Steroidal and nonsteroidal sulfamates as potent inhibitors of steroid sulfatase

Journal of Medicinal Chemistry

Volumn 41, Issue 7, 1998, Pages 1068-1083

  Woo, L W Lawrence ^a   Howarth, Nicola M ^a,c   Purohit, Atul ^b   Hejaz, Hatem A M ^a   Reed, Michael J ^b   Potter, Barry V L ^a  

^a University of Bath   (United Kingdom)

^b ST MARY S HOSPITAL   (United Kingdom)

^c HERIOT WATT UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIMETHYLCOUMARIN 3 O SULFAMATE; 4 METHYLCOUMARIN 7 O SULFAMATE; COUMARIN DERIVATIVE; ENZYME INHIBITOR; ESTRONE 3 O SULFAMATE; INDANONE DERIVATIVE; STERYL SULFATASE; SULFAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CELL STRAIN MCF 7; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; HUMAN; HUMAN CELL; MICROSOME; PLACENTA; STRUCTURE ACTIVITY RELATION;

EID: 0032568366     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970527v     Document Type: Article

References (61)

1. McPherson, K.; Steel, C. M.; Dixon, J. M. Breast cancer epidemiology, risk factors and genetics. Br. Med. J. 1994, 309, 1003-1006.
2. Beatson, G. T. On the treatment of inoperable cases of carcinoma of the mamma: suggestions for a new method of treatment with illustrative cases. Lancet 1896, No. 2, 104-107.
3. James, V. H. T.; Reed, M. J. Steroid hormones and human cancer. Prog. Cancer Res. Ther. 1980, 14, 471-487.
4. Lippman, M. E.; Dickson, R. B.; Gelmann, E. P.; Rosen, N.; Knabbe, C.; Bates, S.; Bronzert, D.; Huff, K.; Kasid, A. Growth regulatory and peptide production by human breast carcinoma cells. J. Steroid Biochem. Mol. Biol. 1988, 30, 53-61.
5. Henderson, I. C.; Cannelles, G. P. Cancer of the breast: the past decade. N. Engl. J. Med. 1980, 320, 17-30.
6. Bonney, R. C.; Reed, M. J.; Davidson, K.; Beranek, P. A.; James, V. H. T. The relationship between 17β-hydroxysteroid dehydrogenase activity and oestrogen concentrations in human breast tumours and in normal breast tissue. Clin. Endocrinol. 1983, 19, 727-739.
7. Van Landeghem, A. A. J.; Poortman, J.; Nabuurs, M.; Thijssen, J. H. H. Endogenous concentration and sub-cellular distribution of estrogens in normal and malignant breast tissue. Cancer Res. 1985, 45, 2900-2906.
8. Vermeulen, A.; Deslypere, J. P.; Pavidaens, R.; Leclercq, G.; Roy, F.; Henson, J. C. Aromatase, 17β-hydroxysteroid dehydrogenase and intra-tissular sex hormone concentrations in cancerous and normal breast tissue in postmenopausal women. Eur. J. Cancer Clin. Oncol. 1986, 26, 515-525.
9. Fishman, J.; Nisselbaum, J. S.; Mendez-Botet, C. S.; Schwartz, M. K. Estrone and estradiol content in human breast tumors: relationship to estradiol receptors. J. Steroid Biochem. Mol. Biol. 1977, 8, 893-896.
10. Castiglione-Gertsch, M. New aromatase inhibitors: more selectivity, less toxicity, unfortunately, the same activity. Eur. J. Cancer 1996, 32A, 393-395.
11. Jonat, W.; Howell, A.; Blomqvist, C.; Eiermann, W.; Winblad, G.; Tyrrell, C.; Mauriac, L.; Roche, H.; Lundgren, S.; Hellmund, R.; Azab, M. A randomised trial comparing two doses of the new selective aromatase inhibitor anastrozole (Arimidex) with megestrol acetate in postmenopausal patients with advanced breast cancer. Eur. J. Cancer 1996, 32A, 404-412.
12. Santner, S. J.; Feil, P. D.; Santen, R. J. In situ estrogen production via the estrone sulfatase pathway in breast tumors: relative importance vs the aromatase pathway. J. Clin. Endocrinol. Metab. 1984, 59, 29-33.
13. Yamamoto, T.; Kitawaki, J.; Urabe, M.; Honjo, H.; Tamura, T.; Noguchi, T.; Okada, H.; Sasaki, H.; Tada, A.; Terashima, Y.; Nakamura, J.; Yoshihama, M. Estrogen productivity of endometrium and endometrial cancer tissue-influence of aromatase on proliferation of endometrial cancer cells. J. Steroid Biochem. Mol. Biol. 1993, 44, 463-468.
14. James, V. H. T.; McNeill, J. M.; Lai, L. C.; Newton, C. J.; Ghilchik, M. W.; Reed, M. J. Aromatase activity in normal breast and breast tumor tissues: in vivo and in vitro studies. Steroids 1987, 50, 269-279.
15. Adams, J. B.; Garcia, M.; Rochefort, H. Estrogenic effects of physiological concentrations of 5-androstene-3β,17β-diol and its metabolism in MCF-7 human breast cancer cells. Cancer Res. 1981, 41, 4720-4726.
16. Poulin, R.; Labrie, F. Stimulation of cell proliferation and oestrogenic response by adrenal C19-δ-5-steroids in the ZR-75-1 human breast cancer cell line. Cancer Res. 1986, 46, 4933-4937.
17. Dauvois, S.; Labrie, F. Androstenedione and androst-5-ene-3β,-17β-diol stimulate DMBA-induced mammary tumours-role of aromatase. Breast Cancer Res. Treat. 1989, 13, 61-69.
18. Poortman, J.; Andriesse, R.; Agema, A.; Donker, G. H.; Schwarz, F.; Thijssen, J. H. H. In Adrenal Androgens; Genazzani, A. R., Thijssen, J. H. H., Siiteri, P. K., Eds.; Raven Press: New York, 1980; pp 219-240.
19. Purohit, A.; Dauvois, S.; Parker, M. G.; Potter, B. V. L.; Williams, G. J.; Reed, M. J. The hydrolysis of oestrone sulphate and dehydroepiandrosterone sulphate by human steroid sulphatase expressed in transfected COS-1 cells. J. Steroid Biochem. Mol. Biol. 1994, 50, 101-104.
20. Townsley, J. D.; Schul, D. A.; Rubin, E. J. Inhibition of steroid3-sulfatase by endogenous steroids. A possible mechanism controlling placental estrogen synthesis from conjugated precursors. J. Clin. Endocrinol. Metab. 1970, 31, 670-678.
21. Evans, J.; Rowlands, M.; Jarman, M.; Coombes, R. C. Inhibition of estrone sulfatase enzyme in human placenta and human breast carcinoma. J. Steroid Biochem. Mol. Biol. 1991, 39, 493-499.
22. Santner, S. J.; Santen, R. J. Inhibition of estrone sulfatase and 17β-hydroxysteroid dehydrogenase by antiestrogens. J. Steroid Biochem. Mol. Biol. 1993, 45, 383-390.
23. Carlstrom, K.; Doberl, A.; Pousette, A.; Rannevik, G.; Wilking, N. Inhibition of steroid sulfatase activity by danazol. Acta Obstet. Gynaec. Scand. 1984, 123 (Suppl.), 107-111.
24. Li, P. K.; Pillai, R.; Yeung, B. L.; Bender, W. H.; Martino, D. M.; Lin, F. T. Synthesis and biochemical studies of estrone sulfatase inhibitors. Steroids 1993, 58, 106-111.
25. Li, P. K.; Pillai, R.; Dibbelt, L. Estrone sulfate analogs as estrone sulfatase inhibitors. Steroids 1995, 60, 299-306.
26. Selcer, K. W.; Jagannathan, S.; Rhodes, M. E.; Li, P. K. Inhibition of placental estrone sulfatase activity and MCF-7 breast cancer cell proliferation by estrone-3-amino derivatives. J. Steroid Biochem. Mol. Biol. 1996, 59, 83-91.
27. Duncan, L.; Purohit, A.; Howarth, N. M.; Potter, B. V. L.; Reed, M. J. Inhibition of estrone sulfatase activity by estrone-3-methylthiophosphonate: a potential therapeutic agent in breast cancer. Cancer Res. 1993, 53, 298-303.
28. 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. 1993, 3, 313-318.
29. Howarth, N. M.; Purohit, A.; Reed, M. J.; Potter, B. V. L. Estrone sulfonates as inhibitors of estrone sulfatase. Steroids 1997, 62, 346-350.
30. Howarth, N. M.; Purohit, A.; Reed, M. J.; Potter, B. V. L. Estrone sulfamates: potent inhibitors of estrone sulfatase with therapeutic potential. J. Med. Chem. 1994, 37, 219-221.
31. Reed, M. J.; Potter, B. V. L. Steroid sulphatase inhibitors. U.S. Patent 5, 616, 574, 1997.
32. 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. 1995, 55, 395-403.
33. Woo, L. W. L.; Lightowler, M.; Purohit, A.; Reed, M. J.; Potter, B. V. L. Heteroatom-substituted analogues of the active site-directed inhibitor estra-1, 3, 5(10)-trien-17-one-3-sulphamate inhibit estrone sulphatase by a different mechanism. J. Steroid Biochem. Mol. Biol. 1996, 57, 79-88.
34. Williams, G. J.; Woo, L. W. L.; Mahon, M. F.; Purohit, A.; Reed, M. J.; Potter, B. V. L. X-ray crystal structure and mechanism of action of oestrone 3-O-sulphamate, a synthetic active site-directed inhibitor of oestrone sulphatase. Pharm. Sci. 1996, 2, 11-16.
35. Li, P. K.; Rhodes, M. E.; Jagannathan, S.; Johnson, D. A. Reversal of scopolamine induced amnesia in rats by the steroid sulfatase inhibitor estrone-3-O-sulfamate. Cognit. Brain Res. 1995, 2, 251-254.
36. Daynes, R. A.; Araneo, B. A.; Dowell, T. A.; Huang, K.; Dudley, D. Regulation of murine lymphokine production in vivo. 3. The lymphoid tissue micro-environment exerts regulatory influences over T-helper cell function. J. Exp. Med. 1990, 171, 979-996.
37. Rook, G. A. W.; Hernandez-Pando, R.; Lightman, S. Hormones, peripherally activated prohormones and regulation of the TH1/ TH2 balance. Immunol. Today 1994, 15, 301-303.
38. Birnböck, H.; Von Angerer, E. Sulfate derivatives of 2-phenylindoles as novel steroid sulfatase inhibitors. Biochem. Pharmacol. 1990, 39, 1709-1713.
39. Li, P. K.; Milano, S.; Kluth, L.; Rhodes, M. E. Synthesis and sulfatase inhibitory activities of nonsteroidal estrone sulfatase inhibitors. J. Steroid Biochem. Mol. Biol. 1996, 59, 41-48.
40. Selcer, K. W.; Hegde, P. V.; Li, P. K. Inhibition of estrone sulfatase and proliferation of human breast cancer cells by nonsteroidal (p-O-sulfamoyl)-N-alkanoyltyramines. Cancer Res. 1997, 57, 702-707.
41. Woo, L. W. L.; Purohit, A.; Reed, M. J.; Potter, B. V. L. Active site-directed inhibition of estrone sulfatase by nonsteroidal coumarin sulfamates. J. Med. Chem. 1996, 39, 1349-1351.
42. Prezewowsky, K.; Laurent, H.; Hofmeister, H.; Wiechert, R.; Neumann, F.; Nishino, Y. 1,3-Oxygenated 8α-estratriene. German Patent 1975, 2 426 778; Chem. Abstr. 1976, 84, 150838c.
43. Prezewowsky, K.; Laurent, H.; Hofmeister, H.; Wiechert, R.; Neumann, F.; Nishino, Y. 1,3-Oxygenated 8α-estratriene. German Patent 1975, 2 426 779; Chem. Abstr. 1977, 86, 106891g.
44. Schwarz, S.; Weber, G.; Kühner, F. Sulfamate des 17α-Äthinylöstradiols. (Sulphamates of 17̈-Ethinyloestradiol.) Zeitschrift fur Chemie 1970, 10, 299-300.
45. Schwarz, S.; Weber, G. Steroid sulfamate: Phasentransfer-katalysierte Veresterung von Östrogenen mit Sulfonyl Chloriden. (Steroid sulphamates. Phase transfer-catalyzed esterification of oestrogens with sulphonyl chlorides.) Zeitschrift fur Chemie 1975, 15, 270-272.
46. Sasmor, E. J. Hydrocortisone 21-cyclohexylsulfamate. British Patent 1988, l 124 720; Chem. Abstr. 1969, 70, 4415 g.
47. Schwarz, S.; Weber, G. Steroid sulfamate. (Steroid sulphamates.) Zeitschrift fur Chemie 1974, 14, 15-16.
48. Schwarz, S.; Weber, G.; Schreiber, M. Sulfonyloxyderivative von Östrogenen. (Sulphonyloxy derivatives of oestrogens.) Pharmazie 1975, 30, 17-21.
49. Schwarz, S.; Weber, G. Sulfamoylation of phenolic hydroxyl groups in steroids. German Patent (East) 1975 114 806; Chem. Abstr. 1976, 85, 63238j.
50. Appel, R.; Berger, G. Über das Hydrazidosulfamid. (On hydrazidosulfamide.). Chem. Ber. 1958, 91, 1339-1341.
51. 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-sulfamate. Biochemistry 1995, 34, 11508-11514.
52. 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 oestrone-3-O-sulphamate. Int. J. Cancer 1995, 63, 106-111.
53. Woo, L. W. L.; Purohit, A.; Reed, M. J.; Potter, B. V. L. Oestrone 3-O-(N-acetyl)sulphamate, a potential molecular probe of the active site of oestrone sulphatase. Bioorg. Med. Chem. Lett. 1997, 7, 3075-3080.
54. Purohit, A.; Woo, L. W. L.; Singh, A.; Winterborn, C. J.; Potter, B. V. L.; Reed, M. J. In vivo activity of 4-methylcoumarin-7-O-sulfamate, a nonsteroidal, nonestrogenic steroid sulfatase inhibitor. Cancer Res. 1996, 56, 4950-4955.
55. Kraus, G. A.; Frazier, K. A.; Roth, B. D.; Taschner, M. J.; Neuenschwander, K. Conversion of lactones into ethers. J. Org. Chem. 1981, 46, 2417-2419.
56. Breytenbach, J. C.; Rall, G. J. H. Structure and synthesis of isoflavonoid analogues from Neorautanenia amboensis Schinz. J. Chem. Soc., Perkin Trans, I 1980, 1804-1809.
57. Pearce, B. C.; Parker, R. A.; Deason, M. E.; Dischino, D. D.; Gillespie, E.; Qureshi, A. A.; Volk, K.; Wright, J. J. K. Inhibitors of cholesterol biosynthesis. 2. Hypocholesterolemic and antioxidant activities of benzopyran and tetrahydronaphthalene analogues of the tocotrienols. J. Med. Chem. 1994, 37, 526-541.
58. Kloek, J. A.; Leschinsky, K. L. An improved synthesis of sulfamoyl chlorides. J. Org. Chem. 1976, 41, 4028-4029.
59. Amakasu, T.; Sato, K. Coumarins II. The acid-catalysed reaction of phenols with simple αβ-unsaturated acids. J. Org. Chem. 1966, 37, 1433-1436.
60. Bisagni, E.; Ducrocq, C.; Hung, N. C. Aromatisation des dihydro-3,4-carbazole(2H)ones-1 par le chlorure de pyridinium. (Aromatisation of dihydro-3,4-carbazole(2H)ones-1 with pyridinium chloride.) Tetrahedron 1980, 36, 1327-1330.
61. Purohit, A.; Vernon, K. A.; Wagenaar-Hummelinck, A. E.; Woo, L. W. L.; Hejaz, H. A. M.; Potter, B. V. L.; Reed, J. M. The development of A-ring modified analogues of oestrone 3-O-sulphamate as potent steroid sulphatase inhibitors with reduced oestrogenicity. J. Steroid Biochem. Mol. Biol. 1998, in press.