Open AccessN-tert-butylmethanimine N-oxide is an efficient spin-trapping probe for EPR analysis of glutathione thiyl radical
Author(s) -
Melanie J. Scott,
Timothy R. Billiar,
Detcho A. Stoyanovsky
Publication year - 2016
Publication title -
scientific reports
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.24
H-Index - 213
ISSN - 2045-2322
DOI - 10.1038/srep38773
Subject(s) - spin trapping , electron paramagnetic resonance , nitrone , chemistry , radical , adduct , photochemistry , context (archaeology) , superoxide , nitroso , nuclear magnetic resonance , medicinal chemistry , organic chemistry , catalysis , paleontology , cycloaddition , biology , enzyme , physics
The electron spin resonance (EPR) spin-trapping technique allows detection of radical species with nanosecond half-lives. This technique is based on the high rates of addition of radicals to nitrones or nitroso compounds (spin traps; STs). The paramagnetic nitroxides (spin-adducts) formed as a result of reactions between STs and radical species are relatively stable compounds whose EPR spectra represent “structural fingerprints” of the parent radical species. Herein we report a novel protocol for the synthesis of N - tert -butylmethanimine N- oxide (EBN), which is the simplest nitrone containing an α-H and a tertiary α′-C atom. We present EPR spin-trapping proof that: (i) EBN is an efficient probe for the analysis of glutathione thiyl radical (GS • ); (ii) β-cyclodextrins increase the kinetic stability of the spin-adduct EBN/ • SG; and (iii) in aqueous solutions, EBN does not react with superoxide anion radical (O 2 −• ) to form EBN/ • OOH to any significant extent. The data presented complement previous studies within the context of synthetic accessibility to EBN and efficient spin-trapping analysis of GS • .