New zinc binding motifs in the design of selective carbonic anhydrase inhibitors

Mini-Reviews in Medicinal Chemistry

Volumn 6, Issue 8, 2006, Pages 921-936

  Winum, Jean Yves ^a   Scozzafava, Andrea ^b   Montero, Jean Louis ^a   Supuran, Claudiu T ^b  

^a UNIV MONTPELLIER   (France)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Cyanamide; Hydroxyurea; Sulfamate anchoring group; Unsubstituted sulfonamides; Zinc binding function (ZBF)

Indexed keywords

ACETAZOLAMIDE; ANTICONVULSIVE AGENT; ANTIGLAUCOMA AGENT; ANTINEOPLASTIC AGENT; ANTIOBESITY AGENT; ANTIULCER AGENT; BICARBONATE; CARBON DIOXIDE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IV; CARBONATE DEHYDRATASE IX; CYANAMIDE; DIURETIC AGENT; HYDROGEN; HYDROLYASE INHIBITOR; HYDROXYUREA; ISOENZYME; RWJ 37497; SULFAMIDE DERIVATIVE; SULFANILAMIDE; SULFONAMIDE; TOPIRAMATE; UNCLASSIFIED DRUG; UREA DERIVATIVE; ZINC;

ARTICLE; BINDING KINETICS; DRUG DESIGN; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG TARGETING; ENZYME DEGRADATION; ENZYME INHIBITION; EPILEPSY; GLAUCOMA; HUMAN; HYDROGEN BOND; MALIGNANT NEOPLASTIC DISEASE; MEDICAL LITERATURE; NEUROLOGIC DISEASE; NEUROMUSCULAR DISEASE; OBESITY; PATHOPHYSIOLOGY; PROTEIN MOTIF; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; ULCER;

BINDING SITES; CARBONIC ANHYDRASE INHIBITORS; CATALYSIS; DRUG DESIGN; ISOENZYMES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; SULFONIC ACIDS; ZINC;

EID: 33746934196     PISSN: 13895575     EISSN: None     Source Type: Journal    
DOI: 10.2174/138955706777934946     Document Type: Article

References (47)

1. The Biological Chemistry of the Elements. The Inorganic Chemistry of Life, J.J.R. Frausto da Silva; R.J.P. Williams Eds., 2nd ed., Oxford University Press, New York, 2001.
2. Hernick, M.; Fierke, C.A. Arch. Biochem. Biophys., 2005, 433, 71-84.
3. Parkin, G. Chem. Rev., 2004, 104, 699-767.
4. Carbonic anhydrase - Its Inhibitors and Activators; Supuran, C. T.; Scozzafava, A.; Conway, J., Eds.; CRC Press: Boca Raton, London, New York, 2004.
5. Scozzafava, A.; Mastrolorenzo, A.; Supuran, CT. Expert Opin. Ther. Patents, 2004, 14, 667-702.
6. Pastorekova, S.; Parkkila, S.; Pastorek, J.; Supuran, C. T. J. Enz. Inhib. Med. Chem., 2004, 19, 199-229.
7. Supuran, C. T.; Scozzafava, A.; Casini, A. Med Res. Rev., 2003, 23, 146-89.
8. Krebs, H.A. Biochem. J, 1948, 43, 525-528.
9. Supuran, C.T.; Scozzafava, A. Expert Opin. Ther. Patents, 2002, 12, 217-242.
10. Supuran, C.T.; Scozzafava, A. Matrix metalloproteinases (MMPs). In Proteinase and Peptidase Inhibition: Recent Potential Targets for Drug Development, Smith, H.J.; Simons, C. Eds., Taylor & Francis, London & New York, pp. 35-61, 2002.
11. Briganti, F.; Pierattelli, A.; Scozzafava, A.; Supuran, C.T., Eur. J. Med. Chem., 1996, 31, 1001-1010.
12. Mincione, F.; Menabuoni, L.; Briganti, F.; Mincione, G.; Scozzafava, A.; Supuran, C.T. J. Enz. Inhib., 1998, 13, 267-284.
13. Supuran, C.T.; Scozzafava, A.; Briganti, F. J. Enz. Inhib., 1999, 14, 289-306.
14. Scozzafava, A.; Supuran, C.T. J. Med. Chem., 2000, 43, 3677-3687.
15. Scozzafava, A.; Banciu, M.D.; Popescu, A.; Supuran, C.T. J. Enz. Inhib., 2000, 15, 443-453.
16. Fenesan, L; Popescu, R.; Scozzafava, A.; Crucin, V.; Mateiciuc, E.; Bauer, R.; Ilies, M.A.; Supuran, C.T. J Enz. Inhib., 2000, 15, 297-310.
17. Scolnick, L.R.; Clements, A.M.; Liao, J.; Crenshaw, L.; Hellberg, M.; May, J., Dean, T.R.; and Christianson, D.W. J. Am. Chem. Soc., 1997, 119, 850-851.
18. (a) Winum, J-Y.; Scozzafava, A.; Montero, J-L.; Supuran, C.T. Med Res. Rev., 2005, 25, 186-228.
19. (b) Winum, J-Y.; Scozzafava, A.; Montero, J-L.; Supuran, C.T. Expert Opin. Ther. Patents, 2004, 14, 1273-1308.
20. Lo, Y.S.; Nolan, J.C.; Maren, T.H.; Welstead, W.J.; Gripshover, D.F.; Shamblee, D.A. J. Med Chem., 1992, 35, 4790-4794.
21. Abbate, F.; Supuran, CT.; Scozzafava, A.; Orioli, P.; Stubbs, M.T.; Klebe, G. J. Med. Chem., 2002, 45, 3583-3587.
22. Maryanoff, B.E.; Nortey, S.O.; Gardocki, J.F.; Shank, R.P.; Dodgson, S.P. J. Med. Chem., 1987, 30, 880-887.
23. Maryanoff, B.E.; Costanzo, M.J.; Nortey, S.O.; Greco, M.N.; Shank, R.P.; Schupsky, J.J.; Ortegon, M.P.; Vaught, J.L. J. Med Chem., 1998, 41, 1315-1343.
24. Recacha, R.; Costanzo, M.J.; Maryanoff, B.E.; Chaftopadhyay, D. Biochem. J., 2002, 361, 437-441.
25. Casini, A.; Antel, J.; Abbate, F.; Scozzafava, A.; David, S.; Waldeck, H.; Schafer, S.; Supuran, C.T. Bioorg. Med. Chem. Lett., 2003, 13, 841-845.
26. Antel, J.; Weber, A.; Sotriffer, C.A.; Klebe, G. In Carbonic anhydrase - Its inhibitors and activators, Supuran CT, Scozzafava A, Conway J Eds, CRC Press, Boca Raton (FL), USA, 2004; pp. 45-66.
27. Nussbaumer, P.; Billich, A. Expert Opin. Ther. Patents, 2003, 13, 605-625.
28. Vicker, N.; Ho, Y.; Robinson, J.; Woo, L.L.; Purohit, A.; Reed, M.J.; Potter, B.V. Bioorg. Med. Chem. Left., 2003, 13, 863-865.
29. Ho, Y.T.; Purohit, A.; Vicker, N.; Newman, S.P.; Robinson, J.J., Leese, M.P.; Ganeshapillai, D.; Woo, L.W.L., Potter, B.V., Reed, M.J. Biochem. Biophys. Res. Commun., 2003, 305, 909-914.
30. Abbate, F.; Winum, J.Y.; Potter, B.V.; Casini, A.; Montero, J.L.; Scozzafava, A.; Supuran, C.T. Moorg. Med Chem. Lett., 2004, 14, 231-234.
31. Pastorekova. S, Pastorek J. Cancer-related carbonic anhydrase isozymes. In Carbonic Anhydrase - Its Inhibitors and Activators, Supuran, C.T.; Scozzafava, A.; Conway, J.; Eds, CRC Press, Boca Raton (FL), USA, 2004, pp. 253-280.
32. Winum, J.Y.; Vullo, D.; Casini, A.; Montero, J-L.; Scozzafava, A.; Supuran, C.T. J. Med. Chem., 2003, 46, 2197-2204.
33. Winum, J.Y.; Vullo, D.; Casini, A.; Montero, J.L.; Scozzafava, A.; Supuran, C.T. J. Med. Chem., 2003, 46, 5471-5477.
34. Bonnac, L.; Innocenti, A.; Winum, J.Y.; Casini, A.; Montero, J.L. Scozzafava, A.; Barragan, V.; Supuran, C.T. J. Enz. Inhib. Med. Chem, 2004, 19, 287-291.
35. Winum, J.Y.; Scozzafava, A.; Montern, J.L.; Supuran, C.T. Expert Opin. Ther. Patents, 2006, 16, 27-47.
36. Casini, A.; Winum, J.Y.; Montero, J.L.; Scozzafava, A.; Supuran, C.T. Bioorg. Med. Chem. Lett., 2003, 13, 837-840.
37. Winum, J.Y.; Innocenti, A.; Nast, J.; Montero, J.L.; Scozzafava, A.; Vullo, D.; Supuran, C.T. Bioorg. Med. Chem. Lett., 2005, 15, 2353-2358.
38. Winum, J.Y.; Cecchi, A.; Montero, I.L.; Innocenti, A.; Scozzafava, A.; Supuran, C.T. Bioorg. Med. Chem. Lett., 2005, 15, 3302-3306.
39. (a) Kurzer, F.; Douragbi-Zadeh, K. Chem. Rev., 1967, 67,107-152;
40. (b) Rabalais, J.W.; McDonald, J.M.; Scherr, V.; McGlynn S.P. Chem. Rev., 1971, 71, 73-95.
41. Khalifah, R.G. J. Biol. Chem., 1971, 246, 2561-2573.
42. Supuran, C.T.; Conroy, C.W.; Maren, T.H. Proteins Struct. Funct. Genet., 1997, 27, 272-278.
43. Briganti, F.; Mangani, S.; Scozzafava, A.; Vernaglione, G.; Supuran, CT. J. Biol. Inorg. Chem., 1999, 4, 528-36.
44. Rogers, J.L; Mukherjee, J.; Khalifah, R.G. Biochemistry, 1987,26, 5672-5679.
45. Xue, Y.; Vidgren, J.; Svensson, L.A.; Liljas, A.; Jonsson, B.H.; Lindskog, S. Proteins Struct. Funct. Genet., 1993, 15, 80-87.
46. Guerri, A.; Briganti, F.; Scozzafava, A.; Supuran, C.T.; Mangani, S. Biochemistry, 2000, 39, 12391-12397.
47. Scozzafava, A.; Supuran, C.T. Bioorg. Med. Chem., 2003, 11, 2241-2246.