Mutational Spectra for 5,6-Dimethylchrysene 1,2-Dihydrodiol 3,4-Epoxides in the supF Gene of pSP189

John E. Page, Jan Szeliga, Anthony Dipple, Shantu Amin, Stephen S. Hecht

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Dihydrodiol epoxides from 5,6-dimethylchrysene exhibit properties similar to those of fjord region-containing hydrocarbon derivatives in that they react extensively with deoxyadenosine residues in DNA and consequently generate substantial numbers of mutations at AT pairs as well as GC pairs. The syn-dihydrodiol epoxide favors reaction with deoxyadenosine (68% of adducts) to a greater extent than does the anti-dihydrodiol epoxide (52% of adducts), and point mutations at AT pairs (72% for syn- and 45% for anti-dihydrodiol epoxide) follow the same trend. A novel feature of the mutagenicity of the 5,6-dimethylchrysene derivatives is that they exhibit a higher fraction of AT → GC transitions (28% and 26% for syn and anti, respectively) than has been seen for other hydrocarbon derivatives to date.

Original languageEnglish (US)
Pages (from-to)143-147
Number of pages5
JournalChemical Research in Toxicology
Volume8
Issue number1
DOIs
StatePublished - Jan 1 1995

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Epoxy Compounds
Genes
Hydrocarbons
Derivatives
Estuaries
Point Mutation
Mutation
5,6-dimethylchrysene
trans-1,2-dihydro-1,2-naphthalenediol
DNA
2'-deoxyadenosine

All Science Journal Classification (ASJC) codes

  • Toxicology

Cite this

Page, John E. ; Szeliga, Jan ; Dipple, Anthony ; Amin, Shantu ; Hecht, Stephen S. / Mutational Spectra for 5,6-Dimethylchrysene 1,2-Dihydrodiol 3,4-Epoxides in the supF Gene of pSP189. In: Chemical Research in Toxicology. 1995 ; Vol. 8, No. 1. pp. 143-147.
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abstract = "Dihydrodiol epoxides from 5,6-dimethylchrysene exhibit properties similar to those of fjord region-containing hydrocarbon derivatives in that they react extensively with deoxyadenosine residues in DNA and consequently generate substantial numbers of mutations at AT pairs as well as GC pairs. The syn-dihydrodiol epoxide favors reaction with deoxyadenosine (68{\%} of adducts) to a greater extent than does the anti-dihydrodiol epoxide (52{\%} of adducts), and point mutations at AT pairs (72{\%} for syn- and 45{\%} for anti-dihydrodiol epoxide) follow the same trend. A novel feature of the mutagenicity of the 5,6-dimethylchrysene derivatives is that they exhibit a higher fraction of AT → GC transitions (28{\%} and 26{\%} for syn and anti, respectively) than has been seen for other hydrocarbon derivatives to date.",
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Mutational Spectra for 5,6-Dimethylchrysene 1,2-Dihydrodiol 3,4-Epoxides in the supF Gene of pSP189. / Page, John E.; Szeliga, Jan; Dipple, Anthony; Amin, Shantu; Hecht, Stephen S.

In: Chemical Research in Toxicology, Vol. 8, No. 1, 01.01.1995, p. 143-147.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Mutational Spectra for 5,6-Dimethylchrysene 1,2-Dihydrodiol 3,4-Epoxides in the supF Gene of pSP189

AU - Page, John E.

AU - Szeliga, Jan

AU - Dipple, Anthony

AU - Amin, Shantu

AU - Hecht, Stephen S.

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N2 - Dihydrodiol epoxides from 5,6-dimethylchrysene exhibit properties similar to those of fjord region-containing hydrocarbon derivatives in that they react extensively with deoxyadenosine residues in DNA and consequently generate substantial numbers of mutations at AT pairs as well as GC pairs. The syn-dihydrodiol epoxide favors reaction with deoxyadenosine (68% of adducts) to a greater extent than does the anti-dihydrodiol epoxide (52% of adducts), and point mutations at AT pairs (72% for syn- and 45% for anti-dihydrodiol epoxide) follow the same trend. A novel feature of the mutagenicity of the 5,6-dimethylchrysene derivatives is that they exhibit a higher fraction of AT → GC transitions (28% and 26% for syn and anti, respectively) than has been seen for other hydrocarbon derivatives to date.

AB - Dihydrodiol epoxides from 5,6-dimethylchrysene exhibit properties similar to those of fjord region-containing hydrocarbon derivatives in that they react extensively with deoxyadenosine residues in DNA and consequently generate substantial numbers of mutations at AT pairs as well as GC pairs. The syn-dihydrodiol epoxide favors reaction with deoxyadenosine (68% of adducts) to a greater extent than does the anti-dihydrodiol epoxide (52% of adducts), and point mutations at AT pairs (72% for syn- and 45% for anti-dihydrodiol epoxide) follow the same trend. A novel feature of the mutagenicity of the 5,6-dimethylchrysene derivatives is that they exhibit a higher fraction of AT → GC transitions (28% and 26% for syn and anti, respectively) than has been seen for other hydrocarbon derivatives to date.

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