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Prophylactic Antiviral Activity of Sulfated Glycomimetic Oligomers and Polymers

  • Laura Soria-Martinez
    Laura Soria-Martinez
    Institute of Cellular Virology, ZMBE, University of Münster, Münster 48149, Germany
    Research Group “ViroCarb: glycans controlling non-enveloped virus infections” (FOR2327), Coordinating University of Tübingen, Tübingen 72074, Germany
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  • , 
  • Sebastian Bauer
    Sebastian Bauer
    Institute of Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-University Düsseldorf, Düsseldorf 40225, Germany
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  • , 
  • Markus Giesler
    Markus Giesler
    Institute of Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-University Düsseldorf, Düsseldorf 40225, Germany
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  • , 
  • Sonja Schelhaas
    Sonja Schelhaas
    European Institute for Molecular Imaging, University of Münster, Münster 48149, Germany
    Cells in Motion Interfaculty Centre CiMIC, University of Münster, Münster 48149, Germany
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  • , 
  • Jennifer Materlik
    Jennifer Materlik
    Institute of Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-University Düsseldorf, Düsseldorf 40225, Germany
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  • , 
  • Kevin Janus
    Kevin Janus
    Institute of Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-University Düsseldorf, Düsseldorf 40225, Germany
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  • , 
  • Patrick Pierzyna
    Patrick Pierzyna
    Institute of Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-University Düsseldorf, Düsseldorf 40225, Germany
    More by Patrick Pierzyna
  • , 
  • Miriam Becker
    Miriam Becker
    Institute of Cellular Virology, ZMBE, University of Münster, Münster 48149, Germany
    Research Group “ViroCarb: glycans controlling non-enveloped virus infections” (FOR2327), Coordinating University of Tübingen, Tübingen 72074, Germany
    More by Miriam Becker
  • , 
  • Nicole L. Snyder
    Nicole L. Snyder
    Research Group “ViroCarb: glycans controlling non-enveloped virus infections” (FOR2327), Coordinating University of Tübingen, Tübingen 72074, Germany
    Department of Chemistry, Davidson College, Davidson, North Carolina 28035, United States
    More by Nicole L. Snyder
  • , 
  • Laura Hartmann*
    Laura Hartmann
    Institute of Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-University Düsseldorf, Düsseldorf 40225, Germany
    Research Group “ViroCarb: glycans controlling non-enveloped virus infections” (FOR2327), Coordinating University of Tübingen, Tübingen 72074, Germany
    *[email protected]
    More by Laura Hartmann
    Orcidhttp://orcid.org/0000-0003-0115-6405
  • , and 
  • Mario Schelhaas*
    Mario Schelhaas
    Institute of Cellular Virology, ZMBE, University of Münster, Münster 48149, Germany
    Research Group “ViroCarb: glycans controlling non-enveloped virus infections” (FOR2327), Coordinating University of Tübingen, Tübingen 72074, Germany
    Cells in Motion Interfaculty Centre CiMIC, University of Münster, Münster 48149, Germany
    *[email protected]
    More by Mario Schelhaas
    Orcidhttp://orcid.org/0000-0002-6735-583X
Cite this: J. Am. Chem. Soc. 2020, 142, 11, 5252–5265
Publication Date (Web):February 27, 2020
https://doi.org/10.1021/jacs.9b13484
Copyright © 2020 American Chemical Society
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    Abstract

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    In this work, we investigate the potential of highly sulfated synthetic glycomimetics to act as inhibitors of viral binding/infection. Our results indicate that both long-chain glycopolymers and short-chain glycooligomers are capable of preventing viral infection. Notably, glycopolymers efficiently inhibit Human Papillomavirus (HPV16) infection in vitro and maintain their antiviral activity in vivo, while the glycooligomers exert their inhibitory function post attachment of viruses to cells. Moreover, when we tested the potential for broader activity against several other human pathogenic viruses, we observed broad-spectrum antiviral activity of these compounds beyond our initial assumptions. While the compounds tested displayed a range of antiviral efficacies, viruses with rather diverse glycan specificities such as Herpes Simplex Virus (HSV), Influenza A Virus (IAV), and Merkel Cell Polyomavirus (MCPyV) could be targeted. This opens new opportunities to develop broadly active glycomimetic inhibitors of viral entry and infection.

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    • Materials and methods for the synthesis of sulfated glycopolymers and glycooligomers; analytical data for sulfated glycopolymers and glycooligomers and according precursors and intermediates; and additional information including materials and methods and supplementary figures for biological assays (PDF)

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