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WHY DOES 5-METHYL CHRYSENE INTERACT WITH DNA LIKE BOTH A PLANAR AND A NON-PLANAR POLYCYCLIC AROMATIC HYDROCARBON? QUANTUM MECHANICAL STUDIES
Citation:
Rabinowitz, J. R., S. Little, AND K. W. Brown. WHY DOES 5-METHYL CHRYSENE INTERACT WITH DNA LIKE BOTH A PLANAR AND A NON-PLANAR POLYCYCLIC AROMATIC HYDROCARBON? QUANTUM MECHANICAL STUDIES. INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY 88(1):99-106, (2001).
Description:
Polycyclic aromatic hydrocarbons are a large class of anthropogenic chemicals found in the environment. Some class members are potent animal carcinogens while other similar class members show little carcinogenic activity. When considering a series of in vitro studies of the interaction of polycyclic aromatic hydrocarbon bay region diol-epoxides with DNA, it was found that molecules with a crowded bay region behaved differently than molecules with a more open bay region. Molecules with a crowded bay region are non-planar while in general polycyclic aromatic hydrocarbons are planar molecules. This dichotomy between planar and non-planar subclasses proved useful but when the experimental data was considered, 5-methylchrysene did not fit well into either class. In this study quantum mechanical calculations are reported that show 5-methyl chrysene and its diol-epoxides are nonplanar molecules but the energy required to force them to be planar is considerably smaller than for most other non-planar polycyclic aromatic hydrocarbons. The relationship to the experimental results that indicated 5-methylchrysene may behave like both a planar polycyclic aromatic hydrocarbon in some experiments and a nonplanar polycyclic aromatic hydrocarbon in others is discussed.