Document Detail


Horseradish peroxidase-catalyzed oxidation of acetaminophen to intermediates that form polymers or conjugate with glutathione.
MedLine Citation:
PMID:  3951429     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Horseradish peroxidase catalyzed the polymerization of acetaminophen. Addition of reduced glutathione (GSH) to reaction mixtures resulted in decreased polymerization and formation of minor amounts of GSH-acetaminophen conjugates. The conjugates were identified as 3-(glutathion-S-yl)acetaminophen and 3-(glutathion-S-yl)diacetaminophen. Horseradish peroxidase also catalyzed polymerization of synthetic 3-(glutathion-S-yl)acetaminophen to a dimer conjugate. In contrast to acetaminophen, 3-(glutathion-S-yl)acetaminophen oxidation was slowly catalyzed by horseradish peroxidase. However, in reaction mixtures containing equimolar concentrations of acetaminophen and synthetic 3-(glutathion-S-yl)acetaminophen, the formation of 3-(glutathion-S-yl)diacetaminophen and 3-(diglutathion-S-yl)diacetaminophen was rapid and accounted for approximately 95% of the products, whereas acetaminophen polymers accounted for only 5% of the products. These findings suggest that horseradish peroxidase catalyzed the one-electron oxidation of acetaminophen to N-acetyl-p-benzosemiquinone imine which preferentially polymerized rather than reacted with GSH. N-Acetyl-p-benzosemiquinone imine may also oxidize 3-(glutathion-S-yl)acetaminophen to form acetaminophen and 3-(glutathion-S-yl)-N-acetyl-p-benzosemiquinone imine. The data indicate that once this conjugate radical is formed it reacts with either N-acetyl-p-benzosemiquinone minine or 3-(glutathion-S-yl)-N-acetyl-p-benzosemiquinone imine via a radical termination mechanism.
Authors:
D W Potter; D W Miller; J A Hinson
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  Molecular pharmacology     Volume:  29     ISSN:  0026-895X     ISO Abbreviation:  Mol. Pharmacol.     Publication Date:  1986 Feb 
Date Detail:
Created Date:  1986-03-28     Completed Date:  1986-03-28     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0035623     Medline TA:  Mol Pharmacol     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  155-62     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Acetaminophen* / analogs & derivatives*
Benzoquinones*
Carbon Radioisotopes / diagnostic use
Chromatography, High Pressure Liquid
Free Radicals
Glutathione*
Horseradish Peroxidase / pharmacology*
Imines
Magnetic Resonance Spectroscopy
Oxidation-Reduction
Peroxidases / pharmacology*
Polymers*
Chemical
Reg. No./Substance:
0/Benzoquinones; 0/Carbon Radioisotopes; 0/Free Radicals; 0/Imines; 0/Polymers; 103-90-2/Acetaminophen; 50700-49-7/N-acetyl-4-benzoquinoneimine; 64889-81-2/3-(glutathion-S-yl)acetaminophen; 70-18-8/Glutathione; 87015-37-0/N-acetyl-4-benzosemiquinone imine; EC 1.11.1.-/Horseradish Peroxidase; EC 1.11.1.-/Peroxidases

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


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