| Sialyl Lewis(x) analogs based on a quinic acid scaffold as the fucose mimic. | |
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MedLine Citation:
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PMID: 15936191 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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(-)-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. |
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Authors:
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Christian Girard; Jennifer Dourlat; Aline Savarin; Christine Surcin; Stefanie Leue; Virginie Escriou; Céline Largeau; Jean Herscovici; Daniel Scherman |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Bioorganic & medicinal chemistry letters Volume: 15 ISSN: 0960-894X ISO Abbreviation: Bioorg. Med. Chem. Lett. Publication Date: 2005 Jul |
Date Detail:
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Created Date: 2005-06-13 Completed Date: 2005-10-11 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 9107377 Medline TA: Bioorg Med Chem Lett Country: England |
Other Details:
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Languages: eng Pagination: 3224-8 Citation Subset: IM |
Affiliation:
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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. christian-girard@enscp.fr |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Cell Adhesion
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drug effects E-Selectin / drug effects*, metabolism Fucose / chemistry HL-60 Cells Humans Inhibitory Concentration 50 Ligands Molecular Mimicry Oligosaccharides / chemical synthesis*, metabolism, pharmacology P-Selectin / drug effects Quinic Acid / chemical synthesis*, pharmacology |
| Chemical | |
Reg. No./Substance:
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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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