Cyclopenta[cd]fluoranthene and its precursors in combustion exhausts: a survey of their bacterial mutagenic activity.
Cyclopenta[cd]fluoranthene (1) and 3-ethynylfluoranthene (2) have both recently been identified in combustion exhausts. In this study, their mutagenic activities were compared to that of fluoranthene (3), one of the most abundant polycyclic aromatic hydrocarbons (PAHs) in combustion exhausts, in the Salmonella/microsome reversion assay (Ames assay) using S. typhimurium strain TA98. The mutagenicity of 1 was modest in comparison to other active cyclopenta PAHs. Unexpectedly, 2 was mutagenic both with and without exogenous metabolic activation (rat liver S9). Furthermore, cyclopenta[cd]fluoranthene-3,4-epoxide (6) was synthesized in order to evaluate its role as the ultimate mutagenic active form of 1. The epoxide 6 was a direct-acting mutagen. In addition, a pyrolysate containing a mixture of 1 (85%), 2 (2%), and 3 (13%) obtained by flash vacuum thermolysis of 3-(1-chloroethenyl)fluoranthene (2a) at 1,050 degrees C was also mutagenic, but a significant mutagenic response was detected only in the presence of S9 activation. The results of this study indicate that 1 and 2 can contribute to the mutagenic activity of combustion exhausts.
Debye Institute, Department of Physical Organic Chemistry, Utrecht University, 3584 CH Utrecht, The Netherlands.
María José
MJ
Otero-Lobato
Leonardus W
LW
Jenneskens
Willem
W
Seinen
D000818:Animals; D005449:Fluorenes / Q000737:chemistry / Q000633:toxicity*; D008297:Male; D008862:Microsomes, Liver / Q000187:drug effects / Q000378:metabolism; D009152:Mutagenicity Tests; D051381:Rats; D017208:Rats, Wistar; D000091243:Ribosomal Protein S9; D012269:Ribosomal Proteins / Q000378:metabolism; D012486:Salmonella typhimurium / Q000187:drug effects / Q000235:genetics; D001335:Vehicle Emissions / Q000032:analysis / Q000633:toxicity*
D005449:Fluorenes; D000091243:Ribosomal Protein S9; D012269:Ribosomal Proteins; D001335:Vehicle Emissions