Pulse radiolysis study on free radical scavenger edaravone (3-methyl-1-phenyl-2-pyrazolin-5-one)

J Photochem Photobiol B. 2007 Nov 12;89(1):36-43. doi: 10.1016/j.jphotobiol.2007.08.001. Epub 2007 Aug 7.

Abstract

The reactions between edaravone and various one-electron oxidants such as (*)OH, N(3)(*), Br(2)(-), and SO(4)(-), have been studied by pulse radiolysis techniques. The transient species produced by the reaction of edaravone with (*)OH radical shows an absorption band with lambda(max)=320 nm, while the oxidation by N(3)(*), Br(2)(-), SO(4)(-) and CCl(3)OO(*) results in an absorption band with lambda(max)=345 nm. Different from the previous reports, the main transient species by the reaction of edaravone with (*)OH radical in the absence of O(2) is attributed to OH-adducts. At neutral condition (pH 7), the rate constants of edaravone reacting with (*)OH, N(3)(*), SO(4)(-), CCl(3)OO(*), and e(aq)(-) are estimated to be 8.5x10(9), 5.8x10(9), 6x10(8), 5.0x10(8) and 2.4x10(9)dm(3)mol(-1)s(-1), respectively. From the pH dependence on the formation of electron adducts and on the rate constant of edaravone with hydrated electron, the pK(a) of edaravone is estimated to be 6.9+/-0.1.

MeSH terms

  • Absorption
  • Antipyrine / analogs & derivatives*
  • Antipyrine / chemistry
  • Edaravone
  • Free Radical Scavengers / chemistry*
  • Free Radicals / chemistry
  • Hydrogen-Ion Concentration
  • Kinetics
  • Oxidation-Reduction
  • Pulse Radiolysis

Substances

  • Free Radical Scavengers
  • Free Radicals
  • Edaravone
  • Antipyrine