Abstract
On-line electrochemistry/liquid chromatography/mass spectrometry was used to simulate the detoxification mechanism of paracetamol in the body. In an electrochemical flow-through cell, paracetamol was oxidized at a porous glassy carbon working electrode at a potential of 600 mV vs. Pd/H2 with formation of a quinoneimine intermediate. The quinoneimine further reacted with glutathione and/or N-acetylcysteine to form isomeric adducts via the thiol function. The adducts were characterized on-line by liquid chromatography/mass spectrometry. These reactions are similar to those occurring between paracetamol and glutathione under catalysis by cytochrome P450 enzymes in the body.
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Financial support by the Deutsche Forschungsgemeinschaft (DFG, Bonn, Germany) and the Fonds der Chemischen Industrie (Frankfurt, Germany) is gratefully acknowledged.
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Awarded a Poster Prize on the occasion of the Conference of the German Mass Spectrometric Society (DGMS) in Mainz, March 5–8, 2006.
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Lohmann, W., Karst, U. Simulation of the detoxification of paracetamol using on-line electrochemistry/liquid chromatography/mass spectrometry. Anal Bioanal Chem 386, 1701–1708 (2006). https://doi.org/10.1007/s00216-006-0801-y
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DOI: https://doi.org/10.1007/s00216-006-0801-y