Production of polycyclic aromatic hydrocarbon metabolites from a peroxynitrite/iron(III) porphyrin biomimetic model and their mutagenicities



Some polycyclic aromatic hydrocarbons (PAHs) are typical promutagens that require metabolic activation to exhibit their mutagenicities and carcinogenicities. The metabolites of three PAHs, pyrene (PY), fluoranthene (FLU), and benzo[a]pyrene (BaP), produced from the peroxynitrite/T(p-Cl)PPFeCl(peroxynitrite/(chloride)iron(III)tetrakis(p-chlorophenyl)porphyrin) system, have been identified with high-performance liquid chromatography coupled with electron spray ionization tandem mass spectrometry. The results demonstrated that three major metabolites were the quinone group, OH group, and nitro group. In the Ames test, all three PAH metabolites became mutagenic without using the enzymatic activating system, whereas their parents did not show positive results. Cell transformation assay indicated that 1,3-nitro-BaP and BaP metabolites produced from this biomimetic system have more serious effects in inducing cancer than the BaP parent. Environ. Toxicol. Chem. 2011; 30:723–729. © 2010 SETAC