N-2-(2-ethoxycarbonyl-propyl) alpha-phenylnitrone: an efficacious lipophilic spin trap for superoxide detection

Arch Biochem Biophys. 2002 Jan 1;397(1):51-6. doi: 10.1006/abbi.2001.2657.

Abstract

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.

MeSH terms

  • Benzene Derivatives
  • Electron Spin Resonance Spectroscopy
  • Hydrogen-Ion Concentration
  • Kinetics
  • Models, Chemical
  • Nitrogen Oxides / chemistry*
  • Spin Labels*
  • Spin Trapping / methods
  • Superoxides / analysis*

Substances

  • Benzene Derivatives
  • N-2-(2-ethoxycarbonylpropyl)phenylnitrone
  • Nitrogen Oxides
  • Spin Labels
  • Superoxides