Environmental oestrogen-mimics display liposomal membrane-antioxidant ability: Importance of molecular modelling predictions

Journal of Chemical Technology and Biotechnology

Volumn 73, Issue 2, 1998, Pages 131-136

  Leadley, Jane ^a   Lewis, David F V ^a   Wiseman, Helen ^b   Goldfarb, Peter S ^a   Wiseman, Alan ^a  

^a UNIVERSITY OF SURREY   (United Kingdom)

^b KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

Environmental oestrogen mimics; Lipid peroxidation; Liposomal membranes; Membrane antioxidants; Molecular modelling; Water environments

Indexed keywords

ANTIOXIDANTS; BIOLOGICAL MEMBRANES; COMPUTER SIMULATION; ESTERS; ETHERS; LIPIDS; METABOLITES; MOLECULAR STRUCTURE; OXIDATION; PHENOLS; WATER POLLUTION;

NONYLPHENOL;

HORMONES;

4,4' ISOPROPYLIDENEDIPHENOL; DETERGENT; ESTRADIOL; ESTROGEN; PHTHALIC ACID DIBUTYL ESTER; TAMOXIFEN;

ARTICLE; BREAST CANCER; ECOTOXICOLOGY; FECES; FISH; HERMAPHRODITISM; LAGOON; LIPID PEROXIDATION; MOLECULAR MODEL; OXIDATIVE STRESS; SEWAGE TREATMENT; WATER POLLUTION;

EID: 0032189744     PISSN: 02682575     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-4660(1998100)73:2<131::AID-JCTB948>3.0.CO;2-B     Document Type: Article

References (32)

1. The Identification and Assessment of Oestrogenic Substances in Sewage Treatment Water Effluents. UK Stationery Office Ltd, 1997.
2. Endocrine-Disrupting Substances in the Environment: What Should be Done? The Environment Agency, Environmental Issues Series, 1998.
3. Environmental Oestrogens: Consequences to Human Health and Wildlife. Institute for Environment and Health, Leicester, 1995.
4. Wiseman, A., Goldfarb, P., Ridgway, T. J. & Wiseman, H., Gender-hazards from oestrogen minics in water environments. J. Chem. Technol. Biotechnol., 71 (1998) 3-5.
5. Harries, J. E., Sheahan, D. D., Jobling, S., Matthiessen, P., Neall, P., Routledge, E. J., Rycroft, R., Sumpter, J. P. & Tylor, T., A survey of estrogenic activity in United Kingdom inland water. Environ. Toxicol. Chem., 15 (1996) 1993-2002.
6. Wiseman, H. & Lewis, D. F. V., The metabolism of tamoxifen by human cytochromes P-450 is rationalized by molecular modelling studies of the enzyme-substrate interactions: potential importance to its proposed anticarcinogenic/carcinogenic action. Carcinogenesis, 17 (1996) 1357-60.
7. Lewis, D. F. V., Sex, drugs and P-450. Chemistry and Industry, 20 October (1997) 831-4.
8. Lewis, D. F. V., Parker, M. G. & King, R. J. B., Molecular modelling of the human oestrogen receptor and ligand interactions based on site-directed mutagenesis and amino acid sequence homology. J. Steroid Biochem. Molec. Biol., 52 (1995) 55-65.
9. Wiseman, H., Cannon, M., Arnstein, H. R. V. & Barlow, D. J., The structural mimicry of membrane sterols by tamoxifen: evidence from its cholesterol coefficients and molecular-modelling for its action as a membrane antioxidant and an anticancer agent. Biochim. Biophys. Acta, 1138 (1992) 197-202.
10. Wiese, T. & Kelce, W. R., An introduction to environmental oestrogens. Chemistry and Industry, 18 August (1997) 648-53.
11. Chatterjee, S. N. & Argwal, S., Liposomes as membrane models for study of lipid peroxidation. Free Rad. Biol. Med., 4 (1988) 51-72.
12. Halliwell, B. & Gutteridge, J. M. C., Free Radicals in Biology and Medicine, 2nd edn. Clarendon Press, Oxford, 1989.
13. Riedl, A., Anderton, M., Shamsi, Z., Goldfarb, P. & Wiseman, A., Differing features of proteins in membranes may result in antioxidant or pro-oxidant action: opposite effects on lipid peroxidation of alcohol dehydrogenase and albumin in liposomal systems. Redox Report, 2(1996) 35-40.
14. Quinlan, G. J., Halliwell, B., Moorhouse, C. P. & Gutteridge, J. M. C., Action of lead(II) and aluminium (III) ions on iron-stimulated lipid peroxidation in liposomes, erythrocytes and rat liver microsomal fractions. Biochim. Biophys. Acta, 962 (1988) 196-200.
15. Wiseman, H., Tamoxifen: Molecular Basis of Use in Cancer Treatment and Prevention. John Wiley, Chichester, 1994.
16. Wiseman, H., Quinn, P. & Halliwell, B., Tamoxifen and related compounds decrease membrane fluidity in liposomes. Mechanism for the antioxidant action of tamoxifen and relevance to its anticancer and cardioprotective actions? FEBS Lett., 330 (1993) 53-6.
17. Wiseman, H., The antioxidant action of a pure antioestrogen: ability to inhibit lipid peroxidation compared to tamoxifen and 17β-oestradiol and relevance to its anticancer potential. Biochem. Pharmacol., 47 (1994) 493-8.
18. Wiseman, H., Dietary influences on membrane function: importance in protection against oxidative damage and disease. J. Nutr. Biochem., 7 (1996) 2-15.
19. Halliwell, B. & Chirico, S., Lipid peroxidation: its mechanism, measurement and significance. Am. J. Clin. Nutr., 57 (1993) 715S-725S.
20. Wiseman, H., Phytochemicals (B) Epidemiological Factors. In Encyclopedia of Human Nutrition, eds M. Sadler & M. Saltmarsh. Academic Press, London, 1998 (in press).
21. Williams, R. L. & Rutledge, T., Recent phytoestrogen research. Chemistry and Industry, 5 January (1998) 14-16.
22. Reinli, K. & Block, G., Phytoestrogen content of foods - a compendium of literature values. Nutr. Cancer, 26 (1998) 123-48.
23. Kirkman, L. M., Lampe, J. W., Campbell, D. R., Martini, M. C. & Slavin, J. L., Urinary lignan and isoflavonoid excretion in men and women consuming vegetable and soy diets. Nutr. Cancer, 24 (1995) 1-12.
24. Xu, X, Harris, K. S., Wang, H.-J., Murphy, P. A. & Hendrich, S., Bioavailability of soybean isoflavones depends upon gut microflora in women. J. Nutr., 125 (1995) 2307-15.
25. Wiseman, H., Role of dietary phyto-oestrogens in the protection against cancer and heart disease. Biochem. Soc Trans., 24 (1996) 795-800.
26. Adlercreutz, C. H. T., Goldin, B. R., Gorbach, S. L., Hockerstedt, K. A. V., Watanabe, S., Hamalainen, E. K., Markkanen, M. H., Makela, T. H., Wahala, K. T., Hase, T. A. & Fotsis, T., Soybean phytoestrogen intake and cancer risk. J. Nutr., 125 (1995) 757s-770s.
27. Cassidy, A., Physiological effects of phyto-oestrogens in relation to cancer and other human health risks. Proc. of the Nutr. Soc., 55 (1996) 399-417.
28. Bingham, S. A., Atkinson, C., Liggins, J., Bluck, L. & Coward, A., Plant oestrogens: where are we now. Br. J. Nutr. (1998) in press.
29. Wiseman, H., O'Reilly, J., Lim, P., Garnett, A. P., Huang, W.-C. & Sanders, T. A. B., Antioxidant properties of the isoflavone phytoestrogen functional ingredient in soya products. In Functional Foods '97, eds M. Sadler, M. Spiro & S. Strain. British Nutrition Foundation/Royal Society of Chemistry, London, 1998 (in press).
30. Ashby, J., Lefevre, P. A., Odum, J., Harris, C. A., Routledge, E. J. & Sumpter, J. P., Synergy between synthetic oestrogens? Nature, 385 (1997) 494.
31. Lynch, J. M. & Wiseman, A. (eds), Environmental Biomonitoring: the Biotechnology Ecotoxicology Interface. Cambridge University Press, Cambridge, 1998.
32. Wiseman, H. & Halliwell, B., Damage to DNA by reactive oxygen and nitrogen species: role in inflammatory disease and progression to cancer. Biochem. J. 313 (1996) 17-29.