PMID: 9436622Jan 22, 1998Paper

Interaction of 1-hydroxyethyl radical with glutathione, ascorbic acid and alpha-tocopherol

Free Radical Biology & Medicine
D A StoyanovskyA I Cederbaum

Abstract

Ethanol has been shown to be oxidized to a free radical metabolite, the 1-hydroxyethyl radical (HER). Interaction of HER with cellular antioxidants may contribute to the known ability of ethanol administration to lower levels of GSH and alpha-tocopherol. Experiments were carried out to establish a model system for the generation of HER and to study its interaction with GSH, ascorbic acid and alpha-tocopherol. A standard reaction for formation of azo-compounds using acetaldehyde and hydroxylamine-O-sulfonic acid was applied for the synthesis of 1,1'-dihydroxyazoethane (CH3CH(OH)-N=N-CH(OH)CH3). Although stable at -70 degrees C, thermal decomposition of this compound at room temperature was shown to produce HER, detected by EPR spectrometry as the PBN/HER or DMPO/HER spin adducts, and validated by computer simulation. GSH, present at the beginning of the experiment, inhibited formation of the PBN/HER signal. However, GSH did not cause any decay of pre-formed PBN/HER spin adduct. GSH was consumed in the presence of the HER-generating system in a reaction largely reversed by addition of NADPH plus glutathione reductase. Ascorbate also inhibited formation of the PBN/HER spin adduct and rapidly reduced the pre-formed adduct. HER ampl...Continue Reading

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Citations

Dec 22, 1999·Archives of Biochemistry and Biophysics·S PuntaruloA I Cederbaum
May 24, 2006·Biometals : an International Journal on the Role of Metal Ions in Biology, Biochemistry, and Medicine·Kassy A MiesAlvin L Crumbliss
Aug 9, 2005·Free Radical Biology & Medicine·Martin J J RonisThomas M Badger
Oct 16, 2002·Life Sciences·Ramón RodrigoCleofina Bosco
Jan 5, 2002·Free Radical Biology & Medicine·Elisa MottaranEmanuele Albano
May 15, 2002·Free Radical Biology & Medicine·Lester A Reinke
Apr 3, 2001·Free Radical Biology & Medicine·K SakuraiA I Cederbaum
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