The development of steroid sulphatase inhibitors

Endocrine-Related Cancer

Volumn 3, Issue 1, 1996, Pages 9-23

  Reed, M J ^a   Purohit, A ^a   Woo, L W L ^b   Potter, B V L ^b  

^a ST MARY S HOSPITAL   (United Kingdom)

^b University of Bath   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYTAMOXIFEN; ANTIESTROGEN; DANAZOL; DIETHYLSTILBESTROL; ENZYME INHIBITOR; ESTRADIOL DERIVATIVE; ESTRONE 3 O METHYLPHOSPHONATE; ESTRONE 3 O METHYLTHIOPHOSPHONATE; ESTRONE DERIVATIVE; FULVESTRANT; MEDROXYPROGESTERONE ACETATE; PROMEGESTONE; STEROID SULPHATASE INHIBITOR; TAMOXIFEN; UNCLASSIFIED DRUG;

BREAST CANCER; DRUG DEVELOPMENT; HORMONAL THERAPY; HUMAN; REVIEW;

EID: 0029945598     PISSN: 13510088     EISSN: None     Source Type: Journal    
DOI: 10.1677/erc.0.0030009     Document Type: Review

References (70)

1. Adams JB, Garcia M & Rochefort H 1981 Estrogenic effects of physiological concentrations of 5-androstene-3β,17β-diol and its metabolism in MCF-7 human breast cancer cells. Cancer Research 41 4720-4726.
2. Anderson CJ, Lucan LJH & Widlanski TS 1995 Molecular recognition in biological systems: phosphate esters vs sulphate esters and the mechanism of action of steroid sulphatases. Journal of the American Chemical Society 117 3889-3890.
3. Bartsch W, Klein H, Schiemann U, Bauer HW & Voight KD 1990 Enzymes of androgen formation and degradation in the human prostate. Annals of the New York Academy of Sciences 595 53-66.
4. Birnbock H & Von Angerer E 1990 Sulphate derivatives of 2-phenylindoles as novel steroid sulphatase inhibitors. Biochemical Pharmacology 39 1709-1713.
5. Bonney RC, Reed MJ, Davidson K, Beranek PA & James VHT 1983 The relationship between 17β hydroxysteroid dehydrogenase activity and oestrogen concentrations in human breast tumours and in normal breast tissue. Clinical Endocrinology 19 727-739.
6. Bonney RC, Scanlon MJ, Jones DL, Beranek PA, Reed MJ & James VHT 1984 The inter-relationship between plasma 5-ene adrenal androgens in normal women. Journal of Steroid Biochemistry 20 1353-1355.
7. Burns GRJ 1983 Purification and partial characterization of arylsulphatase C from human placental microsomes. Biochimica et Biophysica Acta 759 199-204.
8. Carlstrom K, Doberl A, Gershagen S & Rannevik G 1984a Peripheral plasma levels of dehydroepiandrosterone sulphate, dehydroepiandrosterone, androstenedione and testosterone following different doses of Danazol. Acta Obstetrica et Gynecologica Scandinavica 123 (Suppl) 125-129.
9. Carlstrom K, Doberl A, Pousette A, Rannevik G & Wilking N 1984b Inhibition of steroid sulphatase activity by Danazol. Acta Obstetrica et Gynecologica Scandinavica 123 (Suppl) 107-111.
10. Chai CLL & Lowe G 1991 The mechanism and stereochemical course of sulphuryl transfer catalysed by the aryl sulphotransferase from Eubacterium A-44. Bioorganic Chemistry 20 181-188.
11. Chai CLL, Loughlin WA & Lowe G 1992 The stereochemical course of sulphonyl transfer catalysed by aryl sulphatase II from Aspergillus oryzae. Biochemical Journal 287 805-812.
12. Cox RJ, Hoskinson RM & Wong MSF 1979 Antisera reactive directly to oestrone sulphate. Steroids 33 549-562.
13. Dauvois S & Labrie F 1989 Androstenedione and androst-5-ene-3β,17β-diol stimulate DMBA-induced mammary tumours - role of aromatase. Breast Cancer Research and Treatment 13 61-69.
14. Daynes RA, Araneo BA, Ershler WB, Maloney C, Li G-Z & Ryn S-Y 1993 Altered regulation of IL-6 production with normal aging. Journal of Immunology 150 5219-5230.
15. Dibbelt L & Kuss E 1986 Human placental steryl-sulphatase. Biological Chemistry Hoppe Seyler 367 1223-1229.
16. Dibbelt L, Li P-K, Pillai R & Knuppen R 1994 Inhibition of human placental sterylsulphatase by synthetic analogues of oestrone sulphate. Journal of Steroid Biochemistry and Molecular Biology 50 261-266.
17. Dowsett M, Cunningham DC, Stein RC, Evans S, Dehennin L, Medley A & Coombes RC 1989 Dose-related endocrine effects and pharmacokinetics of oral and intramuscular 4-hydroxyandrostenedione in postmenopausal breast cancer patients. Cancer Research 49 1306-1311.
18. Duncan LJ, Purohit A, Howarth NM, Potter BVL & Reed MJ 1993 Inhibition of oestrone sulphatase activity by oestrone-3-methylthiophosphonate: a potential therapeutic agent in breast cancer. Cancer Research 53 298-303.
19. Duncan LJ, Coldham ND & Reed MJ 1994 The interaction of cytokines in regulating oestradiol 17β-hydroxysteroid dehydrogenase activity in MCF-7 cells. Journal of Steroid Biochemistry and Molecular Biology 49 63-68.
20. Evans TRJ, Rowlands MG, Jarman M β Coombes RC 1991 Inhibition of oestrone sulphatase enzyme in human placenta and human breast carcinoma. Journal of Steroid Biochemistry and Molecular Biology 39 493-499.
21. Gniot-Szulzycka J & Januszewska B 1986 Purification of steroid sulphohydrolyase from human placenta microsomes. Acta Biochemica Polonica 33 203-215.
22. Hobkirk R 1993 Steroid sulphation. Trends in Endocrinology and Metabolism 4 69-79.
23. Hotamisligil GS, Arner P, Caro JF, Atkinson RL & Spiegelman BM 1995 Increased adipose tissue expression of tumour necrosis factor a in human obesity and insulin resistance. Journal of Clinical Investigation 95 2409-2415.
24. Howarth NM, Purohit A, Reed MJ & Potter BVL 1994 Oestrone sulphamates: potent inhibitors of oestrone sulphatase with therapeutic potential. Journal of Medicinal Chemistry 37 219-221.
25. James VHT, McNeill JM, Lai LC, Newton CJ, Ghilchik MW & Reed MJ 1987 Aromatase activity in normal breast and breast tumour tissue: in vivo and in vitro studies. Steroids 50 269-279.
26. Johnston SRD, Smith JE, Doody D, Jacobs S, Robertshaw H & Dowsett M 1994 Clinical and endocrine effects of the oral aromatase inhibitor Vorozole in postmenopausal patients with advanced breast cancer. Cancer Research 54 5875-5881.
27. Li P-K, Pillai R, Young BL, Bender WH, Martino DM & Liu F-T 1993 Synthesis and biochemical studies of oestrone sulphatase inhibitors. Steroids 58 106-111.
28. Li P-K, Pillai R & Dibbelt L 1995 Oestrone sulphate analogues as oestrone sulphatase inhibitors. Steroids 60 299-306.
29. Luu-The V, Labrie C, Simard J, Luchance Y, Zhao H-F, Conet J, Lablanc G & Labrie F 1989 Characterization of cDNAs for human oestradiol 17β-dehydrogenase and assignment of the gene to chromosome 17: evidence for two mRNA species with distinct 5′ termini in human placenta. Molecular Endocrinology 3 1301-1309.
30. Macdiarmid F, Wang D, Duncan LJ, Purohit A, Ghilchik MW & Reed MJ 1994 Stimulation of aromatase activity in breast fibroblasts by tumour necrosis factor a. Molecular and Cellular Endocrinology 106 17-21.
31. 3H-oestradiol by normal breast and breast tumour tissues in postmenopausal women. International Journal of Cancer 38 193-196.
32. 4 isomerase (3βHSD), 17β-HSD, 5α-reductase and aromatase activities in the rhesus monkey. Molecular and Cellular Endocrinology 104 103-111.
33. Naitoh K, Honjo H, Yamamoto T, Urabe M, Ogino Y, Yasumura T & Nambara T 1989 Estrone sulphate and sulphatase activity in human breast cancer and endometrial cancer. Journal of Steroid Biochemistry 33 1049-1054.
34. Nguyen B-L, Ferme I, Chetrite G & Pasqualini JR 1993 Action of danazol on the conversion of oestrone sulphate to oestradiol and on the sulphatase activity in the MCF-7, T-47D and MDA-MB-231 human mammary cancer cells. Journal of Steroid Biochemistry and Molecular Biology 46 17-23.
35. Noel CT, Reed MJ, Jacobs HS & James VHT 1981 The plasma concentration of oestrone sulphate in postmenopausal women: lack of diurnal variation, effect of ovariectomy, age and weight. Journal of Steroid Biochemistry 14 1101-1105.
36. Pasqualini JR, Gelly C, Nguyen B-L & Vella C 1989 Importance of oestrogen sulphates in breast cancer. Journal of Steroid Biochemistry 34 155-163.
37. Pasqualini JR, Maloche C, Maroni M & Chetrite G 1994 Effect of progestagen Promegestone (R-5020) on mRNA of the oestrone sulphatase in the MCF-7 human mammary cancer cells. Anticancer Research 14 1589-1594.
38. Poortman J, Andriesse R, Agema A, Donker GH, Schwarz F & Thijssen JHH 1980 Adrenal androgen secretion and metabolism in postmenopausal women. In Adrenal Androgens, pp 219-240. Eds AR Genazzani, JHH Thijssen & PK Siiteri. New York: Raven Press.
39. Poulin R & Labrie F 1986 Stimulation of cell proliferation and oestrogenic response by adrenal C19-delta-5-steroids in the ZR-75-1 human breast cancer cell line. Cancer Research 46 4933-4937.
40. Prost-Avallet O, Oursin J & Adessi GL 1991 In vitro effect of synthetic progestogens on oestrone sulphatase activity in human breast carcinoma. Journal of Steroid Biochemistry and Molecular Biology 39 967-973.
41. Purohit A & Reed MJ 1992 Oestrogen sulphatase activity in hormone-dependent and hormone-independent breast cancer cells: modulation by steroidal and non-steroidal therapeutic agents. International Journal of Cancer 50 901-905.
42. Purohit A, Riaz AA, Ghilchik MW & Reed MJ 1992 The origin of oestrone sulphate in normal and malignant breast tissues in postmenopausal women. Hormone and Metabolic Research 24 532-536.
43. Purohit A, Dauvois S, Parker MG, Potter BVL, Williams GJ & Reed MJ 1994 The hydrolysis of oestrone sulphate and dehydroepiandrosterone sulphate by human steroid sulphatase expressed in transfected COS-1 cells. Journal of Steroid Biochemistry and Molecular Biology 50 101-104.
44. Purohit A, Ghilchik MW, Duncan LJ, Wang DY, Singh A, Walker MM & Reed MJ 1995a Aromatase activity and interleukin-6 production by normal and malignant breast tissues. Journal of Clinical Endocrinology and Metabolism 80 3052-3058.
45. Purohit A, Williams CJ, Howarth NM, Potter BVL & Reed MJ 1995b Inactivation of steroid sulphatase by an active site-directed inhibitor, oestrone-3-O-sulphamate. Biochemistry 34 11508-11514.
46. Purohit A, Williams GJ, Roberts CJ, Potter BVL & Reed MJ 1995c In vivo inhibition of oestrone sulphatase and dehydroepiandrosterone sulphatase by oestrone-3-O-sulphamate. International Journal of Cancer 62 106-111.
47. Reed MJ & Purohit A 1993 Sulphatase inhibitors: the rationale for the development of a new endocrine therapy. Reviews on Endocrine-Related Cancer 45 51-62.
48. Reed MJ & Purohit A 1994 Inhibition of steroid sulphatases. In Design of Enzyme Inhibitors as Drugs, vol 2, pp 481-494. Eds M Sandler & J Smith. Oxford: Oxford University Press.
49. Reed MJ, Owen AM, Lai LC, Coldham NG, Ghilchik MW, Shaikh NA & James VHT 1989 In situ oestrone synthesis in normal breast and breast tumour tissues: effect of treatment with 4-hydroxyandrostenedione. International Journal of Cancer 44 233-237.
50. Reed MJ, Lai LC, Owen AM, Singh A, Coldham NG, Purohit A, Ghilchik MW, Shaikh NA & James VHT 1990 Effect of treatment with 4-hydroxyandrostenedione on the peripheral conversion of androstenedione to oestrone and in vitro tumour aromatase activity in postmenopausal women with breast cancer. Cancer Research 50 193-196.
51. Reed MJ, Topping L, Coldham NG, Purohit A, Ghilchik MW & James VHT 1993 Control of aromatase activity in breast cancer cells: the role of cytokines and growth factors. Journal of Steroid Biochemistry and Molecular Biology 44 589-596.
52. Reed MJ, Purohit A, Duncan LJ, Singh A, Roberts CJ, Williams GJ & Potter BVL 1995 The role of cytokines and sulphatase inhibitors in regulating oestrogen synthesis in breast tumours. Journal of Steroid Biochemistry and Molecular Biology 53 413-420.
53. Rook GAW, Hernandez-Pando R & Lightman S 1994 Hormones, peripherally activated prohormones and regulation of Th1/Th2 balance. Immunology Today 15 301-303.
54. Ruder HJ, Loriaux DL & Lipsett MB 1972 Estrone sulphate: production rate and metabolism in man. Journal of Clinical Investigation 51 1020-1023.
55. Santner SJ & Santen RJ 1993 Inhibition of oestrone sulphatase and 17β-hydroxysteroid dehydrogenase by anti-oestrogens. Journal of Steroid Biochemistry and Molecular Biology 45 383-390.
56. Santner SJ, Feil PD & Santen RJ 1984 In situ oestrogen production via oestrone sulphatase pathway in breast tumours: relative importance versus aromatase pathway. Journal of Clinical Endocrinology and Metabolism 59 29-33.
57. Santner SJ, Levin MC & Santen RJ 1990 Oestrone sulphate stimulates growth of nitrosomethylurea-induced breast carcinoma in vivo in the rat. International Journal of Cancer 46 73-78.
58. Selcer KW & Li P-K 1995 Oestrogenicity, antioestrogenicity and oestrone sulphatase inhibition of oestrone-3-amine and oestrone-3-thiol. Journal of Steroid Biochemistry and Molecular Biology 52 281-286.
59. Snyers L & Content J 1992 Enhancement of IL-6 receptor P chain (gp130) expression by IL-6, IL-1 and TNF in human epithelial cells. Biochemical and Biophysical Research Communications 185 902-908.
60. Soderqvist G, Olsson H, Wilking N, von Schoultz B & Carlstrom K 1994 Metabolism of oestrone sulphate by normal breast tissue: influence of menopausal status and oral contraceptives. Journal of Steroid Biochemistry and Molecular Biology 48 221-229.
61. Svenstrup B, Herrstedt J, Brunner N, Bennett P, Wachmann H & Dombernowsky P 1994 Sex hormone levels in postmenopausal women with advanced metastatic breast cancer treated with CGS 169 49A. European Journal of Cancer 30A 1254-1258.
62. Tseng L, Mazella J, Lee LU & Stone ML 1983 Oestrogen sulphatase and oestrogen sulphotransferase in human primary mammary carcinoma. Journal of Steroid Biochemistry 19 1413-1417.
63. Utsumi T 1989 Local production of oestrogen via aromatase and oestrone sulphatase in breast cancer tissue. Nippon Geka Gakkai Zasshi 90 920-927.
64. Van Landeghem AAJ, Poortman J, Nabaurs M & Thijssen JHH 1985 Endogenous concentration and sub-cellular distribution of estrogens in normal and malignant breast tissue. Cancer Research 45 2900-2904.
65. Wilking N, Carlstrom K, Skoldefors H, Theve NO & Wallgren A 1982 Effects of tamoxifen on the serum levels of oestrogens and adrenocortical steroids in postmenopausal breast cancer patients. Acta Chirurgica Scandinavica 148 345-349.
66. Wilkinson JR, Williams JC, Singh D, Goss PE, Easton D & Coombes RC 1986 Response of nitrosomethylurea-induced rat mammary tumours to endocrine therapy and comparison with clinical response. Cancer Research 46 4862-4865.
67. Williams GJ, Woo LWL, Mahon MF, Purohit A, Reed MJ & Potter BVL 1996 X-ray crystal structure and mechanism of action of oestrone 3-O-sulphamate, a synthetic active site-directed inhibitor of oestrone sulphatase. Pharmaceutical Sciences 2 7-12.
68. Woo LWL, Lightowler M, Purohit A, Reed MJ & Potter BVL 1996a Heteroatom-substituted analogues of the active-site directed inhibitor estra-1,3,5(10)-trien-17-one-3-sulphamate inhibit estrone sulfatase by a different mechanism. Journal of Steroid Biochemistry and Molecular Biology 57 (In Press).
69. Woo LWL, Purohit A, Reed MJ & Potter BVL 1996b Active site-directed inhibition of estrone sulphatase by non-steroidal coumarin sulfamates. Journal of Medicinal Chemistry (In Press).
70. Yamamoto T, Kitawaki J, Urabe M, Honjo H, Tamura T, Noguchi T, Okada H, Sajaki H, Tada A, Terashima Y, Nakamura J & Yoshihama M 1993 Oestrogen productivity of endometrium and endometrial cancer tissue: influence of aromatase on proliferation of endometrial cancer cells. Journal of Steroid Biochemistry and Molecular Biology 44 463-468.