Biotransformation of 1-nitropyrene in intestinal anaerobic bacteria.
Mutagenic nitroaromatic compounds have recently been found in photocopies, urban atmosphere, automobile exhaust and wastewater. 1-Nitropyrene (1-NP) is readily formed when pyrene, ubiquitous in the environment, is exposed to nitrogen dioxide in the urban atmosphere or in automobile exhaust, and is highly mutagenic, inducing 449 his+ revertants/plate/nmol from Salmonella typhimurium strain TA98 in the absence of S9 fraction in the Salmonella-microsome test. It is possible to swallow sputum or some food containing 1-NP and it would come into contact with the normal bacterial flora. We determined the 1-NP nitroreductase activity in environmental and laboratory bacterial strains. We found that the mutagenicity of 1-NP mixed with the feces of a healthy man or a culture of anaerobic bacteria was decreased. The product proved to be 1-aminopyrene (1-AP), based on its fluorescence spectrum, its mass spectrum, and its characteristic thin layer chromatographic and high performance liquid chromatographic patterns. The 1-NP nitroreductase activity of aerobic bacteria was low, but crude extracts from the anaerobic bacteria, i.e., Bacteroides fragilis, B. thetaiotaomicron, B. vulgatus, Fusobacterium mortiferum, F. nucleatum, Clostridium perfringens, C. sporogenes, Bifidobacterium adolescentis, B. bifidum, Eubacterium lentum, E. limosum, and Peptostreptococcus anaerobius, all easily converted 1-NP to 1-AP and proportionally decreased the mutagenic activity of 1-NP.
D000328:Adult; D000632:Aminopyrine / Q000378:metabolism; D001419:Bacteria / Q000378:metabolism*; D001438:Bacteroidaceae / Q000378:metabolism*; D001711:Biotransformation; D005243:Feces / Q000382:microbiology; D006801:Humans; D007422:Intestines / Q000382:microbiology*; D008297:Male; D009152:Mutagenicity Tests; D009154:Mutation / Q000187:drug effects; D009601:Nitroreductases; D010088:Oxidoreductases / Q000378:metabolism* / Q000494:pharmacology; D011721:Pyrenes / Q000378:metabolism*
D011721:Pyrenes; D000632:Aminopyrine; D010088:Oxidoreductases; C037214:1-nitropyrene reductase; D009601:Nitroreductases; C032668:1-nitropyrene