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  • A novel class of carbonic anhydrase inhibitors: glycoconjugate benzene sulfonamides prepared by "click-tailing"

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    JMedChem2006_AUSTRALIAmanuscript_revised_2.pdf (444.1Kb)
    Author(s)
    Wilkinson, Brendan L
    Bornaghi, Laurent F
    Houston, Todd A
    Innocenti, Alessio
    Supuran, Claudiu T
    Poulsen, Sally-Ann
    Griffith University Author(s)
    Poulsen, Sally-Ann
    Houston, Todd A.
    Wilkinson, Brendan L.
    Bornaghi, Laurent
    Year published
    2006
    Metadata
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    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 ...
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    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.
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    Journal Title
    Journal of Medicinal Chemistry
    Volume
    49
    Issue
    22
    Publisher URI
    http://pubs.acs.org/journal/jmcmar?cookieSet=1
    DOI
    https://doi.org/10.1021/jm060967z
    Copyright Statement
    © 2006 American Chemical Society. Self-archiving of the author-manuscript version is not yet supported by this publisher. Please use the hypertext link to access the journal's website or contact the author for more information. Please refer to the journal for the definitive published version.
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Pharmacology and pharmaceutical sciences
    Publication URI
    http://hdl.handle.net/10072/11308
    Collection
    • Journal articles

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