Carbonic anhydrase inhibitors. Inhibition of cytosolic isoforms I and II, and extracellular isoforms IV, IX, and XII with sulfamides incorporating sugar moieties

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 18, 2007, Pages 5086-5090

  Colinas, Pedro A ^a   Bravo, Rodolfo D ^a   Vullo, Daniela ^b   Scozzafava, Andrea ^b   Supuran, Claudiu T ^b  

^a FACULTAD DE CIENCIAS EXACTAS   (Argentina)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Carbonic anhydrase; Isoforms; Sugar; Sulfamide; Tumor associated isozyme

Indexed keywords

CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IV; CARBONATE DEHYDRATASE IX; ISOENZYME; SULFANILAMIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYTOSOL; ENZYME ACTIVITY; ENZYME BINDING; ENZYME GLYCOSYLATION; ENZYME INHIBITION; SUBSTITUTION REACTION;

AMIDES; CARBONIC ANHYDRASE INHIBITORS; ISOENZYMES;

EID: 34547890260     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.07.023     Document Type: Article

References (34)

1. Winum J.-Y., Casini A., Mincione F., Starnotti M., Montero J.-L., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 14 (2004) 225
2. Winum J.-Y., Temperini C., El Cheikh K., Innocenti A., Vullo D., Ciattini S., Montero J.-L., Scozzafava A., and Supuran C.T. J. Med. Chem. 49 (2006) 7024
3. Wilkinson B.L., Bornaghi L.F., Houston T.A., Innocenti A., Supuran C.T., and Poulsen S.A. J. Med. Chem. 49 (2006) 6539
4. Wilkinson B.L., Bornaghi L.F., Houston T.A., Innocenti A., Vullo D., Supuran C.T., and Poulsen S.A. Bioorg. Med. Chem. Lett. 17 (2007) 987
5. Wilkinson B.L., Bornaghi L.F., Houston T.A., Innocenti A., Vullo D., Supuran C.T., and Poulsen S.A. J. Med. Chem. 50 (2007) 1651
6. Winum J.Y., Thiry A., El Cheikh K., Dogné J.M., Montero J.L., Vullo D., Scozzafava A., Masereel B., and Supuran C.T. Bioorg. Med. Chem. Lett. 17 (2007) 2685
7. Scozzafava A., Mastrolorenzo A., and Supuran C.T. Expert Opin. Ther. Pat. 16 (2006) 1627
8. Supuran C.T., Scozzafava A., and Casini A. Med. Res. Rev. 23 (2003) 146
9. Supuran C.T. Curr. Top. Med. Chem. 7 (2007) 825
10. Nair S.K., and Christianson D.W. J. Am. Chem. Soc. 113 (1991) 9455
11. Christianson D.W., and Fierke C.A. Acc. Chem. Res. 29 (1996) 331
12. Whittington D.A., Waheed A., Ulmasov B., Shah G.N., Grubb J.H., Sly W.S., and Christianson D.W. Proc. Natl. Acd. Sci. USA 98 (2001) 9545
13. Supuran C.T., and Scozzafava. Bioorg. Med. Chem. 15 (2007) 4336
14. Pastorekova S., Parkkila S., Pastorek J., and Supuran C.T. J. Enzyme Inhib. Med. Chem. 19 (2004) 199
15. Scozzafava A., Mastrolorenzo A., and Supuran C.T. Expert Opin. Ther. Pat. 14 (2004) 667
16. Thiry A., Dogné J.-M., Masereel B., and Supuran C.T. Trends Pharmacol. Sci. 27 (2006) 566
17. Di Fiore A., Scozzafava A., Winum J.Y., Montero J.L., Pedone C., Supuran C.T., and De Simone G. Bioorg. Med. Chem. Lett. 17 (2007) 1726
18. Mincione F., Scozzafava A., and Supuran C.T. Curr. Top. Med. Chem. 7 (2007) 849
19. Thiry A., Dogné J.M., Supuran C.T., and Masereel B. Curr. Top. Med. Chem. 7 (2007) 855
20. De Simone G., and Supuran C.T. Curr. Top. Med. Chem. 7 (2007) 879
21. Pastorekova S., Parkkila S., and Zavada J. Adv. Clin. Chem. 42 (2006) 167
22. Alterio V., Vitale R.M., Monti S.M., Pedone C., Scozzafava A., Cecchi A., De Simone G., and Supuran C.T. J. Am. Chem. Soc. 128 (2006) 8329
23. Svastova E., Hulikova A., Rafajova M., Zat'ovicova M., Gibadulinova A., Casini A., Cecchi A., Scozzafava A., Supuran C.T., Pastorek J., and Pastorekova S. FEBS Lett. 577 (2004) 439
24. Cecchi A., Hulikova A., Pastorek J., Pastorekova S., Scozzafava A., Winum J.-Y., Montero J.-L., and Supuran C.T. J. Med. Chem. 48 (2005) 4834
25. Dubois, L.; Douma, K.; Supuran, C. T.; Chiu, R. K.; van Zandvoort, M. A.; Pastorekova, S.; Scozzafava, A.; Wouters, B. G.; Lambin, P. Radiother. Oncol., in press.
26. Winum J.-Y., Scozzafava A., Montero J.-L., and Supuran C.T. Curr. Top. Med. Chem. 7 (2007) 835
27. Colinas P.A., and Bravo R.D. Org. Lett. 5 (2003) 4509
28. Colinas P.A., and Bravo R.D. Tetrahedron Lett. 46 (2005) 1687
29. Colinas, P. A.; Bravo, R. D. unpublished results.
30. 13 and represent means from at least three different determinations. Enzyme concentrations in the assay system were: 9.2 nM for hCA I, 7.6 nM for hCA II, 12.5 nM for hCA IV, 14 nM for hCA IX, and 13 nM for hCA XII.
31. Vullo D., Innocenti A., Nishimori I., Pastorek J., Scozzafava A., Pastorekova S., and Supuran C.T. Bioorg. Med. Chem. Lett. 15 (2005) 963
32. Innocenti A., Firnges M., Antel J., Wurl M., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 14 (2004) 5769
33. Pastorekova S., Kopacek J., and Pastorek J. Curr. Top. Med. Chem. 7 (2007) 865
34. Pastorekova S., and Pastorek J. Cancer-related carbonic anhydrase isozymes and their inhibition. In: Supuran C.T., Scozzafava A., and Conway J. (Eds). Carbonic Anhydrase. Its Inhibitors and Activators (2004), CRC Press, Boca Raton (FL) 255-281