Carbonic anhydrase inhibitors: Inhibition of cytosolic/tumor-associated isoforms I, II, and IX with iminodiacetic carboxylates/hydroxamates also incorporating benzenesulfonamide moieties

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 6, 2007, Pages 1538-1543

  Santos, M Amelia ^a   Marques, Sergio ^a   Vullo, Daniela ^b   Innocenti, Alessio ^b   Scozzafava, Andrea ^b   Supuran, Claudiu T ^b  

^a INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Carbonic anhydrase; Carboxylate; Cytosolic isozyme; Hydroxamate; Sulfonamide; Tumor associated isozyme IX; Zinc binding function

Indexed keywords

ACETAZOLAMIDE; BENZENESULFONAMIDE DERIVATIVE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IX; CARBOXYLIC ACID DERIVATIVE; DIGLYCINE; ETHOXZOLAMIDE; HYDROXAMIC ACID DERIVATIVE; INDISULAM; ISOENZYME; MATRIX METALLOPROTEINASE; MEMBRANE ENZYME; METHAZOLAMIDE; SULPIRIDE; ZINC; ZONISAMIDE;

ARTICLE; CYTOSOL; DRUG DESIGN; DRUG SELECTIVITY; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION;

CARBONIC ANHYDRASE INHIBITORS; CELL MEMBRANE; CYTOSOL; HUMANS; HYDROXAMIC ACIDS; INDICATORS AND REAGENTS; ISOENZYMES; NEOPLASMS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 33847161733     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.12.107     Document Type: Article

References (41)

1. Supuran C.T., and Scozzafava A. Metalloproteinase - collagenase inhibitors examples. In: Smith H.J., and Simons C. (Eds). Enzymes and their Inhibition-Drug Development (2005), CRC Press, Boca Raton, London and New York 292-300
2. Supuran C.T., and Scozzafava A. Matrix metalloproteinases (MMPs). In: Smith H.J., and Simons C. (Eds). Proteinase and Peptidase Inhibition: Recent Potential Targets for Drug Development (2002), Taylor & Francis, London & New York 35-61
3. Supuran C.T., Scozzafava A., and Conway J. Carbonic Anhydrase-Its Inhibitors and Activators (2004), CRC Press, Boca Raton, New York, London
4. Pastorekova S., Parkkila S., and Zavada J. Adv. Clin. Chem. 42 (2006) 167
5. Scozzafava A., Mastrolorenzo A., and Supuran C.T. Expert Opin. Ther. Pat. 16 (2006) 1627
6. Pastorekova S., Parkkila S., Pastorek J., and Supuran C.T. J. Enzyme Inhib. Med. Chem. 19 (2004) 199
7. Supuran C.T., Scozzafava A., and Casini A. Development of sulfonamide carbonic anhydrase inhibitors. In: Supuran C.T., Scozzafava A., and Conway J. (Eds). Carbonic Anhydrase-Its Inhibitors and Activators (2004), CRC Press, Boca Raton 67-147
8. Supuran C.T., Scozzafava A., and Casini A. Med. Res. Rev. 23 (2003) 146
9. Scozzafava A., Mastrolorenzo A., and Supuran C.T. Expert Opin. Ther. Pat. 14 (2004) 667
10. Winum J.Y., Scozzafava A., Montero J.L., and Supuran C.T. Med. Res. Rev. 25 (2005) 186
11. Winum J.-Y., Scozzafava A., Montero J.-L., and Supuran C.T. Expert Opin. Ther. Pat. 16 (2006) 27
12. Weber A., Casini A., Heine A., Kuhn D., Supuran C.T., Scozzafava A., and Klebe G. J. Med. Chem. 47 (2004) 550
13. Menchise V., De Simone G., Alterio V., Di Fiore A., Pedone C., Scozzafava A., and Supuran C.T. J. Med. Chem. 48 (2005) 5721
14. De Simone G., Di Fiore A., Menchise V., Pedone C., Antel J., Casini A., Scozzafava A., Wurl M., and Supuran C.T. Biorg. Med. Chem. Lett. 15 (2005) 2315
15. Casini A., Antel J., Abbate F., Scozzafava A., David S., Waldeck H., Schafer S., and Supuran C.T. Bioorg. Med. Chem. Lett. 13 (2003) 841
16. Abbate F., Coetzee A., Casini A., Ciattini S., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 14 (2004) 337
17. Abbate F., Casini A., Owa T., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 14 (2004) 217
18. Scozzafava A., and Supuran C.T. J. Med. Chem. 43 (2000) 3677
19. Santos M.A., Marques S., Gil M., Tegoni M., Scozzafava A., and Supuran C.T. J. Enzyme Inhib. Med. Chem. 18 (2003) 233
20. Whittaker M., Floyd C.D., Brown P., and Gearing A.J.H. Chem. Rev. 99 (1999) 2735
21. Leung D., Abbenante G., and Fairlie D.P. J. Med. Chem. 43 (2000) 305
22. Campestre C., Agamennone M., Tortorella P., Prezioso S., Biasone A., Gavazzo E., Pochetti G., Mazza F., Hiller O., Tschesche H., Consalvi V., and Gallina C. Bioorg. Med. Chem. Lett. 16 (2006) 20
23. Grams F., Crimmin M., Hinnes L., Huxley P., Pieper M., Tschesche H., and Bode W. Biochemistry 34 (1995) 14012
24. Grams F., Reinemer P., Powers J.C., Kleine T., Pieper M., and Tschesche H. Eur. J. Biochem. 228 (1995) 830
25. Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. 11 (2003) 2241
26. Temperini C., Innocenti A., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 16 (2006) 4316
27. 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
28. Yamamoto M., Hirayama R., Naruse K., Yoshino K., Shimada A., Inoue S., Kayagaki N., Yagita H., Okumura K., and Ikeda S. Drug Des. Discov. 16 (1999) 119
29. 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
30. 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
31. Tuccinardi T., Martinelli A., Nuti E., Carelli P., Balzano F., Uccello-Baretta G., Murphy G., and Rossello A. Bioorg. Med. Chem. 14 (2006) 4260
32. Nagase H., and Woessner Jr. J.F. J. Biol. Chem. 274 (1999) 21491
33. 3: 668.15187; found 668.15165.
34. Santos M.A., Marques S.M., Tuccinardi T., Carelli P., Panelli L., and Rossello A. Bioorg. Med. Chem. 14 (2006) 7539
35. Marques S.M., Chaves S., Rossello A., Tuccinardi T., and Santos M.A. Metal Ions in Biology and Medicine Vol. 9 (2006), John Libbey Eurotext, Paris pp. 117-121
36. Chaves S., Marques S.M., Cachudo A., Esteves M.A., and Santos M.A. Eur. J. Inorg. Biochem. (2006) 3853
37. Thiry A., Dogné J.-M., Masereel B., and Supuran C.T. Trends Pharmacol. Sci. 27 (2006) 566
38. 15,18
39. Temperini C., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 16 (2006) 5152
40. Nishimori I., Vullo D., Innocenti A., Scozzafava A., Mastrolorenzo A., and Supuran C.T. Bioorg. Med. Chem. Lett. 15 (2005) 3828
41. Wilkinson B.L., Bornaghi L.F., Houston T.A., Innocenti A., Supuran C.T., and Poulsen S.A. J. Med. Chem. 49 (2006) 6539