and Z. Werb Nat. Rev. Cancer 2 2002 161
13. C.M. Overall, and O. Kleifeld Nat. Rev. Cancer 6 2006 227
14. J.M. Atkinson, C.S. Siller, and J.H. Gill Br. J. Pharmacol. 153 2008 1344
15. D.F. Tang-Wai, A. Brossi, L.D. Arnold, and P. Gros Biochemistry 32 1993 6470
16. J.M. Atkinson, R.A. Falconer, D.R. Edwards, C.J. Pennington, C.S. Siller, S.D. Shnyder, M.C. Bibby, L.H. Patterson, P.M. Loadman, and J.H. Gill Cancer Res. 70 2010 6902
17. G. Szakacs, J.K. Paterson, J.A. Ludwig, C. Booth-Genthe, and M.M. Gottesman Nat. Rev. Drug Disc. 5 2006 219
18. M.L. Gelmi, S. Mottadelli, D. Pocar, A. Riva, E. Bombardelli, R. De Vincenzo, and G. Scambia J. Med. Chem. 42 1999 5272
19. I. Ringel, D. Jaffe, S. Alerhand, O. Boye, A. Muzaffar, and A. Brossi J. Med. Chem. 34 1991 3334
20. R.B. Ravelli, B. Gigant, P.A. Curmi, I. Jourdain, S. Lachkar, A. Sobel, and M. Knossow Nature 428 2004 198
21. P. Labute J. Comput. Chem. 29 2008 1693
22. A. Massarotti, A. Coluccia, R. Silvestri, G. Sorba, and A. Brancale ChemMedChem 7 2012 33
23. K. Pors, J.A. Plumb, R. Brown, P. Teesdale-Spittle, M. Searcey, P.J. Smith, and L.H. Patterson J. Med. Chem. 48 2005 6690
24. I. Ringel, O. Bakshi, W. Mellado, A. Ramu, D. Gibson, and J. Katzhendler Biochem. Pharmacol. 37 1988 2487
25. D.H. Li, S.K. Zhang, Z.G. Hao, K.S. Ma, X.R. Tan, Z.L. Wang, and N.K. Li Chin. Med. J. (Engl.) 93 1980 188
26. C. Stengel, S.P. Newman, M.P. Leese, B.V. Potter, M.J. Reed, and A. Purohit Br. J. Cancer 102 2010 316
27. P.A. Joe, A. Banerjee, and R.F. Luduena Cell Motil. Cytoskeleton 65 2008 476
28. A.L. Risinger, E.M. Jackson, L.A. Polin, G.L. Helms, D.A. LeBoeuf, P.A. Joe, E. Hopper-Borge, R.F. Luduena, G.D. Kruh, and S.L. Mooberry Cancer Res. 68 2008 8881
29. M.A. Jordan, and L. Wilson Nat. Rev. Cancer 4 2004 253
30. J.R. Jackson, D.R. Patrick, M.M. Dar, and P.S. Huang Nat. Rev. Cancer 7 2007 107
31. Q.M. Abdallah, R.M. Phillips, F. Johansson, T. Helleday, L. Cosentino, H. Abdel-Rahman, J. Etzad, R.T. Wheelhouse, K. Kiakos, J.P. Bingham, J.A. Hartley, L.H. Patterson, and K. Pors Biochem. Pharmacol. 83 2012 1514
32. K. Pors, P.M. Loadman, S.D. Shnyder, M. Sutherland, H.M. Sheldrake, M. Guino, K. Kiakos, J.A. Hartley, M. Searcey, and L.H. Patterson Chem. Commun. (Camb.) 47 2011 12062
33. K. Pors, S.D. Shnyder, P.H. Teesdale-Spittle, J.A. Hartley, M. Zloh, M. Searcey, and L.H. Patterson J. Med. Chem. 49 2006 7013