The anti-glycolytic action of (S)-alpha-chlorohydrin on epididymal bovine spermatozoa in vitro.
(S)-alpha-Chlorohydrin interferes with glycolysis in bovine spermatozoa whereas the (R)-isomer is ineffective. The action of the (S)-isomer, which involves inhibition of the reaction catalysed by glyceraldehyde 3-phosphate dehydrogenase, is not immediate but is evident only after a brief period of incubation with the spermatozoa. This inhibitory action is prevented when glycerol is present suggesting that the mechanism of action of (S)-alpha-chlorohydrin requires its oxidation to (S)-3-chlorolactaldehyde which is the active metabolite. Addition of racemic 3-chlorolactaldehyde to bovine spermatozoa caused immediate inhibition of glycolysis. It is proposed that the action of (S)-alpha-chlorohydrin in bovine spermatozoa is similar to that observed in the spermatozoa of other species in being a two-stage process; first, its oxidation to (S)-3-chlorolactaldehyde, and then inhibition of the glycolytic enzyme by this metabolite.
D000447:Aldehydes / Q000378:metabolism; D000818:Animals; D002417:Cattle; D002728:Chlorohydrins / Q000494:pharmacology*; D005632:Fructose / Q000378:metabolism; D005990:Glycerol / Q000378:metabolism; D005994:Glycerophosphates / Q000378:metabolism; D006019:Glycolysis / Q000187:drug effects*; D007536:Isomerism; D007773:Lactates / Q000378:metabolism; D019344:Lactic Acid; D008297:Male; D013094:Spermatozoa / Q000187:drug effects*; D000517:alpha-Chlorohydrin / Q000494:pharmacology*
D000447:Aldehydes; D002728:Chlorohydrins; D005994:Glycerophosphates; D007773:Lactates; D005632:Fructose; D019344:Lactic Acid; C045799:3-chlorolactaldehyde; D000517:alpha-Chlorohydrin; C029620:alpha-glycerophosphoric acid; D005990:Glycerol