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Efficient chemical synthesis of heparin-like octa-, deca- and dodecasaccharides and inhibition of FGF2-and VEGF(165)-mediated endothelial cell functions

Miller, Gavin J.; Hansen, Steen U.; Avizienyte, Egle; Rushton, Graham; Cole, Claire; Jayson, Gordon C.; Gardiner, John M.

Efficient chemical synthesis of heparin-like octa-, deca- and dodecasaccharides and inhibition of FGF2-and VEGF(165)-mediated endothelial cell functions Thumbnail


Authors

Steen U. Hansen

Egle Avizienyte

Graham Rushton

Claire Cole

Gordon C. Jayson

John M. Gardiner



Abstract

A concise chemical synthesis of a series of structurally-defined heparin-like oligosaccharides is described. This work provides an efficient entry to octa-, deca-, and dodecasaccharides, including the first synthesis of (GlcNS6S-IdoA2S)5 and (GlcNS6S-IdoA2S)6. Evaluation of the in vitro activity of these species against FGF2- and VEGF165-dependent endothelial cell proliferation and migration establishes that octa- and decasaccharides are more potent in targeting FGF2-induced effects, where cell migration is affected more significantly than proliferation. These structure–activity relationships exemplify the significance of 6-O-sulfation in regulating the activity of angiogenic growth factors.

Journal Article Type Article
Acceptance Date May 26, 2013
Publication Date May 28, 2013
Publicly Available Date Mar 28, 2024
Journal Chemical Science
Print ISSN 2041-6520
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 4
Issue 8
Pages 3218 - 3222
DOI https://doi.org/10.1039/C3SC51217G
Publisher URL https://doi.org/10.1039/c3sc51217g

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