Some chloro derivatives of polynuclear aromatic hydrocarbons are potent mutagens in Salmonella typhimurium.
A series of chlorinations of some polynuclear aromatic hydrocarbons (PAH) were carried out and the products were tested for mutagenicity on Salmonella typhimurium TA98 and TA100. We conclude that the chlorination of certain PAHs with low mutagenicity, such as pyrene and benzo[e]pyrene, resulted in the formation of two types of product. The chlorination of pyrene was studied in some detail. The major products of this chlorination were chloro-substituted pyrenes. These compounds showed an S9-dependent mutagenicity and were identified as 1-chloro-, 1,6-dichloro-, 1,8-dichloro- and 1,3-dichloropyrene. On tester strain TA100 the mutagenic effect ranged from 1.4 to 14 revertants/nmol, 1,3-dichloropyrene being the most potent of the isomers. Minor products eluting from a chromatograph in a more polar fraction than the major products were also formed. These compounds were less stable than the major products and were identified as pyrene with chloro additions in the 4- and 5-positions, with various chloro substituents at other positions. These minor products showed a high mutagenic effect on Salmonella in the absence of S9. The mutagenic effect on strain TA100 ranged from 10 to 15 revertants per ng which is at least 40 and 4000 times higher than for 1-nitropyrene and pyrenequinones, respectively. These unstable chloro derivatives of pyrene are difficult to analyse chemically because they are easily degraded and give rise to the more stable 4-chloropyrene.
D013058:Mass Spectrometry; D009152:Mutagenicity Tests; D009153:Mutagens / Q000633:toxicity*; D009154:Mutation; D011721:Pyrenes / Q000138:chemical synthesis / Q000633:toxicity*; D012486:Salmonella typhimurium / Q000187:drug effects; D013329:Structure-Activity Relationship
D009153:Mutagens; D011721:Pyrenes; C040345:1-chloropyrene; C040348:1,3-dichloropyrene; C040347:1,6-dichloropyrene; C040346:1,8-dichloropyrene