Carbonic anhydrase inhibitors. Inhibition of the cytosolic human isozymes I and II, and the transmembrane, tumor-associated isozymes IX and XII with substituted aromatic sulfonamides activatable in hypoxic tumors

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 18, 2006, Pages 4846-4851

  Saczewski, Franciszek ^a   Sławiński, Jarosław ^a   Kornicka, Anita ^a   Brzozowski, Zdzisław ^a   Pomarnacka, Elzbieta ^a   Innocenti, Alessio ^b   Scozzafava, Andrea ^b   Supuran, Claudiu T ^b  

^a MEDICAL UNIVERSITY OF GDANSK   (Poland)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Carbonic anhydrase; Disulfides; Hypoxia; Prodrug; Sulfonamides; Tumor

Indexed keywords

ANTINEOPLASTIC AGENT; AROMATIC COMPOUND; BENZENESULFONAMIDE DERIVATIVE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IX; CARBONIC DEHYDRATASE XII; DISULFIDE; ISOENZYME; SULFONAMIDE; SULFONE DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ENZYME INHIBITION; HYPOXIA; OXIDATION; SOLID TUMOR; SUBSTITUTION REACTION;

CARBONIC ANHYDRASE INHIBITORS; CELL HYPOXIA; CELL MEMBRANE; CYTOSOL; HUMANS; ISOENZYMES; MOLECULAR STRUCTURE; NEOPLASMS; SULFONAMIDES; WATER;

EID: 33746836508     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.06.064     Document Type: Article

References (35)

1. Harris A.L. Nat. Rev. Cancer 2 (2002) 38
2. Denny W.A. Expert Opin. Ther. Pat. 15 (2005) 635
3. Stubbs M., McSheehy P.M.J., Griffiths J.R., and Bashford C.L. Mol. Med. Today 6 (2000) 15
4. Helmlinger G., Sckell A., Dellian M., Forbes N.S., and Jain R.K. Clin. Cancer Res. 8 (2002) 1284
5. Fukumura D., Xu L., Chen Y., Gohongi T., Seed B., and Jain R.K. Cancer Res. 61 (2001) 6020
6. Kato Y., Nakayama Y., Umeda M., and Miyazaki K. J. Biol. Chem. 267 (1992) 11424
7. Martinez-Zaguilan R., Lynch R.M., Martinez G.M., and Gillies R.J. Clin. Exp. Metastasis 14 (1992) 176
8. Fischer B., Müller B., Fischer K.G., Baur N., and Kreutz W. Clin. Immunol. 96 (2000) 252
9. Supuran C.T., Scozzafava A., and Casini A. Med. Res. Rev. 23 (2003) 146
10. In: Supuran C.T., Scozzafava A., and Conway J. (Eds). Carbonic Anhydrase-Its Inhibitors and Activators (2004), CRC Press (Taylor and Francis Group), Boca Raton, Florida 1 and references cited therein
11. Casini A., Scozzafava A., Mastrolorenzo A., and Supuran C.T. Curr. Cancer Drug Targets 2 (2002) 55
12. Pastorekova S., Parkkila S., Pastorek J., and Supuran C.T. J. Enzyme Inhib. Med. Chem. 19 (2004) 199
13. Wykoff C.C., Beasley N.J., Watson P.H., Turner K.J., Pastorek J., Sibtain A., Wilson G.D., Turley H., Talks K.L., Maxwell P.H., Pugh C.W., Ratcliffe P.J., and Harris A.L. Cancer Res. 60 (2000) 7075
14. Potter C.P.S., and Harris A.L. Br. J. Cancer 89 (2003) 2
15. Svastova E., Hulikova A., Rafajova M., Zatovicova M., Gibadulinova A., Casini A., Cecchi A., Scozzafava A., Supuran C.T., Pastorek J., and Pastorekova S. FEBS Lett. 577 (2004) 439
16. 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
17. Vullo D., Innocenti A., Nishimori I., Pastorek J., Scozzafava A., Pastorekova S., and Supuran C.T. Biorg. Med. Chem. Lett. 15 (2005) 963
18. Denny W.A. Eur. J. Med. Chem. 36 (2001) 577
19. Jaffar M., and Stratford I.J. Expert Opin. Ther. Pat. 9 (1999) 1371
20. Mabjeesh N.J., Frazier M.C., Simons J.W., and Zhong H. Expert Opin. Ther. Pat. 12 (2002) 777
21. Sławiński J. Eur. J. Med. Chem. 39 (2004) 179
22. Pomarnacka E., and Kornicka A. Acta Pol. Pharm.-Drug Res. 55 (1998) 297
23. Pastorekova S., Casini A., Scozzafava A., Vullo D., Pastorek J., and Supuran C.T. Bioorg. Med. Chem. Lett. 14 (2004) 869
24. Abbate F., Casini A., Owa T., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 14 (2004) 217
25. Vullo D., Franchi M., Gallori E., Pastorek J., Scozzafava A., Pastorekova S., and Supuran C.T. Bioorg. Med. Chem. Lett. 13 (2003) 1005
26. Supuran C.T. Expert Opin. Investig. Drugs 12 (2003) 283
27. Winum J.Y., Cecchi A., Montero J.L., Innocenti A., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 15 (2005) 3302
28. Khalifah R.G. J. Biol. Chem. 246 (1971) 2561
29. Supuran C.T., Casini A., and Scozzafava A. Development of sulfonamide carbonic anhydrase inhibitors (CAIs). In: Supuran C.T., Scozzafava A., and Conway J. (Eds). Carbonic Anhydrase-Its Inhibitors and Activators (2004), CRC Press, Boca Raton (FL), USA 67
30. Chakravarty S., and Kannan K.K. J. Mol. Biol. 243 (1994) 298
31. Boriack P.A., Christianson D.W., Kingery-Wood J., and Whitesides G.M. J. Med. Chem. 38 (1995) 2286
32. Di Fiore A., De Simone G., Menchise V., Pedone C., Casini A., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 15 (2005) 1937
33. Abbate F., Casini A., Scozzafava A., and Supuran C.T. J. Enzyme Inhib. Med. Chem. 18 (2003) 303
34. Abbate F., Casini A., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 14 (2004) 2357
35. Weber A., Casini A., Heine A., Kuhn D., Supuran C.T., Scozzafava A., and Klebe G. J. Med. Chem. 47 (2004) 550