Carbonic anhydrase inhibitors. The mitochondrial isozyme VB as a new target for sulfonamide and sulfamate inhibitors

Journal of Medicinal Chemistry

Volumn 48, Issue 24, 2005, Pages 7860-7866

  Nishimori, Isao ^a   Vullo, Daniela ^b   Innocenti, Alessio ^b   Scozzafava, Andrea ^b   Mastrolorenzo, Antonio ^b   Supuran, Claudiu T ^b  

^a KOCHI MEDICAL SCHOOL   (Japan)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAZOLAMIDE; ANTICONVULSIVE AGENT; ANTIGLAUCOMA AGENT; ANTIOBESITY AGENT; BENZENESULFONAMIDE DERIVATIVE; BENZOLAMIDE; BRINZOLAMIDE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE INHIBITOR; DICLOFENAMIDE; DORZOLAMIDE; ETHOXZOLAMIDE; INDISULAM; METHAZOLAMIDE; MITOCHONDRIAL ENZYME; MITOCHONDRIAL ISOZYME VB; ORPHAN DRUG; SULFAMATE INHIBITOR; SULFANILAMIDE DERIVATIVE; SULFONAMIDE; SULPIRIDE; TOPIRAMATE; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG TARGETING; ENZYME INHIBITION; ENZYME KINETICS; ENZYME PURIFICATION; MOLECULAR CLONING; NUCLEOTIDE SEQUENCE; PROTEIN EXPRESSION;

AMINO ACID SEQUENCE; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASE V; CATALYSIS; CLONING, MOLECULAR; HUMANS; ISOENZYMES; KINETICS; MITOCHONDRIA; MOLECULAR SEQUENCE DATA; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; SULFONIC ACIDS;

EID: 28144452672     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050483n     Document Type: Article

References (49)

1. Pastorekova, S.; Parkkila, S.; Pastorek, J.; Supuran, C. T., Carbonic anhydrases: Current state of the art, therapeutic applications and future prospects. J. Enzyme Inhib. Med. Chem. 2004, 19 (3), 199-229.
2. Lehtonen, J.; Shen, B.; Vihinen, M.; Casini, A.; Scozzafava, A.; Supuran, C. T.; Parkkila, A. K.; Saarnio, J.; Kivela, A. J.; Waheed, A.; Sly, W. S.; Parkkila, S., Characterization of CA XIII, a novel member of the carbonic anhydrase isozyme family. J. Biol. Chem. 2004, 279 (4), 2719-27.
3. Supuran, C. T.; Scozzafava, A.; Casini, A., Carbonic anhydrase inhibitors. Med. Res. Rev. 2003, 23 (2), 146-89.
4. Supuran, C. T.; Vullo, D.; Manole, G.; Casini, A.; Scozzafava, A. Designing of novel carbonic anhydrase inhibitors and activators. Curr. Med. Chem. Cardiovasc. Hematol. Agents 2004, 2 (1), 49-68.
5. Tashian, R. E.; Venta, P. J.; Nicewander, P. H.; Hewett-Emmett, D., Evolution, structure, and expression of the carbonic anhydrase multigene family. Prog. Clin. Biol. Res. 1990, 344, 159-75.
6. Fujikawa-Adachi, K.; Nishimori, I.; Taguchi, T.; Onishi, S., Human mitochondrial carbonic anhydrase VB. cDNA cloning, mRNA expression, subcellular localization, and mapping to chromosome x. J. Biol. Chem. 1999, 274 (30), 21228-33.
7. Nishimori, I.; Onishi, S., Carbonic anhydrase isozymes in the human pancreas. Dig. Liver Dis. 2001, 33 (1), 68-74.
8. (a) Fujikawa-Adachi, K.; Nishimori, I.; Taguchi, T.; Onishi, S., Human carbonic anhydrase XIV (CA14): cDNA cloning, mRNA expression, and mapping to chromosome 1. Genomics 1999, 61 (1), 74-81;
9. (b) Hilvo, M.; Tolvanen, M.; Clark, A.; Shen, B.; Shah, G. N.; Waheed, A.; Halmi, P.; Hanninen, M.; Vihinen, M.; Sly, W. S.; Parkkila, S. Characterization of CA XV, a new GPI-anchored form of carbonic anhydrase. Biochem. J. 2005, in press (Epub August 8, 2005).
10. Dodgson, S. J.; Forster, R. E., 2nd; Storey, B. T.; Mela, L., Mitochondrial carbonic anhydrase. Proc. Natl. Acad. Sci. U.S.A. 1980, 77 (9), 5562-6.
11. Dodgson, S. J.; Forster, R. E., 2nd; Schwed, D. A.; Storey, B. T., Contribution of matrix carbonic anhydrase to citrulline synthesis in isolated guinea pig liver mitochondria. J. Biol. Chem. 1983, 258 (12), 7696-701.
12. Dodgson, S. J.; Forster, R. E., 2nd; Storey, B. T., The role of carbonic anhydrase in hepatocyte metabolism. Ann. N. Y. Acad. Sci. 1984, 429 516-24.
13. Dodgson, S. J.; Forster, R. E., 2nd, Carbonic anhydrase: Inhibition results in decreased urea production by hepatocytes. J. Appl. Physiol. 1986, 60 (2), 646-52.
14. Carter, N. D.; Dodgson, S. J.; Quant, P. A., Expression of hepatic mitochondrial carbonic anhydrase V. Biochim. Biophys. Acta. 1990, 1036 (3), 237-41.
15. Heck, R. W.; Tanhauser, S. M.; Manda, R.; Tu, C.; Laipis, P. J.; Silverman, D. N., Catalytic properties of mouse carbonic anhydrase V. J. Biol. Chem. 1994, 269 (40), 24742-6.
16. Boriack-Sjodin, P. A.; Heck, R. W.; Laipis, P. J.; Silverman, D. N.; Christianson, D. W., Structure determination of murine mitochondrial carbonic anhydrase V at 2.45-A resolution: Implications for catalytic proton transfer and inhibitor design. Proc. Natl. Acad. Sci. U.S.A. 1995, 92 (24), 10949-53.
17. Supuran, C. T.; Scozzafava, A.; Conway, J., Carbonic Anhydrase - Its Inhibitors and Activators. CRC Press: Boca Raton, FL, 2004; pp 1-363.
18. Vullo, D.; Franchi, M.; Gallori, E.; Antel, J.; Scozzafava, A.; Supuran, C. T., Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides. J. Med. Chem. 2004, 47 (5), 1272-9.
19. Winum, J. Y.; Innocenti, A.; Gagnard, V.; Montero, J. L.; Scozzafava, A.; Vullo, D.; Supuran, C. T., Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with organic phosphates and phosphonates. Bioorg. Med. Chem. Lett. 2005, 15 (6), 1683-1686.
20. Innocenti, A.; Vullo, D.; Scozzafava, A.; Casey, J. R.; Supuran, C., Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with carboxylates. Bioorg. Med. Chem. Lett. 2005, 15 (3), 573-8.
21. Innocenti, A.; Antel, J.; Wurl, M.; Scozzafava, A.; Supuran, C. T., Carbonic anhydrase inhibitors: Inhibition of human cytosolic isozyme II and mitochondrial isozyme V with a series of benzene sulfonamide derivatives. Bioorg. Med. Chem. Lett. 2004, 14 (22), 5703-7.
22. Supuran, C. T., Carbonic anhydrase inhibitors in the treatment and prophylaxis of obesity. Expert Opin. Ther. Pat. 2003, 13, 1545-1550.
23. Winum, J. Y.; Scozzafava, A.; Montera, J. L.; Supuran, C. T., Sulfamates and their therapeutic potential. Med. Res. Rev. 2005, 25, 186-228.
24. Hazen, S. A.; Waheed, A.; Sly, W. S.; LaNoue, K. F.; Lynch, C. J., Differentiation-dependent expression of CA V and the role of carbonic anhydrase isozymes in pyruvate carboxylation in adipocytes. Faseb. J. 1996, 10 (4), 481-90.
25. Supuran, C. T.; Scozzafava, A., Carbonic anhydrase inhibitors and their therapeutic potential. Expert Opin. Ther. Pat. 2000, 10, 575-600.
26. Supuran, C. T.; Scozzafava, A. Applications of carbonic anhydrase inhibitors and activators in therapy. Expert Opin. Ther. Pat. 2002, 12, 217-242.
27. Scozzafava, A.; Mastrolorenzo, A.; Supuran, C. T., Modulation of carbonic anhydrase activity and its applications in therapy. Expert Opin. Ther. Pat. 2004, 14, 667-702.
28. Abbate, F.; Casini, A.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the perfluorobenzoyl analogue of methazolamide. Implications for the drug design of fluorinated inhibitors. J. Enzyme Inhib. Med. Chem. 2003, 18 (4), 303-8.
29. Supuran, C. T., Carbonic anhydrases: Catalytic and inhibition mechanisms, distribution and physiological roles. In Carbonic anhydrase-Its inhibitors and activators, Supuran, C. T.; Scozzafava, A.; Conway, J., Eds. CRC Press: Boca Raton, FL, 2004; pp 1-23.
30. Supuran, C. T.; Scozzafava, A.; Casini, A. Development of sulfonamide carbonic anhydrase inhibitors. In Carbonic anhydrase-Its inhibitors and activators, Supuran, C. T.; Scozzafava, A.; Conway, J., Eds. CRC Press: Boca Raton, FL, 2004; pp 67-147.
31. Shah, G. N.; Hewett-Emmett, D.; Grubb, J. H.; Migas, M. C.; Fleming, R. E.; Waheed, A.; Sly, W. S., Mitochondrial carbonic anhydrase CA VB: Differences in tissue distribution and pattern of evolution from those of CA VA suggest distinct physiological roles. Proc. Natl. Acad. Sci. U.S.A. 2000, 97 (4), 1677-82.
32. Liddell, N. E.; Maren, T. H. CO2 retention as a basis for increased toxicity of salicylate with acetazolamide: Avoidance of increased toxicity with benzolamide. J. Pharmacol. Exp. Ther. 1975, 195 (1), 1-7.
33. Casini, A.; Antel, J.; Abbate, F.; Scozzafava, A.; David, S.; Waldeck, H.; Schafer, S.; Supuran, C. T., Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with isozymes I, II and IV. Bioorg. Med. Chem. Lett. 2003, 13 (5), 841-5.
34. Abbate, F.; Coetzee, A.; Casini, A.; Ciattini, S.; Scozzafava, A.; Supuran, C. T., Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the antipsychotic drug sulpiride. Bioorg. Med. Chem. Lett. 2004, 14 (2), 337-41.
35. Abbate, F.; Casini, A.; Owa, T.; Scozzafava, A.; Supuran, C. T., 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. 2004, 14 (1), 217-23.
36. Ilies, M. A.; Vullo, D.; Pastorek, J.; Scozzafava, A.; Ilies, M.; Caproiu, M. T.; Pastorekova, S.; Supuran, C. T. Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX by halogenosulfanilamide and halogenophenylaminobenzolamide derivatives. J. Med. Chem. 2003, 46 (11), 2187-96.
37. Scozzafava, A.; Briganti, F.; Mincione, G.; Menabuoni, L.; Mincione, F.; Supuran, C. T., Carbonic anhydrase inhibitors: Synthesis of water-soluble, aminoacyl/dipeptidyl sulfonamides possessing long-lasting intraocular pressure-lowering properties via the topical route. J. Med. Chem. 1999, 42 (18), 3690-700.
38. Scozzafava, A.; Menabuoni, L.; Mincione, F.; Briganti, F.; Mincione, G.; Supuran, C. T., Carbonic anhydrase inhibitors. Synthesis of water-soluble, topically effective, intraocular pressure-lowering aromatic/heterocyclic sulfonamides containing cationic or anionic moieties: Is the tail more important than the ring? J. Med. Chem. 1999, 42 (14), 2641-50.
39. Supuran, C. T.; Clare, B. W., Quantum theoretic QSAR of benzene derivatives: Some enzyme inhibitors. J. Enzyme Inhib. Med. Chem. 2004, 19 (3), 237-48.
40. Winum, J. Y.; Dogne, J. M.; Casini, A.; de Levai, X.; Montero, J. L.; Scozzafava, A.; Vullo, D.; Innocenti, A.; Supuran, C. T., Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic/membrane-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating hydrazino moieties. J. Med. Chem. 2005, 48 (6), 2121-5.
41. Vullo, D.; Voipio, J.; Innocenti, A.; Rivera, C.; Ranki, H.; Scozzafava, A.; Kaila, K.; Supuran, C. T., Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides. Bioorg. Med. Chem. Lett. 2005, 15 (4), 971-6.
42. Vullo, D.; Innocenti, A.; Nishimori, L; Pastorek, J.; Scozzafava, A.; Pastorekova, S.; Supuran, C. T., Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides-a new target for the design of antitumor and antiglaucoma drugs? Bioorg. Med. Chem. Lett. 2005, 15 (4), 963-9.
43. Winum, J. Y.; Pastorekova, S.; Jakubickova, L.; Montero, J. L.; Scozzafava, A.; Pastorek, J.; Vullo, D.; Innocenti, A.; Supuran, C. T., Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with bis-sulfamates. Bioorg. Med. Chem. Lett. 2005, 15 (3), 579-84.
44. Okuyama, T.; Sato, S.; Zhu, X. L.; Waheed, A.; Sly, W. S., Human carbonic anhydrase IV: cDNA cloning, sequence comparison, and expression in COS cell membranes. Proc. Natl. Acad. Sci. U.S.A. 1992, 89 (4), 1315-9.
45. Tashian, R. E. The carbonic anhydrases: Widening perspectives on their evolution, expression and function. Bioessays 1989, 10 (6), 186-92.
46. Fiore, A. D.; Simone, G. D.; Menchise, V.; Pedone, C.; Casini, A.; Scozzafava, A.; Supuran, C. T., Carbonic anhydrase inhibitors: X-ray crystal structure of a benzenesulfonamide strong CA II and CA IX inhibitor bearing a pentafluorophenylaminothioureido tail in complex with isozyme II. Bioorg. Med. Chem. Lett. 2005, 15 (7), 1937-1942.
47. Svastova, E.; Hulikova, A.; Rafajova, M.; Zat'ovicova, M.; Gibadulinova, A.; Casini, A.; Cecchi, A.; Scozzafava, A.; Supuran, C. T.; Pastorek, J.; Pastorekova, S., Hypoxia activates the capacity of tumor-associated carbonic anhydrase IX to acidify extracellular pH. FEBS Lett. 2004, 577 (3), 439-45.
48. Khalifah, R. G.; Strader, D. J.; Bryant, S. H.; Gibson, S. M., Carbon-13 nuclear magnetic resonance probe of active-site ionizations in human carbonic anhydrase B. Biochemistry 1977, 16 (10), 2241-7.
49. Khalifah, R. G., The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J. Biol. Chem. 1971, 246 (8), 2561-73.