Girard Christian, Dourlat Jennifer, Savarin Aline, Surcin Christine, Leue Stefanie, Escriou Virginie, Largeau Céline, Herscovici Jean, Scherman Daniel
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.
Bioorg Med Chem Lett. 2005 Jul 1;15(13):3224-8. doi: 10.1016/j.bmcl.2005.05.004.
(-)-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.
（-）-奎尼酸被用作制备唾液酸化路易斯（x）模拟物的起始原料，以靶向E-选择素。奎尼酸羟基的空间取向可以模拟L-岩藻糖的羟基。引入以羧酸结尾的侧链以取代碳水化合物识别域中的唾液酸相互作用。测试了第一系列包含与奎尼酸相连的氨基酸的衍生物的亲和力，发现它们与E-选择素相互作用，其半数抑制浓度（IC50）在毫摩尔范围内。
