Characterization of spin adducts obtained with hydrophobic nitrone spin traps

Abstract

Several 5-alkyl-3,3,5-trimethylpyrroline 1-oxides have been prepared and their ability to trap a number of radicals has been investigated. In each case the addition to the nitrone is stereospecific and affords only one of the two possible geometric isomers of the resulting nitroxyl radical. The addition of a hydrogen atom gives nitroxyls containing two non-equivalent α-protons, the spectra of which are very similar to that observed during the red blood cell haemolysis induced by phenylhydrazine in the presence of a similar spin trap. A re-interpretation of the results obtained in the biological system appears to be warranted.