Estrone sulfatase and its inhibitors

Anti-Cancer Agents in Medicinal Chemistry

Volumn 9, Issue 6, 2009, Pages 599-612

  Aidoo Gyamfi, Kwabina ^a   Cartledge, Tim ^a   Shah, Kruti ^a   Ahmed, Sabbir ^a  

^a KINGSTON UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 METHYLCOUMARIN 7 O SULFAMATE; ANDROSTENEDIOL SULFATE; ANTINEOPLASTIC AGENT; AROMATASE; CHROMENONE DERIVATIVE; COUMARIN SULFAMATE DERIVATIVE; DAIDZEIN 4' O SULFATE; DAIDZEIN 4',7 DI O SULFATE; DANAZOL; ESTRADIOL; ESTROGEN RECEPTOR; ESTRONE 3 O METHYLPHOSPHONOTHIONIC ACID; ESTRONE SULFATASE INHIBITOR; HYDROXYTAMOXIFEN; KETONE DERIVATIVE; MADURAHYDROXYLACTONE; PRASTERONE; PRASTERONE SULFATE; STX 213; THIOSEMICARBAZONE DERIVATIVE; UNCLASSIFIED DRUG;

BREAST CANCER; CANCER CELL; CELL GROWTH; CELL STIMULATION; CLINICAL TRIAL; DRUG DESIGN; DRUG EFFICACY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; ESTROGEN ACTIVITY; HORMONE ACTION; HUMAN; IC 50; REVIEW; STRUCTURE ACTIVITY RELATION;

EID: 70349091079     PISSN: 18715206     EISSN: None     Source Type: Journal    
DOI: 10.2174/187152009788679985     Document Type: Review

References (71)

1. Beatson, G. T. On the treatment of inoperable cases of carcinoma of the mama:suggestions for a new method of treatment with illustrative cases. Lancet, 1896, 2, 104-107.
2. James, V. H. T. and Reed, M. J. Steroid hormones and human cancer. Prog. Cancer Res. Ther., 1980, 14, 471-487.
3. Lippman, M. E.; Dickson, R. B.; Gelman, E. P.; Rosen, N.; Knabbe, C.; Bates, S.; Bronzert, D.; Huff, K. and Kasid, A. Growth regulatory and peptide production by human breast carcinoma cells. J. Steroid Biochem. Mol. Biol., 1988, 30, 53-61.
4. Pasqualini, J. R.; Chetrite, G.; Nguyen, B. L.; Maloche, C.; Delalonde, L.; Talbi, M.; Feinstein, M. C.; Blacker, C.; Botella, J. and Paris, J. Estrone sulfate-sulfatase and 17-Beta-hydroxysteroid dehydrogenase-activities - A hypothesis for their role in the evolution of human breast-cancer from hormone-dependence to hormone-independence. J. Steroid Biochem. Mol. Biol., 1995, 53, 407-412.
5. Van Landegham, A.A.J.; Poortman, J.; Nabuurs, M. and Thijsen, J.H.H. Endogenous concentration and subcellular-distribution of estrogens in normal and malignant human-breast tisuue. Cancer Res., 1985, 45, 2900-2906.
6. Pasqualini, J.R.; Gelly, C.; Nguyen, B.L. and Vella, C. Importance of estrogen sulfates in breast cancer. J. Steroid Biochem. Mol. Biol., 1989, 34, 155-163.
7. Hobkirk, R. Steroid sulfation - current concepts. Trends Endocrin. Metabol., 1993, 4, 69-74.
8. Santner, S.J.; Feil, P.D. and Santen, R.J. In-situ estrogen production via the estrone sulfatase pathway in breast tumours: Relative importance versus the aromatase pathway. J. Clin. Endocr. Metabol., 1984, 59, 29-33.
9. Reed, M.J.; Purohit, A.; Woo, L.W.L. and Potter, B.V.L. The development of steroid sulfatase inhibitors. Endocr. Relat. Cancer, 1996, 3, 9-23.
10. Pasqualini, J.R. and Chetrite, G.S. Recent insight on the control of enzymes involved in estrogen formation and transformation in human breast cancer. J. Steroid. Biochem. Mol. Biol., 2005, 93, 221-236.
11. Adams, J.B.; Garcia, M. and Rochefort, H. Estrogenic effects of physiological concentrations of 5-androstene-3β, 17β-diol and its metabolism in MCF7 human breast cancer cells. Cancer Res., 1981, 41, 4720-4726.
12. Carlstrom, K.; Doberl, A.; Pousette, A.;Rannevik, G. and Wilking, N. In Recent Results in Cancer Research. Eds.; Leclercq G., Toma S., Paridaems R., Heuson J.C. Acta Obstet. Gynecol. Scand., 1984a, 123(Suppl.), 107-111.
13. Selcer, K.W.; Jagannathan, S.; Rhodes, M.E. and Li, P.K. Inhibition of placental estrone sulfatase activity and MCF7 breast cancer cell proliferation by estrone-3-amino derivatives. J. Steroid Biochem. Mol. Biol., 1996, 59, 83-91.
14. Purohit, A. and Reed, M.J. Oestrogen sulphatase activity in hormone-dependent and hormone-independent breast cancer cell lines: Modulation by steroidal and non-steroidal therapeutic agents. Int. J. Cancer, 1992, 50, 901-905.
15. Nguyen, B.L.; Ferme, I.; Chetrite, G. and Pasqualini, J.R. Action of danazol on the conversion of estrone sulphate to estradiol and on the sulfatase activity in the MCF-7, T-47D and MDA-MB-231 human mammary-cancer cells. J. Steroid Biochem. Mol. Biol., 1993, 46, 17-23.
16. Cox, R. I.; Hoskinson, R. M. and Wong, M. S. Antisera reactive directly to estrone sulphate. Steroids, 1979, 33, 549-62.
17. Duncan, L.; Purohit, A.; Howarth, N.M.; Potter, B.V.L. and Reed, M.J. Inhibition of estrone sulfatase activity by estrone-3-methylthiophosphonate: A potential therapeutic agent on breast cancer. Cancer Res., 1993, 53, 298-303.
18. Purohit, A.; Williams, G.J.; Howarth, N.M.; Potter, B.V.L. and Reed, M.J. Inactivation of steroid sulfatase by an active site directed inhibitor. Biochemistry, 1995, 34, 11508-11514.
19. Anderson, C.; Freeman, J.; Lucus, L.H.; Farley, M.; Dalhoumi, H. and Widlanski, T.S. Estrone sulfatase: Probing structural requirements for substrate and inhibitor recognition. Biochemistry, 1997, 36, 2586-2594.
20. Woo, L.W.L., Purohit, A., Reed, M.J. and 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.
21. Woo, L.W.L.; Lightowler, M.; Purohit, A.; Reed, M.J. and 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. Steriod Biochem. Molec. Biol., 1996a, 57, 79-88.
22. Howarth, N.M.; Purohit, A.; Reed, M. J. and Potter, B.V.L. Estrone sulfonates as inhibitors of estrone sulfatase. Steroids, 1997, 62, 346-350.
23. Fischer, D.S.; Woo, L.W.L.; Mahon, M.F.; Purohit, A.; Reed, M.J. and Potter, B.V.L. Novel D ring modified steroid derivatives as potent, non-estrogenic steroid sulfatase inhibitors with in vivo activity. Bioorg. Med. Chem., 2003, 11, 1685-1700.
24. Potter, B.V.L.; Reed, M.J. Steroidal compounds for inhibiting steroid sulphatase. Sterix Ltd. WO0232409, 2002c.
25. Foster, P.A.; Newman, S.P.; Chander, S.K.; Stengel, C.; Jhalli, R.; Woo, L.W.L.; Potter, B.V.L.; Reed, M.J. and Purohit, A. In vivo efficacy of STX213, a second generation steroid sulfatase inhibitor, for hormone-dependent breast cancer therapy. Clin. Cancer Res., 2006, 12, 5543-5549.
26. Li, P. K. and Selcer, K. W. Steroid sulfatase inhibitors and methods for making and using the same. Duquesne Univ. of the Holy Ghost: WO09903876, 1999.
27. Li P. K.; Akinaga S., Murakata C. Duquesne Univ. of the Holy Ghost & Kyowa Hakko Kogyo Co. Ltd.: Steroid sulfatase inhibitors and methods for making and using the same. WO0043408, 2000.
28. Li P. K.; Chu G.H.; Guo J.P. Peters A. and Selcer K.W. Development of potent non-estrogenic estrone sulfatase inhibitors. Steroids, 1998, 63: 425-432.
29. Tanabe, M.; Peters, R. H.; Chao, W. R. and Shigeno, K. Sri In-t Estrone sulfamate inhibitors of estrone sulfatase, and associated pharmaceutical compositions and methods of use. WO9933858, 1999.
30. Potter, B. V. L. and Reed, M. J Sterix Ltd.: 17-aryl-linker derivatised estrogen 3-sulphamates as inhibitors of steroid sulphatase. WO0216393, 2002a.
31. Potter, B. V. L. and Reed, M. J. Sterix Ltd.: Thioether-sulphamate steroids as steroid sulphatase inhibitors and anti-cancer compounds. WO0216394, 2002b.
32. Potter, B. V. L. and Reed, M. J. Oestrogen-17-sulphamates as inhibitors of steroid sulphatase. Sterix Ltd.: WO0216392, 2002d.
33. Poirier, D. and Boivin, R.P. 17 α-alkyl- or 17 α-substituted benzyl-17 β-estradiols: A new family of estrone-sulfatase inhibitors. Bioorg. Med. Chem. Lett., 1998c, 8, 1891-1896.
34. Hejaz, H.A.M.; Purohit A.; Mahon M.F.; Reed M.J. and Potter B.V.L. Recent advances in the development of steroid sulphatase inhibitors. J. Med. Chem., 1999, 42, 3188-3192.
35. Peters, R.H.; Chao, W-R.; Sato, B.; Shigeno, K.; Zaveri, N.T. and Tanabe, M. Steroidal oxathiazine inhibitors of estrone sulfatase. Steroids, 2003, 68, 97-110.
36. Woo, L.W.L.; Purohit, A.; Reed, M.J. and Potter, B.V.L. Active site directed inhibition of estrone sulfatase by nonsteroidal coumarin sulfamates J. Med. Chem., 1996b, 39, 1349-1351.
37. Reed, M. J., Potter, B. V. L., Hejaz, H., Purohit, A.Sterix Ltd.: Halogenated sulphamate-, phosphonate-, thiophosphonate-, sulphonate- and sulphonamide- compounds as inhibitors of steroid sulphatase. WO0144268, 2001.
38. Purohit, A.; Vernon, K.A.; Hummelinck, A.E.W.; Woo, L.W.L.; Hejaz, H.A. M.; Potter, B.V.L. and Reed, M.J. 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., 1998b, 64, 269-275.
39. Schreiner, E. P. and Billich, A. Estrone formate: a novel type of irreversible inhibitor of human steroid sulfatase. Bioorg. Med. Chem. Lett., 2004, 14, 4999-5002.
40. Brinbock, H. and Von Angerer, E. Sulfate derivatives of 2-phenylindols as novel steroid sulfatase inhibitors. Biochem. Pharmacol., 1990, 39, 1709-1713.
41. Reed, M.J.; Purohit, A., Woo, L.W.L and Potter, B.V.L. The development of steroid sulfatase inhibitors. Endocr. Relat. Cancer, 1996, 3, 9-23.
42. Chen, C.W.; Oberley, T.D. and Roy, D. Inhibition of stilbene estrogen-induced cell proliferation of renal epithelial cells through the modulation of insulin-like growth factor-I receptor expression. Cancer Lett., 1996, 105, 51-59.
43. Chu, G.H.; Peters, A.; Selcer, K.W. and Li, P.K. Synthesis and sulfatase inhibitory activities of (E)- and (Z)-4-hydroxytamoxifen sulfamates. Bioorg. Med. Chem. Lett., 1999, 9, 141-144.
44. Naoyuki, K.; Akira, O.; Shigeki, I.;Yoshihiro, T.; Takayoshi, N.; Hiroo, T. and Tomohito, F. Phenylsulfamate derivative. Teikoku Hormone MFG Co. Ltd., 2001.
45. Ahmed, S.; James, K.; Owen, C. P. and Patel, C. K. Design, synthesis and biochemical evaluation of AC ring mimics as novel inhibitors of the enzyme estrone sulfatase (ES). Bioorg. Med. Chem. Lett., 2002, 12, 1343-1346.
46. Ahmed, S.; James, K. and Owen, C. P. Design, synthesis and biochemical evaluation of AC ring mimics as novel inhibitors of the enzyme estrone sulfatase (ES). J. Steroid Biochem. Mol. Biol., 2002, 82, 425-435.
47. Nussbaumer, P.; Bilban, M. and Billich, A. 4,4′Benzophenone-O,O′-disulfamate: A potent inhibitor of steroid sulfatase. J. Med. Chem., 2002, 45, 4310-4320.
48. Nussbaumer, P.; Winiski, A.P. and Billich, A. Estrogenic potential of 2-alkyl-4-(thio)chromenone 6-O-sulfamates: Potent inhibitors of human steroid sulfatase. J. Med. Chem., 2003, 46, 5091-5094.
49. Billich, A.; Nussbaumer, P. and Lehr, P. Stimulation of MCF-7 breast cancer cell proliferation by estrone sulfate and dehydroepiandrosterone sulfate: inhibition by novel non-steroidal steroid sulfatase inhibitors. J. Steroid. Biochem. Mol. Biol., 2000, 73, 225-235.
50. Woo, L.W.L.; Howarth, N.M.; Purohit, A.; Hatem, A.M.; Reed, M.J. and Potter, B.V.L. Steroidal and non-steroidal sulphamates as potent inhibitors of steroid sulphatase. J. Med. Chem., 1998, 41, 1068-1083.
51. Malini, B.; Purohit, A.; Ganeshapillai, D.; Woo, L.W.L.; Potter, B.V.L. and Reed, M.J. Inhibition of steroid sulphatase activity by tricyclic coumarin sulphamates. J. Steroid Biochem. Mol. Biol., 2000, 75, 253-258.
52. Stanway, S.J.; Purohit, A.; Woo, L.W.L.; Sufi, S.; Vigushin, D.; Ward, R.; Wilson, R.H.; Stanczyk, F.Z.; Dobbs, N.; Kulinskaya, E.; Elliott, M.; Potter, B.V.L.; Reed, M.J. and Coombes, R.C. Phase I study of STX 64 (667 Coumate) in breast cancer patients: The first study of a steroid sulfatase inhibitor. Clin. Cancer Res., 2006, 12, 1585-1592.
53. Wong, C.K. and Keung, W.M. Daidzein sulfoconjugates are potent inhibitors of steroid sulfatase. Biochem. Biophys. Res. Commun., 1997, 233, 579-583.
54. Li, P. K.; Milano, S.; Kluth, L. and Rhodes, M. E. Synthesis and sulfatase inhibitory activities of non-steroidal estrone sulfatase inhibitors. J. Steroid. Biochem. Mol. Biol., 1996, 59, 41-48.
55. Ciobanu, L. C.; Luu-The V. and Poirier D. Nonsteroidal compounds designed to mimic potent steroid sulfatase inhibitors. J. Steroid Biochem. Mol. Biol., 2002, 80, 339-353.
56. Ahmed, S.; James, K.; Owen, C. P.; Patel, C. K. and Patel, M. Novel inhibitors of the enzyme estrone sulfatase (ES). Bioorg. Med. Chem. Lett., 2001, 11, 841-844.
57. Ahmed, S.; Owen, C.; James, K.; Patel, C. K. and Patel, M. Hydrophobicity, a physicochemical factor in the inhibition of the enzyme estrone sulfatase. Bioorg. Med. Chem. Lett., 2001, 11, 2525-2528.
58. Ahmed, S.; James, K.; Owen, C. P.; Patel, C. K. and Patel, M. Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES). J. Steroid Biochem. Mol. Biol., 2002, 80, 419-427.
59. Ahmed, S.; James, K. and Patel, C. K. First report of the investigation into the importance of pK(a) in the inhibition of estrone sulfatase by sulfamate containing compounds. Biochem. Biophys. Res. Commun., 2000a, 272, 583-585.
60. Ahmed, S.; James, K. and Sampson, L. Synthesis and biochemical evaluation of some novel benzoic acid based esters as potential inhibitors of oestrone sulphatase J. Pharm. Pharmacol., 2003, 1, 85-93.
61. Ahmed, S.; James, K.; Owen, C. P. and Patel, C. K. Structure-activity relationship determination within a group of substituted phenyl sulfamate based compounds against the enzyme oestrone sulfatase. J. Pharm. Pharmacol., 2003, 2, 211-218.
62. Patel, C. K.; Owen, C. P. and Ahmed, S. The design, synthesis, and in vitro biochemical evaluation of a series of esters of 4-[(aminosulfonyl)oxy]benzoate as novel and highly potent inhibitors of estrone sulfatase. Biochem. Biophys. Res. Commun., 2003, 307, 778-781.
63. Patel, C. K.; Owen, C. P. and Ahmed, S. Inhibition of estrone sulfatase (ES) by alkyl and cycloalkyl ester derivatives of 4-[(aminosulfonyl)oxyl]benzoic acid. Bioorg. Med. Chem. Lett., 2004, 14, 605-609.
64. Owen, C. P.; Patel, M.; Patel, C. K.; Cartledge, T. and Ahmed, S. Synthesis and in vitro biochemical evaluation of a series of cycloalkyl esters of 4-sulfamoylated benzoic acid as inhibitors of estrone sulfatase (ES). Lett. Drug Des. Discov., 2007, 4, 394-398.
65. Owen, C. P.; Patel, C. K.; Cartledge, T and Ahmed, S. Synthesis and in vitro biochemical evaluation of a series of cycloalkyl esters of 4-sulfamoylated benzoic acid as inhibitors of estrone sulfatase (ES). Lett. Drug Des. Discov., 2007, 4, 399-403.
66. Ahmed, S.; James, K.; Sampson, L. and Mastri, C. Structure-activity relationship study of steroidal and nonsteroidal inhibitors of the enzyme estrone sulfatase. Biochem. Biophys. Res. Commun., 1999, 254, 811-815.
67. Ahmed, S.; James, K.; Owen, C. P.; Patel, C. K. and Sampson L. Evidence for the mechanism of the irreversible inhibition of oestrone sulphatase (ES) by aminosulphonate based compounds. J. Steroid Biochem. Mol. Biol., 2002, 80, 429-440.
68. Ahmed, S.; James, K. and Patel, C. K. First report of the investigation into the importance of pK(a) in the inhibition of estrone sulfatase by sulfamate containing compounds. Biochem. Biophys. Res. Commun., 2000, 27, 583-585.
69. Ahmed, S.; Owen, C. P.; James, K.; Patel, C. K. and Sampson, L. The mechanism of the irreversible inhibition of estrone sulfatase (ES) through the consideration of a range of methane- and amino-sulfonate-based compound. Bioorg. Med. Chem. Lett., 2002, 12, 1279-1282.
70. Jütten, P.; Schumann, W.; Härtl, A.; Heinisch, L.; Gräfe, U.; Werner, W. and Ulbricht, H. A novel type of nonsteroidal estrone sulfatase inhibitors. Bioorg. Med. Chem. Lett., 2002, 12, 1339-1342.
71. Jütten, P.; Schumann, W.; Härtl, A.; Heinisch, L.; Dahse, H. M. and Grafe, U. Thiosemicarbazones of formyl benzoic acids as novel potent inhibitors of estrone sulfatase. J. Med. Chem., 2007, 50, 3661-3666.