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The Effect of the Structure of Polychlorinated Biphenyls on their Hydroxylation, Oxidation, and Glutathionyl Conjugation Reactions.
MedLine Citation:
PMID:  23336137     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
OBJECTIVE: To compare the nature of the metabolites formed from the phase I metabolism (hydroxylation and oxidation) and phase II metabolism (glutathionyl conjugation) of PCBs that have different chlorine substitution patterns. To discuss the structure-activity relationships and metabolic mechanisms of PCBs. METHODS: 4-Cl-biphenyl (PCB3), 4,4'-Cl-biphenyl (PCB15), 3,4,3',4'-Cl-biphenyl (PCB77) were used for in vitro metabolic study. LC/MS and UV-Vis studies were performed for metabolites identification. RESULTS: The cytochrome P-450 catalyzed hydroxylation rate decreased as the number of chlorine substitutions increased. In this reaction, PCB3 was fully metabolized, approximately half of the PCB15 was metabolized and PCB77 was not metabolized at all. The oxidation rate of PCB15-HQ was higher than that of PCB3-HQ under various oxidation conditions. The LC/MS and UV-Vis data suggest that in the conjugation reaction of PCB15-Q and GSH, the Michael addition reaction occurs preferentially over the displacement reaction. CONCLUSION: The metabolic profiles of polychlorinated biphenyls (PCBs) are dramatically affected by chlorine substitution patterns. It is suggested that the metabolic profiles of PCBs are related to their chlorine substitution patterns, which may have implications for the toxicity of PCB exposure.
Authors:
Er Qun Song; Xiao Yan Ma; Xing Guo Tian; Jing Liu; Li Chao Liu; Hui Dong; Yang Song
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Publication Detail:
Type:  JOURNAL ARTICLE    
Journal Detail:
Title:  Biomedical and environmental sciences : BES     Volume:  26     ISSN:  0895-3988     ISO Abbreviation:  Biomed. Environ. Sci.     Publication Date:  2013 Feb 
Date Detail:
Created Date:  2013-1-22     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8909524     Medline TA:  Biomed Environ Sci     Country:  -    
Other Details:
Languages:  ENG     Pagination:  138-147     Citation Subset:  -    
Copyright Information:
Copyright © 2013 The Editorial Board of Biomedical and Environmental Sciences. Published by China CDC. All rights reserved.
Affiliation:
Key Laboratory of Luminescence and Real-Time Analysis, Ministry of Education, College of Pharmaceutical Sciences, Southwest University, Chongqing 400715, China.
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