外消旋和S(+)α-氯代甘油醇-1-磷酸对3-磷酸甘油醛脱氢酶的作用及其避孕作用的关系

Effect of racemic and S(+) alpha-chlorohydrin-1-phosphate on glyceraldehyde-3-phosphate dehydrogenase in relation to its contraceptive action.

作者信息

Fitzpatrick R W, Jackson H, Dickinson N A

出版信息

Contraception. 1978 Nov;18(5):477-83. doi: 10.1016/0010-7824(78)90032-x.

Abstract

The phosphate esters of racemic (+/-) alpha-chlorohydrin and its S(+)-optical isomer have been prepared as cyclohexylamine salts. In vitro both inhibited glyceraldehyde-3-phosphate dehydrogenase by a competitive mechanism, whereas (+/-) alpha-chlorohydrin did not. The S(+)-isomer was approximately four times as potent as the racemate. These results correlate with data concerning the relative contraceptive activity in rats of racemic and S(+) alpha-chlorohydrin. They support the view that the antifertility mechanism involves in vivo formation of S(+) alpha-chlorohydrin-1-phosphate, with resulting inhibition of glycolysis in sperm.

摘要

外消旋（±）α-氯醇及其S（+）-旋光异构体的磷酸酯已制备成环己胺盐。在体外，两者均通过竞争性机制抑制3-磷酸甘油醛脱氢酶，而（±）α-氯醇则无此作用。S（+）-异构体的效力约为外消旋体的四倍。这些结果与有关外消旋和S（+）α-氯醇在大鼠体内相对避孕活性的数据相关。它们支持这样一种观点，即抗生育机制涉及体内形成S（+）α-氯醇-1-磷酸，从而抑制精子中的糖酵解。