Carbonic anhydrase inhibitors: Possible anticancer drugs with a novel mechanism of action

Drug Development Research

Volumn 69, Issue 6, 2008, Pages 297-303

  Supuran, Claudiu T ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Anticancer drug; Carbonic anhydrase; Hypoxia; Isoform IX; pH regulation; Sulfonamide; Tumor

Indexed keywords

ANTINEOPLASTIC AGENT; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE III; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IV; CARBONATE DEHYDRATASE IX; CARBONATE DEHYDRATASE V; CARBONATE DEHYDRATASE XII; HYPOXIA INDUCIBLE FACTOR 1ALPHA; SULFAMIDE DERIVATIVE; SULFONAMIDE;

ANTINEOPLASTIC ACTIVITY; DRUG MECHANISM; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME KINETICS; ENZYME LOCALIZATION; HUMAN; HYPOXIA; MALIGNANT NEOPLASTIC DISEASE; NONHUMAN; REVIEW; TUMOR GROWTH;

EID: 57749094149     PISSN: 02724391     EISSN: 10982299     Source Type: Journal    
DOI: 10.1002/ddr.20262     Document Type: Review

References (24)

1. Abbate F, Casini A, Owa T, Scozzafava A, Supuran CT. 2004. Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX. Bioorg Med Chem Lett 14:217-223.
2. Alterio V, Vitale RM, Monti SM, Pedone C, Scozzafava A, Cecchi A, De Simone G, Supuran CT. 2006. Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX. J Am Chem Soc 128:8329-8335.
3. Cecchi A, Supuran CT. 2008. Fluorescence- and spin-labeled carbonic anhydrase inhibitors. Curr Pharm Des 14:699-707.
4. Cecchi A, Hulikova A, Pastorek J, Pastorekova S, Scozzafava A, Winum JY, Montero JL, Supuran CT. 2005. Carbonic anhydrase inhibitors. Design of fluorescent sulfonamides as probes of tumor-associated carbonic anhydrase IX that inhibit isozyme IX-mediated acidification of hypoxic tumors. J Med Chem 48:4834-4841.
5. De Simone G, Vitale RM, Di Fiore A, Pedone C, Scozzafava A, Montero JL, Winum JY, Supuran CT. 2006. Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX J Med Chem 49:5544-5551.
6. Garaj V, Pucetti L, Fasolis G, Winum J-Y, Montero J-L, Scozzafava A, Vullo D, Innocenti A, Supuran CT. 2004. Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating 1,2,4-triazine moieties Bioorg Med Chem Lett 14:5427-5433
7. Hilvo M, Innocenti A, Monti SM, De Simone G, Supuran CT, Parkkila S. 2008a. Recent advances in research on the most novel carbonic anhydrases, CA XIII and XV. Curr Pharm Des 2008;14:672-14:678.
8. Hilvo M, Monti SM, De Simone G, Supuran CT, Parkkila S. 2008b. Biochemical characterization of CA IX, one of the most active carbonic anhydrase isozymes. J Biol Chem (in press).
9. Hockel M, Vaupel P. 2001. Tumor hypoxia: definitions and current clinical, biologic, and molecular aspects. J Natl Cancer Inst 93:266-276.
10. Menchise V, De Simone G, Alterio V, Di Fiore A, Pedone C, Scozzafava A, Supuran CT. 2005. Carbonic anhydrase inhibitors: stacking with Phe131 determines active site binding region of inhibitors as exemplified by the X-ray crystal structure of a membrane-impermeant antitumor sulfonamide complexed with isozyme II. J Med Chem 48:5721-5727.
11. Owa T, Yoshino H, Okauchi T, Yoshimatsu K, Ozawa Y, Sugi NH, Nagasu T, Koyanagi N, Kitoh K. 1999. Discovery of novel antitumor sulfonamides targeting G1 phase of the cell cycle. J Med Chem 42: 3789-3799.
12. Parkkila S. 2008. Significance of pH regulation and carbonic anhydrases in tumour progression and implications for diagnostic and therapeutic approaches. BJU Int 101(Suppl 4):16-21.
13. Pastorekova S, Pastorek, J. 2004. Cancer-related carbonic anhydrase isozymes. In: Supuran CT, Scozzafava A, Conway J, editors. Carbonic anhydrase: its inhibitors and activators. Boca Raton: CRC Press. p 253-280.
14. Pastorekova S, Casini A, Scozzafava A, Vullo D, Pastorek J, Supuran CT. 2004. Carbonic anhydrase inhibitors: the first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme IX. Bioorg Med Chem Lett 14:869-873.
15. Pastorekova S, Zatovicova M, Pastorek J. 2008. Cancer-associated carbonic anhydrases and their inhibition. Curr Pharm Des 14:685-698.
16. Semenza GL. 2001. Hypoxia-inducible factor 1: oxygen homeostasis and disease pathophysiology. Trends Mol Med 7:345-350.
17. Supuran, CT. 2003. Indisulam: an anticancer sulfonamide in clinical development. Expert Opin Invest Drugs 12:283-287
18. Supuran CT. 2008. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nature Rev Drug Discov 7:168-181.
19. Supuran CT, Scozzafava A, Casini A. 2003. Carbonic anhydrase inhibitors. Med Res Rev 23:146-189.
20. Svastova E, Hulikova A, Rafajova M, Zatovicova M, Gibadulinova A, Casini A, Cecchi A, Scozzafava A, Supuran CT, Pastorek J, Pastorekova S. 2004. Hypoxia activates the capacity of tumor-associated carbonic anhydrase IX to acidify extracellular pH. FEBS Lett 577:439-445.
21. Swietach P, Wigfield S, Cobden P, Supuran CT, Harris AL, Vaughan-Jones RD. 2008. Tumor-associated carbonic anhydrase 9 spatially co-ordinates intracellular pH in three-dimensional multicellular growths. J Biol Chem 283:20473-20483.
22. Thiry A, Supuran CT, Masereel B, Dogné JM. 2008. Recent developments of carbonic anhydrase inhibitors as potential anticancer drugs. J Med Chem 51:3051-3056.
23. Winum JY, Rami M, Scozzafava A, Montero JL, Supuran C. 2008. Carbonic anhydrase IX: a new druggable target for the design of antitumor agents. Med Res Rev 28:445-463.
24. Wykoff CC, Beasley NJ, Watson PH, Turner KJ, Pastorek J, Sibtain A, Wilson GD, Turley H, Talks KL, Maxwell PH, Pugh CW, Ratcliffe PJ, Harris AL. 2000. Hypoxia-inducible expression of tumor-associated carbonic anhydrases. Cancer Res 60:7075-7083.