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4. Para -Substituted α-Phenyl- N - tert -butyl Nitrones: Spin-Trapping, Redox and Neuroprotective Properties

Author

Deletraz, Anaïs, Tuccio, Béatrice, Roussel, Julien, Combes, Maud, Cohen-Solal, Catherine, Fabre, Paul-Louis, Trouillas, Patrick, Vignes, Michel, Callizot, Noelle, Durand, Grégory, Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Neuro-sys, Pharmacochimie et Biologie pour le Développement (PHARMA-DEV), Institut de Recherche pour le Développement (IRD)-Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT), Ciblage individuel et prévention des risques de traitements immunosupresseurs et de la transplantation (IPPRITT), CHU Limoges-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut Génomique, Environnement, Immunité, Santé, Thérapeutique (GEIST), Université de Limoges (UNILIM)-Université de Limoges (UNILIM), and Palacky University Olomouc

Subjects
[SDV]Life Sciences [q-bio], Monomers, Reaction products, Peptides and proteins, Redox reactions, Nitrogen compounds
Abstract

International audience; In this work, a series of para-substituted α-phenyl-N-tert-butyl nitrones (PBN) were studied. Their radical-trapping properties were evaluated by electron paramagnetic resonance, with 4-CF 3-PBN being the fastest derivative to trap the hydroxymethyl radical (• CH 2 OH). The redox properties of the nitrones were further investigated by cyclic voltammetry, and 4-CF 3-PBN was the easiest to reduce and the hardest to oxidize. This is due to the presence of the electron-withdrawing CF 3 group. Very good correlations between the Hammett constants (σ p) of the substituents and both spin-trapping rates and redox potentials were observed. These correlations were further supported by computationally determined ionization potentials and atom charge densities. Finally, the neuroprotective effect of these derivatives was studied using two different in vitro models of cell death on primary cortical neurons injured by glutamate exposure or on glial cells exposed to t BuOOH. Trends between the protection afforded by the nitrones and their lipophilicity were observed. 4-CF 3-PBN was the most potent agent against t BuOOH-induced oxidative stress on glial cells, while 4-Me 2 N-PBN showed potency in both models.

Published
2020

11. Reactivities of Substituted α-Phenyl- \textitN - \textittert -butyl Nitrones

Author

Rosselin, Marie, Choteau, Fanny, Zéamari, Kamal, Nash, Kevin M., Das, Amlan, Lauricella, Robert, Lojou, Elisabeth, Tuccio, Béatrice, Villamena, Frederick A., Durand, Grégory, Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Chimie, biologie et radicaux libres - UMR 6517 (CBRL), Université de la Méditerranée - Aix-Marseille 2-Université Paul Cézanne - Aix-Marseille 3-Université de Provence - Aix-Marseille 1-Centre National de la Recherche Scientifique (CNRS), Bioénergétique et Ingénierie des Protéines (BIP ), Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de la Matière Condensée de Bordeaux (ICMCB), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Université de Bordeaux (UB), and SAFRAN Messier-Bugatti-Dowty

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience; no abstract

Published
2014

13. Reactivities of Substituted α-Phenyl-N-tert-butyl Nitrones

Author

Rosselin, Marie, primary, Choteau, Fanny, additional, Zéamari, Kamal, additional, Nash, Kevin M., additional, Das, Amlan, additional, Lauricella, Robert, additional, Lojou, Elisabeth, additional, Tuccio, Béatrice, additional, Villamena, Frederick A., additional, and Durand, Grégory, additional

Published
2014
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15. Para -Substituted α-Phenyl- N - tert -butyl Nitrones: Spin-Trapping, Redox and Neuroprotective Properties.

Author

Deletraz A, Tuccio B, Roussel J, Combes M, Cohen-Solal C, Fabre PL, Trouillas P, Vignes M, Callizot N, and Durand G

Abstract

In this work, a series of para -substituted α-phenyl- N - tert -butyl nitrones (PBN) were studied. Their radical-trapping properties were evaluated by electron paramagnetic resonance, with 4-CF 3 -PBN being the fastest derivative to trap the hydroxymethyl radical ( • CH 2 OH). The redox properties of the nitrones were further investigated by cyclic voltammetry, and 4-CF 3 -PBN was the easiest to reduce and the hardest to oxidize. This is due to the presence of the electron-withdrawing CF 3 group. Very good correlations between the Hammett constants (σ p ) of the substituents and both spin-trapping rates and redox potentials were observed. These correlations were further supported by computationally determined ionization potentials and atom charge densities. Finally, the neuroprotective effect of these derivatives was studied using two different in vitro models of cell death on primary cortical neurons injured by glutamate exposure or on glial cells exposed to t BuOOH. Trends between the protection afforded by the nitrones and their lipophilicity were observed. 4-CF 3 -PBN was the most potent agent against t BuOOH-induced oxidative stress on glial cells, while 4-Me 2 N-PBN showed potency in both models., Competing Interests: The authors declare no competing financial interest., (© 2020 American Chemical Society.)

Published
2020
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