Cyclopenta[cd]fluoranthene and its precursors in combustion exhausts: A survey of their bacterial mutagenic activity

• Published in: Environmental and molecular mutagenesis 2004, Vol.44 (4), p.304-312
• Main Authors: Otero-Lobato, María José, Jenneskens, Leonardus W., Seinen, Willem
• Format: Article
• Language: English
• Subjects: Animals; Bacteria; Biological and medical sciences; epoxidation; Fluorenes - chemistry; Fluorenes - toxicity; Fundamental and applied biological sciences. Psychology; Genetics of eukaryotes. Biological and molecular evolution; Male; Medical sciences; Microsomes, Liver - drug effects; Microsomes, Liver - metabolism; Mutagenicity Tests; nonalternant cyclopenta-fused polycyclic aromatic hydrocarbon; pyrolysate; Rats; Rats, Wistar; Ribosomal Proteins - metabolism; Salmonella; Salmonella typhimurium; Salmonella typhimurium - drug effects; Salmonella typhimurium - genetics; Salmonella typhimurium TA98; Toxicology; Vehicle Emissions - analysis; Vehicle Emissions - toxicity
• ISSN: 0893-6692; 1098-2280
• DOI: 10.1002/em.20047

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°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. Environ. Mol. Mutagen. 44:304–312, 2004. © 2004 Wiley‐Liss, Inc.