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Chemical Compound Review:

SureCN232796 (8S,9S,13S,14S,17S)-17- hydroxy-13-methyl-3...

Synonyms: CHEBI:4866, CHEMBL1628111, NSC629909, LMST05020005, AC1L25BO, ...

Wood, C.E. et al., Tseng, L. et al., Pasqualini, J.R. et al., Hobkirk, R. et al., Wood, C.E. et al., et al.

Wood, Gridley, Keller-Wood, Wood,

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High impact information on C08357

The present study was designed to test the hypothesis that exogenous estradiol-3-sulfate stimulates HPA axis activity in late gestation fetal sheep and that it is concentrated by fetal brain tissue [1].
Sulfotransferase 2A1 forms estradiol-17-sulfate and celecoxib switches the dominant product from estradiol-3-sulfate to estradiol-17-sulfate [2].
Additionally, estradiol circulates in the form of estradiol-3-sulfate, a molecular form that is taken up by the fetal brain and deconjugated by steroid sulfatase, which is expressed in the fetal brain [3].
Estradiol-3-sulfate was equipotent with E2 and estradiol-17 beta-glucuronide approx. 10% as potent [4].
It has been demonstrated that different estrogen-3-sulfates (estrone-3-sulfate, estradiol-3-sulfate, estriol-3-sulfate) can provoke important biological responses in different mammary cancer cell lines: there is a significant increase in progesterone receptor [5].

Anatomical context of C08357

We infused estradiol-3-sulfate iv into fetal sheep (125-135 d gestation; term = 147 d) at rates of 0, 0.25, and 1.0 mg/d for 5 d and performed serial sampling of fetal blood before and at the end of the infusion periods [1].
The use of the latter as a natural subd E23S are present in liver, kidney, blood, gallbladder bile, intestine, uterus, and placenta after injection of labelled E2 into mature male and female guinea pigs [6].
However, the average value of the ESFT activity, expressed in nmol of estradiol-3-sulfate (E2S) formed from estradiol (E2)/mg of cytosol protein per hr, was found to be significantly higher in ER +/PGR + tumors (n = 26, 0.18 +/- 0.15, means +/- SD) than in ER -/PGR - tumors (n = 31, 0.08 +/- 0.06, P less than 0.005) [7].

Analytical, diagnostic and therapeutic context of C08357

The high-affinity monoclonal anti-estradiol antibody 9D3 presents a specificity defect towards estradiol-3-sulphate and 3-glucuronide conjugates incompatible with use in direct immunoassays [8].
Specific antisera for the radioimmunoassay of estradiol-3-sulfate [9].

References

Biological activity of 17beta-estradiol-3-sulfate in ovine fetal plasma and uptake in fetal brain. Wood, C.E., Gridley, K.E., Keller-Wood, M. Endocrinology (2003) [Pubmed]
Sulfotransferase 2A1 forms estradiol-17-sulfate and celecoxib switches the dominant product from estradiol-3-sulfate to estradiol-17-sulfate. Wang, L.Q., James, M.O. J. Steroid Biochem. Mol. Biol. (2005) [Pubmed]
Estrogen/hypothalamus-pituitary-adrenal axis interactions in the fetus: The interplay between placenta and fetal brain. Wood, C.E. J. Soc. Gynecol. Investig. (2005) [Pubmed]
Vitellogenin synthesis in cultured hepatocytes; an in vitro test for the estrogenic potency of chemicals. Pelissero, C., Flouriot, G., Foucher, J.L., Bennetau, B., Dunoguès, J., Le Gac, F., Sumpter, J.P. J. Steroid Biochem. Mol. Biol. (1993) [Pubmed]
Importance of estrogen sulfates in breast cancer. Pasqualini, J.R., Gelly, C., Nguyen, B.L., Vella, C. J. Steroid Biochem. (1989) [Pubmed]
In vitro and in vivo studies on the metabolism of estrogens and their sulfates in guinea pigs. Hobkirk, R., Freeman, D.J., Harvey, P.R., Nilsen, M., Jennings, B. Can. J. Biochem. (1977) [Pubmed]
Estrogen sulfatase and estrogen sulfotransferase in human primary mammary carcinoma. Tseng, L., Mazella, J., Lee, L.Y., Stone, M.L. J. Steroid Biochem. (1983) [Pubmed]
Functional characterization of an anti-estradiol antibody by site-directed mutagenesis and molecular modelling: modulation of binding properties and prominent role of the V(L) domain in estradiol recognition. Coulon, S., Pellequer, J.L., Blachère, T., Chartier, M., Mappus, E., Chen Sw, S.W., Cuilleron, C.Y., Baty, D. J. Mol. Recognit. (2002) [Pubmed]
Specific antisera for the radioimmunoassay of estradiol-3-sulfate. Tanaka, T., Suguro, N., Shiratori, Y., Kubodera, A. J. Steroid Biochem. (1985) [Pubmed]

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