Document Detail

Nitroxide metabolites from alkylhydroxylamines and N-hydroxyurea derivatives resulting from reductive inhibition of soybean lipoxygenase.
MedLine Citation:
PMID:  1315759     Owner:  NLM     Status:  MEDLINE    
One proposed mechanism of the inactivation of lipoxygenase by inhibitors is the reduction of the catalytically active ferric form of the enzyme to its ferrous form. Recent studies have shown that compounds containing the hydroxamate moiety are potent inhibitors of lipoxygenase. The hydroxamate portion of the inhibitor is thought to bind to iron at the catalytic site of the enzyme. We now report evidence that the NOH of the hydroxamate group of N-(4-chlorophenyl)-N-hydroxy-N'-(3-chlorophenyl)urea, N-[(E)-3-(3-phenoxyphenyl)prop-2-enyl]acetohydroxamic acid (BW A4C), and N-(1-benzo(b)thien-2-ylethyl)-N-hydroxyurea (Zileuton) is oxidized by lipoxygenase to form their corresponding nitroxides, which are directly detected by electron paramagnetic resonance spectroscopy. It is consistently found that the selected NOH-containing compounds, e.g. alkylhydroxylamines or N-hydroxyureas, are also oxidized by lipoxygenase to form their corresponding nitroxides.
W Chamulitrat; R P Mason; D Riendeau
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Publication Detail:
Type:  Comparative Study; Journal Article    
Journal Detail:
Title:  The Journal of biological chemistry     Volume:  267     ISSN:  0021-9258     ISO Abbreviation:  J. Biol. Chem.     Publication Date:  1992 May 
Date Detail:
Created Date:  1992-06-09     Completed Date:  1992-06-09     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985121R     Medline TA:  J Biol Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  9574-9     Citation Subset:  IM    
National Institute of Environmental Health Sciences, National Institutes of Health, Research Triangle Park, North Carolina 27709.
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MeSH Terms
Electron Spin Resonance Spectroscopy
Free Radicals
Hydroxamic Acids / pharmacology
Hydroxylamines / metabolism*,  pharmacology
Hydroxyurea / analogs & derivatives*,  metabolism*,  pharmacology
Lipoxygenase Inhibitors / metabolism,  pharmacology*
Molecular Structure
Nitrogen Oxides / metabolism*
Soybeans / enzymology*
Structure-Activity Relationship
Reg. No./Substance:
0/Benzeneacetamides; 0/Free Radicals; 0/Hydroxamic Acids; 0/Hydroxylamines; 0/Lipoxygenase Inhibitors; 0/Nitrogen Oxides; 106328-57-8/N-(3-phenoxycinnamyl)acetohydroxamic acid; 127-07-1/Hydroxyurea; 132880-11-6/zileuton; 14332-28-6/nitroxyl

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

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