Ethylene chlorohydrin




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Chlorohydrin uptake was incorporated into the endothelial cells

Time:2015/12/4 2:30:14

The effect of isomer of α-chlorohydrin and racemic β-chlorolactate on the rat kidney

The (R)- and (S)-isomers of the male antifertility agent α-chlorohydrin have been synthesized. When administered to rats, the (R)-isomer induced a period of diuresis and glucosuria, whereas the (S)-isomer, which possesses the antifertility activity, had no detrimental action on the kidney. Neither of the isomers of α-chlorohydrin nor those of an active analogue, 3-amino-1-chloropropan-2-ol, had any inhibitory activity on the oxidative metabolism of glucose or lactate in isolated kidney tubules. However, β-chlorolactate, a metabolite common to both compounds, inhibited the oxidation of glucose, lactate, pyruvate and glutamate to CO2. It is proposed that the antifertility action of the (S)-isomers of α-chlorohydrin and 3-amino-1-chloropropan-2-ol is unrelated to the renal toxicity of the (R)-isomers, a toxic action involving the inhibition of oxidative metabolism by (S)-β-chlorolactate or a further product of this metabolite.

Fatty acid chlorohydrins and bromohydrins are cytotoxic to human endothelial cells

Reaction of unsaturated lipids with the hypohalous acids (hypochlorous acid and hypobromous acid) results in the addition of the halide (X) across double bonds to form halohydrins (-CH2CH(OH)CH(X)CH2-). These modified lipids could be potentially destabilising to cell membranes due to their increased polarity. We have investigated the effect of pre-formed halohydrins on human umbilical vein endothelial cells (HUVEC) by incubating cultured cells with oleic acid micelles containing chlorohydrins or bromohydrins. Cell detachment and necrotic death were observed with increasing doses of halohydrins, whereas the cells were unaffected by equivalent doses of oleic acid. Bromohydrins caused more lysis than did chlorohydrins at equivalent doses. Complete lysis was seen with 200 muM fatty acidchlorohydrin micelles and with 50 muM fatty acidbromohydrin micelles. Chlorohydrin uptake was much less than the oleic acid control whereas bromohydrins were incorporated into the endothelial cells similarly to oleic acid. This difference or the bulkier nature of the bromohydrins could account for their increased toxicity. This study has demonstrated the potential toxicity of the halohydrins, and implications for their formation in inflammation are discussed.