0000000000460337
AUTHOR
Michael Fickler
The 3,4-oxide is responsible for the DNA binding of benzo[ghi]perylene, a polycyclic aromatic hydrocarbon without a “classic” bay-region
Abstract The polycyclic aromatic hydrocarbon (PAH) benzo[ghi]perylene (BghiP) lacks a “classic” bay-region and is therefore unable to form vicinal dihydrodiol epoxides thought to be responsible for the genotoxicity of carcinogenic PAHs like benzo[a]pyrene. The bacterial mutagenicity of BghiP increases considerably after inhibition of the microsomal epoxide hydrolase (mEH) indicating arene oxides as genotoxic metabolites. Two K-region epoxides of BghiP, 3,4-epoxy-3,4-dihydro-BghiP (3,4-oxide) and 3,4,11,12-bisepoxy-3,4,11,12-tetrahydro-BghiP (3,4,11,12-bisoxide) identified in microsomal incubations of BghiP are weak bacterial mutagens in strain TA98 of Salmonella typhimurium with 5.5 and 1.5…
Unexpected DNA damage caused by polycyclic aromatic hydrocarbons under standard laboratory conditions
Abstract The genotoxicity of 15 polycyclic aromatic hydrocarbons was determined with the alkaline version of the comet assay employing V79 lung fibroblasts of the Chinese hamster as target cells. These cells lack the enzymes necessary to convert PAHs to DNA-binding metabolites. Surprisingly, 11 PAHs, i.e., benzo[ a ]pyrene (BaP), benz[ a ]anthracene, 7,12-dimethylbenz[ a ]anthracene, 3-methylcholanthrene, fluoranthene, anthanthrene, 11 H -benzo[ b ]fluorene, dibenz[ a,h ]anthracene, pyrene, benzo[ ghi ]perylene and benzo[ e ]pyrene caused DNA strand breaks even without external metabolic activation, while naphthalene, anthracene, phenanthrene and naphthacene were inactive. When the comet as…