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  • A Sulfonozanamivir Analogue Has Potent Anti-influenza Virus Activity

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    Accepted Manuscript (AM)
    Author(s)
    Hadhazi, Adam
    Li, Linghui
    Bailly, Benjamin
    Maggioni, Andrea
    Martin, Gael
    Dirr, Larissa
    Dyason, Jeffrey C
    Thomson, Robin J
    Gao, George F
    Borbas, Aniko
    Ve, Thomas
    Pascolutti, Mauro
    von Itzstein, Mark
    Griffith University Author(s)
    von Itzstein, Mark
    Thomson, Robin J.
    Maggioni, Andrea
    Pascolutti, Mauro
    Dirr, Larissa E.
    Ve, Thomas
    Year published
    2018
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    Abstract
    Influenza virus infection continues to cause significant, often severe, respiratory illness worldwide. A validated target for the development of anti‐influenza agents is the virus surface protein sialidase. In the current study, we have discovered a highly potent inhibitor of influenza virus sialidase, based on a novel sialosyl sulfonate template. The synthesised 3‐guanidino sialosyl α‐sulfonate, a sulfonozanamivir analogue, inhibits viral replication in vitro at the nanomolar level, comparable to that of the anti‐influenza drug zanamivir. Using protein X‐ray crystallography we show that the sialosyl α‐sulfonate template ...
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    Influenza virus infection continues to cause significant, often severe, respiratory illness worldwide. A validated target for the development of anti‐influenza agents is the virus surface protein sialidase. In the current study, we have discovered a highly potent inhibitor of influenza virus sialidase, based on a novel sialosyl sulfonate template. The synthesised 3‐guanidino sialosyl α‐sulfonate, a sulfonozanamivir analogue, inhibits viral replication in vitro at the nanomolar level, comparable to that of the anti‐influenza drug zanamivir. Using protein X‐ray crystallography we show that the sialosyl α‐sulfonate template binds within the sialidase active site in a 1C4 chair conformation. The C1‐sulfonate moiety forms crucial and strong‐binding interactions with the active site's triarginyl cluster, while the 3‐guanidino moiety interacts significantly with conserved active site residues. This sulfonozanamivir analogue provides a new direction in anti‐influenza virus drug development.
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    Journal Title
    ChemMedChem
    Volume
    13
    Issue
    8
    DOI
    https://doi.org/10.1002/cmdc.201800092
    Copyright Statement
    © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the peer reviewed version of the following article: A Sulfonozanamivir Analogue Has Potent Anti-influenza Virus Activity, ChemMedChem, Volume 13, Issue 8, April 23, 2018, Pages 785-789, which has been published in final form at 10.1002/cmdc.201800092. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving (http://olabout.wiley.com/WileyCDA/Section/id-828039.html)
    Subject
    Medicinal and biomolecular chemistry
    Medicinal and biomolecular chemistry not elsewhere classified
    Organic chemistry
    Pharmacology and pharmaceutical sciences
    Publication URI
    http://hdl.handle.net/10072/385111
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    • Journal articles

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