Carbonic anhydrase inhibitors. Inhibition of cytosolic isozyme XIII with aromatic and heterocyclic sulfonamides: A novel target for the drug design

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 14, 2004, Pages 3757-3762

  Lehtonen, Jonna M ^a   Parkkila, Seppo ^a,b   Vullo, Daniela ^c   Casini, Angela ^c   Scozzafava, Andrea ^c   Supuran, Claudiu T ^c  

^a UNIVERSITY OF TAMPERE   (Finland)

^b UNIVERSITY OF OULU   (Finland)

^c UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOETHYLBENZENESULFONAMIDE; ACETAZOLAMIDE; AMINOBENZOLAMIDE; AROMATIC COMPOUND; CARBONATE DEHYDRATASE; DICLOFENAMIDE; DORZOLAMIDE; HETEROCYCLIC COMPOUND; ISOENZYME; MAFENIDE; METHAZOLAMIDE; NANOPARTICLE; ORTHANILAMIDE; SULFANILAMIDE; SULFONAMIDE; UNCLASSIFIED DRUG; VALDECOXIB;

ARTICLE; BRAIN; CORRELATION ANALYSIS; CYCLIZATION; CYTOSOL; DERIVATIZATION; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; HALOGENATION; INTESTINE; KIDNEY; LUNG; PH; PROBABILITY; REGULATORY MECHANISM; SALIVARY GLAND; UTERUS;

AMINO ACID SEQUENCE; ANIMALS; CARBONIC ANHYDRASE INHIBITORS; CYTOSOL; DRUG DESIGN; HUMANS; HYDROGEN-ION CONCENTRATION; ISOENZYMES; KINETICS; MOLECULAR SEQUENCE DATA; NEOPLASMS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 2942532691     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.04.106     Document Type: Article

References (26)

1. Supuran C.T., Vullo D., Manole G., Casini A., Scozzafava A. Curr. Med. Chem. - Cardiovasc. Hematol. Agents. 2:2004;49-68
2. Supuran C.T., Scozzafava A., Casini A. Med. Res. Rev. 23:2003;146-189
3. Supuran C.T., Scozzafava A. Expert. Opin. Ther. Patents. 12:2002;217-242
4. Supuran C.T., Scozzafava A. Curr. Med. Chem.-Imm.; Endoc. Metab. Agents. 1:2001;61-97
5. Supuran C.T., Scozzafava A. Expert Opin. Ther. Pat. 10:2000;575-600
6. Cox E.H., McLendon G.L., Morel F.M., Lane T.W., Prince R.C., Pickering I.J., Gorge G.N. Biochemistry. 39:2000;12128-12130
7. Lane T.W., Morel F.M. Proc. Natl. Acad. Sci. U.S.A. 97:2000;4627-4631
8. So A.K., Espie G.S., Williams E.B., Shively J.M., Heinhorst S., Cannon G.C. J. Bacteriol. 186:2004;623-630
9. Supuran C.T., Scozzafava A., Conway J. Carbonic anhydrase - Its inhibitors and activators. 2004;1-376 CRC, Boca Raton (FL), USA. and references cited therein
10. Pastorekova, S.; Parkkila, S.; Pastorek, J.; Supuran, C. T. J. Enzym. Inhib. Med. Chem., 2004, 19, in press
11. Weber A., Casini A., Heine A., Kuhn D., Supuran C.T., Scozzafava A., Klebe G. J. Med. Chem. 47:2004;550-557
12. 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. J. Biol. Chem. 279:2004;2719-2727
13. Parkkila S., Kaunisto K., Kellokumpu S., Rajaniemi H. Histochemistry. 95:1991;477-482
14. Ilies M.A., Vullo D., Pastorek J., Scozzafava A., Ilies M., Caproiu M.T., Pastorekova S., Supuran C.T. J. Med. Chem. 46:2003;2187-2196
15. Clare B.W., Supuran C.T. Eur. J. Med. Chem. 34:1999;463-474
16. Supuran C.T., Ilies M.A., Scozzafava A. Eur. J. Med. Chem. 33:1998;739-752
17. Supuran C.T., Clare B.W. Eur. J. Med. Chem. 34:1999;41-50
18. 18 The gel was washed using 10 mM HEPES buffer (pH 7.5) containing 150 mM NaCl and the bound enzyme was eluted using 0.1 M sodium acetate, pH 5.6, containing 0.5 M sodium perchlorate. The purified His-tagged CA XIII was analyzed by two methods: colloidal Coomassie blue protein stain (Invitrogen) and western blotting. The His-tagged and untagged mCA XIII showed practically identical catalytic activity and affinity for sulfonamide inhibitors (data not shown)
19. 2 solutions in water at 20°C were used as substrate. Stock solutions of inhibitors were prepared at a concentration of 1-3 mM (in DMSO-water 1:1, v/v) and dilutions up to 0.1 nM done with the assay buffer mentioned above. Inhibitor and enzyme solutions were preincubated together for 10 min at room temperature prior to assay, in order to allow for the formation of the E-I complex. Triplicate experiments were done for each inhibitor concentration, and the values reported throughout the paper are the mean of such results
20. 14
21. Ferraroni M., Briganti F., Chegwidden W.R., Supuran C.T., Wiebauer K.E., Tashian R.E., Scozzafava A. Biochemistry. 41:2002;6237-6244
22. Ferraroni M., Briganti F., Chegwidden W.R., Supuran C.T., Scozzafava A. Inorg. Chim. Acta. 339:2002;135-144
23. Behravan G., Jonsson B.H., Lindskog S. Eur. J. Biochem. 195:1991;393-396
24. Vullo D., Franchi M., Gallori E., Pastorek J., Scozzafava A., Pastorekova S., Supuran C.T. Bioorg. Med. Chem. Lett. 13:2003;1005-1009
25. Franchi M., Vullo D., Gallori E., Pastorek J., Russo A., Scozzafava A., Pastorekova S., Supuran C.T. J. Enzym. Inhib. Med. Chem. 18:2003;333-338
26. Pastorekova S., Casini A., Scozzafava A., Vullo D., Pastorek J., Supuran C.T. Bioorg. Med. Chem. Lett. 14:2004;869-873