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- W2026673172 abstract "Incubation of rat liver microsomes with radiolabeled 2,4-diaminoanisole (2,4-DAA) in the presence of NADPH and oxygen led to the formation of irreversibly bound products to microsomal protein. The binding was inhibited by a CO:O2 atmosphere and by an antibody against NADPH cytochrome c reductase. In vivo and in vitro inhibitors of cytochrome P-450 decreased the binding and phenobarbital-pretreatment increased binding, whereas β-napthoflavone-pretreatment was without effect. Binding of ring-labeled 2,4-DAA was much higher than with methyl-labeled-2,4-DAA. Experiments with [3H]-ring-and [14C]-ring-labeled-2,4-DAA indicated some loss of tritium; this was confirmed by isolation of labile tritium. Substitution of the hydrogens in the methyl group with deuterium led to increases in both binding and mutagenicity of 2,4-DAA. Formation of formaldehyde and a small amount of methanol could be demonstrated during the oxidative metabolism of methyl-labeled-2,4-DAA. Addition of superoxide dismutase and ascorbic acid inhibited binding, and a small amount of irreversible binding could be demonstrated when NADPH was replaced by a xanthine-xanthine oxidase system. Microsomes from rat kidneys also activated 2.4-DAA in the presence of NADPH. Thin-layer chromatography revealed that 30–40 per cent of 2.4-DAA was oxidized during 10 min of incubation with liver microsomes. And a tentative scheme involving aromatic hydroxylation, oxidative demethylation and N-hydroxylation for the microsomal metabolism of 2,4-DAA is presented. Irreversible binding could also be shown with liver microsomal RNA in vitro, whereas no binding to exogenously added DNA could be found." @default.
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- W2026673172 date "1979-01-01" @default.
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- W2026673172 title "Metabolic activation of 2,4-diaminoanisole, a hair-dye component—II. Role of cytochrome P-450 metabolism in irreversible binding in vitro" @default.
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- W2026673172 doi "https://doi.org/10.1016/0006-2952(79)90268-5" @default.
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