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Allopurinol and its interactions with Cu2+ ions: radical reactions and complex structure (Articolo in rivista)

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Allopurinol and its interactions with Cu2+ ions: radical reactions and complex structure (Articolo in rivista) (literal)

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Tamba M., Torreggiani A. (2003)
Allopurinol and its interactions with Cu2+ ions: radical reactions and complex structure
in Research on chemical intermediates (Print)
(literal)

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Allopurinol (ALP), an inhibitor of the xanthine oxidase enzime, is reported to provide protection against free-radical mediated damage by various mechanisms, including free-radical scavenging and metal chelation (i.e. Cu(II)). To obtain a wider insight into the molecular aspects of the beneficial action of ALP, free ALP and the Cu(II)-ALP system were investigated by radiation chemical and spectroscopic studies. The pulse radiolysis experiments show that ALP is a good .OH scavenger, leading to transient semi-oxidized species(phenoxyl radicals). The latter are also formed by the reaction of ALP with some specific one-electron oxidizing radicals (i.e. N3. and SO4-.). The phenoxyl radicals are stabilized by their resonance properties and scarcely react with oxygen. In addition, the chelation of Cu(II) by ALP does not significantly affect the reactivity of the drug towards .OH. The Raman and the IR spectra support the good chelating ability of ALP, indicating the formation of two Cu(II)-ALP complexes with a slightly different structure. These results suggest that ALP may inhibit oxidative damage both through the direct radical scavenging and the copper chelation mechanism. In fact, both the conversion of an harmful radical, such as .OH, into a less reactive transient species, and the capture of copper ions, which play a relevant role in metal-catalysed generation of reactive oxygen species, will prove beneficial for the cell-protection. (literal)

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