Combretazet-3 a novel synthetic cis-stable combretastatin A-4-azetidinone hybrid with enhanced stability and therapeutic efficacy in colon cancer

Oncology Reports

Volumn 29, Issue 6, 2013, Pages 2451-2458

  Greene, Lisa M ^a   Wang, Shu ^a   O'Boyle, Niamh M ^a   Bright, Sandra A ^a   Reid, Jane E ^a   Kelly, Patrick ^a   Meegan, Mary J ^a   Zisterer, Daniela M ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

Azetidinone ( lactam); Colon cancer; Combretastatin A 4

Indexed keywords

ANTINEOPLASTIC AGENT; AZETIDINONE DERIVATIVE; COMBRETASTATIN A4; COMBRETAZET 3; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; COLON CANCER; CONTROLLED STUDY; DRUG DETERMINATION; DRUG EFFICACY; DRUG STABILITY; DRUG STRUCTURE; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; PRIORITY JOURNAL; SINGLE DRUG DOSE; TREATMENT RESPONSE;

ANIMALS; ANTINEOPLASTIC AGENTS; AUTOPHAGY; AZETIDINES; CELL LINE, TUMOR; CELL SURVIVAL; COLONIC NEOPLASMS; DRUG STABILITY; FEMALE; G2 PHASE CELL CYCLE CHECKPOINTS; GUAIACOL; HUMANS; HYDROGEN-ION CONCENTRATION; INHIBITORY CONCENTRATION 50; INJECTIONS, INTRAPERITONEAL; MICE; MICE, INBRED BALB C; MICE, NUDE; MICROSOMES, LIVER; TUMOR BURDEN; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84876279820     PISSN: 1021335X     EISSN: 17912431     Source Type: Journal    
DOI: 10.3892/or.2013.2379     Document Type: Article

References (23)

1. Pettit GR, Singh SB, Hamel E, Lin CM, Alberts DS and Garcia-Kendall D: Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A-4. Experientia 45: 209-211, 1989. (Pubitemid 19062390)
2. Marrelli M, Conforti F, Statti GA, Cachet X, Michel S, Tillequin F and Menichini F: Biologicalpotential and structure-activity relationships of most recently developed vascular disrupting agents: an overview of new derivatives of natural combretastatin a-4. Curr Med Chem 18: 3035-3081, 2011.
3. Dowlati A, Robertson K, Cooney M, Petros WP, Stratford M, Jesberger J, Rafie N, Overmoyer B, Makkar V, Stambler B, Taylor A, Waas J, Lewin JS, McCrae KR and Remick SC: A phase I pharmacokinetic and translational study of the novel vascular targeting agent combretastatin a-4 phosphate on a single-dose intravenous schedule in patients with advanced cancer. Cancer Res 62: 3408-3416, 2002. (Pubitemid 34651387)
4. Delmonte A and Sessa C: AVE8062: a new combretastatin derivative vascular disrupting agent. Expert Opin Investig Drugs 18: 1541-1548, 2009.
5. Beale TM, Myers RM, Shearman JW, Charnock-Jones SD, Brenton JD, Gergely FV and Ley SV: Antivascular and anticancer activity of dihalogenated A-ring analogues of combretastatin A-4. Med Chem Commun 1: 202-208, 2010.
6. Shan Y, Zhang J, Liu Z, Wang M and Dong Y: Developments of combretastatin A-4 derivatives as anticancer agents. Curr Med Chem 18: 523-538, 2011.
7. O'Boyle NM, Greene LM, Bergin O, Fichet JB, McCabe T, Lloyd DG, Zisterer DM and Meegan MJ: Synthesis, evaluation and structural studies of antiproliferative tubulin-targeting azetidin-2-ones. Bioorg Med Chem 19: 2306-2325, 2011.
8. Carr M, Greene LM, Knox AJ, Lloyd DG, Zisterer DM and Meegan MJ: Lead identification of conformationally restricted beta-lactam type combretastatin analogues: synthesis, antiproliferative activity and tubulin targeting effects. Eur J Med Chem 45: 5752-5766, 2010.
9. O'Boyle NM, Carr M, Greene LM, Bergin O, Nathwani SM, McCabe T, Lloyd DG, Zisterer DM and Meegan MJ: Synthesis and evaluation of azetidinone analogues of combretastatin A-4 as tubulin targeting agents. J Med Chem 53: 8569-8584, 2010.
10. Greene LM, O'Boyle NM, Nolan DP, Meegan MJ and Zisterer DM: The vascular targeting agent Combretastatin-A4 directly induces autophagy in adenocarcinoma-derived colon cancer cells. Biochem Pharmacol 84: 612-624, 2012.
11. O'Boyle NM, Carr M, Greene LM, Keely NO, Knox AJ, McCabe T, Lloyd DG, Zisterer DM and Meegan MJ: Synthesis, biochemical and molecular modelling studies of antiproliferative azetidinones causing microtubule disruption and mitotic catastrophe. Eur J Med Chem 46: 4595-4607, 2011.
12. Schobert R, Effenberger-Neidnicht K and Biersack B: Stable combretastatin A-4 analogues with sub-nanomolar efficacy against chemoresistant HT-29 cells. Int J Clin Pharmacol Ther 49: 71-72, 2011.
13. Ohsumi K, Nakagawa R, Fukuda Y, Hatanaka T, Morinaga Y, Nihei Y, Ohishi K, Suga Y, Akiyama Y and Tsuji T: Novel combretastatin analogues effective against murine solid tumors: design and structure-activity relationships. J Med Chem 41: 3022-3032, 1998. (Pubitemid 28359938)
14. Hinnen P and Eskens FA: Vascular disrupting agents in clinical development. Br J Cancer 96: 1159-1165, 2007 (Pubitemid 46625071)
15. Patterson DM, Zweifel M, Middleton MR, Price PM, Folke LK, Stratford MR, Ross P, Halford S, Peters J, Balkissoon J, Chaplin DJ, Padhani AR and Rustin GJ: Phase I clinical and pharmacokinetic evaluation of the vascular-disrupting agent OXi4503 in patients with advanced solid tumors. Clin Cancer Res 18: 1415-25, 2012.
16. Greene LM, Nathwani SM, Bright SA, Fayne D, Croke A, Gagliardi M, McElligott AM, O'Connor L, Carr M, Keely NO, O'Boyle NM, Carroll P, Sarkadi B, Conneally E, Lloyd DG, Lawler M, Meegan MJ and Zisterer DM: The vascular targeting agent combretastatin-A4 and a novel cis-restricted β-lactam analogue, CA-432, induce apoptosis in human chronic myeloid leukemia cells and ex vivo patient samples including those displaying multidrug resistance. J Pharmacol Exp Ther 335: 302-313, 2010.
17. Greene LM, Carr M, Keeley NO, Lawler M, Meegan MJ and Zisterer DM: BubR1 is required for the mitotic block induced by combretastatin-A4 and a novel cis-restricted β-lactam analogue in human cancer cells. Int J Mol Med 27: 715-723, 2011.
18. Rubinsztein DC, Codogno P and Levine B: Autophagy modul ation as a potential therapeutic target for diverse diseases. Nat Rev Drug Discov 11: 709-730, 2012.
19. Leslie EM, Deeley RG and Cole SP: Toxicological relevance of the multidrug resistance protein 1, MRP1 (ABCC1) and related transporters. Toxicology 167: 3-23, 2001. (Pubitemid 32830943)
20. Lee HY, Chang JY, Nien CY, Kuo CC, Shih KH, Wu CH, Chang CY, Lai WY and Liou JP: 5-Amino-2-aroylquinolines as highly potent tubulin polymerization inhibitors. Part 2. The impact of bridging groups at position C-2. J Med Chem 54: 8517-8525, 2011.
21. Romagnoli R, Baraldi PG, Salvador MK, Preti D, Aghazadeh Tabrizi M, Brancale A, Fu XH, Li J, Zhang SZ, Hamel E, Bortolozzi R, Basso G and Viola G: Synthesis and evaluation of 1,5-disubstituted tetrazoles as rigid analogues of combretastatin A-4 with potent antiproliferative and antitumor activity. J Med Chem 55: 475-488, 2012.
22. Rustin GJ, Galbraith SM, Anderson H, Stratford M, Folkes LK, Sena L, Gumbrell L and Price PM: Phase I clinical trial of weekly combretastatin A4 phosphate: clinical and pharmacokinetic results. J Clin Oncol 21: 2815-2822, 2003. (Pubitemid 46621828)
23. Eikesdal HP, Schem BC, Mella O and Dahl O: The new tubulin-inhibitor combretastatin A-4 enhances thermal damage in the BT4An rat glioma. Int J Radiat Oncol Biol Phys 46: 645-652, 2000. (Pubitemid 30100642)