A computational study on the relative reactivity of reductively activated 1,4-benzoquinone and its isoelectronic analogs

Journal of Computer-aided Molecular Design
Y H Mariam, A Sawyer

Abstract

The redox capacities of p-benzoquinone (I) and its analogs p-benzoquinone imine (VI) and p-benzoquinone diimine (XI) as the simplest model systems for the biochemically important quinone site of the pharmacophores of the anthracyclines has been investigated by AM1 semi-empirical and ab initio methods. The reductive activation of the parent (Q) model systems to their various redox states (quinone radical anion (Q.-), semiquinone (QH.), semiquinone anion (QH-) and hydroquinone (QH2)), the internal geometrical reorganization and the redox capacities of the redox states have been examined by using energy-partitioning analysis, reaction enthalpies/energies for electron and proton attachments, adiabatic ionization potentials (IPad) and electron affinities (EAad), adiabatic electronegativities (Xad), dipole moments, electrostatic potentials and spin-density surfaces. EAad data and results of energy-partitioning analysis suggest that the one-electron Q to Q.- reducibility of VI is diminished when compared to that of I. The data also predict that reduction to QH., QH- and QH2 is more favorable in VI (cf. I). Deprotonation enthalpy/energy calculations predict that the oxidizability of the reduced forms of VI is diminished when compared t...Continue Reading

References

Dec 1, 1975·Journal of the National Cancer Institute·S K Carter
Oct 1, 1991·The Biochemical Journal·G CiarrocchiA Montecucco
Feb 1, 1974·Annals of Internal Medicine·R H Blum, S K Carter
Jul 18, 1983·Biochemical and Biophysical Research Communications·H Nohl, W Jordan
Nov 1, 1986·Proceedings of the National Academy of Sciences of the United States of America·R G Pearson

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Citations

Dec 3, 2013·The Journal of Chemical Physics·R BreitwieserP Lang
Aug 16, 2011·Pharmacology & Therapeutics·Rene KizekMarie Stiborova
Apr 13, 2000·Journal of Chemical Information and Computer Sciences·D J Livingstone
Dec 4, 2009·Chemical Research in Toxicology·Pierantonio MennaGiorgio Minotti
Dec 11, 2007·Bioelectrochemistry·Mirela EnacheElena Volanschi

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