Bacterial mutagenic evaluation of a series of 4' substituted derivatives of 3-benzylidenamino-5H-1,2,3-triazin[5,4b]indol-4-one.
The mutagenicity of ten triazinoindole derivatives was studied in bacteria. The compounds form part of a 3-(4'-substituted-benzylidenamino)-5H-1,2,3-triazin[5,4-b]in dol-4-one series and differ in the physicochemical properties of the substituent at the 4' position of the benzylidenamino group: -H, -OH, -COOH, -OCH3, -COOCH3, -NHCOCH3, -C1, -NO2, -C6H5, and -OC6H5. They were tested in the TA97, TA98, TA100, and TA102 strains of Salmonella typhimurium, both with and without metabolic activation, using the preincubation procedure. Only the derivatives with phenyl and phenoxy substituents were non-mutagenic. The remaining compounds significantly increased the number of His+ revertants and showed three patterns of activity based upon their mutagenic potency and their response to metabolic activation. Size and hydrophobicity of the 4'-substituents are the physicochemical characteristics that most differentiate the mutagenic triazinoindole derivatives from the nonmutagenic ones.
García
E
E
Toxicología Genética, C.I.F.A., Universidad de Navarra, Pamplona, Spain.
Lopez-de-Cerain
A
A
Gullón
A
A
Arrarás
J A
JA
Monge
A
A
D016368:Frameshift Mutation / Q000235:genetics; D007211:Indoles / Q000633:toxicity*; D016297:Mutagenesis, Site-Directed / Q000235:genetics; D009152:Mutagenicity Tests; D009153:Mutagens / Q000633:toxicity*; D012486:Salmonella typhimurium / Q000235:genetics; D014227:Triazines / Q000633:toxicity*
D007211:Indoles; D009153:Mutagens; D014227:Triazines; C075775:3-benzylidenamino-5H-1,2,3-triazin(5,4b)indol-4-one