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Hydrocarbon-deoxyribonucleoside adducts formed by syn and anti 5,6-dimethylchrysene 1,2- dihydrodiol 3,4-epoxides

  1. Author:
    Szeliga, J.
    Amin, S.
    Hilton, B. D.
    Chmurny, G. N.
    Dipple, A.
    1. Year of Conference: 1997
  2. Conference Name: Annual Meeting of the American Association for Cancer Research
    1. 38
    2. Pages: A3006
  4. Type of Work: Meeting Abstract
  1. Abstract:

    Exploration of the chemistry of DNA adduct formation by polycyclic aromatic hydrocarbons was extended by examining products of DNA reaction for both syn and anti 5,6-dimethylchrysene 1,2- dihydrodiol 3,4-epoxides (DMCDE). Approximately 32% of anti DMCDE and 24% of syn DMCDE was trapped by calf thymus DNA in aqueous solutions. Specific adducts were separated by HPLC and identified and characterized by UV, CD and NMR spectroscopy. The major products of reaction with DNA arose by bans opening of the epoxide ring by both deoxyguanosine and deoxyadenosine residues for anti DMCDE and from cis opening of the epoxide ring by deoxyadenosine residues for syn DMCDE. The relative yields of dAdo/dGuo adducts were 2.1/1 for syn DMCDE and 1.1/1 for anti DMCDE, respectively. 5,6-Dimethylchrysene has a sterically hindered bay region, resulting from the methyl groups at the 5- and 6-positions, that distorts the molecule from planarity. Presumably, as a result of this, the chemistry of adduct formation by DMCDE is similar to that of compounds containing fiord regions, e.g benzo[g]chrysene and benzo[c]phenanthrene, since these also react extensively with deoxyadenosine residues in DNA as well as with deoxyguanosine residues.

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