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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
6
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pubmed:dateCreated |
1989-5-2
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pubmed:abstractText |
The mutagenicity of benzyl 1,2,3,4,4-pentachlorobutadienyl sulfide (BPBS) and benzyl 1,2-dichlorovinyl sulfide (BDVS) was studied in the Ames preincubation assay to investigate the hypothesis that the mutagenic effect of the cysteine S-conjugates S-(pentachlorobutadienyl)-L-cysteine and S-(1,2-dichlorovinyl)-L-cysteine is associated with their metabolism to unstable thiols. Under conditions enabling cytochrome P-450-dependent benzylic hydroxylation of BPBS and BDVS, both benzyl sulfides were mutagenic. These results in combination with the lack of mutagenicity observed with benzaldehyde and with the tert-butyl analogues, which cannot be metabolized to a hemimercaptal, indicate that the formation of unstable thiols is responsible for the mutagenic effects of the benzyl sulfides and the corresponding cysteine S-conjugates. Benzyl 2-chloro-1,1,2-trifluoroethyl sulfide, which also undergoes benzylic hydroxylation, was negative in the Ames-Test; this is in agreement with the observed lack of mutagenicity of the corresponding S-conjugate S-(2-chloro-1,1,2-trifluoroethyl)-L-cysteine. Also, benzyl 2-chloroethyl sulfide, which, along with the corresponding S-conjugate S-(2-chloroethyl)-L-cysteine, does not require bioactivation, was a potent, direct-acting mutagen in the Ames-Test.
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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/Benzyl Compounds,
http://linkedlifedata.com/resource/pubmed/chemical/Cysteine,
http://linkedlifedata.com/resource/pubmed/chemical/Cytochrome P-450 Enzyme System,
http://linkedlifedata.com/resource/pubmed/chemical/Sulfhydryl Compounds,
http://linkedlifedata.com/resource/pubmed/chemical/Sulfides,
http://linkedlifedata.com/resource/pubmed/chemical/Tissue Extracts
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pubmed:status |
MEDLINE
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pubmed:month |
Mar
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pubmed:issn |
0006-2952
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:day |
15
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pubmed:volume |
38
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
935-9
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pubmed:dateRevised |
2007-11-14
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pubmed:meshHeading |
pubmed-meshheading:2930594-Animals,
pubmed-meshheading:2930594-Benzyl Compounds,
pubmed-meshheading:2930594-Biotransformation,
pubmed-meshheading:2930594-Cysteine,
pubmed-meshheading:2930594-Cytochrome P-450 Enzyme System,
pubmed-meshheading:2930594-DNA Damage,
pubmed-meshheading:2930594-Microsomes, Liver,
pubmed-meshheading:2930594-Mutagenicity Tests,
pubmed-meshheading:2930594-Oxidation-Reduction,
pubmed-meshheading:2930594-Rats,
pubmed-meshheading:2930594-Sulfhydryl Compounds,
pubmed-meshheading:2930594-Sulfides,
pubmed-meshheading:2930594-Tissue Extracts
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pubmed:year |
1989
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pubmed:articleTitle |
Mutagenicity of benzyl S-haloalkyl and S-haloalkenyl sulfides in the Ames-test.
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pubmed:affiliation |
Institut für Toxikologie, Universität Würzburg, Federal Republic of Germany.
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pubmed:publicationType |
Journal Article,
Comparative Study,
Research Support, U.S. Gov't, P.H.S.,
Research Support, U.S. Gov't, Non-P.H.S.,
Research Support, Non-U.S. Gov't
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