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Chemical Compound Review:

EMATE (8S,9S,13S,14S)-13-methyl-17- oxo-3...

Synonyms: Emate compound, CHEMBL122708, SureCN305660, CHEBI:301043, NSC-685426, ...

Purohit, A. et al., Ciobanu, L.C. et al., Ciobanu, L.C. et al., Ho, Y.T. et al., Flood, J.F. et al., et al.

Raobaikady, Purohit, Chander, Woo, Leese, Potter, Reed, Flood, Farr, Johnson, Li, Morley, Hoffmann, Rot, Niiyama, Billich,

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of Emate compound

COUMATE did not stimulate the growth of MCF-7 breast cancer cells or uteri of ovariectomized rats, in contrast to estrone-3-O-sulfamate [1].

Psychiatry related information on Emate compound

Reversal of scopolamine induced amnesia in rats by the steroid sulfatase inhibitor estrone-3-O-sulfamate [2].

High impact information on Emate compound

Using an ovariectomized mouse model, we show that the first generation of steroid sulfatase inhibitors tested, 3-sulfamoyloxy-17alpha-p-tert-butylbenzyl(or benzyl)estra-1,3,5 (10)-trien-17beta-ols and estrone-3-O-sulfamate, are estrogenic compounds stimulating estrogen-sensitive uterine growth [3].
Differential effects of estrone and estrone-3-O-sulfamate derivatives on mitotic. Arrest, apoptosis, and microtubule assembly in human breast cancer cells [4].
In this study, in vitro and in vivo techniques have been used to confirm that COUMATE, in contrast to the steroidal steroid sulfatase inhibitor estrone-3-O-sulfamate, is devoid of estrogenic activity [1].
Other compounds that contain an aryl sulphamate moiety, for example, oestrone-3-O-sulphamate, are sequestered into red blood cells (RBCs) [5].
Estrone-3-O-sulfamate (EMATE), a steroid sulfatase inhibitor, potentiates the effect of DHEAS on memory retention such that lower doses of DHEAS improve memory retention [6].

Biological context of Emate compound

Pharmacokinetics of oestrone-3-O-sulphamate [7].
In the test for estrogenicity, estrone and estrone-3-O-sulfamate significantly stimulated MCF-7 cell growth [8].
The MCF-7 cell proliferation assay revealed that estrone and estrone-3-O-sulfamate were both estrogenic, but the (p-O-sulfamoyl)-N-alkanoyl phenylalkyl amines were not [9].
The IC50 values of compound 10 are similar to that of 17alpha-t-butylbenzyl-estradiol, which was previously reported by our group as a good steroid sulfatase reversible inhibitor, but remains higher than that of the potent inactivators estrone-3-O-sulfamate (EMATE) and 17alpha-t-butylbenzyl-EMATE [10].

Anatomical context of Emate compound

Measurement of oestrone sulphatase activity in white blood cells to monitor in vivo inhibition of steroid sulphatase activity by oestrone-3-O-sulphamate [11].
2-MeOE2bisMATE was found to retain its STS inhibitory activity and in a placental microsome assay system it was equipotent with oestrone-3-O-sulphamate (EMATE) [12].

Associations of Emate compound with other chemical compounds

Using a 96-well plate assay, oestrone-3-O-sulphamate (EMATE) and two coumarin-based sulphamate drugs (667 COUMATE and STX 118) were found to have IC(50) values of 25-59 nM for the inhibition of hCAII activity [13].

Gene context of Emate compound

Steroid sulfatase activity was inhibited by estrone-3-O-sulfamate, a specific inhibitor of steroid sulfatase, in a concentration-dependent way [14].
Three treatment groups, 5-15 weeks of age were used: controls, estrone and STS inhibitor (estrone-3-O-sulfamate), (n=8 per group) [15].

References

In vivo activity of 4-methylcoumarin-7-O-sulfamate, a nonsteroidal, nonestrogenic steroid sulfatase inhibitor. Purohit, A., Woo, L.W., Singh, A., Winterborn, C.J., Potter, B.V., Reed, M.J. Cancer Res. (1996) [Pubmed]
Reversal of scopolamine induced amnesia in rats by the steroid sulfatase inhibitor estrone-3-O-sulfamate. Li, P.K., Rhodes, M.E., Jagannathan, S., Johnson, D.A. Brain research. Cognitive brain research. (1995) [Pubmed]
Inhibition of estrone sulfate-induced uterine growth by potent nonestrogenic steroidal inhibitors of steroid sulfatase. Ciobanu, L.C., Luu-The, V., Martel, C., Labrie, F., Poirier, D. Cancer Res. (2003) [Pubmed]
Differential effects of estrone and estrone-3-O-sulfamate derivatives on mitotic. Arrest, apoptosis, and microtubule assembly in human breast cancer cells. MacCarthy-Morrogh, L., Townsend, P.A., Purohit, A., Hejaz HAM, n.u.l.l., Potter BVL, n.u.l.l., Reed, M.J., Packham, G. Cancer Res. (2000) [Pubmed]
Pharmacokinetics of the nonsteroidal steroid sulphatase inhibitor 667 COUMATE and its sequestration into red blood cells in rats. Ireson, C.R., Chander, S.K., Purohit, A., Parish, D.C., Woo, L.W., Potter, B.V., Reed, M.J. Br. J. Cancer (2004) [Pubmed]
Peripheral steroid sulfatase inhibition potentiates improvement of memory retention for hippocampally administered dehydroepiandrosterone sulfate but not pregnenolone sulfate. Flood, J.F., Farr, S.A., Johnson, D.A., Li, P.K., Morley, J.E. Psychoneuroendocrinology (1999) [Pubmed]
Pharmacokinetics of oestrone-3-O-sulphamate. Hidalgo Aragones, M.I., Purohit, A., Parish, D., Sahm, U.G., Pouton, C.W., Potter, B.V., Reed, M.J. J. Steroid Biochem. Mol. Biol. (1996) [Pubmed]
Development of potent non-estrogenic estrone sulfatase inhibitors. Li, P.K., Chu, G.H., Guo, J.P., Peters, A., Selcer, K.W. Steroids (1998) [Pubmed]
Development of (p-O-sulfamoyl)-N-alkanoyl-phenylalkyl amines as non-steroidal estrone sulfatase inhibitors. Kolli, A., Chu, G.H., Rhodes, M.E., Inoue, K., Selcer, K.W., Li, P.K. J. Steroid Biochem. Mol. Biol. (1999) [Pubmed]
3Beta-sulfamate derivatives of C19 and C21 steroids bearing a t-butylbenzyl or a benzyl group: synthesis and evaluation as non-estrogenic and non-androgenic steroid sulfatase inhibitors. Ciobanu, L.C., Boivin, R.P., Luu-The, V., Poirier, D. Journal of enzyme inhibition and medicinal chemistry. (2003) [Pubmed]
Measurement of oestrone sulphatase activity in white blood cells to monitor in vivo inhibition of steroid sulphatase activity by oestrone-3-O-sulphamate. Purohit, A., Froome, V.A., Wang, D.Y., Potter, B.V., Reed, M.J. J. Steroid Biochem. Mol. Biol. (1997) [Pubmed]
Inhibition of MCF-7 breast cancer cell proliferation and in vivo steroid sulphatase activity by 2-methoxyoestradiol-bis-sulphamate. Raobaikady, B., Purohit, A., Chander, S.K., Woo, L.W., Leese, M.P., Potter, B.V., Reed, M.J. J. Steroid Biochem. Mol. Biol. (2003) [Pubmed]
Inhibition of carbonic anhydrase II by steroidal and non-steroidal sulphamates. Ho, Y.T., Purohit, A., Vicker, N., Newman, S.P., Robinson, J.J., Leese, M.P., Ganeshapillai, D., Woo, L.W., Potter, B.V., Reed, M.J. Biochem. Biophys. Res. Commun. (2003) [Pubmed]
Steroid sulfatase in the human hair follicle concentrates in the dermal papilla. Hoffmann, R., Rot, A., Niiyama, S., Billich, A. J. Invest. Dermatol. (2001) [Pubmed]
Steroid sulfatase inhibitor alters blood pressure and steroid profiles in hypertensive rats. Valigora, S.D., Lib, P.K., Dunphy, G., Turner, M., Ely, D.L. J. Steroid Biochem. Mol. Biol. (2000) [Pubmed]

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