Document Detail

Mercapturic acid formation is an activation and intermediary step in the metabolism of hexachlorobutadiene.
MedLine Citation:
PMID:  3516155     Owner:  NLM     Status:  MEDLINE    
14C-hexachlorobutadiene (HCBD), a mutagenic and nephrocarcinogenic pollutant, was administered by oral gavage of 100 mg/kg to female rats, and the radioactivity in 24 hr urine pooled. The average amount of radioactivity recovered in urine was 5.4% of the total 14C-activity ingested. Solvent extraction, high performance liquid chromatography (HPLC), radio gas chromatography and gas chromatography/mass spectrometry were used for separation and identification of metabolites. After solvent extraction and HPLC four fractions were separated containing 1%, 5%, 15% and 80% of radioactivity. In the 80% fraction one metabolite was identified after derivatization and comparison with the authentic compound as the mercapturic acid of HCBD (N-acetyl-S-1,1,2,3,4-pentachlorobutadienyl)-L-cysteine). The mercapturic acid accounts for 10% of the urinary 14C-activity. In a first attempt the mutagenic potential of the mercapturic acid was determined on Salmonella typhimurium TA 100 with and without metabolic activating S9 mix. In the presence of S9 mix the mercapturic acid exerts a strong mutagenic effect which proved to be about 80 times higher than that of HCBD. The results identify the formation of the mercapturic acid via direct glutathione conjugation as an activating and intermediary step in the metabolism of hexachlorobutadiene.
D Reichert; S Schütz
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Biochemical pharmacology     Volume:  35     ISSN:  0006-2952     ISO Abbreviation:  Biochem. Pharmacol.     Publication Date:  1986 Apr 
Date Detail:
Created Date:  1986-05-14     Completed Date:  1986-05-14     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0101032     Medline TA:  Biochem Pharmacol     Country:  ENGLAND    
Other Details:
Languages:  eng     Pagination:  1271-5     Citation Subset:  IM    
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MeSH Terms
Acetylcysteine / metabolism*
Butadienes / metabolism*,  poisoning
Carbon Radioisotopes / diagnostic use
Gas Chromatography-Mass Spectrometry
Mutagens / metabolism
Rats, Inbred Strains
Salmonella typhimurium / drug effects
Reg. No./Substance:
0/Butadienes; 0/Carbon Radioisotopes; 0/Mutagens; 616-91-1/Acetylcysteine; 87-68-3/hexachlorobutadiene

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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