Effect of Nitro Orientation on Ras -Protooncogene Mutation in Liver Tumors from 7-Nitrodibenz[ a,h ]anthracene-Treated Mice

Fu, Peter P.; Tungeln, Linda S. Von; Xia, Qingsu; Zhan, Daqian; Heflich, Robert H.

doi:10.1080/10406630290104004

Cited by 2 publications

(1 citation statement)

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“…Possible factors for the differences include hydrophobicity, metabolism, ability to intercalate, orientation prior to binding, and DNA sequence specificity for binding (20). To rationalize the differences, Fu et al and Rosenkrantz (4,(21)(22)(23)(24) proposed that the nitro group orientation relative to the aromatic moiety may be correlated with observed mutagenicity. Such a proposal was the subject of a previous study (9) where the nitro group orientation of nitro-PAHs with 1-4 aromatic benzenoid rings was examined with the density functional theoretical (DFT) method B3LYP/6-31G*.…”

Section: Introductionmentioning

confidence: 95%

Density Functional Theoretical Study of Mono-Nitrated Fluoranthenes

Onchoke

2008

Polycyclic Aromatic Compounds

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The molecules 1-, 2-, 3-, 7-, and 8-nitrofluoranthenes are well-known mutagens and carcinogens. These environmental pollutants are emitted into the atmosphere via anthropogenic activities including diesel combustion emissions, residential home heating and reactions of nitrogen oxide (NO x ) gases with fluoranthene. The differential mutagenic potency between nitrated fluoranthenes has been proposed to emanate from the orientation of the nitro group relative to the aromatic plane. To establish the validity of the structure-function correlations requires specific crystal structures, which are unavailable. Fortunately, electronic structure calculations can be done. In this report, the structures of fluoranthene and its mono nitrated derivatives were investigated with the density functional theoretical theory at B3LYP/6-311+G** level. The structure-function correlations were examined by comparing reported mutagenicity data with calculated bond lengths, angles and dihedral angles. The relationships between the calculated structures and the reported mutagenicity in the chemical literature are discussed.

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