Steroid sulfatase inhibitors for estrogen- and androgen-dependent cancers

Journal of Endocrinology

Volumn 212, Issue 2, 2012, Pages 99-110

  Purohit, Atul ^a   Foster, Paul A ^b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b Centre for Endocrinology   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 [N (4 BROMOBENZYL) N (1,2,4 TRIAZOL 4 YL)AMINO]BENZONITRILE; ANASTROZOLE; ANDROGEN; ANDROSTENEDIOL; ANDROSTENEDIONE; ANTINEOPLASTIC HORMONE AGONISTS AND ANTAGONISTS; DANAZOL; ESTROGEN; ESTRONE 3 O SULFAMATE; IROSUSTAT; KW 2581; LETROZOLE; MESSENGER RNA; PRASTERONE SULFATE; SR 16157; STERYL SULFATASE; STX 1938; STX 213; STX 681; UNCLASSIFIED DRUG;

ANDROGEN BLOOD LEVEL; ANDROGEN METABOLISM; ANTINEOPLASTIC ACTIVITY; BINDING AFFINITY; BREAST CANCER; CANCER PATIENT; CANCER RISK; CANCER SURVIVAL; CASTRATION RESISTANT PROSTATE CANCER; CELL PROLIFERATION; DRUG EFFICACY; DRUG HALF LIFE; DRUG MECHANISM; DRUG POTENCY; ENDOMETRIOSIS; ENDOMETRIUM CANCER; ENDOPLASMIC RETICULUM; ESTROGEN BLOOD LEVEL; ESTROGEN METABOLISM; ESTROGEN SYNTHESIS; HUMAN; IC 50; IMMUNOHISTOCHEMISTRY; IN VITRO STUDY; MITOGENESIS; MULTIPLE CYCLE TREATMENT; NONHUMAN; OVARY CANCER; PHASE 1 CLINICAL TRIAL (TOPIC); PHASE 2 CLINICAL TRIAL (TOPIC); POSTMENOPAUSE; PRIORITY JOURNAL; PROSTATE CANCER; PROTEIN EXPRESSION; REVIEW; TUMOR XENOGRAFT;

ANDROGENS; ANIMALS; ANTINEOPLASTIC AGENTS, HORMONAL; AROMATASE INHIBITORS; BREAST NEOPLASMS; ENZYME INHIBITORS; ESTROGENS; FEMALE; HUMANS; MALE; MOLECULAR TARGETED THERAPY; NEOPLASM PROTEINS; NEOPLASMS, HORMONE-DEPENDENT; PROSTATIC NEOPLASMS; RECEPTORS, ANDROGEN; RECEPTORS, ESTROGEN; STERYL-SULFATASE;

EID: 84856786322     PISSN: 00220795     EISSN: 14796805     Source Type: Journal    
DOI: 10.1530/JOE-11-0266     Document Type: Review

References (105)

1. Anderson C, Freeman J, Lucas LH, Farley M, Dalhoumi H & Widlanski TS, 1997 Estrone sulfatase: probing structural requirements for substrate and inhibitor recognition. Biochemistry 36 2586-2594.
2. Aspinall SR, Stamp S, Davison A, Shenton BK & Lennard TW, 2004 The proliferative effects of 5-androstene-3 beta, 17 beta-diol and 5 alpha-dihydrotestosterone on cell cycle analysis and cell proliferation in MCF7, T47D, and MDAMB231 breast cancer cell lines. Journal of Steroid Biochemistry and Molecular Biology 88 37-51.
3. Bernstein L & Ross RK, 1993 Endogenous hormones and breast cancer risk. Epidemiologic Reviews 15 48-65.
4. Birnböck H & von Angerer E, 1990 Sulfate derivatives of 2-phenylinodes as novel steroid sulfatase inhibitors: an in vitro study on structure-activityrelationship. Biochemical Pharmacology 39 1709-1713.
5. Bonney RC, Reed MJ, Davidson K, Beranek PA & James VH, 1983 The relationship between 17b-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, Reed MJ, Jones DL, Beranek PA & James VH, 1984 Adrenal androgen concentrations in breast tumours and in normal breast tissue. The relationship to oestradiol metabolism. Journal of Steroid Biochemistry 20 501-504.
7. de Bono JS, Logothetis CJ, Molina A, Fizazi K, North S, Chu L, Chi KN, Jones RJ, Goodman OB Jr, Saad F et al. 2011 Abiraterone and increased survival in metastatic prostate cancer. New England Journal of Medicine 364 1995-2005.
8. Calhoun KE, Pommier RF, Muller P, Fletcher WS & Toth-Fejel S, 2003 Dehydroepiandrosterone sulfate causes proliferation of estrogen receptorpositive breast cancer cells despite treatment with fulvestrant. Archives of Surgery 138 879-883.
9. Carlstrom K, Doberl A, Gershagen S & Rannevik G, 1984 Peripheral levels of dehydroepiandrosterone sulfate, dehydroepiandrosterone, androstendione, and testosterone following different doses of danazol. Acta Obstetricia et Gynecologica Scandinavica 123 125-129.
10. Carruba G, 2007 Estrogens and prostate cancer: an eclipsed truth in an androgen-dominated scenario. Journal of Cellular Biochemistry 102 899-911.
11. Chanplakorn N, Chanplakorn P, Suzuki T, Ono K, Chan MS, Miki Y, Saji S, Ueno T, Toi M & Sasano H, 2010 Increased estrogen sulfatase (STS) and 17beta-hydroxysteroid dehydrogenase type-1 (17beta-HSD1) following neoadjuvant aromatase inhibitor therapy in breast cancer patients. Breast Cancer Research and Treatment 120 639-648.
12. Chura JC, Blomquist CH, Ryu HS & Argenta PA, 2009 Estrone sulfatase activity in patients with advanced ovarian cancer. Gynecologic Oncology 112 205-209.
13. Davison SL & Davis SR, 2004 Androgens in women. Journal of Steroid Biochemistry and Molecular Biology 85 363-366.
14. Dibbelt L, Li P-K, Pillai R & Knuppen R, 1994 Inhibition of human placental sterylsulfatase by synthetic analogs of estrone sulfate. Journal of Steroid Biochemistry and Molecular Biology 50 261-266.
15. Duncan L, Purohit A, Howarth NM, Potter BVL & Reed MJ, 1993 Inhibition of estrone sulfatase activity by estrone-3-methylthiophosphonate: a potential therapeutic agent in breast cancer. Cancer Research 53 289-303.
16. Edery M, Goussard J, Dehennin L, Scholler R, Reiffsteck J & Drosdowsky MA, 1981 Endogenous oestradiol-17beta concentration in breast tumours determined by mass fragmentography and by radioimmunoassay: relationship and receptor content. European Journal of Cancer 17 115-120.
17. Evan TRJ, Rowlands MG, Jarman M & Coombes RC, 1991 Inhibition of estrone sulfatase enzyme in human placenta and human breast carcinoma. Journal of Steroid Biochemistry and Molecular Biology 39 493-499.
18. Evans TR, Rowlands MG, Silva MC, Law M & Coombes RC, 1993 Prognostic significance of aromatase and estrone sulfatase enzymes in human breast cancer. Journal of Steroid Biochemistry and Molecular Biology 44 583-587.
19. Evans TR, Rowlands MG, Law M & Coombes RC, 1994 Intratumoral oestrone sulphatase activity as a prognostic marker in human breast carcinoma. British Journal of Cancer 69 555-561.
20. Falany JL & Falany CN, 1996 Expression of cytosolic sulfotransferases in normal mammary epithelial cells and breast cancer cell lines. Cancer Research 56 1551-1555.
21. Falany JL,Macrina N & Falany CN, 2002 Regulation of MCF-7 breast cancer cell growth by beta-estradiol sulfation. Breast Cancer Research and Treatment 74 16776.
22. Farnsworth WE, 1973 Human prostatic dehydroepiandrosterone sulfate sulfatase. Steroids 21 647-654.
23. Fischer DS, Chander SK, Woo LWL, Fenton JC, Purohit A, Reed MJ & Potter BVL, 2003a Novel D-ring modified steroid derivatives as potent, non-estrogenic steroid sulfatase inhibitors with in vivo activity. Journal of Steroid Biochemistry and Molecular Biology 84 343-349.
24. Fischer DS,Woo LWL, Mahon MF, Purohit A, Reed MJ & Potter BVL, 2003b D-ring modified estrone derivatives as novel potent inhibitors of steroid sulfatase. Bioorganic and Medicinal Chemistry 11 1685-1700.
25. Fishman J, Nisselbaum JS, Menende-Botel CJ & Schwartz MK, 1977 Estrone and estradiol content in human breast tumors: relationship to estradiol receptors. Journal of Steroid Biochemistry 8 893-896.
26. Foster PA, Newman SP, Chander SK, Stengel C, Jhalli R, Woo LWL, Potter BVL, Reed MJ & Purohit, A, 2006 In vivo efficacy of STX213, a second generation steroid sulfatase inhibitors, for hormone dependent breast cancer therapy. Clinical Cancer Research 12 5543-5549.
27. Foster PA, Chander SK, Newman SP, Woo LWL, Sutcliffe OB, Bubert C, Zhou D, Chen S, Potter BVL, Reed MJ et al. 2008a A new therapeutic strategy against hormone-dependent breast cancer: the preclinical development of a dual aromatase and sulfatase inhibitor. Clinical Cancer Research 14 6469-6477.
28. Foster PA, Chander SK, Parson MF, Newman SP, Woo LWL, Potter BVL, Reed MJ & Purohit A, 2008b Efficacy of three potent steroid sulfatase inhibitors: pre-clinical investigations for their use in the treatment of hormone-dependent breast cancer. Breast Cancer Research and Treatment 111 129-138.
29. Foster PA, Woo LWL, Potter BVL, Reed MJ & Purohit A, 2008c The use of steroid sulfatase inhibitors as a novel therapeutic strategy against hormonedependent endometrial cancer. Endocrinology 149 4035-4042.
30. Geisler J, Sasano H, Chen S & Purohit A, 2011 Steroid sulphatase inhibitors: promising new tools for breast cancer therapy? Journal of Steroid Biochemistry and Molecular Biology 125 39-45
31. Giton F, Taille A, Allory Y, Galons H, Vacherot F, Soyeux P, Abbou CC, Loric S, Cussenot O, Raynaud JP et al. 2008 Estrone sulfate, a prognosis marker for tumor aggressiveness in prostate cancer. Journal of Steroid Biochemistry and Molecular Biology 109 158-167.
32. Harrkonen PL & Makela SI, 2004 Role of estrogens in the development of prostate cancer. Journal of Steroid Biochemistry and Molecular Biology 92 297-305.
33. Ho SM, 2004 Estrogens and antioestrogens: key mediators of prostate carcinogenesis and new therapeutic candidates. Journal of Cellular Biochemistry 91 491-505.
34. Hobkirk R, 1993 Steroid sulfation. Trends in Endocrinology and Metabolism 4 69-74.
35. Howarth NH, Purohit A, Reed MJ & Potter BVL, 1994 Estrone sulfamates: potent inhibitors of estrone sulfatase with therapeutic potential. Journal of Medicinal Chemistry 37 219-221.
36. Howarth NM, Purohit A, Reed MJ & Potter BVL, 1997 Estrone sulfonates as inhibitors of estrone sulfatase. Steroids 62 346-350.
37. Howarth NM, Purohit A, Robinson JJ, Vicker N, Reed MJ & Potter BVL, 2002 Estrone 3-sulfate mimics inhibitors of estrone sulfatase activity: homology model construction and docking studies. Biochemistry 41 14801-14814.
38. Ibrahim AR & Abul-Hajj YJ 1990, Aromatase inhibition by flavanoids. Journal of Steroid Biochemistry and Molecular Biology 37 257-260.
39. Ishida H, Nakata T, Suzuki M, Shiotsu Y, Tanaka H, Sato N, Terasaki Y, Takebayashi M, Anazawa H, Murakata C et al. 2007a A novel steroid selective steroid sulfatase inhibitor KW-2581 inhibits sulphated-estrogen dependent growth of breast cancer cells in vitro and in animal models. Breast Cancer Research and Treatment 106 215-227.
40. Ishida H, Nakata T, Sato N, Li PK, Kuwabara T & Akinaga S, 2007b Inhibition of steroid sulfatase activity and cell proliferation in ZR-75-1 and BT-474 human breast cancer cells by KW-2581 in vitro and in vivo. Breast Cancer Research and Treatment 104 211-219.
41. Ishida H, Sato N, Hosogi J, Tanaka H & Kuwabara T, 2008 Inactivation of recombinant human steroid sulfatase by KW-2581. Journal of Steroid Biochemistry and Molecular Biology 108 17-22.
42. Jackson T,Woo LWL, Trusselle MN, Purohit A, Reed MJ & Potter BVL, 2007 Dual aromatase-sulfatase inhibitors based on the anastrozole template: synthesis, in vitro SAR, molecular modelling and in vivo activity. Organic and Biomolecular Chemistry 21 2940-2952.
43. James VHL & Reed MJ, 1980 Steroid hormones and human cancer. Progression in Cancer Research Therapy 14 471-487.
44. James VHT, McNeill JM, Lai LC, Newton CJ, Ghilchik MW & Reed MJ, 1987 Aromatase activity in normal breast and breast tumor tissue: in vivo and in vitro studies. Steroids 50 269-279.
45. James MR, Skaar TC, Lee RY, MacPherson A, Zwiebel JA, Ahluwalia BS, Ampy F & Clarke R, 2001 Constitutive expression of the steroid sulfatase gene supports growth of MCF-7 human breast cancer cells in vitro and in vivo. Endocrinology 142 1497-1505.
46. Kellis JT & Vickery LE, 1984 Inhibition of human estrogen synthetase (aromatase) by flavones. Science 225 1032-1034.
47. Knudsen KE & Penning TM, 2010 Partners in crime: deregulation of AR activity and androgen synthesis in prostate cancer. Trends in Endocrinology and Metabolism 21 315-324.
48. Kroboth PD, Salek FS, Pittenger AL, Pittenger AL, Fabian TJ & Frye RF, 1999 DHEA and DHEA-S: a review. Journal of Clinical Pharmacology 39 327-348.
49. Kudoh M, Susaki Y, Ideyama Y, Nanya T, Okada M, Shikama H & Fujikura T, 1995 The potent and selective inhibition of estrogen production by nonsteroidal aromatase inhibitor, YM511. Journal of Steroid Biochemistry and Molecular Biology 54 265-271.
50. Labrie F, Cusan L, Gomez J, Luu-The V, Candas B, Bélanger A & Labrie C, 2004 Major impact of hormonal therapy in localised prostate cancer-death can already be an exception. Journal of Steroid Biochemistry and Molecular Biology 92 327-344.
51. Lacassagne A, 1955 Endocrine factors concerned in the genesis of experimental mammary carcinoma. Journal of Endocrinology 13 9-18.
52. Li P-K, Pillai R, Young BL, Bender WH, Martino DM & Lin FT, 1993 Synthesis and biochemical studies of estrone sulfatase inhibitors. Steroids 58 106-111.
53. Li P-K, Pillai R & Dibbelt L, 1995 Estrone sulfatase analogs as estrone sulfatase inhibitors. Steroids 60 299-306.
54. Li P-K, Milano S, Kluth L & Rhodes ME, 1996 Synthesis and sulfatase inhibitory activities of non-steroidal estrone sulfatase inhibitors. Journal of Steroid Biochemistry and Molecular Biology 59 41-48.
55. Li P-K, Chu GH, Peters A & Selcer KW, 1998 Development of potent nonestrogenic sulfatase inhibitors. Steroids 63 423-432.
56. Lipton A, Santen RJ, Santner SJ, Harvey HA, Sanders SI & Matthews YL, 1992 Prognostic value of breast cancer aromatase. Cancer 70 1951-1955.
57. Lloyd MD, Pederick RL, Natesh R,Woo LWL, Purohit A, Reed MJ, Acharya KR & Potter BVL, 2005 Crystal structure of human carbonic anhydrase II at 1.95 A resolution in complex with 667-coumate, a novel anti-cancer agent. Biochemical Journal 385 715-720.
58. Lonning PE, DowsettM& Powles TJ, 1990 Postmenopausal estrogen synthesis and metabolism: alterations caused by aromatase inhibitors used for the treatment of breast cancer. Journal of Steroid Biochemistry 35 355-366.
59. López-Marure R, Contreras PG & Dillon JS, 2011 Effects of dehydroepiandrosterone on proliferation, migration, and death of breast cancer cells. European Journal of Pharmacology 660 268-274.
60. MacDonald PC, Edman CD, Hemsell DL, Porter JC & Siiteri PK, 1978 Effect of obesity on conversion of plasma androstendione to estrone in postmenopausal women with and without endometrial cancer. American Journal of Obstetrics and Gynecology 130 448-455.
61. Maltais R & Poirier D, 2011 Steroid sulfatase inhibitors: a review covering the promising 2000-2010 decade. Steroids 76 929-948.
62. Miyoshi Y, Ando A, Hasegawa S, Ishitobi M, Taguchi T, Tamaki Y & Noguchi S, 2003 High expression of steroid sulfatase mRNA predicts poor prognosis in patients with estrogen receptor-positive breast cancer. Clinical Cancer Research 9 2288-2293.
63. Morphy R & Rankovic Z, 2005 Designed multiple ligands. An emerging drug discovery paradigm. Journal of Medicinal Chemistry 48 6523-6543.
64. Nakamura Y, Suzuki T & Fukuda T. 2006 Steroid sulfatase and estrogen sulphotransferase in human prostate cancer. Prostate 66 1005-1012.
65. Noel CT, Reed MJ, Jacobs HS & James VHL, 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.
66. Palmieri C, Januszewski A, Stanway S & Coombes RC, 2011 Irusostat: a first-generation steroid sulfatase inhibitor in breast cancer. Expert Review of Anticancer Therapy 11 179-183.
67. Pasqualini JR, Gelly C, Nguyen BL & Vella C, 1989 Importance of estrogen sulfate in breast cancer. Journal of Steroid Biochemistry 34 155-163.
68. Pasqualini JR, Chetrite G, Blacker C, Feinstein MC, Delalonde L, Talbi M & Maloche C, 1996 Concentrations of estrone, estradiol, and estrone sulfate and evaluation of sulfatase and aromatase activities in pre- and postmenopausal breast cancer patients. Journal of Clinical Endocrinology and Metabolism 81 1460-1464.
69. Purohit A, Howarth NM, Potter BVL & Reed MJ, 1994 Inhibition of steroid sulphatase activity by steroidal methylthiophosphonates: potential therapeutic agents in breast cancer. Journal of Steroid Biochemistry and Molecular Biology 48 523-527.
70. Purohit A, William GJ, Howarth NM, Potter BVL & Reed MJ, 1995a Inactivation of steroid sulfatase by an active site-directed inhibitor, estrone-3-O-sulfamate. Biochemistry 34 11508-11514.
71. Purohit A, Williams GJ, Roberts CJ, Potter BVL & Reed MJ, 1995b In vivo inhibition of estrone sulphatase and dehydroepiandrosterone sulphatase by estrone-3-O-sulphamate. International Journal of Cancer 62 106-111.
72. Purohit A, Reed MJ, Morris NC, Williams GJ & Potter BVL, 1996a Regulation and inhibition of steroid sulfatase activity in breast cancer. Annals of the New York Academy of Sciences 784 40-49.
73. Purohit A, Woo LWL, Singh A, Winterborn CJ, Potter BVL & Reed MJ, 1996b In vivo activity of 4-methylcoumarin-7-O-sulfamate, a nonsteroidal, nonestrogenic steroid sulfatase inhibitor. Cancer Research 56 4950-4955.
74. Purohit A, Vernon KA, Hummelinck AE,Woo LWL, Hejaz HA, Potter BVL & Reed MJ, 1998 The development of A-ring modified analogues of oestrone-3-O-sulphamate as potent steroid sulphatase inhibitors with reduced oestrogenicity. Journal of Steroid Biochemistry and Molecular Biology 64 269-275.
75. Purohit A, Hejaz HAM, Woo LWL, van Strien AE, Potter BVL & Reed MJ, 1999 Recent advances in the development of steroid sulphatase inhibitors. Journal of Steroid Biochemistry and Molecular Biology 69 227-238.
76. Purohit A,Woo LW, Potter BVL & Reed MJ, 2000 In vivo inhibition of estrone sulfatase activity and growth in nitrosomethylurea-induced mammary tumors by 667 Coumate. Cancer Research 60 3394-3396.
77. Purohit A, Woo LWL, Barrow D, Hejaz HA, Nicholson RI, Potter BVL & Reed MJ, 2001 Non-steroidal and steroidal sulfamates: new drugs for cancer therapy. Molecular and Cellular Endocrinology 171 129-135.
78. Purohit A, Woo LWL, Chander SK, Newman SP, Ireson C, Ho Y, Grasso A, Leese MP, Potter BVL & Reed MJ, 2003 Steroid sulphatase inhibitors for breast cancer therapy. Journal of Steroid Biochemistry and Molecular Biology 86 423-432.
79. Raobaikady B, Purohit A, Chander SK, Woo LWL, Leese MP, Potter BVL & Reed MJ, 2003 Inhibition of MCF-7 breast cancer cell proliferation and in vivo steroid sulphatase activity by 2-methoxyoestradiol-bis-sulphamate. Journal of Steroid Biochemistry and Molecular Biology 84 351-358.
80. Rasmussen LM, Zaveri NT, Stenvang J, Peters RH & Lykkesfeldt AE, 2007 A novel dual-target steroid sulfatase inhibitor and antiestrogen: SR 16157, a promising agent for the therapy of breast cancer. Breast Cancer Research and Treatment 106 191-203.
81. Rausch L, Green C, Steinmetz K, Levalley S, Catz P, Zaveri N, Schweikart K, Tomaszewski J & Mirsalis J, 2011 Preclinical, pharmacokinetic, toxilogical and biomarker evaluation of SR16157, a novel dual-acting steroid sulfatase inhibitor and selective estrogen modulator. Cancer Chemotherapy and Pharmacology 67 1341-1352.
82. Reed MJ & Murray MAF, 1979 The Oestrogens. In Hormones in Blood, edn 3, pp 263-266. Eds CH Gray & VHT James. London: Academic Press.
83. Reed MJ & Purohit A, 1993 Sulphatase inhibitors: the rationale for the development of a new endocrine therapy. Endocrine-Related Cancer 45 51-62.
84. Reed MJ & Purohit A, 1994 Inhibition of steroid sulphatases. In Design of enzyme inhibitors as drugs, pp 481-494. Eds M Sandler & HJ Smith. Oxford University Press.
85. Reed MJ, Hutton JD, Baxendale PM, James VH, Jacobs HS & Fisher RP, 1979 The conversion of androstendione to oestrone and production of oestrone in women with endometrial cancer. Journal of Steroid Biochemistry 11 905-911.
86. Reed MJ, Purohit A, Woo LWL & Potter BVL, 1996 The development of steroid sulphatase inhibitors. Endocrine-Related Cancer 3 9-23.
87. Reed MJ, Purohit A, Woo LW, Newman SP & Potter BVL, 2005 Steroid sulfatase: molecular biology, regulation, and inhibition. Endocrine Reviews 26 171-202.
88. Rosenfeld RS, Rosenberg BJ, Fukushima DK & Hellman L, 1975 24-Hour secretory pattern of dehydroisoandrosterone and dehydroisoandrosterone sulfate. Journal of Clinical Endocrinology and Metabolism 40 850-855.
89. Ruder HJ, Loriaux DL & Lipsett MB, 1972 Estrone sulfate: production rate and metabolism in man. Journal of Clinical Investigation 51 1020-1033.
90. Santen SJ, Feil PD & Santen RJ, 1984 In situ estrogen production via the estrone sulfatase pathway in breast tumors: relative importance versus the aromatase pathway. Journal of Clinical Endocrinology and Metabolism 54 29-33.
91. Sasano H, Nagasaki S, Miki Y & Suzuki T, 2009 New developments in intracrinology of human breast cancer: estrogen sulfatase and sulfotransferase. Annals of the New York Academy of Sciences 1155 76-79.
92. Soto AM & Sonnenschein C, 2010 Environmental causes of cancer: endocrine disruptors as carcinogens. Nature Reviews. Endocrinology 6 363-370.
93. Stanway SJ, Purohit A,Woo LWL, Sufi S, Vigushin D,Ward R, Wilson RH, Stanczyk FZ, Dobbs N, Kulinskaya E et al. 2006 Phase I study of STX64 (667 Coumate) in breast cancer patients: the first study of a steroid sulfatase inhibitor. Clinical Cancer Research 12 1585-1592.
94. Stanway SJ,Delavault P, PurohitA,Woo LWL, ThurieauC, Potter BVL&Reed MJ, 2007 Steroid sulfatase: a new target for the endocrine therapy of breast cancer. Oncologist 12 370-374.
95. Stott CA, 2002 Sulfonation and molecular action. Endocrine Reviews 23 703-732.
96. Suzuki T, Miki Y, Nakamura Y, Ito K & Sasano H, 2011 Steroid sulfatase and estrogen sulfotransferase in human carcinomas. Molecular and Cellular Endocrinology 340 148-153.
97. Taylor RE, Powles TJ, Humphreys J, Bettelheim R, Dowsett M, Casey AJ, Neville AM & Coombes RC, 1982 Effects of endocrine therapy on steroid-receptor content of breast cancer. British Journal of Cancer 45 80-85.
98. Utsumi T, Yoshimura N, Maruta M, Takeuchi S, Ando J, Maeda K & Harada N, 1999 Significance of steroid sulfatase expression in breast cancer. Breast Cancer 6 298-300.
99. Utsumi T, Yoshimura N, Takeuchi S, Maruta M, Maeda K & Harada N, 2000 Elevated steroid sulfatase expression in breast cancer. Journal of SteroidBiochemistry and Molecular Biology 73 141-145.
100. Van Landeghem AAJ, Poortman J, Nabuurs M & Thijssen JHH, 1985 Endogenous concentrations and sub-cellular distribution of estrogens in normal and malignant breast tissue. Cancer Research 45 2900-2904.
101. Woo LWL, Howarth NM, Purohit A, Hejaz HA, Reed MJ & Potter BVL, 1998 Steroidal and non-steroidal sulfamates as potent inhibitors of steroid sulfatase. Journal of Medicinal Chemistry 41 1068-1083.
102. Woo LWL, Sutcliffe OB, Bubert C, Grasso A, Chander SK, Purohit A, Reed MJ & Potter BVL, 2003 First dual aromatase-steroid sulfatase inhibitors. Journal of Medicinal Chemistry 46 3193-3196.
103. Woo LWL, Purohit A & Potter BVL, 2011 Development of steroid sulfatase inhibitors. Molecular and Cellular Endocrinology 340 175-185.
104. Wood PM, Woo LWL, Labrosse JR, Thomas MP, Mahon MF, Chander SK, Purohit A, Reed MJ & Potter BVL, 2010 Bicyclic derivatives of the potent dual aromatase-steroid sulfatase inhibitor 2-bromo-4-{[(4-cyanophenyl)(4h-1,2,4-triazol-4-yl)amino]methyl}phenylsulfamate: synthesis, SAR, crystal structure, and in vitro and in vivo activities. ChemMedChem 5 1577-1593.
105. Wood PM, Woo LWL, Thomas MP, Mahon MF, Purohit A & Potter BVL, 2011 Aromatase and dual-aromatase-steroid sulfatase inhibitors from the letrozole and vorozole templates. ChemMedChem 6 1423-1438.