The line asymmetry of electron spin resonance spectra as a tool to determine the cis:trans ratio for spin-trapping adducts of chiral pyrrolines N-oxides: the mechanism of formation of hydroxyl radical adducts of EMPO, DEPMPO, and DIPPMPO in the ischemic-reperfused rat liver

Free Radical Biology & Medicine
Marcel CulcasiSylvia Pietri

Abstract

Nonstereospecific addition of free radicals to chiral nitrones yields cis/trans diastereoisomeric nitroxides often displaying different electron spin resonance (ESR) characteristics. Glutathione peroxidase-glutathione (GPx-GSH) reaction was applied to reduce the superoxide adducts (nitrone/*OOH) to the corresponding hydroxyl radical (HO*) adducts (nitrone/*OH) of two nitrones increasingly used in biological spin trapping, namely 5-diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide (DEPMPO) and 5-ethoxycarbonyl-5-methyl-1-pyrroline N-oxide, and of 5-diisopropoxyphosphoryl-5-methyl-1-pyrroline N-oxide (DIPPMPO), a sterically hindered DEPMPO analogue. The method offered improved conditions to record highly resolved ESR spectra and by accurate simulation of line asymmetry we obtained clear evidence for the existence of previously unrecognized isomer pairs of cis- and trans-[DEPMPO/*OH] and [DIPPMPO/*OH]. Additional nitrone/*OH generation methods were used, i.e. photolysis of hydrogen peroxide and the Fenton reaction. We developed a kinetic model involving first- and second-order decay and a secondary conversion of trans to cis isomer to fully account for the strongly configuration-dependent behavior of nitrone/*OH. In the reductive sy...Continue Reading

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Citations

Sep 11, 2009·The Journal of Biological Chemistry·Eiri HeynoAnja Krieger-Liszkay
Dec 7, 2010·Free Radical Research·Sergey I DikalovIgor A Grigor'ev
Oct 30, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Dana DvoranováVlasta Brezová
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Jan 8, 2011·Bioorganic & Medicinal Chemistry·Klaus StolzeThomas Rosenau
Oct 6, 2009·Bioorganic & Medicinal Chemistry·Klaus StolzeThomas Rosenau
Aug 19, 2008·Bioorganic & Medicinal Chemistry·Klaus StolzeThomas Rosenau
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