N-tert-butylmethanimine N-oxide is an efficient spin-trapping probe for EPR analysis of glutathione thiyl radical

作者：Scott Melanie J; Billiar Timothy R; Stoyanovsky Detcho A^*

来源：Scientific Reports, 2016, 6(1): 38773.

DOI：10.1038/srep38773

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 a-H and a tertiary alpha'-C atom. We present EPR spin-trapping proof that: (i) EBN is an efficient probe for the analysis of glutathione thiyl radical (GS(center dot)); (ii) beta-cyclodextrins increase the kinetic stability of the spinadduct EBN/(center dot)SG; and (iii) in aqueous solutions, EBN does not react with superoxide anion radical (O-2 -(center dot)) to form EBN/(OOH)-O-center dot 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(center dot).

• 出版日期2016-12-12