Mutagenicity in Salmonella typhimurium and structure-activity relationships of wastewater components emanating from the manufacture of trinitrotoluene.
The mutagenicity of 36 polynitroaromatic compounds was investigated with five strains of Salmonella typhimurium. Isomeric trinitrotoluenes (TNT), with the exception of 2,4,6-TNT and 2,3,4-TNT, exhibit mutagenicity independently of nitroreductase enzymes, but isomeric aminodinitrotoluenes (ADNT) and isomeric dinitrotoluenes (DNT) need nitroreductase to induce mutation. Within groups of isomeric TNTs, DNTs, and ADNTs, mutagenic response was enhanced by a para orientation of nitro groups. The mutagenic response of isomeric DNTs was found to correlate with the compound's ability to undergo charge-transfer complexation with reductive enzymes, whereas further complexation (such as a Janovsky complex) appears to be required for inducing mutation in dinitrobenzenes. These results indicate that polynitroaromatic compounds in TNT wastewaters possess a significant potential for biologic activity.
D001711:Biotransformation; D004136:Dinitrobenzenes / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D007536:Isomerism; D009152:Mutagenicity Tests; D009153:Mutagens; D009574:Nitro Compounds / Q000378:metabolism; D009578:Nitrobenzenes / Q000494:pharmacology; D009601:Nitroreductases; D010088:Oxidoreductases / Q000378:metabolism; D012486:Salmonella typhimurium / Q000187:drug effects; D013329:Structure-Activity Relationship; D014303:Trinitrotoluene / Q000494:pharmacology*; D014877:Water Pollution, Chemical
D004136:Dinitrobenzenes; D009153:Mutagens; D009574:Nitro Compounds; D009578:Nitrobenzenes; D014303:Trinitrotoluene; C016403:2,4-dinitrotoluene; D010088:Oxidoreductases; D009601:Nitroreductases