D-葡萄糖的O-甲基磺酰基衍生物作为靶向脑药物递送潜在烷基化剂的合成。评估它们与人类红细胞GLUT1己糖转运蛋白的相互作用。
Synthesis of O-methylsulfonyl derivatives of D-glucose as potential alkylating agents for targeted drug delivery to the brain. Evaluation of their interaction with the human erythrocyte GLUT1 hexose transporter.
作者信息
Halmos T, Santarromana M, Antonakis K, Scherman D
机构信息
UMR 133 CNRS/Rhône-Poulenc Rorer, Laboratoire de Chimie Organique Biologique, Villejuif, France.
出版信息
Carbohydr Res. 1997 Mar 26;299(1-2):15-21. doi: 10.1016/s0008-6215(96)00328-x.
In order to obtain hydrophilic analogues of 1,4-dimethylsulfonyloxybutane (busulfan) with enhanced selectivity and improved brain penetration, we have synthesized 6-O-methylsulfonyl-D-glucose, 3-O-methylsulfonyl-D-glucose, 3,6-di-O-methylsulfonyl-D-glucose, 4-O-methylsulfonyl-D-glucose, and 4,6-di-O-methylsulfonyl-D-glucose, and we have studied their interactions with the human erythrocyte GLUT1 hexose transport system. Mesylation of OH-4 and OH-6 of glucose resulted in a slightly diminished affinity for the GLUT1 glucose transporter, whereas mesylation of OH-3 led to complete loss of affinity.
为了获得具有更高选择性和更好脑渗透性的1,4 - 二甲磺酰氧基丁烷（白消安）的亲水性类似物，我们合成了6 - O - 甲基磺酰基 - D - 葡萄糖、3 - O - 甲基磺酰基 - D - 葡萄糖、3,6 - 二 - O - 甲基磺酰基 - D - 葡萄糖、4 - O - 甲基磺酰基 - D - 葡萄糖和4,6 - 二 - O - 甲基磺酰基 - D - 葡萄糖，并研究了它们与人红细胞GLUT1己糖转运系统的相互作用。葡萄糖的OH - 4和OH - 6甲磺酰化导致对GLUT1葡萄糖转运蛋白的亲和力略有降低，而OH - 3甲磺酰化导致亲和力完全丧失。
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