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  • The synthesis and biological evaluation of lactose-based sialylmimetics as inhibitors of rotaviral infection

    Author(s)
    Liakatos, A
    Kiefel, MJ
    Fleming, F
    Coulson, B
    von Itzstein, M
    Griffith University Author(s)
    von Itzstein, Mark
    Kiefel, Milton
    Year published
    2006
    Metadata
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    Abstract
    Rotaviruses are the most significant cause of gastroenteritis in young children and are responsible for over 600,000 infant deaths annually. The rotaviral haemagglutinin protein (VP8*) of some strains has been implicated in early recognition and binding events of host cell-surface sialoglycoconjugates, and is therefore an attractive target for potential therapeutic intervention. Since N-acetylneuraminic acid a(2,3)-linked to galactose is believed to be the minimum binding epitope of rotavirus to host cells, we report here our development of an efficient and flexible synthetic route to a range of lactose-based sialylmimetics ...
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    Rotaviruses are the most significant cause of gastroenteritis in young children and are responsible for over 600,000 infant deaths annually. The rotaviral haemagglutinin protein (VP8*) of some strains has been implicated in early recognition and binding events of host cell-surface sialoglycoconjugates, and is therefore an attractive target for potential therapeutic intervention. Since N-acetylneuraminic acid a(2,3)-linked to galactose is believed to be the minimum binding epitope of rotavirus to host cells, we report here our development of an efficient and flexible synthetic route to a range of lactose-based sialylmimetics of a(2,3)-linked thiosialosides. These compounds were biologically evaluated as inhibitors of rotaviral infection using an in vitro neutralisation assay. The results suggest that these lactose-based sialylmimetics are not inhibitors of the rhesus rotavirus strain; however, they do exhibit modest inhibition of the human (Wa) strain, presumably through inhibition of the rotaviral adhesion process.
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    Journal Title
    Bioorganic & Medicinal Chemistry
    Volume
    14
    Publisher URI
    http://www.elsevier.com/wps/find/journaldescription.cws_home/129/description#description
    DOI
    https://doi.org/10.1016/j.bmc.2005.08.057
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Pharmacology and pharmaceutical sciences
    Biochemistry and cell biology
    Publication URI
    http://hdl.handle.net/10072/13716
    Collection
    • Journal articles

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