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• W1966205220 abstract "1. The influence of a change in the type of halogen substituent on phase II metabolism of 2-fluoro-4-halophenol metabolites formed from 3-halo-fluorobenzenes was studied in vivo and in vitro using 19F nmr and spectroscopic assays.2. The ratio of sulphation to glucuronidation of 2-fluoro-4-halophenol metabolites formed from 3-halofluorobenzenes decreased from 48 to 13 to 6 when the halogen substituent varied from fluorine to chlorine to bromine.3. When the 2-fluoro-4-halophenols themselves were administered to the rats, the ratio of sulphation to glucuronidation was not affected by the type of halogen substituent at C4 and at a constant value of 0.6, i.e. significantly lower.4. Kinetic data for P450 catalysed hydroxylation of the 3-halo-fluorobenzenes and for sulphation and glucuronidation of their 2-fluoro-4-halophenol metabolites were obtained from in vitro microsomal and cytosolic incubations. These data demonstrate that the effects of varying the halogen substituent on phase II metabolism of the 2-fluoro-4-halophenol metabolites can be mainly ascribed to an apparently decreased Km for the glucuronidation of the 2-fluoro-4-halophenols with a change in the halo substituent from fluorine to chlorine to bromine.5. Results from calculations on electronic and structural characteristics of the three 4-halo-2-fluorophenols demonstrate that the best explanation for the decrease in the apparent Km of the glucuronidation from 2,4-difluoro-to 4-chloro-2 fluoro to 4-bromo-2-fluorophenol might be an increase in the hydrophobicity of the phenol. An increase in the hydrophobicity of the phenol would provide an increased possibility for substrate accumulation in the hydrophobic membrane environment of the UDP-glucuronyltransferases, resulting in an apparently decreased Km." @default.
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• W1966205220 date "1994-01-01" @default.
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• W1966205220 title "Influence of the type of halogen substituent on<i>in vivo</i>and<i>in vitro</i>phase II metabolism of 2-fluoro-4-halophenol metabolites formed from 3-halo-fluorobenzenes" @default.
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• W1966205220 doi "https://doi.org/10.3109/00498259409043276" @default.
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