title: The effect of alpha-chlorohydrin on the oxidation of fructose by rabbit spermatozoa in vitro.
abstract: (R,S)-alpha-Chlorohydrin inhibits the oxidative metabolism of fructose in mature rabbit spermatozoa in vitro. This effect is not noticeable at concentrations of the compound up to 10 mM, is evident at 50 mM but at 100 mM is apparently accompanied by cell damage. At a concentration of 50 mM, (R,S)-alpha-chlorohydrin causes the specific inhibition of the enzyme glyceraldehyde 3-phosphate dehydrogenase and is metabolised by the spermatozoa to 3-chlorolactaldehyde of unknown configuration. Exogenous (R,S)-3-chlorolactaldehyde (5 mM and 10 mM) appears to inhibit glyceraldehyde 3-phosphate dehydrogenase in rabbit spermatozoa as well as affecting other metabolic pathways. The ineffectiveness of (R,S)-alpha-chlorohydrin as an anti-fertility agent in male rabbits may be due to the inability of the spermatozoa to produce a sufficient amount of the inhibitory metabolite (S)-3-chlorolactaldehyde.
mesh_terms: D000818:Animals; D002728:Chlorohydrins / Q000494:pharmacology*; D003272:Contraceptive Agents, Male / Q000494:pharmacology*; D005632:Fructose / Q000378:metabolism*; D005993:Glycerolphosphate Dehydrogenase / Q000037:antagonists & inhibitors; D006019:Glycolysis / Q000187:drug effects; D066298:In Vitro Techniques; D008297:Male; D010084:Oxidation-Reduction / Q000187:drug effects; D011817:Rabbits; D013045:Species Specificity; D013094:Spermatozoa / Q000187:drug effects* / Q000378:metabolism; D000517:alpha-Chlorohydrin / Q000378:metabolism / Q000494:pharmacology*
chemical_list: D002728:Chlorohydrins; D003272:Contraceptive Agents, Male; D005632:Fructose; D000517:alpha-Chlorohydrin; D005993:Glycerolphosphate Dehydrogenase