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  • Sulfonamide linked neoglycoconjugates – a new class of inhibitors for cancer-associated carbonic anhydrases

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    Author(s)
    Lopez, Marie
    Bornaghi, Laurent F
    Innocenti, Alessio
    Vullo, Daniela
    Charman, Susan A
    Supuran, Claudiu T
    Poulsen, Sally-Ann
    Griffith University Author(s)
    Poulsen, Sally-Ann
    Bornaghi, Laurent
    Lopez, Marie
    Year published
    2010
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    Abstract
    The contribution of membrane-bound carbonic anhydrases (CAs) to hypoxic tumor growth and progression in cancer implicates cancer-associated CAs as a promising drug target for oncology. In this paper, we present a new class of sulfonamide-linked neoglycoconjugate that was designed to selectively target and inhibit the extracellular domains of the cancer-relevant CA isozymes. We describe the application of novel, yet straightforward, chemistry toward the synthesis of inhibitors that comprise both S-glycosyl sulfenamides and S-glycosyl sulfonamides.We also present the CA inhibition profile of our new neoglycoconjugates, ...
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    The contribution of membrane-bound carbonic anhydrases (CAs) to hypoxic tumor growth and progression in cancer implicates cancer-associated CAs as a promising drug target for oncology. In this paper, we present a new class of sulfonamide-linked neoglycoconjugate that was designed to selectively target and inhibit the extracellular domains of the cancer-relevant CA isozymes. We describe the application of novel, yet straightforward, chemistry toward the synthesis of inhibitors that comprise both S-glycosyl sulfenamides and S-glycosyl sulfonamides.We also present the CA inhibition profile of our new neoglycoconjugates, more specifically a library of 30 compounds (3-32) that were designed to optimize both SAR (structure-activity relationship) and SPR (structure-property relationship) characteristics. We show that our approach produces neutral, water-soluble, and potent inhibitors (Kis in the low nanomolar range) that target cancer-associated CAs.
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    Journal Title
    Journal of Medicinal Chemistry
    Volume
    53
    DOI
    https://doi.org/10.1021/jm901888x
    Copyright Statement
    This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Medicinal Chemistry, copyright 2010 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jm901888x.
    Subject
    Medicinal and biomolecular chemistry
    Biologically active molecules
    Organic chemistry
    Pharmacology and pharmaceutical sciences
    Publication URI
    http://hdl.handle.net/10072/32513
    Collection
    • Journal articles

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