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Radical trapping properties of imidazolyl nitrones

Reybier, Karine and Boyer, Jeremie and Farines, Vincent and Camus, Fabrice and Souchard, Jean-Pierre and Monje, Marie-Carmen and Bernardes-Genisson, Vania and Goldstein, Solo and Nepveu, Françoise Radical trapping properties of imidazolyl nitrones. (2006) Free Radical Research, 40 (1). 11-20. ISSN 1071-5762

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Official URL: https://doi.org/10.1080/10715760500329598


The ability of ten imidazolyl nitrones to directly scavenge free radicals (R√) generated in polar (√OH, cysteinyl, √CH3) or in apolar (CH3–√CH–CH3) media has been studied. When oxygen or sulfur-centered radicals are generated in polar media, EPR spectra are not or weakly observed with simple spectral features. Strong line intensities and more complicated spectra are observed with the isopropyl radical generated in an apolar medium. Intermediate results are obtained with √CH3 generated in a polar medium. EPR demonstrates the ability of these nitrones to trap radicals to the nitrone C(α) atom (alpha radical adduct) and to the imidazol C(5) atom (5-radical adduct). Beside the nucleophilic addition of the radical to the C(α) atom, the EPR studies suggest a two-step mechanism for the overall reaction of R√ attacking the imidazol core. The two steps seem to occur very fast with the √OH radical obtained in a polar medium and slower with the isopropyl radical prepared in benzene. In conclusion, imidazolyl nitrones present a high capacity to trap and stabilize carbon-centered radicals.

Item Type:Article
HAL Id:hal-02143180
Audience (journal):International peer-reviewed journal
Uncontrolled Keywords:
Institution:Other partners > Institut de Recherches SERVIER (FRANCE)
French research institutions > Institut de Recherche pour le Développement - IRD (FRANCE)
Université de Toulouse > Université Toulouse III - Paul Sabatier - UT3 (FRANCE)
Other partners > Université de Namur - UNamur (BELGIQUE)
Laboratory name:
Deposited On:07 Mar 2019 10:15

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