Efficient chemical synthesis of heparin-like octa-, deca- and dodecasaccharides and inhibition of FGF2- and VEGF165-mediated endothelial cell functions | Zendy

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

Open Access

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

Author(s) -

Gavin J. Miller,

Steen U. Hansen,

Egle Avizienyte,

Graham Rushton,

Claire L. Cole,

Gordon C. Jayson,

John M. Gardiner

Publication year - 2013

Publication title -

chemical science

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 3.687

H-Index - 172

eISSN - 2041-6539

pISSN - 2041-6520

DOI - 10.1039/c3sc51217g

Subject(s) - sulfation , cell growth , heparin , in vitro , chemistry , endothelial stem cell , angiogenesis , stereochemistry , biochemistry , microbiology and biotechnology , biology , cancer research

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.

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