Jones A R, Ford S A
Contraception. 1984 Sep;30(3):261-9. doi: 10.1016/0010-7824(84)90089-1.
(S)-alpha-Chlorohydrin inhibits the conversion of fructose to lactate by mature guinea pig spermatozoa in vitro. At a concentration of 2mM, there is a specific inhibition of glyceraldehyde-phosphate dehydrogenase resulting in the accumulation of fructose-1,6-bisphosphate, dihydroxyacetone phosphate and glyceraldehyde-3-phosphate and a concomitant decrease in the concentration of endogenous lactate. (R,S)-[3-36Cl]-alpha-Chlorohydrin is metabolised by the spermatozoa to 3-chlorolactaldehyde of unknown configuration. Exogenous (R,S)-3-chlorolactaldehyde (2mM) is an inhibitor of glyceraldehyde-phosphate dehydrogenase in guinea pig spermatozoa, whereas (R)-alpha-chlorohydrin (10mM) has no significant effect on the metabolism of fructose. 6-Chloro-6-deoxyglucose (10mM) inhibits glyceraldehyde-phosphate dehydrogenase in guinea pig spermatozoa in vitro and is metabolised to 3-chlorolactaldehyde which is presumably the (S)-isomer. The anti-glycolytic actions of (S)-alpha-chlorohydrin and 6-chloro-6-deoxyglucose in guinea pig spermatozoa are suggested to be due to the action of a common metabolite, (S)-3-chlorolactaldehyde.
(S)-α-氯醇在体外可抑制成熟豚鼠精子将果糖转化为乳酸的过程。在2mM的浓度下,它能特异性抑制磷酸甘油醛脱氢酶,导致果糖-1,6-二磷酸、磷酸二羟丙酮和3-磷酸甘油醛积累,同时内源性乳酸浓度降低。(R,S)-[3-³⁶Cl]-α-氯醇被精子代谢为构型未知的3-氯乙醛。外源性(R,S)-3-氯乙醛(2mM)是豚鼠精子中磷酸甘油醛脱氢酶的抑制剂,而(R)-α-氯醇(10mM)对果糖代谢无显著影响。6-氯-6-脱氧葡萄糖(10mM)在体外可抑制豚鼠精子中的磷酸甘油醛脱氢酶,并被代谢为3-氯乙醛,推测其为(S)-异构体。(S)-α-氯醇和6-氯-6-脱氧葡萄糖在豚鼠精子中的抗糖酵解作用被认为是由于共同代谢产物(S)-3-氯乙醛的作用。