TY - JOUR
T1 - Reactions of dihydrodiol epoxides of 5-methylchrysene and 5,6- dimethylchrysene with DNA and deoxyribonucleotides
AU - Szeliga, Jan
AU - Amin, Shantu
AU - Zhang, Fang Jie
AU - Harvey, Ronald G.
PY - 1999/4
Y1 - 1999/4
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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U2 - 10.1021/tx980228o
DO - 10.1021/tx980228o
M3 - Article
C2 - 10207124
AN - SCOPUS:0032939933
SN - 0893-228X
VL - 12
SP - 347
EP - 352
JO - Chemical research in toxicology
JF - Chemical research in toxicology
IS - 4
ER -