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N-acetyl-S-(2-hydroxyethyl)-L-cysteine as a potential tool in biological monitoring studies?

A critical evaluation of possibilities and limitations

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Abstract

In mammalian species, including man, N-acetyl-S-(2-hydroxyethyl)-L-cysteine (2-HEMA) is a common urinary metabolite of a large number of structurally different xenobiotic chemicals. It is a common urinary end product of glutathione pathway metabolism of a variety of chemicals possessing electrophilic properties and, in most cases, also a genotoxic potential. Five different chemically reactive intermediates, with different electrophilic properties, may be involved in the formation of 2-HEMA. An inventory of chemicals known to lead to the formation of 2-HEMA, or based on their chemical structure expected to do so, is presented. Furthermore, an attempt is made to evaluate the possibilities and limitations in terms of the potential use of urinary 2-HEMA as a tool in biomonitoring studies. Two other related, sulfur-containing urinary metabolites, i. e. N-acetyl-(S-carboxymethyl)-L-cysteine and thio-diacetic acid, are proposed as possible alternatives to urinary 2-HEMA. It is suggested that 2-HEMA might be seen as a potentially useful and sensitive signal parameter for the assessment of exposure of animals and man to a variety of electrophilic and therefore potentially toxic xenobiotic chemicals.

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Authors and Affiliations

  1. Department of Pharmacochemistry, Molecular Toxicology, Free University, De Boelelaan 1083, 1081, HV Amsterdam, The Netherlands

    N. P. E. Vermeulen, J. de Jong, E. J. C. van Bergen & R. T. H. van Welie

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  1. N. P. E. Vermeulen
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  2. J. de Jong
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  3. E. J. C. van Bergen
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  4. R. T. H. van Welie
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Vermeulen, N.P.E., de Jong, J., van Bergen, E.J.C. et al. N-acetyl-S-(2-hydroxyethyl)-L-cysteine as a potential tool in biological monitoring studies?. Arch Toxicol 63, 173–184 (1989). https://doi.org/10.1007/BF00316366

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  • DOI: https://doi.org/10.1007/BF00316366

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