Estradiol chemistry

Loe, D.W., Almquist, K.C., Cole, S.P. and Deeley, R.G. (1996) ATP-dependent 17 beta-estradiol 17 - (beta-D-glucuronide) transport by multidrug resistance protein (MRP). Inhibition by cholestatic steroids. Journal of Biological Chemistry, 271, 9683-9689. 

B7. Buscarlet, L., Volland, H., Dupret-Carruel, J., Jolivet, M., Grass , J., Creminon, C., Taran, R, and Pradelles, R, Use of free radical chemistry in an immunometric assay for 17jS-estradiol. Clin. Chem. 47, 102-109 (2001). 

Holthaus et al. (2002) The potential for estradiol and ethinylestradiol to sorb to suspended and bed sediments in some English rivers. Environmental Toxicology and Chemistry 21 2526-2535. 

Korte J.J, M.D. Kahl, K.M. Jensen, M.S. Pasha, L.G. Parks, G.A. LeBlanc, and G.T. Ankley (2000). Fathead minnow vitellogenin Complementary DNA sequence and messenger RNA and protein expression after 17 3-estradiol treatment. Environmental Toxicology and Chemistry 19 972-981. 

In the early days of organic chemistry, the word aromatic was used to describe certain fragrant substances from fruits, trees, and other natural sources. Chemists soon realized, however, that substances grouped as aromatic behaved in a chemically different manner from most other organic compounds. Today, the term aromatic refers to the class of compounds that can be represented as having a six-membered ring with three double bonds. Benzene is the simplest aromatic compound, but aspirin, the steroid sex hormone estradiol, and many other important compounds also contain aromatic rings. 

An extension to this work appeared recently when pyridin-2-yl hydrazine based classical chelators were introduced through an ethinyl or ethenyl moiety at position 17. Although still model complexes, this type of derivatization and complexation can easily be transferred to the corresponding 99mTc chemistry. It could be shown that the relative binding affinity was essentially retained and compared favourably with other reported estradiol-derived carbonyl complexes [106]. 

Horwitz, K.B. and McGuire, W.L. (1978) Nuclear mechanisms of estrogen action. Effects of estradiol and anti-estrogens on estrogen receptors and nuclear receptor processing. The Journal of Biological Chemistry, 253, 8185-8191. 

Bucourt, R., Vignau, M. and Torelli, V. (1978) New biospecific adsorbents for the purification of estradiol receptor. The Journal of Biological Chemistry, 253, 8221-8228. 

The reaction involves three steps and has been the subject of considerable mechanistic interest (Figure 10.15). Androstanedione is converted to estrone, testosterone to 17 3-estradiol, and 16-hydroxy DHEA to estriol. The first two steps are relatively straightforward, for example, RCHj RCHjOH —> CHO (at Cl9). The third step was difficult to rationalize with classic FeO " chemistry, and there has been general acceptance of a FeOO -based mechanism originally developed by Robinson and Akhtar, and further developed in models by Coon and Vaz. ... 

Rearrangements of cyclopropanes. Cyclopropanes are interesting not only by themselves, but also because they are easily converted into important synthons in organic chemistry. Recently, rearrangements of cyclopropanes have appeared in the synthesis of, namely, steroids (pregn-4-en-one) [58], 19-norsteroids (estrone, 19-norandrost-4-en-3-17-dione, estradiol-17,8)and 19-nortestosterone [59], insect juvenile hormone analogs [60]. 

Johns, W.F. (1961) Retropinacol rearrangement of estradiol 3-methyl ether. Journal of Organic Chemistry, 26,4583-4591. 

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