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A mechanism for the formation of bis-glutathione conjugates of propargyl alcohol

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Abstract:



Our earlier research clearly revealed glutathione (GSH) conjugation as a major pathway for the metabolism of propargyl alcohol (2-propyn-1-ol) in rats and in mice. The identification of the metabolite 3,3-bis[(2-acetylamino-2-carboxyethyl)thio]-1-propanol (I) and its congeners represented the first example of multi-glutathione addition to a triple bond, and invoked further research to determine the mechanism for bis-conjugation. To determine whether GSH conjugated directly with propargyl alcohol or after oxidation of the latter to 2-propynal, urinary metabolites from rats administered deuterium-labeled propargyl alcohol were characterized. Following TLC separation and HPLC purification, mass spectrometry was used to show a single mass unit increase for metabolite I over that of the chemically synthesized standard. This result indicates that conjugation of propargyl alcohol with GSH to form the bis-conjugates occurred after initial oxidation to 2-propynal, a reaction that is analogous to a Michael addition.

© 2003 Society of Chemical Industry

Keywords: bis-glutathione of PA; deuterated-PA

Document Type: Research Article

DOI: http://dx.doi.org/10.1002/ps.641

Affiliations: 1: * 2: Chemical Industry Institute of Toxicology, Research Triangle Park, NC 27709, USA

Publication date: March 1, 2003

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