Electrochemistry-mass spectrometry unveils the formation of reactive triclocarban metabolites

A. Baumann, W. Lohmann, T. Rose, K. C. Ahn, B. D. Hammock, U. Karst, Nils Helge Schebb

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38 Scopus citations

Abstract

Triclocarban (3,4,4′-trichlorocarbanilide, TCC) is a widely used antibacterial agent in personal care products and is frequently detected as an environmental pollutant in waste waters and surface waters. In this study, we report novel reactive metabolites potentially formed during biotransformation of TCC. The oxidative metabolism of TCC has been predicted using an electrochemical cell coupled online to liquid chromatography and electrospray ionization mass spectrometry. The electrochemical oxidation unveils the fact that hydroxylated metabolites of TCC may form reactive quinone imines. Moreover, a so-far unknown dechlorinated and hydroxylated TCC metabolite has been identified. The results were confirmed by in vitro studies with human and rat liver microsomes. The reactivity of the newly discovered quinone imines was demonstrated by their covalent binding to glutathione and macromolecules, using β-lactoglobulin A as a model protein. The results regarding the capability of the electrochemical cell to mimic the oxidative metabolism of TCC are discussed. Moreover, the occurrence of reactive metabolites is compared with findings from earlier in vivo studies and their relevance in vivo is argued.

Original languageEnglish (US)
Pages (from-to)2130-2138
Number of pages9
JournalDrug Metabolism and Disposition
Volume38
Issue number12
DOIs
StatePublished - Dec 2010

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ASJC Scopus subject areas

  • Pharmacology
  • Pharmaceutical Science

Cite this

Baumann, A., Lohmann, W., Rose, T., Ahn, K. C., Hammock, B. D., Karst, U., & Schebb, N. H. (2010). Electrochemistry-mass spectrometry unveils the formation of reactive triclocarban metabolites. Drug Metabolism and Disposition, 38(12), 2130-2138. https://doi.org/10.1124/dmd.110.034546