Sialyl Lewis(x) analogs based on a quinic acid scaffold as the fucose mimic |
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Authors: | Girard Christian Dourlat Jennifer Savarin Aline Surcin Christine Leue Stefanie Escriou Virginie Largeau Céline Herscovici Jean Scherman Daniel |
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Institution: | 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 |
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Abstract: | (-)-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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