Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Letter
  • Published:

Metabolic activation of benzo(a)pyrene proceeds by a diol-epoxide

Abstract

CARCINOGENIC polycyclic hydrocarbons such as the widespread environmental contaminant, benzo(a)pyrene (Fig. 1a), undoubtedly require metabolic activitation. Boyland1 proposed that epoxides, whose formation is catalysed by the NADPH-dependent microsomal mono-oxygenases2,3, are the initial products of double-bond oxidation and we have suggested that epoxides are the important reactive metabolites responsible for the biological effects of these carcinogens4.

This is a preview of subscription content, access via your institution

Access options

Buy this article

Prices may be subject to local taxes which are calculated during checkout

Similar content being viewed by others

References

  1. Boyland, E., Biochem. Soc. Symp., 5, 40–54 (1950).

    CAS  Google Scholar 

  2. Jerina, D. M., Daly, J. W., Witkop, B., Zaltzman-Nirenberg, P., and Udenfriend, S., Biochemistry, 9, 147–156 (1970).

    Article  CAS  Google Scholar 

  3. Grover, P. L., Hewer, A., and Sims, P., Biochem. Pharmac., 21, 2713–2726 (1972).

    Article  CAS  Google Scholar 

  4. Grover, P. L., and Sims, P., Biochem. Pharmac., 22, 661–666 (1973).

    Article  CAS  Google Scholar 

  5. Sims, P., and Grover, P. L., Adv. Cancer Res., 20, 165–274 (1974).

    Article  CAS  Google Scholar 

  6. Baird, W. M., Dipple, A., Grover, P. L., Sims, P., and Brookes, P., Cancer Res., 33, 2386–2392 (1973).

    CAS  PubMed  Google Scholar 

  7. Grover, P. L., Hewer, A., and Sims, P., Biochem. Pharmac., 23, 323–332 (1974).

    Article  CAS  Google Scholar 

  8. Swaisland, A. J., Grover, P. L., and Sims, P., Chem. Biol. Interactions (in the press).

  9. Borgen, A., Darvey, H., Castagnoli, N., Crocker, T. T., Rasmussen, R. E,, and Wang, I. Y., J. Med. Chem., 16, 502–506 (1973).

    Article  CAS  Google Scholar 

  10. Sims, P., Biochem. Pharmac., 19, 795–818 (1970).

    Article  CAS  Google Scholar 

  11. Grover, P. L., and Sims, P., Biochem. J., 110, 159 (1968).

    Article  CAS  Google Scholar 

  12. Booth, J., Keysell, G. R., Pal, K., and Sims, P., FEBS Lett., 43, 341–344 (1974).

    Article  CAS  Google Scholar 

  13. Oesch, F., Xenobiotica, 3, 305–340 (1973).

    Article  CAS  Google Scholar 

  14. Boyland, E., and Williams, K., Biochem. J., 94, 190–197 (1965).

    Article  CAS  Google Scholar 

  15. Grover, P. L., Forrester, J. A., and Sims, P., Biochem. Pharmac., 20, 1297–1302 (1971).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

SIMS, P., GROVER, P., SWAISLAND, A. et al. Metabolic activation of benzo(a)pyrene proceeds by a diol-epoxide. Nature 252, 326–328 (1974). https://doi.org/10.1038/252326a0

Download citation

  • Received:

  • Accepted:

  • Issue date:

  • DOI: https://doi.org/10.1038/252326a0

This article is cited by

Search

Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing