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.

  • Article
  • Published:

All oxygens in nucleic acids react with carcinogenic ethylating agents

Abstract

Over 80% of ethylnitrosourea and ethylnitrosoguanidine modification of nucleic acids is on oxygens. The reactivity of oxygens (other than ribose and phosphate) in single-stranded RNA is: O2of C > O2 of U > O6 of G > O4 of U. In double-stranded DNA the order is: O2 of T = O6 of G > O4 of T O2 of C. Oxygen reactivity of single-stranded DNA resembles RNA. The glycosidic bond of O2-alkylpyrimidines is labilised.

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. Singer, B., Progr. Nucl. Acids Res. molec. Biol., 15, 219–284, 330–332 (1975).

    Article  CAS  Google Scholar 

  2. Loveless, A., Nature, 223, 206–207 (1969).

    Article  ADS  CAS  Google Scholar 

  3. Lawley, P. D., and Thatcher, C. J., Biochem. J., 116, 693–707 (1970).

    Article  CAS  Google Scholar 

  4. Lawley, P. D., and Shah, S. A., Biochem. J., 128, 117–132 (1972).

    Article  CAS  Google Scholar 

  5. Lawley, P. D., Orr, D. J., Shah, S. A., Farmer, P. B., and Jarman, M., Biochem. J., 135, 193–201 (1973).

    Article  CAS  Google Scholar 

  6. Walker, I. G., and Ewart, D. F., Mutat. Res., 19, 331–341 (1973).

    Article  CAS  Google Scholar 

  7. Kleihues, P., and Magee, P. N., J. Neurochem., 20, 595–600 (1973).

    Article  CAS  Google Scholar 

  8. Goth, R., and Rajewsky, M. F., Z. Krebsforsch., 82, 37–64 (1974).

    Article  CAS  Google Scholar 

  9. Margison, G. P., and Kleihues, P., Biochem. J., 148, 521–525 (1975).

    Article  CAS  Google Scholar 

  10. Singer, B., and Fraenkel-Conrat, H., Biochemistry, 14, 772–782 (1975).

    Article  CAS  Google Scholar 

  11. Sun, L., and Singer, B., Biochemistry, 14, 1795–1802 (1975).

    Article  CAS  Google Scholar 

  12. Singer, B., and Kusmierek, J. T., Biochemistry (in the press).

  13. Singer, B., FEBS Lett., 63, 85–88 (1976).

    Article  CAS  Google Scholar 

  14. Kuśmierek, J. T., and Singer, B., Biochim. biophys. Acta (in the press).

  15. Singer, B., Biochemistry, 12, 3939–3947 (1972).

    Article  Google Scholar 

  16. Sun, L., and Singer, B., Biochemistry, 13, 1905–1913 (1974).

    Article  CAS  Google Scholar 

  17. Singer, B., Sun, L., and Fraenkel-Conrat, H., Biochemistry, 13, 1913–1920 (1974).

    Article  CAS  Google Scholar 

  18. Singer, B., Biochemistry, 14, 4353–4357 (1975).

    Article  CAS  Google Scholar 

  19. Singer, B., in Handbook of Biochemistry and Molecular Biology (edit. by Fasman, G. D.): Nucleic Acids, 1, 409 (1975).

    Google Scholar 

  20. Kuśmierek, J. T., and Singer, B., Nucleic Acids Res., 3, 989–1000 (1976).

    Article  Google Scholar 

  21. Herriott, R. M., J. gen. Physiol., 32, 221–239 (1948).

    Article  CAS  Google Scholar 

  22. Auerbach, C., and Robson, J. M. Nature, 157, 302 (1946).

    Article  ADS  CAS  Google Scholar 

  23. Ludlum, D. B., J. biol. Chem., 245, 477–482 (1970).

    CAS  PubMed  Google Scholar 

  24. Gerchman, L. L., and Ludlum, D. B., Biochim. biophys. Acta, 308, 310–316 (1973).

    Article  CAS  Google Scholar 

  25. Craddock, V. M., Biochim. biophys. Acta, 312, 202–210 (1973).

    Article  CAS  Google Scholar 

  26. Kirtikar, D. M., and Goldthwait, D. A., Proc. natn. Acad. Sci. U.S.A., 71, 2022–2026 (1974).

    Article  ADS  CAS  Google Scholar 

  27. Goth, R., and Rajewsky, M. F. Proc. natn. Acad. Sci. U.S.A., 71, 639–643 (1974).

    Article  ADS  CAS  Google Scholar 

  28. Kleihues, P., and Margison, G. P. J. natn. Cancer Inst., 53, 1839–1841 (1974).

    CAS  Google Scholar 

  29. Rajewsky, M. F., Goth, R., Laerum, O. D., Biessmann, H., and Hülser, D. F. VIth Int. Symp. Princess Takamatsu Cancer Research Fund (in the press).

  30. Nicoll, J. W., Swann, P. F., and Pegg, A. E. Nature, 254, 261–262 (1975).

    Article  ADS  CAS  Google Scholar 

  31. Kleihues, P., and Margison, G. P., Nature, 259, 153–155 (1976).

    Article  ADS  CAS  Google Scholar 

  32. Singer, B., Sun, L., and Fraenkel-Conrat, H., Proc. natn. Acad. Sci. U.S.A., 72, 2232–2236 (1975).

    Article  ADS  CAS  Google Scholar 

  33. Robins, M. J., Naik, S. R., and Lee, A. S. K., J. Org. Chem., 39, 1891–1899 (1974).

    Article  CAS  Google Scholar 

  34. Sukhorukov, B. I., Gukovskaya, A. S., Sukhoruchkina, L. V., and Laurrenova, G. I., Biophysica, 17, 5–11 (1972).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Singer, B. All oxygens in nucleic acids react with carcinogenic ethylating agents. Nature 264, 333–339 (1976). https://doi.org/10.1038/264333a0

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1038/264333a0

This article is cited by

Comments

By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.

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