Reactions of dihydrodiol epoxides of 5-methylchrysene and 5,6- dimethylchrysene with DNA and deoxyribonucleotides

Jan Szeliga, Shantu Amin, Fang Jie Zhang, Ronald G. Harvey

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Both syn and anti dihydrodiol epoxides from 5-methylchrysene (5-MCDE) and 5,6-dimethylchrysene (5,6-DMCDE) were reacted under the same conditions with native DNA, denatured DNA, and purine deoxyribonucleotides, and the products were quantified. The extents of reaction with the deoxyribonucleotides were consistently greater for 5,6-DMCDE than for 5- MCDE. The yield of adducts in the reaction with DNA ranged from being a few- fold to 50-fold greater than those found in the corresponding deoxyribonucleotide reactions for both 5-MCDE and 5,6-DMCDE. The DNA- dependent enhancement of product yield was greater for 5-MCDE than for 5,6- DMCDE with a few exceptions among cis and trans deoxyadenosine adducts. The most substantial differences in DNA-dependent enhancement were found for deoxyguanosine adducts; thus, steric hindrance between the 6-methyl group in the 5,6-DMCDE and the minor groove in the DNA double helix may account for the greater DNA-dependent enhancement found in the 5-MCDE reactions.

Original languageEnglish (US)
Pages (from-to)347-352
Number of pages6
JournalChemical Research in Toxicology
Volume12
Issue number4
DOIs
StatePublished - Apr 1 1999

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Deoxyribonucleotides
Epoxy Compounds
DNA
Deoxyguanosine
trans-1,2-dihydro-1,2-naphthalenediol
5,6-dimethylchrysene
5-methylchrysene

All Science Journal Classification (ASJC) codes

  • Toxicology

Cite this

@article{40cf3ec4fdde49ccb4848a156b8e7673,
title = "Reactions of dihydrodiol epoxides of 5-methylchrysene and 5,6- dimethylchrysene with DNA and deoxyribonucleotides",
abstract = "Both syn and anti dihydrodiol epoxides from 5-methylchrysene (5-MCDE) and 5,6-dimethylchrysene (5,6-DMCDE) were reacted under the same conditions with native DNA, denatured DNA, and purine deoxyribonucleotides, and the products were quantified. The extents of reaction with the deoxyribonucleotides were consistently greater for 5,6-DMCDE than for 5- MCDE. The yield of adducts in the reaction with DNA ranged from being a few- fold to 50-fold greater than those found in the corresponding deoxyribonucleotide reactions for both 5-MCDE and 5,6-DMCDE. The DNA- dependent enhancement of product yield was greater for 5-MCDE than for 5,6- DMCDE with a few exceptions among cis and trans deoxyadenosine adducts. The most substantial differences in DNA-dependent enhancement were found for deoxyguanosine adducts; thus, steric hindrance between the 6-methyl group in the 5,6-DMCDE and the minor groove in the DNA double helix may account for the greater DNA-dependent enhancement found in the 5-MCDE reactions.",
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Reactions of dihydrodiol epoxides of 5-methylchrysene and 5,6- dimethylchrysene with DNA and deoxyribonucleotides. / Szeliga, Jan; Amin, Shantu; Zhang, Fang Jie; Harvey, Ronald G.

In: Chemical Research in Toxicology, Vol. 12, No. 4, 01.04.1999, p. 347-352.

Research output: Contribution to journalArticle

TY - JOUR

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AU - Amin, Shantu

AU - Zhang, Fang Jie

AU - Harvey, Ronald G.

PY - 1999/4/1

Y1 - 1999/4/1

N2 - Both syn and anti dihydrodiol epoxides from 5-methylchrysene (5-MCDE) and 5,6-dimethylchrysene (5,6-DMCDE) were reacted under the same conditions with native DNA, denatured DNA, and purine deoxyribonucleotides, and the products were quantified. The extents of reaction with the deoxyribonucleotides were consistently greater for 5,6-DMCDE than for 5- MCDE. The yield of adducts in the reaction with DNA ranged from being a few- fold to 50-fold greater than those found in the corresponding deoxyribonucleotide reactions for both 5-MCDE and 5,6-DMCDE. The DNA- dependent enhancement of product yield was greater for 5-MCDE than for 5,6- DMCDE with a few exceptions among cis and trans deoxyadenosine adducts. The most substantial differences in DNA-dependent enhancement were found for deoxyguanosine adducts; thus, steric hindrance between the 6-methyl group in the 5,6-DMCDE and the minor groove in the DNA double helix may account for the greater DNA-dependent enhancement found in the 5-MCDE reactions.

AB - Both syn and anti dihydrodiol epoxides from 5-methylchrysene (5-MCDE) and 5,6-dimethylchrysene (5,6-DMCDE) were reacted under the same conditions with native DNA, denatured DNA, and purine deoxyribonucleotides, and the products were quantified. The extents of reaction with the deoxyribonucleotides were consistently greater for 5,6-DMCDE than for 5- MCDE. The yield of adducts in the reaction with DNA ranged from being a few- fold to 50-fold greater than those found in the corresponding deoxyribonucleotide reactions for both 5-MCDE and 5,6-DMCDE. The DNA- dependent enhancement of product yield was greater for 5-MCDE than for 5,6- DMCDE with a few exceptions among cis and trans deoxyadenosine adducts. The most substantial differences in DNA-dependent enhancement were found for deoxyguanosine adducts; thus, steric hindrance between the 6-methyl group in the 5,6-DMCDE and the minor groove in the DNA double helix may account for the greater DNA-dependent enhancement found in the 5-MCDE reactions.

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