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Journal of Pharmacology and Toxicology

Year: 2007  |  Volume: 2  |  Issue: 1  |  Page No.: 54 - 62

Molecular Modelling Analysis of the Metabolic Activation of Ethylene Glycol

Fazlul Huq and Deena Ababneh


Molecular modelling analyses based on molecular mechanics, semi-empirical (PM3) and DFT (at B3LYP/6-31G* level) calculations using the programs Spartan `02 and HyperChem 7.0 show that glycolic acid has high thermodynamic stability and low kinetic lability so that the reaction in which glycolic acid is converted to glyoxylic acid is indeed rate-determining. The metabolite glyoxal has the lowest LUMO-HOMO energy difference that makes it most kinetically labile. The high kinetic lability and the presence of electron-deficient region on the molecular surface may make glyoxal the most toxic metabolite as it can cause depletion of cellular glutathione, thus compromising antioxidant status of the cell.

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