Dinitro and mononitrobenzo(ghi)perylenes and mononitrocoronene are highly mutagenic in the Ames Salmonella assay.
Benzo(ghi)perylene (B(ghi))Per, (191-24-2)) and coronene (Cor, (191-07-1)) are major constituents of the polycyclic aromatic hydrocarbons (PAH) found in automobile exhaust and polluted air [eg, Grimmer et al, 1981]. Nitration of these PAH by NO2 and traces of HNO3, which are also formed in automobile exhaust, seems highly probable. To identify the presence of these nitroarenes in environmental samples and to examine their mutagenic potencies we synthesized and characterized nitro derivatives of both PAH. 5-NO2B(ghi)Per (81316-87-2) and 1-NO2Cor (81316-84-9) produced 405 and 340 revertants/nmole respectively in TA98 in the presence of 0.6 mg of microsomal enzymes (S-9) per plate in the Ames test. 5,8-diNO2B(ghi)Per (83292-25-5) and 5,10-diNO2B(ghi)Per (83292-26-6) produced 21,500 and 4,000 revertants/nmole in TA98 without microsomal activation. Mutagenicity for the dinitrobenzo(ghi)perylenes was also high in TA98NR and TA97 but was reduced by 97% in TA98-1,8DNP. There is close similarity in the orientation and distances between reactive sites (nitrenium ion and carbocation) on the dinitrobenzo(ghi)perylenes and 1,6-dinitropyrene (42397-64-8) and 1,8-dinitropyrene (42397-65-9).
D000818:Animals; D001551:Benz(a)Anthracenes / Q000633:toxicity; D001711:Biotransformation; D008862:Microsomes, Liver / Q000378:metabolism; D009152:Mutagenicity Tests; D009153:Mutagens / Q000378:metabolism; D010569:Perylene / Q000031:analogs & derivatives / Q000633:toxicity; D011083:Polycyclic Compounds / Q000633:toxicity*; D051381:Rats; D012475:Salmonella / Q000187:drug effects; D013329:Structure-Activity Relationship
D001551:Benz(a)Anthracenes; D009153:Mutagens; D011083:Polycyclic Compounds; D010569:Perylene; C040176:1-nitrocoronene