Document Detail

Sialyl Lewis(x) analogs based on a quinic acid scaffold as the fucose mimic.
MedLine Citation:
PMID:  15936191     Owner:  NLM     Status:  MEDLINE    
(-)-Quinic acid was used as a starting material for the preparation of sialyl Lewis(x) mimetics in order to target E-selectin. Spatial orientation of the hydroxyl groups of quinic acid could mimic the l-fucose ones. Introduction of a side chain ending with a carboxylic acid was effected to replace the sialic acid interaction at the carbohydrate recognition domain. A first series of derivatives, incorporating amino acids linked to quinic acid, were tested for their affinity and found to interact with E-selectin with IC(50) within the millimolar range.
Christian Girard; Jennifer Dourlat; Aline Savarin; Christine Surcin; Stefanie Leue; Virginie Escriou; Céline Largeau; Jean Herscovici; Daniel Scherman
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Bioorganic & medicinal chemistry letters     Volume:  15     ISSN:  0960-894X     ISO Abbreviation:  Bioorg. Med. Chem. Lett.     Publication Date:  2005 Jul 
Date Detail:
Created Date:  2005-06-13     Completed Date:  2005-10-11     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9107377     Medline TA:  Bioorg Med Chem Lett     Country:  England    
Other Details:
Languages:  eng     Pagination:  3224-8     Citation Subset:  IM    
Laboratoire de Pharmacologie Chimique and Génétique (UMR 8151 CNRS/U 640 INSERM), Ecole Nationale Supérieure de Chimie de Paris, 11 rue P. and M. Curie, 75005 Paris, France.
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MeSH Terms
Cell Adhesion / drug effects
E-Selectin / drug effects*,  metabolism
Fucose / chemistry
HL-60 Cells
Inhibitory Concentration 50
Molecular Mimicry
Oligosaccharides / chemical synthesis*,  metabolism,  pharmacology
P-Selectin / drug effects
Quinic Acid / chemical synthesis*,  pharmacology
Reg. No./Substance:
0/5-acetylneuraminyl-(2-3)-galactosyl-(1-4)-(fucopyranosyl-(1-3))-N-acetylglucosamine; 0/E-Selectin; 0/Ligands; 0/Oligosaccharides; 0/P-Selectin; 3713-31-3/Fucose; 77-95-2/Quinic Acid

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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