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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

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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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Publication details

The article was received on 03 May 2013, accepted on 26 May 2013 and first published on 28 May 2013


Article type: Edge Article
DOI: 10.1039/C3SC51217G
Chem. Sci., 2013,4, 3218-3222

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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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