Synthesis and biochemical activities of antiproliferative amino acid and phosphate derivatives of microtubule-disrupting β-lactam combretastatins

European Journal of Medicinal Chemistry

Volumn 62, Issue , 2013, Pages 705-721

  O'Boyle, Niamh M ^a   Greene, Lisa M ^a   Keely, Niall O ^a   Wang, Shu ^a   Cotter, Tadhg S ^a   Zisterer, Daniela M ^a   Meegan, Mary J ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

Antiproliferative; Beta lactam; Combretastatin A 4; Prodrug; Solubility; Tubulin

Indexed keywords

2 AMINO N (2 METHOXY 5 (4 OXO 3 PHENYL 1 (3,4,5 TRIMETHOXYPHENYL)AZETIDIN 2 YL)PHENYL) 3 METHYLBUTANAMIDE; 2 AMINO N (4 (2 (4 METHOXYPHENYL) 4 OXO 1 (3,4,5TRIMETHOXYPHENYL)AZETIDIN 3 YL)PHENYL) 3 PHENYLPROPANAMIDE; 2 METHOXY 5 (4 OXO 3 PHENYL 1 (3,4,5 TRIMETHOXYPHENYL) AZETIDIN 2 YL)PHENYL DIHYROGEN PHOSPHATE; BETA LACTAM PHOSPHATE ESTER DERIVATIVE; COMBRETASTATIN; ORGANOPHOSPHATE; UNCLASSIFIED DRUG;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BIOTRANSFORMATION; BREAST CARCINOMA; CELL DISRUPTION; CONTROLLED STUDY; FLOW CYTOMETRY; HUMAN; HUMAN CELL; PROTEIN BINDING; PROTEIN POLYMERIZATION; SYNTHESIS;

AMINO ACIDS; ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; MCF-7 CELLS; MICROTUBULES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOSPHATES; SOLUBILITY; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84876006690     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.01.016     Document Type: Article

References (40)

1. J. Rautio, H. Kumpulainen, T. Heimbach, R. Oliyai, D. Oh, T. Jarvinen, and J. Savolainen Nat. Rev. Drug Discov. 7 2008 255 270
2. P. Ettmayer, G.L. Amidon, B. Clement, and B. Testa J. Med. Chem. 47 2004 2393 2404
3. D. Fleisher, R. Bong, and B.H. Stewart Adv. Drug Deliv. Rev. 19 1996 115 130
4. N.M. O'Boyle, M. Carr, L.M. Greene, O. Bergin, S.M. Nathwani, T. McCabe, D.G. Lloyd, D.M. Zisterer, and M.J. Meegan J. Med. Chem. 53 2010 8569 8584
5. N.M. O'Boyle, L.M. Greene, O. Bergin, J.-B. Fichet, T. McCabe, D.G. Lloyd, D.M. Zisterer, and M.J. Meegan Bioorg. Med. Chem. 19 2011 2306 2325
6. P.D. Davis, G.J. Dougherty, D.C. Blakey, S.M. Galbraith, G.M. Tozer, A.L. Holder, M.A. Naylor, J. Nolan, M.R.L. Stratford, D.J. Chaplin, and S.A. Hill Cancer Res. 62 2002 7247 7253
7. J.W. Lippert Bioorg. Med. Chem. 15 2007 605 615
8. G.R. Pettit, C. Temple Jr., V.L. Narayanan, R. Varma, M.J. Simpson, M.R. Boyd, G.A. Rener, and N. Bansal Anticancer Drug Des. 10 1995 299 309
9. G.R. Pettit, and J.W. Lippert Anticancer Drug Des. 15 2000 203 216
10. G.R. Pettit, A. Thornhill, N. Melody, and J.C. Knight J. Nat. Prod. 72 2009 380 388
11. G.R. Pettit, H.J. Rosenberg, R. Dixon, J.C. Knight, E. Hamel, J.C. Chapuis, R.K. Pettit, F. Hogan, B. Sumner, K.B. Ain, and B. Trickey-Platt J. Nat. Prod. 75 2012 385 393
12. G.J.S. Rustin, S.M. Galbraith, H. Anderson, M. Stratford, L.K. Folkes, L. Sena, L. Gumbrell, and P.M. Price J. Clin. Oncol. 21 2003 2815 2822
13. Available from: www.clinicaltrials.gov, (accessed 3.03.12).
14. G.R. Pettit, B. Toki, D.L. Herald, P. Verdier-Pinard, M.R. Boyd, E. Hamel, and R.K. Pettit J. Med. Chem. 41 1998 1688 1695
15. K. Ohsumi, R. Nakagawa, Y. Fukuda, T. Hatanaka, Y. Morinaga, Y. Nihei, K. Ohishi, Y. Suga, Y. Akiyama, and T. Tsuji J. Med. Chem. 41 1998 3022 3032
16. K. Strebhardt, and A. Ullrich Nat. Rev. Cancer 8 2008 473 480
17. G.R. Pettit, C.R. Anderson, D.L. Herald, M.K. Jung, D.J. Lee, E. Hamel, and R.K. Pettit J. Med. Chem. 46 2003 525 531
18. M. Carr, L.M. Greene, A.J. Knox, D.G. Lloyd, D.M. Zisterer, and M.J. Meegan Eur. J. Med. Chem. 45 2010 5752 5766
19. P.G.M. Wuts, and T.W. Greene Greene's Protective Groups in Organic Synthesis fourth ed. 2007 John Wiley & Sons, Inc. Hoboken, New Jersey
20. L.A. Carpino, and G.Y. Han J. Org. Chem. 37 1972 3404 3409
21. K. Ohsumi, T. Hatanaka, R. Nakagawa, Y. Fukuda, Y. Morinaga, Y. Suga, Y. Nihei, K. Ohishi, Y. Akiyama, and T. Tsuji Anticancer Drug Des. 14 1999 539 548
22. M. Ueki, N. Nishigaki, H. Aoki, T. Tsurusaki, and T. Katoh Chem. Lett. 1993 721 724
23. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Adv. Drug Deliv. Rev. 23 1997 3 25
24. G.R. Pettit, C. Temple Jr., V.L. Narayanan, R. Varma, M.J. Simpson, M.R. Boyd, G.A. Rener, and N. Bansal Anticancer Drug Des. 10 1995 299 309
25. M. Castedo, J.-L. Perfettini, T. Roumier, K. Andreau, R. Medema, G. Kroemer, Oncogene 23 2825-2837.
26. N.M. O'Boyle, M. Carr, L.M. Greene, A.J.S. Knox, D.G. Lloyd, D.M. Zisterer, and M.J. Meegan Eur. J. Med. Chem. 46 2011 4595 4607
27. I. Vitale, A. Antoccia, C. Cenciarelli, P. Crateri, S. Meschini, G. Arancia, C. Pisano, and C. Tanzarella Apoptosis 12 2007 155 166
28. C. Cenciarelli, C. Tanzarella, I. Vitale, C. Pisano, P. Crateri, S. Meschini, G. Arancia, and A. Antoccia Apoptosis 13 2008 659 669
29. S.M. Nabha, R.M. Mohammad, M.H. Dandashi, B. Coupaye-Gerard, A. Aboukameel, G.R. Pettit, and A.M. Al-Katib Clin. Cancer Res. 8 2002 2735 2741
30. D. Simoni, R. Romagnoli, R. Baruchello, R. Rondanin, M. Rizzi, M.G. Pavani, D. Alloatti, G. Giannini, M. Marcellini, T. Riccioni, M. Castorina, M.B. Guglielmi, F. Bucci, P. Carminati, and C. Pisano J. Med. Chem. 49 2006 3143 3152
31. J.P. Liou, Y.L. Chang, F.M. Kuo, C.W. Chang, H.Y. Tseng, C.C. Wang, Y.N. Yang, J.Y. Chang, S.J. Lee, and H.P. Hsieh J. Med. Chem. 47 2004 4247 4257
32. R. Gastpar, M. Goldbrunner, D. Marko, and E. von Angerer J. Med. Chem. 41 1998 4965 4972
33. R.B.G. Ravelli, B. Gigant, P.A. Curmi, I. Jourdain, S. Lachkar, A. Sobel, and M. Knossow Nature 428 2004 198 202
34. 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 6116
35. S.J. Hecker, and M.D. Erion J. Med. Chem. 51 2008 2328 2345
36. S.B. Bedford, C.P. Quarterman, D.L. Rathbone, J.A. Slack, R.J. Griffin, and M.F.G. Stevens Bioorg. Med. Chem. Lett. 6 1996 157 160
37. I.G. Kirwan, P.M. Loadman, D.J. Swaine, D.A. Anthoney, G.R. Pettit, J.W. Lippert, S.D. Shnyder, P.A. Cooper, and M.C. Bibby Clin. Cancer Res. 10 2004 1446 1453
38. MOE: www.chemcomp.com/software.htm, 2011, Chemical Computing Group.
39. B.L. Flynn, G.P. Flynn, E. Hamel, and M.K. Jung Bioorg. Med. Chem. Lett. 11 2001 2341 2343
40. G. La Regina, T. Sarkar, R. Bai, M.C. Edler, R. Saletti, A. Coluccia, F. Piscitelli, L. Minelli, V. Gatti, C. Mazzoccoli, V. Palermo, C. Mazzoni, C. Falcone, A.I. Scovassi, V. Giansanti, P. Campiglia, A. Porta, B. Maresca, E. Hamel, A. Brancale, E. Novellino, and R. Silvestri J. Med. Chem. 52 2009 7512 7527