In Vitro and In Vivo Research on Phototoxic Xenobiotics: Structure-Reactivity Relationships

  • G. M. J. Beijersbergen van Henegouwen
Part of the Archives of Toxicology book series (TOXICOLOGY, volume 12)


Simultaneous exposure to (sun)light and a xenobiotic may provoke phototoxic effects. Effects often concern the skin. However, normal photobiological processes in man, such as light-induces vitamin D3 production or the conversion of bilirubin with visible light, as well as animal experiments with xenobiotics (Beijersbergen van Henegouwen et al. 1988), show that systemic effects may also occur. Xenobiotics involved are present in drugs, cosmetics, food products, chemicals used in agriculture, the household, etc. The variety in molecular structure of phototoxic compounds is immense, which implies that they can be found in virtually all classes of xenobiotics. An important objective of research is to identify that part of the molecular structure of a given xenobiotic that causes the unwanted effects. This would provide an opportunity to alter the structure in such a way that the phototoxicity would be diminished whereas the desired properties of the xenobiotic, e.g., a drug, would be conserved. This aim may be achieved by combinating data from three different research lines:
  1. 1.

    Photoreactivity in vitro of the phototoxic xenobiotic and structure analogues whether or not in the presence of essential bio(macro)molecules

  2. 2.

    Phototoxicity in microbiological test systems (bacteria, yeast, mammalian cell cultures)

  3. 3.

    Phototoxicity in experimental animals



Mammalian Cell Culture Irreversible Binding Human Plasma Protein Photobiological Effect Photobiological Process 
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  1. Bakri A, Beijersbergen van Henegouwen GMJ (1988) Photopharmacology of diazepam-N4-oxide in the rat (Submitted for publication)Google Scholar
  2. Bakri A, Beijersbergen van Henegouwen GMJ, Chanal JL (1983) Photopharmacology of the tranquilizer chlordiazepoxide in relation to its phototoxicity. Photochem Photobiol 38:177–183PubMedCrossRefGoogle Scholar
  3. Bakri A, Beijersbergen van Henegouwen GMJ, Chanal JL (1985) Involvement of the N4-oxide group in the phototoxicity of chlordiazepoxide in the rat. Photodermatol 2:205–212PubMedGoogle Scholar
  4. Bakri A, Beijersbergen van Henegouwen GMJ, Sedee AGJ (1986) Irreversible binding of chlordiazepoxide to human plasma protein induced by UV-A radiation. Photochem Photobiol 44:181–185PubMedCrossRefGoogle Scholar
  5. Bakri A, Beijersbergen van Henegouwen GMJ, De Vries H (1988) Photobinding of some 7-chloro-1.4-benzodiazepines to human plasma protein in vitro and photopharmacology of diazepam in the rat. Pharm Weekbl [Sci] 10:122–129CrossRefGoogle Scholar
  6. Beijersbergen van Henegouwen GMJ, Busker RW, De Vries H, Schoonderwoerd SA (1988) Systemic photobiological effects from xenobiotics. In: Chambers PL et al (eds) Mechanisms and models in toxicology. Arch Toxicol [Suppl]Google Scholar
  7. Cornelissen PJG, Beijersbergen van Henegouwen GMJ (1980) Photochemical decomposition of 1.4-benzodiazepines: quantitative analysis of decomposed solutions of chlordiazepoxide and diazepam. Pharm Weekbl [Sci] 2:39–48Google Scholar
  8. Cornelissen PJG, Beijersbergen van Henegouwen GMJ, Mohn GR (1980) Structure and photobiological activity of 7-chloro-1.4-benzodiazepines. Studies on the phototoxic effects of chlordiazepoxide, desmethylchlordiazepoxide and demoxepam using a bacterial indicator system. Photochem Photobiol 32:653–661PubMedCrossRefGoogle Scholar
  9. De Vries H, Beijersbergen van Henegouwen GMJ, Wouters R (1983) Correlation between phototoxicity of some 7-chloro-1.4-benzodiazepines and their (photo)chemical properties. Pharm Weekbl [Sci] 5:302–308CrossRefGoogle Scholar
  10. De Vries H, Beijersbergen van Henegouwen GMJ, Bakri A (1988) The effect of glutathione on the oxaziridine mediated phototoxicity of chlordiazepoxide. (Submitted for publication)Google Scholar

Copyright information

© Springer-Verlag 1988

Authors and Affiliations

  • G. M. J. Beijersbergen van Henegouwen
    • 1
  1. 1.Center for Bio-Pharmaceutical SciencesState University of LeydenLeydenThe Netherlands

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