Estrogen chemistry

Bhavnani, B.R. (1998) Pharmacokinetics and pharmacodynamics of conjugated equine estrogens chemistry and metabolism. Proc. Soc. Exp. Biol. Med., 217, 6-16. 

In the following decades, chemists tried to utilize more and more the knowledge on reactions which had already been gained. A number of landmark syntheses represent the change to modern chemistry, such as the synthesis of the estrogenic steroid equilenin (W. Bachmann, 1939), of pyridoxine (K. Folkers, 1939), and of quinine (R.B. Woodward, W. von E. Doering, 1944) [23]. 

Soimenschein C, Soto AM, Eemandez ME, et al. 1995. Development of a marker of estrogenic exposure in human serum. Clinical Chemistry 41(12 Suppl) 1888-1895. 

Fisch, H. and Golden, R. (2003). Environmental estrogens and sperm counts. Pure and Applied Chemistry 75, 2181-2193. 

Harries, J.E., Janbakhsh, A., and Jobling, S. et al. (1999). Estrogenic potency of effluent from two sewage treatment works in the United Kingdom. Environmental Toxicology and Chemistry 18, 932-937. 

Metzger, D., Ah, S., Bomert, J.M., and Chambon, P. (1995). Characterization of the amino-terminal transcriptional activation function of the human estrogen-receptor in animal and yeast-ceUs. Journal of Biological Chemistry 270, 9535-9542. 

Routledge, E.J. and Sumpter, J.P. (1996). Estrogenic activity of surfactants and some of their degradation products assessed using a recombinant yeast screen. Environmental Toxicology and Chemistry 15, 241-248. 

Sheahan, D.A., Brighty, G.C., Daniel, M., and Kirby, S.J. et al. (2002). Estrogenic activity measured in a sewage treatment works treating industrial inputs containing high concentrations of alkylphenohc compounds—a case study. Environmental Toxicology and Chemistry 21, 507-514. 

Vermeirssen, E.L.M., Burki, R., and Joris, C. et al. (2005). Characterization of the estrogenic-ity of Swiss midland rivers using a recombinant yeast bioassay and plasma vitellogenin concentrations in feral male brown trout. Environmental Toxicology and Chemistry 24, 2226-2233. 

Westerlund, L., Billsson, K., and Andersson, P.L. et al. (2000). Early life stage mortality in zebrafish (Danio rerio) following maternal exposnre to polychlorinated biphenyls and estrogen. Environmental Toxicology and Chemistry 19, 1582-1588. 

Bakke et al. (1982) have shown how montmorillonite catalyses chlorination and nitration of toluene nitration leads to 56 % para and 41 % ortho derivative compared to approximately 40 % para and 60 % ortho derivatives in the absence of the catalyst. Montmorillonite clays have an acidity comparable to nitric acid / sulphuric acid mixtures and the use of iron-exchanged material (Clayfen) gives a remarkable improvement in the para, ortho ratio in the nitration of phenols. The nitration of estrones, which is relevant in making various estrogenic drugs, can be improved in a remarkable way by using molecular engineered layer structures (MELS), while a reduction in the cost by a factor of six has been indicated. With a Clayfen type catalyst, it seems possible to manipulate the para, ortho ratio drastically for a variety of substrates and this should be useful in the manufacture of fine chemicals. In principle, such catalysts may approach biomimetic chemistry our ability to predict selectivity is very limited. 

SMLs have been established for the monomers commonly used in making PET (Table 14.2). Studies conducted using monomers and PET intermediates indicated that these materials are essentially non-toxic and pose no threats to human health. The chemistry of compounds that are used to manufacture PET shows no evidence of estrogenic activity (International Life Sciences Institute, 2000). 

Approaches from medicinal chemistry that resulted in the discovery of first-and second-generation SERMS have been reviewed extensively [149] and will not be discussed in this section. The more recently published chemical structures of anti-estrogen were derived from different classes, e.g. stilbestriol. 

Nazrullaev, S. S., Bessonova, I. A. and Akhmedkhodzhaeva, K. S. 2001. Estrogenic activity as a function of chemical structure in Haplophyllum quinoline alkaloids. Chemistry of Natural Compounds, 31(6) 551-555. 

Huang C-H. and D.L. Sedlak (2001). Analysis of estrogenic hormones in municipal wastewater effluent and surface water using enzyme-linked immunosorbent assay and gas chromato-graphy/tandem mass spectrometry. Environmental Toxicology and Chemistry 20 133-139. 

Kirk L.A., C.R. Tyler, C.M. Lye, and J.P. Sumpter (2002). Changes in estrogenic and androgenic activities at different stages of treatment in wastewater treatment works. Environmental Toxicology and Chemistry 21 972-979. 

Lange R., T.H. Hutchinson, C.P. Croudace, F. Siegmund, H. Schweinfurth, P. Hampe, G.H. Panter, and J.R Sumpter (2001). Effects of the synthetic estrogen 17a-ethinylestradiol on the life-cycle of the fathead minnow Pimephales promelas). Environmental Toxicology and Chemistry 20 1216-1227. 

Kirby, M.F., Allen, Y.T., Dyer, R.A., Feist, S.W., Katsiadiki, I., Matthiessen, P., Scott, A.P., Smith, A., Stentiford, G.D., Thain, J.E., Thomas, K.V., ToUiurst, L., Waldock, M.J. (2004). Surveys of plasma vitellogenin and intersex in male flounder (Platichthys flesus) as measures of endocrine disruption by estrogenic contamination in United Kingdom estuaries temporal trends, 1996 to 2001. Environmental Toxicology and Chemistry, 23 748-758. 

Thomas, K.V, Balaam, J., Hurst, M., Nedyalkova, Z., Mekenyan, O. (2004). Potency and characterization of estrogen-receptor agonists in United Kingdom estuarine sediments. Environmental Toxicology and Chemistry. 23 471-479. 

Vethaak, A.D., Schrap, S.M., de Voogt, P. (editors) (2006). Estrogens and xenoestrogens in the aquatic environment an integrated approach for field monitoring and effect assessment. Pensacola (FI) Society of Environmental Toxicology and Chemistry (SETAC). 512 pp. 

At that time (1994-96), I had research support for a project on estrogenic compounds funded by the Chemical Manufacturers Association (CMA) my only official contact with the association was Ann Mason, Director of Scientific and Regulatory Affairs (Chlorine Chemistry Council, CMA), who asked for a yearly report. My opinions on the endocrine disruptor hypothesis have been based on analysis of scientific publications and have been consistent prior to, during, and after the research (not personal) support from the CMA. 

Walden CE, Knopp RH, Johnson JL, Heiss G, Wahl PW, 183. Hoover JJ. Effect of estrogen/progestin potency on clinical chemistry measures. The Lipid Research Clinics Program 184. Prevalence Study. Am J Epidemiol 1986 123(3) 517—31. 

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