O- and S-methylated bromothiocatechols.
Bromobenzene is metabolized by the Hartley guinea pig to two different bromothiocatechols, 4-bromo-2-hydroxythiophenol and 5-bromo-2-hydroxythiophenol. Both the thiol and phenol functional groups of thiocatechol undergo biological methylation. Methylation at the thiol group leads to the formation of (methylthio)bromophenol (S-methylated bromothiocatechol), while methylation of the phenol group leads to methoxybromothiophenol (O-methylated bromothiocatechol). This resulted in the urinary excretion of four O- and S-methylated bromothiocatechols. Bromothiocatechols could be formed by dehydrogenation of their corresponding bromodihydrobenzene thiolols. Both the 3-S- and 4-S-bromodihydrobenzene thiolols, as S-methylated products, were found as urinary metabolites of bromobenzene in the Hartley guinea pig. All four O- and S-methylated bromothiocatechols and two S-methylated bromodihydrobenzene thiolols were also found as urinary metabolites of bromobenzene in the golden Syrian hamster.
Lertratanangkoon
K
K
Department of Pharmacology and Toxicology, University of Texas Medical Branch, Galveston 77555-1031.
D000818:Animals; D001711:Biotransformation; D001969:Bromobenzenes / Q000378:metabolism*; D002396:Catechols / Q000378:metabolism* / Q000652:urine; D002849:Chromatography, Gas; D008401:Gas Chromatography-Mass Spectrometry; D006168:Guinea Pigs; D008297:Male; D008745:Methylation; D013438:Sulfhydryl Compounds / Q000378:metabolism / Q000652:urine
D001969:Bromobenzenes; D002396:Catechols; D013438:Sulfhydryl Compounds; C032036:bromobenzene