Natural Resources Management and Policy Commons^™

Sar Models For Futile Metabolism: One-Electron Reduction Of Quinones, Phenols And Nitrobenzenes, Steven P. Bradbury, Ovanes Mekenyan, G. D. Veith, N. Zaharieva

Steven P. Bradbury

Benzoquinones, naphthoquinones and aziridinylbenzoquinones, can be reduced by flavoproteins to semiquinones that react with molecular oxygen to form superoxide anion with the subsequent regeneration of the parent compounds. This redox cycling, a form of futile metabolism, produces reactive oxygen species and depletes the reducing equivalents of cells without concomitant energy production. The ability of a toxicant to redox cycle is related to its one-electron reduction potential, and this study attempted to estimate reduction potential from structure using semi-empirical quantum chemical models for a diverse set of chemicals. The results of this study suggest that one-electron reduction potentials, within structural classes …