Reactivity of an indolinonic aminoxyl with superoxide anion and hydroxyl radicals.
The increasing knowledge on the participation of free radicals in many diverse clinical and pathological conditions, has consequently expanded the search for new and versatile antioxidants aimed at combating oxidative stress. Our interest in this field concerns aromatic indolinonic aminoxyls (nitroxides) which efficiently react with alkoxyl, peroxyl, aminyl, arylthiyl and alkyl radicals to give non-paramagnetic species. This prompted us to test their antioxidant activity on different biological systems exposed to free radical-induced oxidative stress and the results obtained so far have been very promising. However little is known about their behaviour towards superoxide and hydroxyl radicals. Here, we report on the reactivity of an indolinonic aminoxyl, with the two above mentioned radicals using hypoxanthine/xanthine oxidase and potassium superoxide for generating the former and the Fenton reagent for the latter. Besides performing the deoxyribose assay for studying the reaction of the aminoxyl with hydroxyl radical and monitoring spectral changes of the aminoxyl in the presence of superoxide radical, macroscale reactions were performed in both cases and the products of the reactions isolated and identified. The EPR technique was used in this study to help elucidate the data obtained. The results show that this compound efficiently reacts with both hydroxyl and superoxide radicals and furthermore, it is capable of maintaining iron ions in its oxidized form. The results thus contribute to increasing the knowledge on the reactivity of indolinonic aminoxyls towards free radical species and as a consequence, these compounds and/or other aminoxyl derivatives, may be considered as complementary, and sometimes alternative sources for combating oxidative damage.
Damiani
E
E
Dipartimento di Scienze dei Materiali e della Terra, Università, Ancona, Italy. liz@popcsi.unian.it
Carloni
P
P
Stipa
P
P
Greci
L
L
D003497:Cyclic N-Oxides / Q000737:chemistry*; D003855:Deoxyribose / Q000737:chemistry; D004578:Electron Spin Resonance Spectroscopy; D016166:Free Radical Scavengers / Q000737:chemistry*; D017665:Hydroxyl Radical / Q000737:chemistry*; D019271:Hypoxanthine / Q000378:metabolism; D015394:Molecular Structure; D013053:Spectrophotometry; D013481:Superoxides / Q000737:chemistry*; D017392:Thiobarbituric Acid Reactive Substances; D014969:Xanthine Oxidase / Q000378:metabolism
C121894:1,2-dihydro-2-methyl-2-phenyl-3H-indol-3-one-1-oxyl; D003497:Cyclic N-Oxides; D016166:Free Radical Scavengers; D017392:Thiobarbituric Acid Reactive Substances; D013481:Superoxides; D019271:Hypoxanthine; D017665:Hydroxyl Radical; D003855:Deoxyribose; D014969:Xanthine Oxidase