Carbonic anhydrase inhibitors. X-ray crystal studies of the carbonic anhydrase II-trithiocarbonate adduct-An inhibitor mimicking the sulfonamide and urea binding to the enzyme

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 2, 2010, Pages 474-478

  Temperini, Claudia ^a   Scozzafava, Andrea ^a   Supuran, Claudiu T ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Anion inhibitor; Carbonic anhydrase; Sulfonamide; Trithiocarbonate; Urea; X ray crystallography

Indexed keywords

CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONIC ACID DERIVATIVE; SULFONAMIDE; TRITHIOCARBONATE; UNCLASSIFIED DRUG; UREA; WATER; ZINC ION;

ARTICLE; BINDING KINETICS; BINDING SITE; CRYSTAL STRUCTURE; DRUG POTENCY; DRUG STRUCTURE; ENZYME ACTIVE SITE; ENZYME BINDING; HYDROGEN BOND; X RAY CRYSTALLOGRAPHY;

BINDING SITES; CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; CATALYTIC DOMAIN; CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; PROTEIN BINDING; SULFONAMIDES; THIONES; UREA;

MAMMALIA;

EID: 72249106865     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.11.124     Document Type: Article

References (41)

1. Innocenti A., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 19 (2009) 1855
2. Franchi M., Vullo D., Gallori E., Antel J., Wurl M., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 13 (2003) 2857
3. Vullo D., Franchi M., Gallori E., Pastorek J., Scozzafava A., Pastorekova S., and Supuran C.T. J. Enzyme Inhib. Med. Chem. 18 (2003) 403
4. 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., and Parkkila S. J. Biol. Chem. 279 (2004) 2719
5. Innocenti A., Lehtonen J.M., Parkkila S., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 14 (2004) 5435
6. Innocenti A., Vullo D., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 15 (2005) 567
7. Innocenti A., Firnges M.A., Antel J., Wurl M., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 14 (2004) 5769
8. Vullo D., Ruusuvuori E., Kaila K., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 16 (2006) 3139
9. Nishimori I., Innocenti A., Vullo D., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 17 (2007) 1037
10. Innocenti A., Vullo D., Pastorek J., Scozzafava A., Pastorekova S., Nishimori I., and Supuran C.T. Bioorg. Med. Chem. Lett. 17 (2007) 1532
11. Nishimori I., Innocenti A., Vullo D., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. 15 (2007) 6742
12. Nishimori I., Minakuchi T., Onishi S., Vullo D., Cecchi A., Scozzafava A., and Supuran C.T. J. Enzyme Inhib. Med. Chem. 29 (2009) 70
13. Innocenti A., Vullo D., Scozzafava A., Casey J.R., and Supuran C.T. Bioorg. Med. Chem. Lett. 15 (2005) 573
14. Supuran C.T. Nat. Rev. Drug Disc. 7 (2008) 168
15. In: Supuran C.T., and Winum J.Y. (Eds). Drug Design of Zinc Enzyme Inhibitors-Functional, Structural, and Disease Applications (2009), Wiley, Hoboken (USA) 1-1022
16. Supuran C.T., Scozzafava A., and Casini A. Med. Res. Rev. 23 (2003) 146
17. Supuran C.T., and Scozzafava A. Exp. Opin. Ther. Patents 12 (2002) 217
18. Pastorekova S., Parkkila S., Pastorek J., and Supuran C.T. J. Enzyme Inhib. Med. Chem. 18 (2004) 199
19. In: Supuran C.T., Scozzafava A., and Conway J. (Eds). Carbonic Anhydrase-Its Inhibitors and Activators (2004), CRC Press, Boca Raton (FL), USA 1-363 and references cited therein
20. Almajan G.L., Innocenti A., Puccetti L., Manole G., Barbuceanu S., Saramet I., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 15 (2005) 2347
21. Supuran C.T., Scozzafava A., Saramet I., and Banciu M.D. J. Enzyme Inhib. 13 (1998) 177
22. Barrese A.A., Genis C., Fisher S.Z., Orwenyo J.N., Kumara M.T., Dutta S.K., Phillips E., Kiddle J.J., Tu C., Silverman D.N., Govindasamy L., Agbandje-McKenna M., McKenna R., and Tripp B.C. Biochemistry 47 (2008) 3174
23. Innocenti A., Maresca A., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 18 (2008) 3938
24. Alterio V., Di Fiore A., D'Ambrosio K., Supuran C.T., and De Simone G. X-ray Crystallography of CA Inhibitors and its Importance in Drug Design. In: Supuran C.T., and Winum J.Y. (Eds). Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications (2009), Wiley, Hoboken 73-138
25. Alterio V., Hilvo M., Di Fiore A., Supuran C.T., Pan P., Parkkila S., Scaloni A., Pastorek J., Pastorekova S., Pedone C., Scozzafava A., Monti S.M., and De Simone G. Proc. Natl. Acad. Sci. U.S.A. 106 (2009) 16233
26. 15
27. 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
28. 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
29. Winum J.Y., Temperini C., El Cheikh K., Innocenti A., Vullo D., Ciattini S., Montero J.L., Scozzafava A., and Supuran C.T. J. Med. Chem. 49 (2006) 7024
30. Güzel O., Temperini C., Innocenti A., Scozzafava A., Salman A., and Supuran C.T. Bioorg. Med. Chem. Lett. 18 (2008) 152
31. Xue Y., Vidgren J., Svensson L.A., Liljas A., Jonsson B.H., and Lindskog S. Proteins 15 (1993) 80
32. Oxford Diffraction. crysalis red. Version 1.171.32.2; Oxford Diffraction Ltd, 2006.
33. Jones T.A., Zhou J.Y., Cowan S.W., and Kjeldoard M. Acta Crystallogr., Sect. A 47 (1991) 110
34. Emsley P., and Cowtan K. Acta Crystallogr., Sect. D 60 (2004) 2126
35. Laskowski R.A., MacArthur M.W., Moss D.S., and Thornton J.M. J. Appl. Crystallogr. 26 (1993) 283
36. Gattow G., and Krebs Z. Z. Anorg. Allg. Chem 323 (1963) 13
37. Wng X., Fu H., Du D., Zhou Z., Zhang A., Su C., and Ma K. Chem. Phys. Lett. 460 (2008) 339
38. Briganti F., Mangani S., Scozzafava A., Vernaglione G., and Supuran C.T. J. Biol. Inorg. Chem. 4 (1999) 528
39. Guerri A., Briganti F., Scozzafava A., Supuran C.T., and Mangani S. Biochemistry 39 (2000) 12391
40. Sjoblom B., Polentarutti M., and Djinovic-Carugo K. Proc. Natl. Acad. Sci. U.S.A. 106 (2009) 10609
41. Adam I.S., and Anthemidis A.N. Talanta 15 (2009) 1160