title: Comparative study on the mutagenicity of three structurally related substituted aniline mustards in the Salmonella/microsome assay.
abstract: The ortho, meta and para isomers of N,N-bis(2-chloroethyl)aminocinnamic acid were tested for their ability to mutate Salmonella typhimurium strains in the Salmonella/microsome mutagenicity test. The aim of the work was to establish a structure-activity relationship between these three isomers. The drugs were found to induce base-pair substitutions, causing dose-dependent increases in his+ revertants, in strains TA100 and TA1535. The study showed that the position of the substituent groups influenced the mutagenic activity of the compounds. The ortho isomer exhibited a poorer mutagenic effect than meta and this was found to be a weaker mutagen than para. The presence of metabolic activation enzymes in the test system induced a further increase in his+ revertants, in strains TA100 and TA1535, which is consistent with the findings for melphalan, a cancer chemotherapeutic agent with a chemical structure similar to that of the isomers tested.
authors.affiliation: Institute of Biology, National Research Center Democritus, Athens, Greece.
authors.forename: G
authors.initials: G
authors.lastname: Voutsinas
authors.forename: A
authors.initials: A
authors.lastname: Kappas
authors.forename: N A
authors.initials: NA
authors.lastname: Demopoulos
authors.forename: P
authors.initials: P
authors.lastname: Catsoulacos
mesh_terms: D000816:Aniline Mustard / Q000737:chemistry / Q000378:metabolism / Q000633:toxicity*; D016009:Chi-Square Distribution; D002934:Cinnamates / Q000737:chemistry / Q000378:metabolism / Q000633:toxicity; D004305:Dose-Response Relationship, Drug; D008110:Liver Extracts; D008862:Microsomes, Liver / Q000201:enzymology; D009152:Mutagenicity Tests; D009153:Mutagens / Q000633:toxicity*; D017354:Point Mutation; D015203:Reproducibility of Results; D012486:Salmonella typhimurium / Q000187:drug effects* / Q000235:genetics; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D002934:Cinnamates; D008110:Liver Extracts; D009153:Mutagens; D000816:Aniline Mustard