Skip to main content

Redox Activation of Benzotriazine N-Oxides: Mechanisms and Potential as Anticancer Drugs

  • Chapter

Part of the book series: NATO ASI Series ((NSSA,volume 198))

Abstract

A distinguishing feature of solid tumors compared to most, if not all, normal tissues is their regions of low oxygen tension1. Because hypoxic cells are resistant both to radiation-induced cell killing and to the cytotoxic action of some chemotherapeutic drugs, they have long been considered to be a problem for the radiotherapist and, in some cases, for cancer treatment by cytotoxic drugs. More recently, however, tumor hypoxia is beginning to be regarded as a potentially exploitable difference between normal and neoplastic tissue which might be manipulated for therapeutic benefit, and there are a number of different ways in which this might be achieved.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. J. E. Moulder and S. Rockwell, Hypoxic fractions of solid tumors: experimental techniques, methods of analysis, and a survey of existing data, Int. J. Radiat. Oncol. Biol. Phys. 10:695–712 (1984).

    Article  PubMed  CAS  Google Scholar 

  2. M. A. Baker, E. M. Zeman, V. K. Hirst, and J. M. Brown, Metabolism of SR 4233 by Chinese hamster ovary cells: Basis of selective hypoxic cytotoxicity, Cancer Res. 48: 5947–5952 (1988).

    PubMed  CAS  Google Scholar 

  3. E. M. Zeman and J. M. Brown, Modifiers of SR 4233 cytotoxicity, Abstract of 35th Annual Meeting of Radiation Research Society, 1987 (1987).

    Google Scholar 

  4. E. M. Zeman, M. A. Baker, M. J. Lemmon, C. I. Pearson, J. A. Adams, J. M. Brown, W. W. Lee, and M. Tracy, Structure-activity relationships for benzotriazine di-N-oxides, Int. J. Radiat. Oncol. Biol. Phys. 16: 977–981 (1989).

    Article  PubMed  CAS  Google Scholar 

  5. A. J. Varghese and G. F. Whitmore, Detection of a reactive metabolite of misonidazole in human urine, Int. J. Radiat. Oncol. Biol. Phys. 10:1361–1363 (1984).

    Article  PubMed  CAS  Google Scholar 

  6. Y. C. Taylor and A. M. Rauth, Differences in the toxicity and metabolism of the 2-nitroimidazole misonidazole (Ro-07–0582) in HeLa and Chinese hamster ovary cells, Cancer Res. 38:2745–2752 (1978).

    PubMed  CAS  Google Scholar 

  7. K. Laderoute, P. Wardman and A. M. Rauth, Molecular mechanisms for the hypoxia-dependent activation of 3-amino-1,2,4-benzotriazine-1,4-dioxide (SR 4233), Biochem. Pharmacol. 37:1487–1495 (1988).

    Article  PubMed  CAS  Google Scholar 

  8. E. M. Zeman and J. M. Brown, Pre- and post-irradiation radio-sensitization by SR 4233, Int. J. Radiat. Oncol. Biol. Phys. 16:967–971 (1989).

    Article  PubMed  CAS  Google Scholar 

  9. K. W. Kohn, L. C. Erickson, R. A. Ewig,, and C. A. Friedman, Fractionation of DNA from mammalian cells by alkaline elution, Biochemistry 15:4629–4637 (1976).

    Article  PubMed  CAS  Google Scholar 

  10. A. Giaccia, R. Weinstein, J. Hu, and T. D. Stamato, Cell-cycle dependent repair of double-strand breaks in the gamma-ray-sensitive Chinese hamster cell, Somat. Cell and Molec. Gent. 11:485–491 (1985).

    Article  CAS  Google Scholar 

  11. R. F. Kallman and M. J. Dorie, Tumor oxygenation and reoxygenation during radiation therapy: their importance in predicting tumor response, Int. J. Radiat. Oncol. Biol. Phys. 12:681–685 (1986).

    Article  PubMed  CAS  Google Scholar 

  12. E. M. Zeman, V. K. Hirst, M. J. Lemmon, and J. M. Brown, Enhancement of radiation-induced tumor cell killing by the hypoxic cell toxin SR 4233, Radiother. Oncol. 12:209–218 (1988).

    Article  PubMed  CAS  Google Scholar 

  13. D. B. Cater, C. M. B. Grigson, and D. A. Watkinson, Changes of oxygen tension in tumors induced by vasoconstrictor and vasodilator drugs, Acta Radiol. 58:401–408 (1962).

    Article  PubMed  CAS  Google Scholar 

  14. D. J. Chaplin and B. Acker, The effect of hydralazine on the tumor cytotoxicity of the hypoxic cell cytotoxin RSU-1069: evidence for therapeutic gain, Int. J. Radiat. Oncol. Biol. Phys. 13:579–585 (1987).

    Article  PubMed  CAS  Google Scholar 

  15. D. J. Chaplin, Potentiation of RSU-1069 tumour cytotoxicity by 5-hydroxytryptamine (5-HT), Br. J. Cancer 54:727–731 (1986).

    Article  PubMed  CAS  Google Scholar 

  16. P. F. Dodion, J. Abrams, B. Gerard, N. Crespeigne, B. Peeters, B. C. Van, and Y, Kenis, Clinical and pharmacokinetic phase 1 trial with the diethylaminoester of flavone acetic acid (LM985, NSC 293015), Eur. J. Cancer Clin. Oncol. 23:837–842 (1987).

    Article  PubMed  CAS  Google Scholar 

  17. T. H. Corbett, M. C. Bissery, A. Wozniak, J. Plowman,, L. Polin, E. Tapazoglou, J. Dieckman, and F. Valeriote, Activity of flavone acetic acid (NSC-347512) against solid tumors of mice. Invest. New Drugs 4: 207–220 (1986).

    Article  PubMed  CAS  Google Scholar 

  18. M. C. Bibby, J. A. Double, P. M. Loadman, and C.V. Duke, Reduction of tumor blood flow by flavone acetic acid: A possible component of therapy. J. Natl. Cancer Inst. 81:216–220 (1989).

    Article  PubMed  CAS  Google Scholar 

  19. J. M. Brown, Exploitation of bioreductive agents with vasoactive drugs, Proceedings of the 8th International Conference of Radiation Research, 719–724 (1988).

    Google Scholar 

  20. J. R. Sun and J. M. Brown, Enhancement of the antitumor effect of flavone acetic acid by the bioreductive cytotoxic drug SR 4233, Cancer Res. 49: 5664–5670 (1989).

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1990 Springer Science+Business Media New York

About this chapter

Cite this chapter

Brown, J.M. (1990). Redox Activation of Benzotriazine N-Oxides: Mechanisms and Potential as Anticancer Drugs. In: Adams, G.E., Breccia, A., Fielden, E.M., Wardman, P. (eds) Selective Activation of Drugs by Redox Processes. NATO ASI Series, vol 198. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-3768-7_12

Download citation

  • DOI: https://doi.org/10.1007/978-1-4615-3768-7_12

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-6679-9

  • Online ISBN: 978-1-4615-3768-7

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics