title: Fine-tuning the amphiphilicity: a crucial parameter in the design of potent alpha-phenyl-N-tert-butylnitrone analogues.
abstract: A new series of hydrophilic, lipophilic, and amphiphilic alpha-phenyl-N-tert-butylnitrone (PBN) derivatives were synthesized to explore the relationship between their hydrophilic-lipophilic properties and antioxidant potency. Very potent protective effects of amphiphilic lactobionamide and tris(hydroxymethyl)aminomethane PBN derivatives were observed in mitochondrial preparations, in cell cultures, and in rotifers exposed to unspecific and mitochondria targeted oxidotoxins.
authors.affiliation: Laboratoire de Chimie BioOrganique et des Systèmes Moléculaires Vectoriels, Faculté des Sciences, Université d'Avignon et des Pays de Vaucluse, 33 Rue Louis Pasteur, 84000 Avignon, France.
authors.forename: Grégory
authors.initials: G
authors.lastname: Durand
authors.forename: Burkhard
authors.initials: B
authors.lastname: Poeggeler
authors.forename: Jutta
authors.initials: J
authors.lastname: Böker
authors.forename: Simon
authors.initials: S
authors.lastname: Raynal
authors.forename: Ange
authors.initials: A
authors.lastname: Polidori
authors.forename: Miguel A
authors.initials: MA
authors.lastname: Pappolla
authors.forename: Rüdiger
authors.initials: R
authors.lastname: Hardeland
authors.forename: Bernard
authors.initials: B
authors.lastname: Pucci
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002478:Cells, Cultured; D003497:Cyclic N-Oxides / Q000737:chemistry*; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015195:Drug Design; D042967:Electron Transport Complex I / Q000378:metabolism; D066298:In Vitro Techniques; D009589:Nitrogen Oxides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D051381:Rats; D012403:Rotifera / Q000187:drug effects; D013329:Structure-Activity Relationship; D013367:Submitochondrial Particles / Q000187:drug effects / Q000378:metabolism; D014325:Tromethamine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000975:Antioxidants; D003497:Cyclic N-Oxides; D004187:Disaccharides; D009589:Nitrogen Oxides; C522311:lactobionamide; C015388:nitrones; D014325:Tromethamine; C029217:phenyl-N-tert-butylnitrone; D042967:Electron Transport Complex I