Formation and Reactivity of a Quinone Methide in Biological Systems

  • David Thompson
  • Peter Moldéus
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 283)


The formation of reactive electrophilic intermediates during xenobiotic metabolism which interact with cellular macromolecules is the foundation of current hypotheses on the mechanism of toxicity and carcinogenicity of many chemicals. Aromatic compounds which contain one or more oxygen atoms in functional groups attached to the ring have been extensively studied. These compounds include phenols, hydroquinones and catechols which are oxidized to quinones. Quinones are cytotoxic by virtue of their ability to redox cycle and generate reactive oxygen species and also by their ability to alkylate cellular macromolecules. More recently, compounds such as acetaminophen and phenetidine have been shown to form quinoneimines which are also highly cytotoxic (Dahlin, D.C. et al., 1984; Ross, D. et al., 1985). It is now becoming apparent that other derivatives of the quinonoid moiety may also be highly reactive; for example, quinone methides and imine methides (Mizutani, T. et al., 1982; Yost, G.S., 1989). For comparison, the chemical structures of a quinone, quinoneimine and quinone methide are shown in Figure 1.


Cumene Hydroperoxide Phenoxyl Radical Coniferyl Alcohol Cellular Macromolecule Glutathione Conjugate 
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Copyright information

© Plenum Press, New York 1991

Authors and Affiliations

  • David Thompson
    • 1
  • Peter Moldéus
    • 1
  1. 1.Department of ToxicologyKarolinska InstitutetStockholmSweden

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