Mutagenicity of chlorinated polycyclic aromatic compounds.

The catalytic chlorination of polycyclic aromatic hydrocarbons leads to the formation of complex mixtures of isomers analogous to those found in fly ash samples of an incineration plant for radioactive waste. Therefore chlorination mixtures of chrysene, pyrene, and fluoranthene were analyzed and characterized by gas chromatography-mass spectrometry. Determination of the exact position of each chlorosubstituent within the molecule was not possible either by mass spectrometry or by comparison with well-defined methyl analogs. The toxic as well as mutagenic effects of such mixtures of isomers was compared with those of their parent hydrocarbons in the microtiter fluctuation test using Salmonella typhimurium TA 98 and TA 100 in a concentration range of 0.5 to 5.0 microgram/ml. No toxic effect could be observed, but the chlorinated products in contrast to their parent compounds were found to be strong mutagens to the S. typhimurium test strains and showed a positive response even without enzymatic activation. Frameshift mutations as well as base pair alterations were detected.