Inhibition of carbonic anhydrase isozymes with benzene sulfonamides incorporating thio, sulfinyl and sulfonyl glycoside moieties.
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.
Singer
Mathilde
M
Eskitis Institute, Griffith University, Nathan, Queensland, Australia.
Lopez
Marie
M
Bornaghi
Laurent F
LF
Innocenti
Alessio
A
Vullo
Daniela
D
Supuran
Claudiu T
CT
Poulsen
Sally-Ann
SA
D001554:Benzene / Q000737:chemistry* / Q000378:metabolism; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis* / Q000378:metabolism; D002256:Carbonic Anhydrases / Q000378:metabolism*; D005697:Galactosides / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology*; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000494:pharmacology*; D006801:Humans; D007527:Isoenzymes / Q000037:antagonists & inhibitors / Q000378:metabolism; D013449:Sulfonamides / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology*; D000096926:Benzenesulfonamides
D001554:Benzene; D002257:Carbonic Anhydrase Inhibitors; D002256:Carbonic Anhydrases; D005697:Galactosides; D006001:Glycoconjugates; D007527:Isoenzymes; D013449:Sulfonamides; C519519:4-(4-((2',3',4',6'-tetra-O-acetylgalactopyranosyl)oxymethyl)-1H-1,2,3-triazol-1-yl)benzenesulfonamide; D000096926:Benzenesulfonamides