Semiquinone anion radicals formed by the reaction of quinones with glutathione or amino acids

Abstract

Using ESR spectroscopy, we show that benzoquinone, 1,4-naphthoquinone and 5-hydroxy-1,4-naphthoquinone react readily with thiol containing compounds, such as glutathione, to form their respective semiquinone anion radicals. These quinones react similarly, but less readily, with the amino group of amino acids. The therapeutic or toxicological significance of the formation of semiquinone anion radicals from the reaction of quinones with nucleophiles, such as thiols and amines, remains to be assessed.