N-2-(2-ethoxycarbonyl-propyl) alpha-phenylnitrone: an efficacious lipophilic spin trap for superoxide detection.
The spin trap N-2-(2-ethoxycarbonyl-propyl) alpha-phenylnitrone, EPPN 1, synthesized by methods previously described, has been purified by recrystallization. A measure of its octanol-phosphate buffer partition coefficient (P(oct) = 29.8) indicated that EPPN was quite lipophilic, yet it could be easily solubilized in water up to 60 mmol L(-1). Although this nitrone was unsuitable for detecting hydroxyl radical, it efficiently trapped several carbon-centered radicals as well as superoxide in aqueous media, without yielding any artifactual signals. Kinetic studies of the superoxide adduct decay gave rate constants k(D) of 2 x 10(-3) and 2.1 x 10(-3) s(-1) at pH 5.6 and pH 7, respectively. EPPN can be considered as an easily prepared and highly pure spin trap, allowing efficient detection of superoxide in aqueous environments.
Roubaud
Valérie
V
UMR 6517 CNRS, Universités d'Aix-Marseille 1 et 3, 13397 Marseille Cedex 20, France.
Lauricella
Robert
R
Bouteiller
Jean-Claude
JC
Tuccio
Béatrice
B
D001555:Benzene Derivatives; D004578:Electron Spin Resonance Spectroscopy; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D008956:Models, Chemical; D009589:Nitrogen Oxides / Q000737:chemistry*; D013113:Spin Labels; D019097:Spin Trapping / Q000379:methods; D013481:Superoxides / Q000032:analysis*
D001555:Benzene Derivatives; C447030:N-2-(2-ethoxycarbonylpropyl)phenylnitrone; D009589:Nitrogen Oxides; D013113:Spin Labels; D013481:Superoxides