Carbonic anhydrase inhibitors: Inhibition of the tumor-associated isozyme IX with fluorine-containing sulfonamides. The first subnanomolar CA IX inhibitor discovered

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 9, 2004, Pages 2351-2356

  Vullo, Daniela ^a   Scozzafava, Andrea ^a   Pastorekova, Silvia ^b   Pastorek, Jaromir ^b   Supuran, Claudiu T ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b INSTITUTE OF VIROLOGY   (Slovakia)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAZOLAMIDE; ANTINEOPLASTIC AGENT; BRINZOLAMIDE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE INHIBITOR; DICLOFENAMIDE; DORZOLAMIDE; ETHOXZOLAMIDE; FLUORINE DERIVATIVE; ISOENZYME; METHAZOLAMIDE; SULFONAMIDE; TUMOR PROTEIN;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG PROTEIN BINDING; DRUG SYNTHESIS; ENZYME INHIBITION; FLUORINATION; STRUCTURE ACTIVITY RELATION;

CARBONIC ANHYDRASE INHIBITORS; FLUORINE; ISOENZYMES; SULFONAMIDES;

EID: 1842790839     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.01.095     Document Type: Article

References (48)

1. Maren T.H. Botrè F., Gros G., Storey B.T. Carbonic Anhydrase - from Biochemistry and Genetics to Physiology and Clinical Medicine. 1991;186-207 VCH, Weinheim.
2. Wistrand P.J., Lindqvist A. Botrè F., Gros G., Storey B.T. Carbonic Anhydrase - from Biochemistry and Genetics to Physiology and Clinical Medicine. 1991;352-378 VCH, Weinheim.
3. Supuran C.T., Scozzafava A. Exp. Opin. Ther. Patents. 10:2000;575-600.
4. Supuran C.T., Scozzafava A. Exp. Opin. Ther. Patents. 12:2002;217-242.
5. Supuran C.T., Scozzafava A. Curr. Med. Chem.- Imm., Endoc. Metab. Agents. 1:2001;61-97.
6. Supuran C.T., Scozzafava A., Casini A. Med. Res. Rev. 23:2003;146-189.
7. Supuran C.T., Scozzafava A., Conway J. Carbonic Anhydrase - its Inhibitors and Activators. 2004;1-368 CRC, Boca Raton, Florida. and references cited therein.
8. Supuran C.T. Exp. Opin. Ther. Patents. 13:2003;1545-1550.
9. Pastorek J., Pastorekova S., Callebaut I., Mornon J.P., Zelnik V., Opavsky R., Zatovicova M., Liao S., Portetelle D., Stanbridge E.J., Zavada J., Burny A., Kettmann R. Oncogene. 9:1994;2877-2888.
10. Opavsky R., Pastorekova S., Zelnik V., Gibadulinova A., Stanbridge E.J., Zavada J., Kettmann R., Pastorek J. Genomics. 33:1996;480-487.
11. Pastorekova S., Parkkila S., Parkkila A.K., Opavsky R., Zelnik V., Saarnio J., Pastorek J. Gastroenterology. 112:1997;398-408.
12. Liao S.Y., Brewer C., Zavada J., Pastorek J., Pastorekova S., Manetta A., Berman M.L., DiSaia P.J., Stanbridge E.J. Am. J. Pathol. 145:1994;598-609.
13. Liao S.Y., Aurelio O.N., Jan K., Zavada J., Stanbridge E.J. Cancer Res. 57:1997;2827-2831.
14. Vermylen P., Roufosse C., Burny A., Verhest A., Bossehaerts T., Pastorekova S., Ninane V., Sculier J.P. Eur. Respir. J. 14:1999;806-811.
15. Turner J.R., Odze R.D., Crum C.P., Resnick M.B. Hum. Pathol. 28:1997;740-744.
16. Scozzafava A., Owa T., Mastrolorenzo A., Supuran C.T. Curr. Med. Chem. 10:2003;925-953.
17. Casini A., Scozzafava A., Mastrolorenzo A., Supuran C.T. Curr. Cancer Drug Targets. 2:2002;55-75.
18. Owa T., Yoshino H., Okauchi T., Yoshimatsu K., Ozawa Y., Sugi N.H., Nagasu T., Koyanagi N., Kitoh K. J. Med. Chem. 42:1999;3789-3799.
19. Supuran C.T. Exp. Opin. Invest. Drugs. 12:2003;283-287.
20. Abbate F., Casini A., Owa T., Scozzafava A., Supuran C.T. Bioorg. Med. Chem. Lett. 14:2004;217-223.
21. Funahashi Y., Sugi N.H., Semba T., Yamamoto Y., Hamaoka S., Tsukahara-Tamai N., Ozawa Y., Tsuruoka A., Nara K., Takahashi K., Okabe T., Kamata J., Owa T., Ueda N., Haneda T., Yonaga M., Yoshimatsu K., Wakabayashi T. Cancer Res. 62:2002;6116-6123.
22. Ozawa Y., Sugi N.H., Nagasu T., Owa T., Watanabe T., Koyanagi N., Yoshino H., Kitoh K., Yoshimatsu K. Eur. J. Cancer. 37:2001;2275-2282.
23. van Kesteren C., Beijnen J.H., Schellens J.H. Anticancer Drugs. 13:2002;989-997.
24. Punt C.J., Fumoleau P., van de Walle B., Faber M.N., Ravic M., Campone M. Ann. Oncol. 12:2001;1289-1293.
25. Raymond E., ten Bokkel Huinink W.W., Taieb J., Beijnen J.H., Faivre S., Wanders J., Ravic M., Fumoleau P., Armand J.P., Schellens J.H. J. Clin. Oncol. 20:2002;3508-3521.
26. Winum J.-Y., Vullo D., Casini A., Montero J.-L., Scozzafava A., Supuran C.T. J. Med. Chem. 46:2003;2197-2204.
27. Vullo D., Franchi M., Gallori E., Pastorek J., Scozzafava A., Pastorekova S., Supuran C.T. Bioorg. Med. Chem. Lett. 13:2003;1005-1009.
28. 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.
29. 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.
30. Winum J.-Y., Vullo D., Casini A., Montero J.-L., Scozzafava A., Supuran C.T. J. Med. Chem. 46:2003;5471-5477.
31. Scozzafava A., Menabuoni L., Mincione F., Briganti F., Mincione G., Supuran C.T. J. Med. Chem. 43:2000;4542-4551.
32. Abbate F., Casini A., Scozzafava A., Supuran C.T. J. Enzy. Inhib. Med. Chem. 18:2003;303-308.
33. Abbate F., Supuran C.T., Scozzafava A., Orioli P., Stubbs M.T., Klebe G. J. Med. Chem. 45:2002;3583-3587.
34. Casini A., Abbate F., Scozzafava A., Supuran C.T. Bioorg. Med. Chem. Lett. 13:2003;2759-2763.
35. Casini A., Antel J., Abbate F., Scozzafava A., David S., Waldeck H., Schäfer S., Supuran C.T. Bioorg. Med. Chem. Lett. 13:2003;841-845.
36. Medina J.C., Shan B., Beckmann H., Farrell R.P., Clark D.L., Learned R.M., Roche D., Li A., Baichwal V., Case C., Baeuerle P.A., Rosen T., Jaen J.C. Bioorg. Med. Chem. Lett. 8:1998;2653-2656.
37. Medina J.C., Roche D., Shan B., Learned R.M., Frankmoelle W.P., Clark D.L., Rosen T., Jaen J.C. Bioorg. Med. Chem. Lett. 9:1999;1843-1846.
38. Shan B., Medina J.C., Santha E., Frankmoelle W.P., Chou T.C., Learned R.M., Narbut M.R., Scott D., Wu P., Jaen J.C., Rosen T., Timmermans P.B.M., Beckmann H. Proc. Natl. Acad. Sci. U.S.A. 96:1999;5686-5691.
39. Scozzafava A., Mastrolorenzo A., Supuran C.T. Exp. Opin. Ther. Patents. 11:2001;765-787.
40. Scozzafava A., Casini A., Supuran C.T. Curr. Med. Chem. 9:2002;1167-1185.
41. Supuran C.T., Ilies M.A., Scozzafava A. Eur. J. Med. Chem. 33:1998;739-751.
42. Supuran C.T., Clare B.W. Eur. J. Med. Chem. 34:1999;41-50.
43. Clare B.W., Supuran C.T. Eur. J. Med. Chem. 34:1999;463-474.
44. 3: 3/7).
45. -1.
46. 2 solutions in water at 20°C were used as substrate. Stock solutions of inhibitors were prepared at a concn 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.
47. 21.
48. Wingo T., Tu C., Laipis P.J., Silverman D.N. Biochem. Biophys. Res. Commun. 288:2001;666-669.