Please use this identifier to cite or link to this item: https://hdl.handle.net/1959.11/22910
Title: A Novel Class of Carbonic Anhydrase Inhibitors: Glycoconjugate Benzene Sulfonamides Prepared by "Click-Tailing"
Contributor(s): Wilkinson, Brendan (author)orcid ; Bornaghi, Laurent F (author); Houston, Todd A (author); Innocenti, Alessio (author); Supuran, Claudiu T (author); Poulsen, Sally-Ann (author)
Publication Date: 2006
DOI: 10.1021/jm060967z
Handle Link: https://hdl.handle.net/1959.11/22910
Abstract: Aryl and heteroaryl sulfonamides (ArSO₂NH₂) are therapeutically used to inhibit the catalytic activity of carbonic anhydrases (CAs). Using a "click-tail" approach a novel class of glycoconjugate benzene sulfonamides have been synthesized that contain diverse carbohydrate-triazole tails. These compounds were assessed for their ability to inhibit three human CA isozymes in vitro: cytosolic hCA I and hCA II and transmembrane, tumor-associated hCA IX. This isozyme has a minimal expression in normal tissue but is overexpressed in hypoxic tumors and its inhibition is a current approach toward new cancer therapies. The qualitative structure-activity for all derivatives demonstrated that the stereochemical diversity present within the carbohydrate tails effectively interrogated the CA active site topology, to generate several inhibitors that were potent and selective toward hCA IX, an important outcome in the quest for potential cancer therapy applications based on CA inhibition.
Publication Type: Journal Article
Source of Publication: Journal of Medicinal Chemistry, 49(22), p. 6539-6548
Publisher: American Chemical Society
Place of Publication: United States
ISSN: 1520-4804
0022-2623
Field of Research (FOR): 030499 Medicinal and Biomolecular Chemistry not elsewhere classified
030504 Organic Green Chemistry
030401 Biologically Active Molecules
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
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