Abstract.
Dibromoacetonitrile (DBAN) is a disinfection byproduct of chlorination of drinking water. Epidemiological studies indicate that it might present a potential hazard to human health. The present work provides evidence for DBAN activation to cyanide (CN–) by the hypoxanthine (HX)/xanthine oxidase (XO)/iron (Fe) system in vitro. Optimum conditions for the oxidation of DBAN to CN–were characterized. Addition of the sulfhydryl compounds glutathione, N-acetyl-L-cysteine or dithiothreitol significantly enhanced the rate of CN–release. A high positive correlation existed between hydroxyl free radical (•OH) generation and CN– formation. Addition of the •OH scavengers mannitol or dimethylthiourea to the reaction mixtures resulted in a significant decrease in the rate of DBAN oxidation. Addition of the antioxidant enzymes catalase or superoxide dismutase resulted in a significant decrease in the rate of DBAN oxidation. The iron chelator desferrioxamine significantly decreased CN– formation. The maximum velocity (V max) and Michaelis-Menten constant (K m) of the reaction were assessed. Allopurinol competitively inhibited the reaction, while folic acid uncompetitively inhibited the reaction. In conclusion, •OH generated by the HX/XO/Fe system are implicated in DBAN oxidation. The present results represent a novel pathway for DBAN activation and might be important in explaining DBAN-induced toxicity.
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Mohamadin, A.M., Abdel-Naim, A.B. In vitro activation of dibromoacetonitrile to cyanide: role of xanthine oxidase. Arch Toxicol 77, 86–93 (2003). https://doi.org/10.1007/s00204-002-0418-7
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DOI: https://doi.org/10.1007/s00204-002-0418-7