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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
5
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pubmed:dateCreated |
1992-3-2
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pubmed:abstractText |
The in vitro S-oxygenation of thiobencarb (Bolero; p-chlorobenzyl N,N-diethylthiocarbamate) in the presence of hepatic microsomes from freshwater- and seawater-adapted striped bass was investigated. Thiobencarb S-oxide was the principal metabolite and accounted for 98% of the total thiobencarb metabolized by striped bass liver microsomes. Studies on the biochemical mechanisms for striped bass hepatic S-oxygenation suggest that this reaction is catalyzed largely by the flavin-containing monooxygenase and to a lesser extent by cytochromes P-450. Following the short incubation period used, no thiobencarb sulfone was detected and no evidence was found for a contribution of cooxidation in the S-oxidation of thiobencarb. This conclusion was supported by studies with microsomes and purified mammalian monooxygenases which also metabolized thiobencarb without cooxidizing factors. Highly purified cytochrome P-450IIB-1 S-oxygenated thiobencarb more efficiently than highly purified hog liver flavin-containing monoxygenase. Thiobencarb S-oxide and thiobencarb sulfone were efficient carbamylating agents and reacted with thiol and amine nucleophiles, whereas thiobencarb itself was relatively stable to transthiocarbamylation. Monooxygenase-catalyzed S-oxygenation of thiobencarb by striped bass liver microsomes may represent a bioactivation process which could explain the known toxicity of thiobencarb in fish.
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pubmed:grant | |
pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Cytochrome P-450 Enzyme System,
http://linkedlifedata.com/resource/pubmed/chemical/Insecticides,
http://linkedlifedata.com/resource/pubmed/chemical/Oxygenases,
http://linkedlifedata.com/resource/pubmed/chemical/Sulfones,
http://linkedlifedata.com/resource/pubmed/chemical/Thiocarbamates,
http://linkedlifedata.com/resource/pubmed/chemical/benthiocarb,
http://linkedlifedata.com/resource/pubmed/chemical/dimethylaniline monooxygenase...
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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 |
3
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
433-40
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pubmed:dateRevised |
2007-11-14
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pubmed:meshHeading |
pubmed-meshheading:2133094-Animals,
pubmed-meshheading:2133094-Bass,
pubmed-meshheading:2133094-Cytochrome P-450 Enzyme System,
pubmed-meshheading:2133094-Insecticides,
pubmed-meshheading:2133094-Microsomes, Liver,
pubmed-meshheading:2133094-Oxidation-Reduction,
pubmed-meshheading:2133094-Oxygenases,
pubmed-meshheading:2133094-Rats,
pubmed-meshheading:2133094-Sulfones,
pubmed-meshheading:2133094-Swine,
pubmed-meshheading:2133094-Thiocarbamates
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pubmed:articleTitle |
S-oxygenation of thiobencarb (Bolero) in hepatic preparations from striped bass (Morone saxatilis) and mammalian systems.
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pubmed:affiliation |
Department of Pharmaceutical Chemistry, School of Pharmacy, University of California, San Francisco, California 94143-0446.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.,
Research Support, Non-U.S. Gov't
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