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Issue 8, 2013
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Efficient chemical synthesis of heparin-like octa-, deca- and dodecasaccharides and inhibition of FGF2- and VEGF165-mediated endothelial cell functions†

Gavin J. Miller,‡a   Steen U. Hansen,§a   Egle Avizienyte,b   Graham Rushton,b   Claire Cole,b   Gordon C. Jaysonb  and  John M. Gardiner*a  
Author affiliations

* Corresponding authors

a Manchester Institute of Biotechnology, School of Chemistry, Faculty of Engineering and Physical Sciences, The University of Manchester, 131 Princess Street, Manchester M1 7DN, UK
E-mail: gardiner@manchester.ac.uk
Tel: +44 (0)161 306 4530

b School of Cancer and Enabling Sciences, University of Manchester, UK
E-mail: Gordon.Jayson2@christie.nhs.uk
Fax: +44 (0)161 446 8565
Tel: +44 (0)161 446 3740

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.

Graphical abstract: Efficient chemical synthesis of heparin-like octa-, deca- and dodecasaccharides and inhibition of FGF2- and VEGF165-mediated endothelial cell functions

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Article information

https://doi.org/10.1039/C3SC51217G
Submitted
03 May 2013
Accepted
26 May 2013
First published
28 May 2013
Chem. Sci., 2013,4, 3218-3222
Article type
Edge Article
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Efficient chemical synthesis of heparin-like octa-, deca- and dodecasaccharides and inhibition of FGF2- and VEGF165-mediated endothelial cell functions

G. J. Miller, S. U. Hansen, E. Avizienyte, G. Rushton, C. Cole, G. C. Jayson and J. M. Gardiner, Chem. Sci., 2013, 4, 3218
DOI: 10.1039/C3SC51217G

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