Gavin Miller g.j.miller@keele.ac.uk
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.
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 |
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