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

  1. Author:
    Szeliga, J.
    Amin, S.
    Zhang, F. J.
    Harvey, R. G.

  2. Author Address

    Szeliga J NCI, Chem Carcinogenesis Lab, ABL Basic Res Program, Frederick Canc Res & Dev Ctr Frederick, MD 21702 USA NCI, Chem Carcinogenesis Lab, ABL Basic Res Program, Frederick Canc Res & Dev Ctr Frederick, MD 21702 USA Amer Hlth Fdn, Naylor Dana Inst Dis Prevent Valhalla, NY 10595 USA Univ Chicago, Ben May Inst Canc Res Chicago, IL 60637 USA
    1. Year: 1999
  2. Journal: Chemical Research in Toxicology
    1. 12
    2. 4
    3. Pages: 347-352
  4. Type of Article: Article
  1. 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 6-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 B-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. [References: 28]

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