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Exploring Rigid and Flexible Core Trivalent Sialosides for Influenza Virus Inhibition

Pallavi Kiran, Sumati Bhatia Orcid Logo, Daniel Lauster, Stevan Aleksić, Carsten Fleck, Natalija Peric, Wolfgang Maison, Susanne Liese, Bettina G. Keller, Andreas Herrmann, Rainer Haag Orcid Logo

Chemistry – A European Journal, Volume: 24, Issue: 72, Pages: 19373 - 19385

Swansea University Author: Sumati Bhatia Orcid Logo

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DOI (Published version): 10.1002/chem.201804826

Abstract

Herein, the chemical synthesis and binding analysis of functionalizable rigid and flexible core trivalent sialosides bearing oligoethylene glycol (OEG) spacers interacting with spike proteins of influenza A virus (IAV) X31 is described. Although the flexible Tris-based trivalent sialosides achieved...

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Published in: Chemistry – A European Journal
ISSN: 0947-6539 1521-3765
Published: Wiley 2018
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URI: https://cronfa.swan.ac.uk/Record/cronfa64872
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Abstract: Herein, the chemical synthesis and binding analysis of functionalizable rigid and flexible core trivalent sialosides bearing oligoethylene glycol (OEG) spacers interacting with spike proteins of influenza A virus (IAV) X31 is described. Although the flexible Tris-based trivalent sialosides achieved micromolar binding constants, a trivalent binder based on a rigid adamantane core dominated flexible tripodal compounds with micromolar binding and hemagglutination inhibition constants. Simulation studies indicated increased conformational penalties for long OEG spacers. Using a systematic approach with molecular modeling and simulations as well as biophysical analysis, these findings emphasize on the importance of the scaffold rigidity and the challenges associated with the spacer length optimization.
Keywords: Adamantane, influenza inhibitors, oligoethylene glycol, trivalent sialoside, viruses
College: Faculty of Science and Engineering
Issue: 72
Start Page: 19373
End Page: 19385

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