Vascular disrupting activity of tubulin-binding 1,5-diaryl-1H-imidazoles

Journal of Medicinal Chemistry

Volumn 52, Issue 23, 2009, Pages 7906-7910

  Bonezzi, Katiuscia ^a   Taraboletti, Giulia ^a   Borsotti, Patrizia ^a   Bellina, Fabio ^b   Rossi, Renzo ^b   Giavazzi, Raffaella ^a  

^a MARIO NEGRI INSTITUTE FOR PHARMACOLOGICAL RESEARCH   (Italy)

^b UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,5 DIARYL 1H IMIDAZOLE DERIVATIVE; 1,5 DIARYL 1H IMIDAZOLE HYDROCHLORIDE DERIVATIVE; IMIDAZOLE DERIVATIVE; TUBULIN; UNCLASSIFIED DRUG; VASCULAR TARGETING AGENT;

ANGIOGENESIS; ARTICLE; CAPILLARY; CELL STRUCTURE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG PROTEIN BINDING; ENDOTHELIUM CELL; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MOLECULAR INTERACTION; TARGET ORGAN; TUMOR NECROSIS;

ANIMALS; BINDING SITES; BLOOD VESSELS; CELL LINE, TUMOR; ENDOTHELIAL CELLS; HUMANS; HYDROCHLORIC ACID; IMIDAZOLES; ISOMERISM; MICE; NEOPLASMS; TUBULIN;

EID: 72249107517     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900968s     Document Type: Article

References (21)

1. Jordan, M. A.; Wilson, L. Microtubules as a target for anticancer drugs. Nat. Rev. Cancer 2004, 4, 253-265.
2. Giavazzi, R.; Bonezzi, K.; Taraboletti, G. Microtubule targeting agents and angiogenesis. In Microtubules as Targets for Cancer Therapies; Fojo, T., Ed.; Humana Press: Totowa, NJ, 2008; pp 519-530.
3. Schwartz, E. L. Antivascular actions of microtubule-binding drugs. Clin. Cancer Res. 2009, 15, 2594-2601
4. Tozer, G. M.; Kanthou, C.; Baguley, B. C. Disrupting tumour blood vessels. Nat. Rev. Cancer 2005, 5, 423-435.
5. Griggs, J.; Metcalfe, J. C.; Hesketh, R. Targeting tumour vasculature: the development of combretastatin A4. Lancet Oncol. 2001, 2, 82-87. (Pubitemid 33585919)
6. Chaplin, D. J.; Horsman, M. R.; Siemann, D. W. Current development status of small-molecule vascular disrupting agents. Curr. Opin. Investig. Drugs 2006, 7, 522-528.
7. Hinnen, P.; Eskens, F. A. Vascular disrupting agents in clinical development. Br. J. Cancer 2007, 96, 1159-1165.
8. Lippert, J. W., III. Vascular disrupting agents. Bioorg. Med. Chem. 2007, 15, 605-615.
9. West, C. M.; Price, P. Combretastatin A4 phosphate. Anticancer Drugs 2004, 15, 179-187.
10. Nam, N. H. Combretastatin A-4 analogues as antimitotic antitumor agents. Curr. Med. Chem. 2003, 10, 1697-1722
11. Aprile, S.; Del Grosso, E.; Tron, G. C.; Grosa, G. In vitro metabolism study of combretastatin A-4 in rat and human liver microsomes. Drug Metab. Dispos. 2007, 35, 2252-2261.
12. Cirla, A.; Mann, J. Combretastatins: from natural products to drug discovery. Nat. Prod. Rep. 2003, 20, 558-564.
13. Tron,G.C.; Pirali,T.; Sorba, G.;Pagliai,F.;Busacca, S.;Genazzani, A.A. Medicinal chemistry of combretastatin A4: present and future directions. J. Med. Chem. 2006, 49, 3033-3044.
14. Wang, L; Woods, K. W.; Li, Q.; Barr, K. J.; McCroskey, R. W.; Hannick, S. M.; Gherke, L.; Credo, R. B.; Hui, Y.-H-; Marsh, K.; Warner, R.; Lee, J. Y.; Zielinski-Mozng, N.; Frost, D.; Rosenberg, S. H.; Sham, H. L. Potent, orally-active heterocyclic-based combretastatin A-4 analogues: synthesis, structure-activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation. J. Med. Chem. 2002, 45, 1697-1711.
15. Bellina, F.; Cauteruccio, S.;Mannina, L.; Rossi, R.; Viel, S. Regioselective synthesis of 1,5-diaryl-1H-imidazoles by palladiumcatalyzed direct arylation of 1-aryl-1H-imidazoles. J. Org. Chem. 2005, 70, 3997-4005.
16. Bellina, F.; Cauteruccio, S.; Rossi, R. Palladium- and Copper- Mediated Direct C-2 Arylation of Azoles;Including Free (NH)- Imidazole, -Benzimidazole and -Indole;Under Base-Free and Ligandless Conditions. Eur. J. Org. Chem. 2006, 1379-1382.
17. Bellina, F.; Calandri, C.; Cauteruccio, S.; Rossi, R. Efficient and highly regioselective direct C-2 arylation of azoles, including free (NH)-imidazole, -benzimidazole and -indole, with aryl halides. Tetrahedron 2007, 63, 1970-1980.
18. Bellina, F.; Cauteruccio, S.; Monti, S.; Rossi, R. Novel imidazolebased combretastatin A-4 analogues: evaluation of their in vitro antitumor activity and molecular modeling study of their binding to the colchicine site of tubulin. Bioorg. Med. Chem. Lett. 2006, 16, 5757-5762.
19. Carreira, L. A. SPARC Online Calculator; Department of Chemistry, University of Georgia: Athens, GA, 2004; http://ibmcl2.chem.uga. edu/sparc.
20. Kanthou, C.; Tozer, G. M. The tumor vascular targeting agent combretastatin A-4-phosphate induces reorganization of the actin cytoskeleton and early membrane blebbing in human endothelial cells. Blood 2002, 99, 2060-2069.
21. Micheletti, G.; Poli, M.; Borsotti, P.; Martinelli, M.; Imberti, B.; Taraboletti, G.; Giavazzi, R. Vascular-targeting activity of ZD6126, a novel tubulin-binding agent. Cancer Res. 2003, 63, 1534-1537. (Pubitemid 36373640)