Dinitropyrenes

Nitroaromatic compounds have been identified in diesel engine emissions (Salmeen et al. 1984), and attention has been directed particularly to 1,8- and 1,6-dinitropyrene that are mutagenic, and possibly carcinogenic (Nakagawa et al. 1983). 

Nakagawa R, S Kitamori, K Horikawa, K Nakashima, H Tokiwa (1983) Identification of dinitropyrenes in diesel-exhaust particles. Their probable presence as the major mutagens. Mutation Res 124 201-211. 

Recently, Bryant t al. (70) examined the metabolism of 1,8-dinitropyrene in several S. typhimurium strains and found reduction to l-amino-8-nitropyrene and 1,8-diaminopyrene. In addition, other unidentified metabolites were detected in strains which were sensitive to 1,8-dinitropyrene-induced mutations (TA98 and TA98NR) but not in the resistant strains, TA98/1,8-DNP and TA98NR/1,8-DNP6. 

Figure 13 Chromatogram of an airborne particulate sample. Peaks 1 = 1,6-dinitropyr-ene 2 = 1,8-dinitropyrene 3 = 1,3-dinitropyrene 4 = 2-fluoro-7-nitrofluorene 5 = 1-nitropyrene. (From Ref. 60.)...

Tokiwa H, Nakagawa R, Horikawa K. 1985. Mutagenic/carcinogenic agents in indoor pollutants The dinitropyrenes, generated by kerosene heaters and fuel gas and liquefied petroleum gas burners. Mutat Resl57(l) 39-47. 

YG1024 is 30 times more sensitive than TA98 to 1,8-dinitropyrene (2,150,000 vs 72,200 rev/nmol -S9). For example, Legzdins and co-workers (1994) used the enhanced response of strain YG1021 to determine the mutagenicities of 14 PAHs, and several nitroarenes, S-atom PACs, and O-atom PACs in the ambient air of Hamilton, Ontario, Canada. 

The human cell mutagenicities of several mono- and dinitropyrenes were determined by Busby and coworkers (1994b) in a forward mutation assay using a metabolically competent line of MCL-5 cells. Minimum detectable mutagen concentrations (MMC, in nmol ml-1 the smaller the detectable concentration, the greater the potency) were as follows 1,6-dinitropyrene, 0.8 1,8-dinitropyrene, 1.5 4-nitropyrene, 3.1 1-nitro-pyrene, 9.1. Other PACs tested, 2-nitropyrene, 1,3-dinitropyrene, and pyrene, were nonmutagens in this... 

Initially, major attention was focused on emissions of diesel soot from light- and heavy-duty motor vehicles, because the particle extracts contained such direct-acting bacterial mutagens and animal and possible human carcinogens (IARC Group 2B, 1989) as 1-nitropyrene (1-N02-PY) and the 1,6- and 1,8-dinitropyrenes (DNP), as well as a third isomer, 1,3-dinitropyrene, IARC Group III. For example, Paputa-Peck and coworkers (Paputa-Peck et al., 1983 IARC, 1989) reported 100 nitro-PAHs (17 positively identified) in... 

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