Mutagenicity of (p-nitrophenyl)adenines in Salmonella typhimurium.
Adenine derivatives having a p-nitrophenyl group at position 2, 8, or 9 were directly mutagenic towards Salmonella typhimurium strains TA98 and TA100, whereas N6-(p-nitrophenyl)adenine was not mutagenic. 2,9- And 8,9-bis-(p-nitrophenyl)adenines were also mutagenic, but N6,9-bis-(p-nitrophenyl)adenine was not. The study on 13 (p-nitrophenyl)adenine derivatives for their Salmonella mutagenicity indicates that only those having a p-nitrophenyl ring directly linked to the purine ring are mutagenic, implying the importance of the coplanar character of the nitrophenyl and the purine rings. The nitro group seems essential for the mutagenicity, as shown from the results of assays using nitroarene-sensitive and -insensitive Salmonella strains. The mutagenic potency of this class of compounds is high, comparable to that of 2-nitrofluorene.
Matsuda
A
A
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.
Akashi
M
M
Ohara
Y
Y
Wataya
Y
Y
Hayatsu
H
H
Ueda
T
T
D000225:Adenine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism / Q000633:toxicity; D004249:DNA Damage; D004261:DNA Replication / Q000187:drug effects; D007364:Intercalating Agents / Q000378:metabolism; D009152:Mutagenicity Tests; D009153:Mutagens; D009596:Nitrophenols / Q000737:chemistry / Q000378:metabolism / Q000633:toxicity*; D012486:Salmonella typhimurium / Q000187:drug effects / Q000235:genetics*; D013329:Structure-Activity Relationship
D007364:Intercalating Agents; D009153:Mutagens; D009596:Nitrophenols; D000225:Adenine