Improved antiviral properties of chain end lipophilic fucoidan-mimetic glycopolymers synthesized by RAFT polymerization

[Display omitted] •O-sulfated glycopolymers with different lipophilic end groups were synthesized.•Short glycopolymers with lipophilic end groups improved the antiviral properties.•The viral infection was completely inhibited and the spreading stopped.•The lipoglycopolymers did not show virucidal pr...

Full description

Saved in:
Bibliographic Details
Published in:European polymer journal 2018-01, Vol.98, p.285-294
Main Authors: Tengdelius, Mattias, Cheung, Kwan Yee, Griffith, May, Påhlsson, Peter, Konradsson, Peter
Format: Article
Language:English
Subjects:
Addition polymerization
Antiviral
Antiviral drugs
Bearing
Chemical synthesis
Copolymers
Glycopolymers
Herpes simplex virus-1
Lipoglycopolymers
Medical research
Oligosaccharides
Polymerization
Polymers
Polysaccharides
Properties (attributes)
RAFT polymerization
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:[Display omitted] •O-sulfated glycopolymers with different lipophilic end groups were synthesized.•Short glycopolymers with lipophilic end groups improved the antiviral properties.•The viral infection was completely inhibited and the spreading stopped.•The lipoglycopolymers did not show virucidal properties. 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 α-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.
ISSN:0014-3057
1873-1945
1873-1945
DOI:10.1016/j.eurpolymj.2017.11.025