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  • Carbonic anhydrase inhibitors: inhibition of isozymes I, II and IX with triazole-linked O-glycosides of benzene sulfonamides

    Author(s)
    Wilkinson, Brendan L
    Bornaghi, Laurent F
    Houston, Todd A
    Innocenti, Alessio
    Vullo, Daniela
    Supuran, Claudiu T
    Poulsen, Sally-Ann
    Griffith University Author(s)
    Poulsen, Sally-Ann
    Houston, Todd A.
    Wilkinson, Brendan L.
    Bornaghi, Laurent
    Year published
    2007
    Metadata
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    Abstract
    We report the synthesis of a series of benzene sulfonamides containing triazole-O-glycoside tails for evaluation as carbonic anhydrase (CA) inhibitors. These glycoconjugates were synthesized by the 1,3-dipolar cycloaddition reaction of 4-azidobenzenesulfonamide with O-propynyl glycosides. Compounds were assessed for their ability to inhibit the enzymatic activity of the physiologically dominant isozymes hCA I and II and the tumor-associated isozyme hCA IX (h = human). Against hCA I these compounds were either micromolar or low nanomolar inhibitors, while against hCA II and IX inhibition in the range of 6.8-53 nM and 9.7-107 ...
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    We report the synthesis of a series of benzene sulfonamides containing triazole-O-glycoside tails for evaluation as carbonic anhydrase (CA) inhibitors. These glycoconjugates were synthesized by the 1,3-dipolar cycloaddition reaction of 4-azidobenzenesulfonamide with O-propynyl glycosides. Compounds were assessed for their ability to inhibit the enzymatic activity of the physiologically dominant isozymes hCA I and II and the tumor-associated isozyme hCA IX (h = human). Against hCA I these compounds were either micromolar or low nanomolar inhibitors, while against hCA II and IX inhibition in the range of 6.8-53 nM and 9.7-107 nM, respectively was observed. The most potent inhibitor against hCA IX was the galactose derivative 8 (Ki = 9.7 nM), this is so far the most potent glycoconjugate inhibitor reported for the tumor-associated hCA IX. These carbohydrate-tethered sulfonamides may prove interesting lead candidates to target tumor-associated CA isozymes, wherein the CA domain is located extracellularly.
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    Journal Title
    Journal of Medicinal Chemistry
    Volume
    50
    Issue
    7
    Publisher URI
    http://pubs.acs.org/journal/jmcmar
    DOI
    https://doi.org/10.1021/jm061320h
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Pharmacology and pharmaceutical sciences
    Publication URI
    http://hdl.handle.net/10072/18264
    Collection
    • Journal articles

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