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Improved antiviral properties of chain end lipophilic fucoidan-mimetic glycopolymers synthesized by RAFT polymerization
Linköping University, Department of Physics, Chemistry and Biology, Chemistry. Linköping University, Faculty of Science & Engineering.
Linköping University, Department of Clinical and Experimental Medicine, Division of Cell Biology. Linköping University, Faculty of Medicine and Health Sciences.
Linköping University, Department of Clinical and Experimental Medicine, Division of Cell Biology. Linköping University, Faculty of Medicine and Health Sciences. Univ Montreal, Canada; Univ Montreal, Canada.ORCID iD: 0000-0003-1222-6720
Linköping University, Department of Clinical and Experimental Medicine, Division of Cell Biology. Linköping University, Faculty of Medicine and Health Sciences.
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2018 (English)In: European Polymer Journal, ISSN 0014-3057, E-ISSN 1873-1945, Vol. 98, p. 285-294Article in journal (Refereed) Published
Abstract [en]

Sulfated polysaccharides and synthetic glycopolymers are promising candidates as antiviral drugs but have failed in clinical trials most likely due to lack of virucidal activity. However, studies have shown that incorporation of lipophilic end groups to oligosaccharide chains is a mean to gain the desired virucidal properties. Here, we describe the introduction of lipophilic end groups to sulfated alpha-L-fucoside-pendant polymethacrylamides, also known as fucoidan-mimetic glycopolymers, by RAFT polymerization. RAFT agents bearing octadecyl, dioctadecyl and cholesteryl groups were used to synthesize lipoglycopolymers of different chain lengths. Short lipoglycopolymers bearing lipophilic end groups showed an improved ability to block viral entry and infection of cells compared to glycopolymers without lipophilic end groups. Short lipoglycopolymers bearing octadecyl or dioctadecyl end groups, also completely stopped the spreading of the viral infection. However, these lipoglycopolymers did not show actual virucidal properties. Nevertheless, we have described a first step towards obtaining virucidal synthetic glycopolymers for clinical use.

Place, publisher, year, edition, pages
PERGAMON-ELSEVIER SCIENCE LTD , 2018. Vol. 98, p. 285-294
Keywords [en]
Glycopolymers; Lipoglycopolymers; RAFT polymerization; Herpes simplex virus-1; Antiviral
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:liu:diva-145802DOI: 10.1016/j.eurpolymj.2017.11.025ISI: 000425561700029OAI: oai:DiVA.org:liu-145802DiVA, id: diva2:1192347
Note

Funding Agencies|Linkopings Universitet

Available from: 2018-03-22 Created: 2018-03-22 Last updated: 2018-03-22

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Tengdelius, MattiasCheung, KittGriffith, MayPåhlsson, PeterKonradsson, Peter
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European Polymer Journal
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