Inhibition of carbonic anhydrase isozymes with benzene sulfonamides incorporating thio, sulfinyl and sulfonyl glycoside moieties.

Article Details

Citation

Copy to clipboard

Singer M, Lopez M, Bornaghi LF, Innocenti A, Vullo D, Supuran CT, Poulsen SA

Inhibition of carbonic anhydrase isozymes with benzene sulfonamides incorporating thio, sulfinyl and sulfonyl glycoside moieties.

Bioorg Med Chem Lett. 2009 Apr 15;19(8):2273-6. doi: 10.1016/j.bmcl.2009.02.086. Epub 2009 Feb 26.

PubMed ID

19286378 [ View in PubMed

]

Abstract

A series of benzene sulfonamides incorporating thio, sulfinyl or sulfonyl glycoside moieties were synthesized. These glycoconjugates were investigated for their ability to inhibit the enzymatic activity of four human carbonic anhydrases (hCA): isozymes I, II and tumour-associated isozymes IX and XII. The oxidation state of the sulfur in the carbohydrate tail moiety did not influence either enzyme inhibition potency or isozyme selectivity even though presenting opportunities for differing interactions with the target isozymes.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Acetazolamide	Carbonic anhydrase 1	Ki (nM)	900	N/A	N/A	Details
Acetazolamide	Carbonic anhydrase 12	Ki (nM)	5.7	N/A	N/A	Details
Acetazolamide	Carbonic anhydrase 2	Ki (nM)	12	N/A	N/A	Details
Brinzolamide	Carbonic anhydrase 1	Ki (nM)	450	N/A	N/A	Details
Brinzolamide	Carbonic anhydrase 2	Ki (nM)	3	N/A	N/A	Details
Dorzolamide	Carbonic anhydrase 1	Ki (nM)	500	N/A	N/A	Details
Dorzolamide	Carbonic anhydrase 2	Ki (nM)	9	N/A	N/A	Details