The reaction rate of edaravone (3-methyl-1-phenyl-2-pyrazolin-5-one (MCI-186)) with hydroxy radical

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  • Abe Shinji
    Department of Pharmacology, The University of Tokushima School of Medicine
  • Kirima Kazuyoshi
    Department of Pharmacology, The University of Tokushima School of Medicine
  • Tsuchiya Koichiro
    Department of Clinical Pharmacology, Graduate School of Pharmaceutical Sciences, The University of Tokushima
  • Okamoto Masumi
    Department of Pharmacology, The University of Tokushima School of Medicine
  • Hasegawa Toyoshi
    Department of Pharmacology, The University of Tokushima School of Medicine
  • Houchi Hitoshi
    Department of Pharmacy, The University of Tokushima School of Medicine
  • Yoshizumi Masanori
    Department of Pharmacology, The University of Tokushima School of Medicine
  • Tamaki Toshiaki
    Department of Pharmacology, The University of Tokushima School of Medicine

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タイトル別名
  • The Reaction Rate of Edaravone (3-Methyl-1-phenyl-2-pyrazolin-5-one (MCI-186)) with Hydroxyl Radical
  • Reaction Rate of Edaravone 3 Methyl 1 phenyl 2 pyrazolin 5 one MCI 186 with Hydroxyl Radical

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抄録

The pyrazoline derivative edaravone is a potent hydroxyl radical scavenger that has been approved for attenuation of brain damage caused by ischemia-reperfusion. In the present work, we first determined the rate constant, kr, at which edaravone scavenges radicals generated by a Fenton reaction in aqueous solution in the presence of the spin trap agent, 5,5-dimethyl-1-pyrroline-N-oxide (DMPO), which competed with edaravone. We detected the edaravone radicals in the process of hydroxyl radical scavenging and found that edaravone reacts with hydroxyl radical around the diffusion limit (kr=3.0×1010 M−1 s−1). The EPR (electron paramagnetic resonance) spectrum of the edaravone radical was observed by oxidation with a horseradish peroxidase–hydrogen peroxide system using the fast-flow method. This radical species is unstable and changed to another radical species with time. In addition, it was found that edaravone consumed molecular oxygen when it was oxidized by horseradish peroxidase (HRP)–H2O2 system, and that edaravone was capable of providing two electrons to the electrophiles. The possible mechanisms for oxidation of edaravone were investigated from these findings.

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