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  • Design, Synthesis, and Biological Evaluation of Novel Carbohydrate-Based Sulfamates as Carbonic Anhydrase Inhibitors

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    Author(s)
    Lopez, Marie
    Trajkovic, Jonathan
    Bornaghi, Laurent F
    Innocenti, Alessio
    Vullo, Daniela
    Supuran, Claudiu T
    Poulsen, Sally-Ann
    Griffith University Author(s)
    Poulsen, Sally-Ann
    Bornaghi, Laurent
    Lopez, Marie
    Trajkovic, Jonathan
    Year published
    2011
    Metadata
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    Abstract
    Carbonic anhydrases (CAs) IX and XII are enzymes with newly validated potential for the development of personalized, first-in-class cancer chemotherapies. Here we present the design and synthesis of novel carbohydrate-based CA inhibitors, several of which were very efficient inhibitors (Ki<10 nM) with good selectivity for cancer-associated CA isozymes over off-target CA isozymes. All inhibitors comprised a carbohydrate core with one hydroxyl group derivatized as a sulfamate. Five different carbohydrates were chosen to present a selection of molecular shapes with subtle stereochemical differences to the CA enzymes ...
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    Carbonic anhydrases (CAs) IX and XII are enzymes with newly validated potential for the development of personalized, first-in-class cancer chemotherapies. Here we present the design and synthesis of novel carbohydrate-based CA inhibitors, several of which were very efficient inhibitors (Ki<10 nM) with good selectivity for cancer-associated CA isozymes over off-target CA isozymes. All inhibitors comprised a carbohydrate core with one hydroxyl group derivatized as a sulfamate. Five different carbohydrates were chosen to present a selection of molecular shapes with subtle stereochemical differences to the CA enzymes active site. Variable modifications of the remaining sugar hydroxyl groups were incorporated to provide an incremental coverage of chemical property parameters that are associated with biopharmaceutical performance. All sulfamate inhibitors displayed ligand efficiencies that are consistent with those reported for good drug lead candidates.
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    Journal Title
    Journal of Medicinal Chemistry
    Volume
    54
    Issue
    5
    DOI
    https://doi.org/10.1021/jm101525j
    Copyright Statement
    This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Medicinal Chemistry, copyright 2011 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/jm101525j.
    Subject
    Medicinal and biomolecular chemistry
    Biologically active molecules
    Organic chemistry
    Pharmacology and pharmaceutical sciences
    Publication URI
    http://hdl.handle.net/10072/41765
    Collection
    • Journal articles

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