Skip to main content

Research Repository

Advanced Search

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
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

Files

G Miller - Efficient chemical synthesis of heparin-like octa- deca- and dodecasaccharides and inhibition....pdf (726 Kb)
PDF







You might also like



Downloadable Citations