LUMO energies and hydrophobicity as determinants of mutagenicity by nitroaromatic compounds in Salmonella typhimurium.
Quantitative structure-activity relationships have been derived for the mutagenic activity of 47 nitroaromatic compounds acting on Salmonella typhimurium (TA100) and 66 acting on TA98. The mutagenicity is linearly dependent on the energy of the lowest occupied molecular orbital and bilinearly dependent on the hydrophobicity (octanol/water log P) of the mutagens. The mechanism of action is considered in the light of these findings.
Lopez de Compadre
R L
RL
Department of Chemistry, Pomona College, Claremont, California 91711.
Debnath
A K
AK
Shusterman
A J
AJ
Hansch
C
C
D001711:Biotransformation; D008433:Mathematics; D008956:Models, Chemical; D015394:Molecular Structure; D009152:Mutagenicity Tests; D009153:Mutagens; D009574:Nitro Compounds / Q000633:toxicity*; D009578:Nitrobenzenes / Q000378:metabolism; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds / Q000633:toxicity*; D011789:Quantum Theory; D012486:Salmonella typhimurium / Q000187:drug effects; D012995:Solubility; D013329:Structure-Activity Relationship; D013816:Thermodynamics; D014969:Xanthine Oxidase / Q000378:metabolism
D009153:Mutagens; D009574:Nitro Compounds; D009578:Nitrobenzenes; D011083:Polycyclic Compounds; D014969:Xanthine Oxidase