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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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spelling v2 64872 2023-11-01 Exploring Rigid and Flexible Core Trivalent Sialosides for Influenza Virus Inhibition a6b1181ebdbe42bd03b24cbdb559d082 0000-0002-5123-4937 Sumati Bhatia Sumati Bhatia true false 2023-11-01 CHEM 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. Journal Article Chemistry – A European Journal 24 72 19373 19385 Wiley 0947-6539 1521-3765 Adamantane, influenza inhibitors, oligoethylene glycol, trivalent sialoside, viruses 20 12 2018 2018-12-20 10.1002/chem.201804826 http://dx.doi.org/10.1002/chem.201804826 COLLEGE NANME Chemistry COLLEGE CODE CHEM Swansea University 2024-01-02T13:09:42.7852973 2023-11-01T10:41:21.6228351 Faculty of Science and Engineering School of Engineering and Applied Sciences - Chemistry Pallavi Kiran 1 Sumati Bhatia 0000-0002-5123-4937 2 Daniel Lauster 3 Stevan Aleksić 4 Carsten Fleck 5 Natalija Peric 6 Wolfgang Maison 7 Susanne Liese 8 Bettina G. Keller 9 Andreas Herrmann 10 Rainer Haag 0000-0003-3840-162x 11 64872__29336__2c46b9456ce1428a980a5c6823ca1e9a.pdf 64872.VOR.pdf 2024-01-02T11:43:23.6562265 Output 1221046 application/pdf Version of Record true © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. Distributed under the terms of a Creative Commons Attribution Non Commercial 4.0 License (CC BY-NC 4.0). true eng https://creativecommons.org/licenses/by-nc/4.0/
title Exploring Rigid and Flexible Core Trivalent Sialosides for Influenza Virus Inhibition
spellingShingle Exploring Rigid and Flexible Core Trivalent Sialosides for Influenza Virus Inhibition
Sumati Bhatia
title_short Exploring Rigid and Flexible Core Trivalent Sialosides for Influenza Virus Inhibition
title_full Exploring Rigid and Flexible Core Trivalent Sialosides for Influenza Virus Inhibition
title_fullStr Exploring Rigid and Flexible Core Trivalent Sialosides for Influenza Virus Inhibition
title_full_unstemmed Exploring Rigid and Flexible Core Trivalent Sialosides for Influenza Virus Inhibition
title_sort Exploring Rigid and Flexible Core Trivalent Sialosides for Influenza Virus Inhibition
author_id_str_mv a6b1181ebdbe42bd03b24cbdb559d082
author_id_fullname_str_mv a6b1181ebdbe42bd03b24cbdb559d082_***_Sumati Bhatia
author Sumati Bhatia
author2 Pallavi Kiran
Sumati Bhatia
Daniel Lauster
Stevan Aleksić
Carsten Fleck
Natalija Peric
Wolfgang Maison
Susanne Liese
Bettina G. Keller
Andreas Herrmann
Rainer Haag
format Journal article
container_title Chemistry – A European Journal
container_volume 24
container_issue 72
container_start_page 19373
publishDate 2018
institution Swansea University
issn 0947-6539
1521-3765
doi_str_mv 10.1002/chem.201804826
publisher Wiley
college_str Faculty of Science and Engineering
hierarchytype
hierarchy_top_id facultyofscienceandengineering
hierarchy_top_title Faculty of Science and Engineering
hierarchy_parent_id facultyofscienceandengineering
hierarchy_parent_title Faculty of Science and Engineering
department_str School of Engineering and Applied Sciences - Chemistry{{{_:::_}}}Faculty of Science and Engineering{{{_:::_}}}School of Engineering and Applied Sciences - Chemistry
url http://dx.doi.org/10.1002/chem.201804826
document_store_str 1
active_str 0
description 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.
published_date 2018-12-20T13:09:44Z
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score 11.013731

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