Skip to main content

Metabolic Activation of Bromopropyl Compounds

  • Chapter
  • First Online:
Book cover Biological Reactive Intermediates—II

Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 136))

Abstract

The possible health risks involved with the use of flame retardants were recognized when it was shown that tris(2,3-dibromopropyl)phosphate (Tris-BP), the major chemical used in US sleepwear between 1973 and 1977, was a potent mutagen in the Salmonella test1,2. It was subsequently demonstrated that Tris-BP caused kidney tubular adenomas and carcinomas in long-term feeding experiments in rats and mice3. This flame retardant can be absorbed from fabric worn by people, because one of its hydrolysis products, 2,3-dibromopropanol (2,3-DBP), wad excreted in the urine of children wearing Tris-BP treated garments4.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
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

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. M.J. Prival, E.C. McCoy, B. Gutter, and H.S. Rosenkranz, Tris(2,3-dibromopropyl)phosphate: mutagenicity of a widely used flame retardant, Science 195: 76 (1977).

    CAS  PubMed  Google Scholar 

  2. A. Blum and B.N. Ames, Flame retardant additives as possible cancer hazards. The main flame retardant in children’s pajamas is a mutagen and should not be used, Science 195: 17 (1977).

    CAS  Google Scholar 

  3. G. Reznik, J.M. Ward, J.F. Hardisty, and A. Russfield, Renal carcinogenic and nephrotoxic effects of the flame retardant tris(2,3-dibromopropyl)phosphate in F344 rats and (C57 BL/6N x C3H/HeN)F mice, J. Natl. Cancer Inst. 63: 205 (1979).

    Google Scholar 

  4. A. Blum, M.D. Gold, B.N. Ames, C. Kenyon, F.R. Jones, E.A. Nett, R.C. Dougherty, E.C. Horning, I. Dzidic, D.I. Carroll, R.N. Stilwell, and J.-P. Thenot, Children absorb tris-BP flame retardant from sleepwear: urine contains the mutagenic metabolite, 2,3-dibromopropanol,_Science 201: 1020 (1978).

    Google Scholar 

  5. E.J. Söderlund, S.D. Nelson, and E. Dybing, Mutagenic activation of tris(2,3-dibromopropyl)phosphate: the role of microsomal oxidative metabolism. Acta Pharmacol. Toxicol. 45: 112 (1979).

    Article  Google Scholar 

  6. L.E. St. John, Jr., M.E. Eldefrawi, and D.J. Lisk, Studies of possible absorption of a flame retardant from treated fabrics worn by rats and humans, Bull. Environ. Contamin. Toxicol. 15: 192 (1976).

    Google Scholar 

  7. J.M. Kennish, K. Wong, N. Gerber, and R.K. Lynn, Pharmacokinetics of the flame retardant tris(2,3-dibromopropyl)phosphate (tris) in the rat: plasma concentrations, excretion and distribution, Pharmacologist 21: 216 (1979).

    Google Scholar 

  8. E. Söderlund, E. Dybing, and S.D. Nelson, Nephrotoxicity and hepatotoxicity of tris(2,3-dibromopropyl)phosphate in the rat, Toxicol. Appl. Pharmacol. in press.

    Google Scholar 

  9. J.A. Miller, Carcinogenesis by chemicals - an overview. G.H.A. Clowes Memorial Lecture, Cancer Res. 30: 559 (1970).

    Google Scholar 

  10. J. McCann, E. Choi, E. Yamasaki, and B.N. Ames, Detection of carcinogens in the Salmonella/microsome test: assay of 300 chemicals, Proc. Natl. Acad. Sci. USA 72: 5135 (1975).

    Google Scholar 

  11. J.B. Hook, K.M. McCormack, and W.M. Kluwe, Biochemical mechanisms of nephrotoxicity, in: “Reviews in Biochemical Toxicology”, vol. 1, E. Hodgson, J.R. Bend, and R.M. Philpot, eds., Elsevier/North-Holland, New York (1979).

    Google Scholar 

  12. J.R. Mitchell, S.D. Nelson, S.S. Thorgeirsson, R.J. McMurtry, and E. Dybing, Metabolic activation: biochemical basis for many drug-induced liver injuries, in: “Progress in Liver Disease”, vol. 5, H. Popper and F. SEhaffner, eds., Grune and Stratton, New York (1976).

    Google Scholar 

  13. E. J. Söderlund, S.D. Nelson, and E. Dybing, In vitro and in vivo covalent binding of the kidney carcinogen tris(2,3-dibromopropyl)phosphate, Cancer Res. submitted.

    Google Scholar 

  14. T. Omura and R.Sato, The carbon monoxide-binding protein of rat liver microsomes. I. Evidence for its hemoprotein nature, J. Biol. Chem. 239: 1370 (1964).

    Google Scholar 

  15. G.E. Neal, A:2. Mattocks, and D.J. Judah, The microsomal activation of aflatoxin B and 2-(N-ethylcarbamoyloxymethyl)- furan in vitro using a novel diffusion apparatus, Biochim. Biophys. Acta 585: 134 (1979).

    Google Scholar 

  16. A. Viviani and W.K. Lutz, Modulation of the binding of the carcinogen benzo(a)pyrene to rat liver DNA in vivo by selective induction of microsomal and nuclear aryl hydrocarbon hydroxylase activity, Cancer Res. 38: 4640 (1978).

    CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1982 Springer Science+Business Media New York

About this chapter

Cite this chapter

Dybing, E., Söderlund, E.J., Nelson, S.D. (1982). Metabolic Activation of Bromopropyl Compounds. In: Snyder, R., et al. Biological Reactive Intermediates—II. Advances in Experimental Medicine and Biology, vol 136. Springer, New York, NY. https://doi.org/10.1007/978-1-4757-0674-1_47

Download citation

  • DOI: https://doi.org/10.1007/978-1-4757-0674-1_47

  • Published:

  • Publisher Name: Springer, New York, NY

  • Print ISBN: 978-1-4757-0676-5

  • Online ISBN: 978-1-4757-0674-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics