Document Detail

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.
MedLine Citation:
PMID:  7703369     Owner:  NLM     Status:  MEDLINE    
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)
A A Elfarra; J E Sharer; R J Duescher
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Chemical research in toxicology     Volume:  8     ISSN:  0893-228X     ISO Abbreviation:  Chem. Res. Toxicol.     Publication Date:    1995 Jan-Feb
Date Detail:
Created Date:  1995-05-10     Completed Date:  1995-05-10     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  8807448     Medline TA:  Chem Res Toxicol     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  68-76     Citation Subset:  IM    
Department of Comparative Biosciences, University of Wisconsin, Madison 53706, USA.
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MeSH Terms
Acetylcysteine / metabolism*
Carcinogens / metabolism*
Epoxy Compounds / metabolism*
Mutagens / metabolism*
Rats, Sprague-Dawley
Grant Support
Reg. No./Substance:
0/Carcinogens; 0/Epoxy Compounds; 0/Mutagens; 616-91-1/Acetylcysteine; 930-22-3/3,4-epoxy-1-butene

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