QSAR for clastogenic effects induced by regioisomers of PAH quinones
In this paper the experimental results on chromosomal aberrations and spindle disturbances in mammalian liver cells for eight regioisomers of pyrene, benzo(a)pyrene and phenanthrene quinones were compared with the AM1 calculated stereoelectronic descriptors. The electronic structure of the parent compounds as well as the corresponding radical anions, were evaluated. Two groups of reactivity descriptors were specified evaluating the mechanisms of genotoxicity of quinones that were recently proposed by the authors. The first group of parameters (eg electronic gap) describes potency of chemicals as crosslinkers of cellular macromolecules, whereas the second group (eg electronegativity frontier orbital energies, their displacement and energy equivalence when going from quinones to the respective intermediate anion-radicals) the one electron reduction efficiency. The ordering of quinones, according to their theoretically estimated reactivities, was found to be consistent with the experimental genotoxicity data. It was concluded that genotoxic activity of studied quinones is an integrated effect of two mechanisms. The prevailing of one of these mechanisms affects the qualitative difference in the genotoxic effect of quinones. The benzo(a)pyrene and pyrene quinones were predicted to be more active crosslink inducers and more effective oxidants than phenanthrene quinones.
Bibliographic Reference: Paper presented : Fifteenth International Symposium on Polycyclic Aromatic Compounds, Belgirate (IT), September 19-22, 1995
Availability: Available from (1) as Paper EN 39931 ORA
Record Number: 199610961 / Last updated on: 1996-09-30
Original language: en
Available languages: en