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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
1
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pubmed:dateCreated |
1992-3-9
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pubmed:abstractText |
Crotonaldehyde (2-butenal), which reacts with DNA and is mutagenic and carcinogenic, was identified as a hepatic microsomal metabolite of the hepatocarcinogen N-nitrosopyrrolidine. Incubation mixtures of N-nitrosopyrrolidine, cofactors, and hepatic microsomes from Aroclor pretreated or control F344 rats were derivatized with (2,4-dinitrophenyl)hydrazine reagent and the resulting mixtures analyzed by high-performance liquid chromatography. Crotonaldehyde (2,4-dinitrophenyl)hydrazone was identified by its retention time in two different systems and by its ultraviolet and mass spectrum. The ratio of 4-hydroxybutyraldehyde, which has previously been identified as a metabolite of NPYR, to crotonaldehyde was 1.5-2 over a range of substrate concentrations. The approximate values of Km and nu max for crotonaldehyde were 5.8 mM and 0.6 nmol/min/mg of protein and for 4-hydroxybutyraldehyde 14.1 mM and 1.7 nmol/min/mg of protein, for substrate concentrations between 1 and 8 mM, with microsomes from Aroclor pretreated rats. The ratio of 4-hydroxybutyraldehyde to crotonaldehyde was 1.9 upon esterase-catalyzed solvolysis of alpha-acetoxy-N-nitrosopyrrolidine, a stable precursor to the initial product of N-nitrosopyrrolidine alpha-hydroxylation. These results demonstrate that crotonaldehyde is formed upon metabolic alpha-hydroxylation of N-nitrosopyrrolidine and suggest that it may be involved in N-nitrosopyrrolidine-macromolecule interactions.
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pubmed:grant | |
pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:issn |
0893-228X
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:volume |
1
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
28-31
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pubmed:dateRevised |
2007-11-14
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pubmed:meshHeading |
pubmed-meshheading:2979707-Aldehydes,
pubmed-meshheading:2979707-Animals,
pubmed-meshheading:2979707-Biotransformation,
pubmed-meshheading:2979707-Chromatography, High Pressure Liquid,
pubmed-meshheading:2979707-Hydroxylation,
pubmed-meshheading:2979707-Kinetics,
pubmed-meshheading:2979707-Male,
pubmed-meshheading:2979707-Microsomes, Liver,
pubmed-meshheading:2979707-N-Nitrosopyrrolidine,
pubmed-meshheading:2979707-Rats,
pubmed-meshheading:2979707-Rats, Inbred F344
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pubmed:articleTitle |
Identification of crotonaldehyde as a hepatic microsomal metabolite formed by alpha-hydroxylation of the carcinogen N-nitrosopyrrolidine.
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pubmed:affiliation |
Division of Chemical Carcinogenesis, American Health Foundation, Valhalla, New York 10595.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.
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