Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the antipsychotic drug sulpiride

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 2, 2004, Pages 337-341

  Abbate, Francesco ^a   Coetzee, Anita ^b   Casini, Angela ^c   Ciattini, Samuele ^c   Scozzafava, Andrea ^c   Supuran, Claudiu T ^c  

^a Bruker Corporation   (United States)

^b Bruker Nonius BV   (Netherlands)

^c UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAZOLAMIDE; ANTIGLAUCOMA AGENT; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IV; CELECOXIB; CYCLOOXYGENASE 2 INHIBITOR; DICLOFENAMIDE; INDISULAM; METHAZOLAMIDE; NEUROLEPTIC AGENT; PHENYLALANINE; PYRROLIDINE DERIVATIVE; SULFONAMIDE; SULPIRIDE; TOPIRAMATE; VALDECOXIB; WATER; ZINC;

ARTICLE; CRYSTAL STRUCTURE; CYTOSOL; DRUG ACTIVITY; DRUG BINDING; ENZYME ACTIVE SITE; ENZYME INHIBITION; HYDROGEN BOND; X RAY CRYSTALLOGRAPHY;

EID: 0347360282     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.11.014     Document Type: Article

References (36)

1. (a) Scozzafava A., Owa T., Mastrolorenzo A., Supuran C.T. Curr. Med. Chem. 10:2003;925
2. (b) Casini A., Scozzafava A., Mastrolorenzo A., Supuran C.T. Curr. Cancer Drug Targets. 2:2002;55
3. (c) Supuran C.T., Casini A., Scozzafava A. Med. Res. Rev. 23:2003;535.
4. (a) Supuran C.T., Scozzafava A., Casini A. Med. Res. Rev. 23:2003;146
5. (b) Supuran C.T., Scozzafava A. Curr. Med. Chem. Imm. Endoc. Metab. Agents. 1:2001;61.
6. (a) Supuran C.T., Scozzafava A. Exp. Opin. Ther. Pat. 12:2002;217
7. (b) Supuran C.T., Scozzafava A. Exp. Opin. Ther. Pat. 10:2000;575.
8. Maryanoff B.E., Costanzo M.J., Nortey S.O., Greco M.N., Shank R.P., Shupsky J.J., Ortegon M.P., Vaught J.L. J. Med. Chem. 41:1998;1315.
9. Casini A., Antel J., Abbate F., Scozzafava A., David S., Waldeck H., Schäfer S., Supuran C.T. Bioorg. Med. Chem. Lett. 13:2003;841.
10. (a) Owa T., Yoshino H., Okauchi T., Yoshimatsu K., Ozawa Y., Sugi N.H., Nagasu T., Koyanagi N., Kitoh K. J. Med. Chem. 42:1999;3789
11. (b) Supuran C.T. Exp. Opin. Invest. Drugs. 12:2003;283.
12. Abbate, F.; Casini, A.; Owa, T.; Scozzafava, A.; Supuran, C.T. Bioorg. Med. Chem. Lett., in press.
13. (a) Woo L.W.L., Howarth N.M., Purohit A., Hejaz H.A.M., Reed M.J., Potter B.V.L. J. Med. Chem. 41:1998;1068
14. (b) Malini B., Purohit A., Ganeshapillai D., Woo L.W.L., Potter B.V.L., Reed M.J. J. Steroid Biochem. Mol. Biol. 75:2000;253.
15. Abbate, F.; Winum, J. -Y.; Potter, B. V. L.; Casini, A.; Montero, J.-L.; Scozzafava, A.; Supuran, C. T. Bioorg. Med. Chem. Lett., in press.
16. (a) Talley J.J. Exp. Opin. Ther. Pat. 7:1997;55
17. (b) Penning T.D., Talley J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Docter S., Graneto M.J., Lee L.F., Malecha J.W., Miyashiro J.M., Rogers R.S., Rogier D.J., Yu S.S., Anderson G.D., Burton E.G., Cogburn J.N., Gregory S.A., Koboldt C.M., Perkins W.E., Seibert K., Veenhuizen A.W., Zhang Y.Y., Isakson P.C. J. Med. Chem. 40:1997;1347.
18. Weber, A.; Casini, A.; Heine, A.; Kuhn, D.; Supuran, C. T.; Scozzafava, A.; Klebe, G. J. Med. Chem., in press.
19. (a) Pani L. Curr. Med. Res. Opin. 18(Suppl.):2002;3
20. (b) Pani L., Gessa G.L. Mol. Psychiatry. 7:2002;247.
21. (a) Muller M.J., Hartter S., Kohler D., Hiemke C. Pharmacopsychiatry. 34:2001;27
22. (b) Drago F., Arezzi A., Virzi A. Eur. Neuropsychopharmacol. 10:2000;437
23. (c) Ferreri M., Florent C., Gerard D. Encephale. 26:2000;58.
24. Pocker Y., Stone J.T. Biochemistry. 6:1967;668.
25. Khalifah R.G. J. Biol. Chem. 246:1971;2561.
26. The hCA II-6 complex data were collected at the Bruker-Nonius facility in Delft (The Netherlands). The sample was measured on a prototype microfocus rotating anode generator (0.1×1 mm focus), running at 2.4 kW. This is 90% of the capacity of the Bruker Nonius Microstar. Montel optics were used, with a 0.3 mm collimator and a ProteumR (Smart6000) detector. An exposure time of 60 s/frame and a frame width of 0.3° have been employed. The acquisition and the manipulation of the data was achieved with the Proteum package and Cosmo for strategy calculation, while Saint+ was used for integration and processing, ProScale for Scaling and SHELXTL for solution and refinement of the structure. The size of the crystal was 0.125×0.125×0.125 mm.
27. Proteum package, Cosmo, Saint+, ProScale and SHELXTL from Bruker Nonius Company.
28. Jones T.A., Cowan S.W., Kjeldgaard M. Acta Crystallogr. A47:1991;110.
29. Gruneberg S., Wendt B., Klebe G. Angew. Chem., Int. Ed. 40:2001;389.
30. Abbate F., Supuran C.T., Scozzafava A., Orioli P., Stubbs M., Klebe G. J. Med. Chem. 45:2002;3583.
31. Abbate F., Casini A., Scozzafava A., Supuran C.T. J. Enzyme Inhib. Med. Chem. 18:2003;303.
32. Casini A., Abbate F., Scozzafava A., Supuran C.T. Bioorg. Med. Chem. Lett. 13:2003;2763.
33. (a) Baptista T., Araujo de Baptista E., Ying Kin N.M., Beaulieu S., Walker D., Joober R., Lalonde J., Richard D. Brain Res. 957:2002;144
34. (b) Baptista T., Lacruz A., Paez X., Hernandez L., Beaulieu S. Eur. J. Pharmacol. 447:2002;91.
35. (a) Hebebrand, J.; Antel, J.; Preuschoff, U.; David, S.; Sann, H.; Weske, M. WO Patent 2002, 07821. (b) Supuran C.T. Exp. Opin. Ther. Pat. 13:2003;1545.
36. The coordinates of the hCA II - sulpiride adduct are available immediately from claudiu.supuran@unifi.it.