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Structure Activity Relationships for the Chemical Behaviour and Toxicity of Electrophilic Quinones/Quinone Methides

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Biological Reactive Intermediates VI

Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 500))

Abstract

Electrophilic quinones and quinone methides from a variety of natural and synthetic compounds have been classified as likely toxic reactive metabolites. This includes the quinones/quinone methides of catechol-type metabolites from estrogens and polycyclic aromatic hydrocarbons1, 2, 3. Metabolic activation of estrogens to redox active and/or electrophilic metabolites has been proposed as one of the mechanisms responsible for the link between estrogen exposure and the risk of developing cancer1, 2.Especially catechol (ortho-diol)-type of metabolites resulting from cytochrome P450 catalysed hydroxylation of estrogens(Figure.1) may be involved.

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Authors and Affiliations

  1. Laboratory of Biochemistry, Wageningen University, Dreijenlaan 3, Wageningen, HA, 6703, The Netherlands

    Ivonne M. C. M. Rietjens, Hanem M. Awad, Marelle G. Boersma & Jacques Vervoort

  2. Wageningen University, Division of Toxicology, Tuinlaan 5, Wageningen, HE, 6703, The Netherlands

    Ivonne M. C. M. Rietjens, Jacques Vervoort & Peter J. van Bladeren

  3. TNO/WU Centre for Food Toxicology, PO Box 8000, Wageningen, EA, 6700, The Netherlands

    Ivonne M. C. M. Rietjens, Marlou L. P. S. van Iersel, Jacques Vervoort & Peter J. van Bladeren

Authors
  1. Ivonne M. C. M. Rietjens
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  2. Hanem M. Awad
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  3. Marelle G. Boersma
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  4. Marlou L. P. S. van Iersel
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  5. Jacques Vervoort
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  6. Peter J. van Bladeren
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Editor information

Editors and Affiliations

  1. Université René Descartes, Paris, France

    Patrick M. Dansette

  2. Rutgers University and The Environmental & Occupational Health Sciences Institute, Piscataway, New Jersey, USA

    Robert Snyder

  3. CNRS, Paris, France

    Marcel Delaforge

  4. University of Surrey, Guildford, Surrey, England

    G. Gordon Gibson

  5. Institute of Toxicology and Environmental Health, The Technical University of Munich, Munich, Germany

    Helmut Greim

  6. Medical University of South Carolina, Charleston, South Carolina, USA

    David J. Jollow

  7. University of Texas, Austin, Texas, USA

    Terrence J. Monks

  8. University of Arizona, Tucson, Arizona, USA

    I. Glenn Sipes

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© 2001 Springer Science+Business Media New York

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Rietjens, I.M.C.M., Awad, H.M., Boersma, M.G., van Iersel, M.L.P.S., Vervoort, J., van Bladeren, P.J. (2001). Structure Activity Relationships for the Chemical Behaviour and Toxicity of Electrophilic Quinones/Quinone Methides. In: Dansette, P.M., et al. Biological Reactive Intermediates VI. Advances in Experimental Medicine and Biology, vol 500. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-0667-6_2

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  • DOI: https://doi.org/10.1007/978-1-4615-0667-6_2

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-5185-6

  • Online ISBN: 978-1-4615-0667-6

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