A focused sulfated glycoconjugate Ugi library for probing heparan sulfate-binding angiogenic growth factors

Liu, Ligong, Li, Caiping, Cochran, Siska, Feder, Daniel, Guddat, Luke W. and Ferro, Vito (2012) A focused sulfated glycoconjugate Ugi library for probing heparan sulfate-binding angiogenic growth factors. Bioorganic & Medicinal Chemistry Letters, 22 19: 6190-6194.


Author Liu, Ligong
Li, Caiping
Cochran, Siska
Feder, Daniel
Guddat, Luke W.
Ferro, Vito
Title A focused sulfated glycoconjugate Ugi library for probing heparan sulfate-binding angiogenic growth factors
Journal name Bioorganic & Medicinal Chemistry Letters   Check publisher's open access policy
ISSN 0960-894X
1464-3391
Publication date 2012-08-10
Sub-type Article (original research)
DOI 10.1016/j.bmcl.2012.08.001
Volume 22
Issue 19
Start page 6190
End page 6194
Total pages 5
Place of publication Oxford, United Kingdom
Publisher Pergamon
Collection year 2013
Language eng
Formatted abstract A library of small molecule heparan sulfate (HS) mimetics was synthesized by employing the Ugi four-component condensation of d-mannopyranoside-derived isocyanides with formaldehyde as the carbonyl component and a selection of carboxylic acids and amines, followed by sulfonation. The library was used to probe the subtle differences surrounding the ionic binding sites of three HS-binding angiogenic growth factors (FGF-1, FGF-2 and VEGF). Each compound features 3 or 4 sulfo groups which serve to anchor the ligand to the HS-binding site of the protein, with a diverse array of functionality in place extending from C-1 or C-6 to probe for adjacent favorable binding interactions. Selectivity of binding to these proteins was clearly observed and supported by molecular docking calculations.
Keyword Glycoconjugates
Growth Factors
Heparan sulfate mimetics
Inhibitors
Ugi condensation
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2013 Collection
School of Chemistry and Molecular Biosciences
Institute for Molecular Bioscience - Publications
 
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Created: Tue, 02 Oct 2012, 10:01:10 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences