title: PBN derived amphiphilic spin-traps. II/Study of their antioxidant properties in biomimetic membranes.
abstract: The work reported herein deals with the evaluation of the antioxidant properties of bitailed amphiphilic α-phenyl-N-tert-butylnitrone derivatives (BPBNs) towards oxidation of an unsaturated lipid, the 1,2-dilinoleoyl-sn-glycero-3-phosphocholine (DLoPC). Oxidation was induced either by UV light irradiation or radical initiators, i.e. the water soluble AAPH and the Fenton reaction, and the antioxidant evaluation was carried out using two biomimetic systems, namely Langmuir monolayers and large unilamellar vesicles. Measurement of the molecular area and the membrane fluidity of pure nitrone monolayers before and after UV-irradiation demonstrated the better stability and antioxidant properties of B17PBN, the derivative with two C17H35 alkyl chains, compared to its analogue B11PBN with two C11H23 alkyl chains. At only 5% molar ratio of nitrone in mixed DLoPC/nitrone monolayers, a complete inhibition of the molecular area decrease was observed for B17PBN whereas B11PBN showed lower protection. The oxidation of mixed DLoPC/nitrones large unilamellar vesicles in the presence of free radicals arising from AAPH decomposition or Fenton reaction was assessed by measuring lipid conjugated dienes and thiobarbituric acid reactive substances on the whole series of nitrone, i.e. C11-, C13-, C15- and C17-based compounds. Compared to the saturated 1,2-dimyristoyl-sn-glycero-3-phosphocholine, all bitailed amphiphilic nitrones were able to decrease conjugated dienes and TBARS in both oxidative paradigms, demonstrating therefore antioxidant property. The inhibition of phospholipids oxidation was increased when increasing the concentration of nitrone with the two B11PBN and B13PBN derivatives exhibiting higher potency. This study underlines the importance in the choice of a model membrane system when evaluating the potency of antioxidants against lipid oxidation.
authors.affiliation: Université d'Avignon et des Pays de Vaucluse, Equipe Chimie Bioorganique et Systèmes Amphiphiles, 33 rue Louis Pasteur, F-84000 Avignon, France; Unité Mixte de Recherche 5247, Centre National de la Recherche Scientifique and Universités de Montpellier 1&2, Institut des Biomolécules Max Mousseron, Faculté de Pharmacie, 15 avenue Charles Flahault, F-34093 Montpellier Cedex 05, France.
authors.forename: Stéphanie
authors.initials: S
authors.lastname: Ortial
authors.affiliation: Université Claude Bernard Lyon I, UMR-CNRS 5013, Laboratoire de Physico-Chimie Biologique, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne Cedex, France; Université de Technologie de Compiègne, FRE CNRS 3580 Génie enzymatique et cellulaire, Centre de Recherche Royallieu, rue Roger Couttolenc CS 60319, F-60203 Compiègne Cedex, France.
authors.forename: Sandrine
authors.initials: S
authors.lastname: Morandat
authors.affiliation: Université Claude Bernard Lyon I, UMR-CNRS 5013, Laboratoire de Physico-Chimie Biologique, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne Cedex, France.
authors.forename: Muriel
authors.initials: M
authors.lastname: Bortolato
authors.affiliation: Université Claude Bernard Lyon I, UMR-CNRS 5013, Laboratoire de Physico-Chimie Biologique, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne Cedex, France.
authors.forename: Bernard
authors.initials: B
authors.lastname: Roux
authors.affiliation: Université d'Avignon et des Pays de Vaucluse, Equipe Chimie Bioorganique et Systèmes Amphiphiles, 33 rue Louis Pasteur, F-84000 Avignon, France; Unité Mixte de Recherche 5247, Centre National de la Recherche Scientifique and Universités de Montpellier 1&2, Institut des Biomolécules Max Mousseron, Faculté de Pharmacie, 15 avenue Charles Flahault, F-34093 Montpellier Cedex 05, France.
authors.forename: Ange
authors.initials: A
authors.lastname: Polidori
authors.affiliation: Université d'Avignon et des Pays de Vaucluse, Equipe Chimie Bioorganique et Systèmes Amphiphiles, 33 rue Louis Pasteur, F-84000 Avignon, France; Unité Mixte de Recherche 5247, Centre National de la Recherche Scientifique and Universités de Montpellier 1&2, Institut des Biomolécules Max Mousseron, Faculté de Pharmacie, 15 avenue Charles Flahault, F-34093 Montpellier Cedex 05, France.
authors.forename: Bernard
authors.initials: B
authors.lastname: Pucci
authors.affiliation: Université d'Avignon et des Pays de Vaucluse, Equipe Chimie Bioorganique et Systèmes Amphiphiles, 33 rue Louis Pasteur, F-84000 Avignon, France; Unité Mixte de Recherche 5247, Centre National de la Recherche Scientifique and Universités de Montpellier 1&2, Institut des Biomolécules Max Mousseron, Faculté de Pharmacie, 15 avenue Charles Flahault, F-34093 Montpellier Cedex 05, France. Electronic address: gregory.durand@univ-avignon.fr.
authors.forename: Grégory
authors.initials: G
authors.lastname: Durand
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry*; D032701:Biomimetics / Q000379:methods*; D008081:Liposomes / Q000737:chemistry; D008567:Membranes, Artificial; D009589:Nitrogen Oxides / Q000737:chemistry
chemical_list: D000975:Antioxidants; D008081:Liposomes; D008567:Membranes, Artificial; D009589:Nitrogen Oxides; C015388:nitrones
keywords: Antioxidants; Free radicals; Langmuir monolayers; Lipid oxidation; Liposomes; Spin traps