Development of potent non-estrogenic estrone sulfatase inhibitors

Steroids

Volumn 63, Issue 7-8, 1998, Pages 425-432

  Li, Pui Kai ^a   Chu, Guo Hua ^a   Guo, Jingping ^a   Peters, Amy ^b   Selcer, Kyle W ^b  

^a DUQUESNE UNIVERSITY   (United States)

^b BAYER CORPORATION   (United States)

Author keywords

Estrogen endent cancers; Estrone sulfatase; Mammary carcinoma; Sulfatase inhibitors

Indexed keywords

ANTIESTROGEN; ENZYME INHIBITOR; ESTRONE; ESTRONE SULFATASE INHIBITOR; ESTRONE SULFATE; SULFATASE; UNCLASSIFIED DRUG;

ARTICLE; BREAST CANCER; CONTROLLED STUDY; DRUG DESIGN; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; ESTROGEN ACTIVITY; ESTRONE BLOOD LEVEL; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION;

BREAST NEOPLASMS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; ENZYME INHIBITORS; ESTRADIOL CONGENERS; ESTRONE; FEMALE; HUMANS; SUBSTRATE SPECIFICITY; SULFATASES; TUMOR CELLS, CULTURED; TYRAMINE;

EID: 0031842368     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(98)00044-0     Document Type: Article

References (21)

1. Samojlik E., Santen R.J., Worgul T.J. Plasma estrone sulfate assessment of reduced estrogen production during treatment of metastatic breast cancer . Steroids. 39:1982;497-503.
2. Pasqualini J.R., Chetrite G., Nguyen B.-L., Maloche C., Delalonde L., Talbi M., Feinstein M.-C., Blacker C., Botella J., Paris J. Estrone sulfate-sulfatase and 17β-Hydroxysteroid dehydrogenase activities a hypothesis for their role in the evolution of human breast cancer from hormone-dependence to hormone-independence . J Steroid Biochem Molec Biol. 53:1995;407-412.
3. Santen R.J., Leszczynski D., Tilson-Mallet N., Feil P.D., Wright C., Manni A., Santner S.J. Enzymatic control of estrogen production in human breast cancer Relative significance of aromatase versus sulfatase pathways . Ann N Y Acad Sci. 464:1986;126-137.
4. Evans T.R.J., Rowlands M.G., Jarman M., Coombes R.C. Inhibition of estrone sulfatase enzyme in human placenta and human breast carcinoma. J Steroid Biochem Molec Biol. 39:1991;493-499.
5. Duncan L., Puroit A., Howarth N.M., Potter B.V.L., Reed M.J. Inhibition of estrone sulfate activity by estrone-3-methylthiophosphonate. Cancer Res. 53:1993;298-303.
6. Howarth N.M., Cooper G., Purohit A., Duncan L., Reed M.J., Potter B.V.L. Phosphonates and thiophosphonates as sulfate surrogates Synthesis of estrone-3-methylthiophosphonate, a potent inhibitor of estrone sulfatase . Bioorg Med Chem Lett. 3:1993;313-318.
7. Howarth N.M., Purohit A., Reed M.J., Potter B.V.L. Estrone sulfamates Potent inibitors of estrone sulfatase with therapeutic potential . J Med Chem. 37:1994;219-221.
8. Li P.K., Pillai R., Young B.L., Bender W., Martino D.M., Lin F.T. Synthesis and biochemical studies of estrone sulfatase inhibitors. Steroids. 58:1993;106-111.
9. Dibbelt L., Li P.K., Pillai R., Knuppen R. Inhibition of human placental sterylsulfatase by synthetic analogs of estrone sulfate. J Steroid Biochem Mol Biol. 52:1995;281-286.
10. Li P.K., Pillai R., Dibbelt L. Estrone sulfate analogs as estrone sulfatase inhibitors. Steroids. 60:1995;299-306.
11. Woo L.W.L., Purohit A., Reed M.J., Potter B.V.L. Active site directed inhibition of estrone sulfatase by nonsteroidal coumarin sulfatase. J Med Chem. 39:1996;1349-1351.
12. Li P.K., Milano S., Kluth L., Rhodes M.E. Synthesis and sulfatase inhibitory activities of nonsteroidal sulfatase inhibitors. J Steroid Biochem Mol Biol. 59:1996;41-48.
13. Purohit A., Williams G.J., Howarth N.M., Potter B.V.L., Reed M.J. Inactivation of steroid sulfatase by an active-site directed inhibitor, estrone-3-O-sulphamate. Biochemistry. 34:1995;11508-11514.
14. Purohit A., Williams G.J., Roberts C.J., Potter B.V.L., Reed M.J. In vivo inhibition of oestrone sulphatase and dehydroepiandrosterone sulphatase by estrone-3-sulphamate. Int J Cancer. 63:1995;106-111.
15. Elger W., Schwarz S., Hedden A., Reddersen G., Schneider B. Sulfamates of various estrogens - prodrugs with increased systemic and reduced hepatic estrogenicity at oral application. J Steroid Biochem Mol Biol. 55:1995;396-403.
16. Holt D.A., Levy M.L., Ladd D.L., Oh H.J., Erb J.M., Heaslip J.I., Brandt M., Metcalf B.W. Steroidal A ring aryl carboxylic acids A new class of steroidal 5α-reductase inhibitors . J Med Chem. 33:1990;937-942.
17. Selcer K.W., Hedge P., Li P.K. Inhibition of estrone sulfatase and proliferation of human breast cancer cells by nonsteroidal (p-O-sulfamoyl)-N-alkanoyltyramines. Cancer Res. 57:1997;702-707.
18. Numazawa M., Osawa Y. Synthesis of 16α-bromoacetoxy androgens and 17β-bromoacetylamino-4-androsten-3-one Potential affinity labels of human placental aromatase . Steroids. 38:1981;149-159.
19. Selcer K.W., Jagannathan S., Li P.K. Inhibition of placental estrone sulfatase activity and MCF-7 breast cancer cell proliferation by estrone-3-amino derivatives. J Steroid Biochem Molec Biol. 59:1996;83-91.
20. Soto A.M., Chung K.L., Sonnenschein C. The pesticides endosulfan, toxaphene, and dieldrin have estrogenic effects on human estrogen sensitive cells. Environ Health Perspect. 102:1994;380-383.
21. Soto A.M., Sonnenschein C. The role of estrogens on the proliferation of human breast tumor cells (MCF-7). J Steroid Biochem. 23:1985;87-94.