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National Institute of Environmental Health Sciences

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Your Environment. Your Health.

Publication Detail

Title: Synthesis and characterization of N-acetyl-L-cysteine S-conjugates of butadiene monoxide and their detection and quantitation in urine of rats and mice given butadiene monoxide.

Authors: Elfarra, A A; Sharer, J E; Duescher, R J

Published In Chem Res Toxicol, (1995 Jan-Feb)

Abstract: Butadiene monoxide (BM), a mutagen and carcinogen, is the major metabolite of 1,3-butadiene in rats and mice. Because mercapturic acids (N-acetyl-L-cysteine S-conjugates) were expected in vivo metabolites of BM, reference BM-mercapturic acids were prepared by the reaction of racemic BM with N-acetyl-L-cysteine. Four isomers were purified and characterized as diastereomeric pairs of S-(2-hydroxy-3-buten-1-yl)-N-acetyl-L-cysteine (I) and S-(1-hydroxy-3-buten-2-yl)-N-acetyl-L-cysteine (II) based on analyses by 1H NMR, fast atom bombardment mass spectrometry, and high resolution electron impact mass spectrometry. Regioisomers I and II were identified in the urine of rats and mice administered (ip) BM based on GC/MS analyses performed after HPLC fractionation followed by esterification and silylation of the carboxyl and hydroxyl groups, respectively, and comparison of GC retention times with synthetic standards. S-(4-Hydroxy-2-buten-1-yl)-N-acetyl-L-cysteine, a rearrangement product formed during chemical synthesis or storage of both I and II under acidic conditions, was not detected; no other BM metabolites were evident in urine samples using this method. When rats were given BM at a dose of 71.5 to 285 mumol/kg, their urinary excretion of I and II within 8 h of BM administration exhibited linear relationships with the administered BM dose; the total amount of the BM dose excreted as combined I and II averaged 17 +/- 4% (mean +/- SD, n = 15). No metabolites were detected in urine samples collected between 8 and 24 h after BM dosing.(ABSTRACT TRUNCATED AT 250 WORDS)

PubMed ID: 7703369 Exiting the NIEHS site

MeSH Terms: Acetylcysteine/metabolism*; Animals; Carcinogens/metabolism*; Epoxy Compounds/metabolism*; Male; Mice; Mutagens/metabolism*; Rats; Rats, Sprague-Dawley

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