Carbonic anhydrase inhibitors: Inhibition of human cytosolic isozyme II and mitochondrial isozyme V with a series of benzene sulfonamide derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 22, 2004, Pages 5703-5707

  Innocenti, Alessio ^a   Antel, Jochen ^b   Wurl, Michael ^b   Scozzafava, Andrea ^a   Supuran, Claudiu T ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b Solvay Pharmaceuticals GmbH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENESULFONAMIDE DERIVATIVE; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE V; MITOCHONDRIAL ENZYME;

ARTICLE; DRUG DESIGN; DRUG EFFECT; DRUG SPECIFICITY; DRUG TARGETING; ENZYME INHIBITION; IC 50;

BENZENE DERIVATIVES; CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASE V; CYTOSOL; HUMANS; ISOENZYMES; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 5144220555     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.07.085     Document Type: Article

References (33)

1. C.T. Supuran, A. Scozzafava, and J. Conway Carbonic Anhydraseâ €"its inhibitors and activators 2004 CRC Boca Raton (FL), USA pp 1â€"363, and references cited therein
2. C.T. Supuran, A. Scozzafava, and A. Casini Med. Res. Rev. 23 2003 146 189
3. C.T. Supuran, and A. Scozzafava Exp. Opin. Ther. Patents 12 2002 217 242
4. K.S. Smith, and J.G. Ferry FEMS Microbiol. Rev. 24 2000 335 366
5. A. Scozzafava, A. Mastrolorenzo, and C.T. Supuran Exp. Opin. Ther. Patents 14 2004 67 702
6. D. Vullo, M. Franchi, E. Gallori, J. Pastorek, A. Scozzafava, S. Pastorekova, and C.T. Supuran Bioorg. Med. Chem. Lett. 13 2003 1005 1009
7. M.A. Ilies, D. Vullo, J. Pastorek, A. Scozzafava, M. Ilies, M.T. Caproiu, S. Pastorekova, and C.T. Supuran J. Med. Chem. 46 2003 2187 2196
8. J.-Y. Winum, D. Vullo, A. Casini, J.-L. Montero, A. Scozzafava, and C.T. Supuran J. Med. Chem. 46 2003 2197 2204
9. S. Pastorekova, A. Casini, A. Scozzafava, D. Vullo, J. Pastorek, and C.T. Supuran Bioorg. Med. Chem. Lett. 14 2004 869 873
10. J.R. Casey, P.E. Morgan, D. Vullo, A. Scozzafava, A. Mastrolorenzo, and C.T. Supuran J. Med. Chem. 47 2004 2337 2347
11. C.T. Supuran Exp. Opin. Investig. Drugs 12 2003 283 287
12. F. Abbate, A. Casini, T. Owa, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 14 2004 217 223
13. S.J. Dodgson J. Appl. Physiol. 63 1987 2134 2141
14. S.J. Dodgson, and K. Cherian Am. J. Physiol. 257 1989 E791 E796
15. I.M. Spencer, I. Hargreaves, and W.R. Chegwidden Biochem. Soc. Trans. 16 1988 973 974
16. W.R. Chegwidden, S.J. Dodgson, and I.M. Spencer W.R. Chegwidden Y. Edwards N. Carter The Carbonic Anhydrases - New Horizons 2000 Birkhäuser Basel 343 363
17. C.J. Lynch, H. Fox, S.A. Hazen, B.A. Stanley, S.J. Dodgson, and K.F. Lanoue Biochem. J. 310 1995 197 202
18. S.A. Hazen, A. Waheed, W.S. Sly, K.F. Lanoue, and C.J. Lynch FASEB J. 10 1996 481 490
19. P.V. Atwood Int. J. Biochem. Cell Biol. 27 1995 231 249
20. J.B. Alldred, and K.E. Reilly Prog. Lipid Res. 35 1997 371 385
21. R.E. Forster, and S.J. Dodgson W.R. Chegwidden Y. Edwards N. Carter The Carbonic Anhydrases - New Horizons 2000, Birkhäuser Basel 263 280
22. C.T. Supuran Exp. Opin. Ther. Patents 13 2003 1545 1550
23. S. Pastorekova, S. Parkkila, J. Pastorek, and C.T. Supuran J. Enz. Inhib. Med. Chem. 19 2004 199 229
24. D. Vullo, M. Franchi, E. Gallori, J. Antel, A. Scozzafava, and C.T. Supuran J. Med. Chem. 47 2004 1272 1279
25. Hebebrand, J.; Antel, J.; Preuschoff, U.; David, S.; Sann, H.; Weske, M. WO Patent 2002, 07821
26. Winum, J.-Y.; Dogné, J. M.; Casini, A.; de Leval, X.; Montero, J. L.; Scozzafava, A.; Vullo, D.; Innocenti, A.; Supuran, C. T. J. Med. Chem., in press
27. A. Casini, A. Scozzafava, F. Mincione, L. Menabuoni, M.A. Ilies, and C.T. Supuran J. Med. Chem. 43 2000 4884 4892
28. A. Scozzafava, L. Menabuoni, F. Mincione, F. Briganti, G. Mincione, and C.T. Supuran J. Med. Chem. 42 1999 2641 2650
29. A. Scozzafava, and C.T. Supuran J. Enz. Inhib. 13 1998 103 123
30. 2 solutions in water at 20°C were used as substrate. Stock solutions of inhibitors were prepared at a concentration of 10-50 mM (in the assay buffer) and dilutions up to 0.1 μM done with the assay buffer mentioned above. Enzyme concentrations were 1 μM for both CA II and CA V. Inhibition constants were calculated as described by R.G. Khalifah J. Biol. Chem. 246 1971 2561 2573
31. M. Franchi, D. Vullo, E. Gallori, J. Antel, M. Wurl, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 13 2003 2857 2861
32. 30 and that of the truncated form were practically identical, but the truncated form is much more stable than the full length one
33. R.G. Khalifah, D.J. Strader, S.H. Bryant, and S.M. Gibson Biochemistry 16 1977 2241 2247