593
Views
44
CrossRef citations to date
0
Altmetric
Reviews

Sulfatase inhibitors: a patent review

, PhD
Pages 79-98 | Published online: 08 Nov 2012

Bibliography

  • Hanson SR, Best MD, Wong C-H. Sulfatases: structure, mechanism, biological activity, inhibition, and synthetic utility. Angew Chem Int Ed 2004;43:5736-63
  • von Figura K, Schmidt B, Selmer T, Dierks T. A novel protein modification generating an aldehyde group in sulfatases: its role in catalysis and disease. Bioessays 1998;20:505-10
  • Bojarova P, Williams SJ. Sulfotransferases, sulfatases and formylglycine-generating enzymes: a sulfation fascination. Curr Opin Chem Biol 2008;12:573-81
  • Hagelueken G, Adams TM, Wiehlmann L, The crystal structure of SdsA1, an alkylsulfatase from Pseudomonas aeruginosa, defines a third class of sulfatases. Proc Natl Acad Sci USA 2006;103:7631-6
  • Chapman E, Best MD, Hanson SR, Wong C-H. Sulfotransferases: structure, mechanism, biological activity, inhibition, and synthetic utility. Angew Chem Int Ed 2004;43:3526-48
  • Bojarova P, Williams SJ. Aryl sulfamates are broad spectrum inactivators of sulfatases: effects on sulfatases from various sources. Bioorg Med Chem Lett 2009;19:477-80
  • Reddy DS. Neurosteroids: endogenous role in the human brain and therapeutic potentials. Prog Brain Res 2010;186:113-37
  • Lin SX, Chen J, Mazumdar M, Molecular therapy of breast cancer: progress and future directions. Nat Rev Endocrinol 2010;6:485-93
  • Woo LWL, Purohit A, Potter BVL. Development of steroid sulfatase inhibitors. Mol Cell Endocrinol 2011;340:175-85
  • Barrios C, Forbes JF, Jonat W, The sequential use of endocrine treatment for advanced breast cancer: where are we? Ann Oncol 2012;23:1378-86
  • Elger W, Barth A, Hedden A, Estrogen sulfamates: a new approach to oral estrogen therapy. Reprod Fertil Dev 2001;13:297-305
  • Maltais R, Poirier D. Steroid sulfatase inhibitors: a review covering the promising 2000 – 2010 decade. Steroids 2011;76:929-48
  • Nussbaumer P, Billich A. Steroid sulfatase inhibitors. Med Res Rev 2004;24:529-76
  • Purohit A, Foster PA. Steroid sulfatase inhibitors for estrogen- and androgen-dependent cancers. J Endocrinol 2012;212:99-110
  • Poirier D, Ciobanu LC, Maltais R. Steroid sulfatase inhibitors. Expert Opin Ther Patents 1999;9:1-17
  • Horvath A, Billich A. Steroid sulfatase inhibitors. Expert Opin Ther Patents 2005;15:1541-53
  • Bond CS, Clements PR, Ashby SJ, Structure of a human lysosomal sulfatase. Structure 1997;5:277-89
  • Lukatela G, Krauss N, Theis K, Crystal structure of human arylsulfatase A: the aldehyde function and the metal ion at the active site suggest a novel mechanism for sulfate ester hydrolysis. Biochemistry 1998;37:3654-64
  • Bojarova P, Denehy E, Walker I, Direct evidence for ArO-S bond cleavage upon inactivation of Pseudomonas aeruginosa arylsulfatase by aryl sulfamates. ChemBioChem 2008;9:613-23
  • Hernandez-Guzman FG, Higashiyama T, Pangborn W, Structure of human estrone sulfatase suggests functional roles of membrane association. J Biol Chem 2003;278:22989-97
  • Boltes I, Czapinska H, Kahnert A, 1.3 A structure of arylsulfatase from Pseudomonas aeruginosa establishes the catalytic mechanism of sulfate ester cleavage in the sulfatase family. Structure 2001;9:483-91
  • Myette JR, Soundararajan V, Behr J, Heparin/Heparan Sulfate N-Sulfamidase from Flavobacterium heparinum. J Biol Chem 2009;284:35189-200
  • Ghayee H, Auchus R. Basic concepts and recent developments in human steroid hormone biosynthesis. Rev Endocr Metab Dis 2007;8:289-300
  • Payne AH, Hales DB. Overview of steroidogenic enzymes in the pathway from cholesterol to active steroid hormones. Endocr Rev 2004;25:947-70
  • Purohit A, Woo LWL, Potter BVL. Steroid sulfatase: a pivotal player in estrogen synthesis and metabolism. Mol Cell Endocrinol 2011;340:154-60
  • Lin A, Mu J, Yang J, Roach PJ. Self-glucosylation of glycogenin, the initiator of glycogen biosynthesis, involves an inter-subunit reaction. Arch Biochem Biophys 1999;363:163-70
  • Utsumi T, Yoshimura N, Takeuchi S, Steroid sulfatase expression is an independent predictor of recurrence in human breast cancer. Cancer Res 1999;59:377-81
  • Colette S, Defrere S, Lousse JC, Inhibition of steroid sulfatase decreases endometriosis in an in vivo murine model. Hum Reprod 2011;26:1362-70
  • Preglem. WO2009037539; 2009
  • Duquesne University of the Holy Ghost. US5763492; 1998
  • Duquesne University of the Holy Ghost. US5556847; 1996
  • Celltech Therapeutics; University College London. WO9526717; 1995
  • Janssen Pharmaceutical. WO03077924; 2003
  • Novartis. WO2006097293; 2006
  • Preglem. WO2010013187; 2010
  • Imperial College of Science, Technology and Medicine. WO9305064; 1993
  • Imperial College of Science, Technology and Medicine. WO9113083; 1991
  • Duquesne University of the Holy Ghost. US5571933; 1996
  • Chander SK, Purohit A, Woo LWL, The role of steroid sulphatase in regulating the oestrogenicity of oestrogen sulphamates. Biochem Biophys Res Commun 2004;322:217-22
  • Woo LWL, Fischer DS, Sharland CM, Anticancer steroid sulfatase inhibitors: synthesis of a potent fluorinated second-generation agent, in vitro and in vivo activities, molecular modeling, and protein crystallography. Mol Cancer Ther 2008;7:2435-44
  • Winum J-Y, Vullo D, Casini A, Carbonic anhydrase inhibitors. Inhibition of cytosolic isozymes I and II and transmembrane, tumor-associated isozyme IX with sulfamates including EMATE also acting as steroid sulfatase inhibitors. J Med Chem 2003;46:2197-204
  • Howarth NM, Purohit A, Reed MJ, Potter BVL. Estrone sulfamates: potent inhibitors of estrone sulfatase with therapeutic potential. J Med Chem 1994;37:219-21
  • Purohit A, Williams GJ, Howarth NM, Inactivation of steroid sulfatase by an active site-directed inhibitor, estrone-3-O-sulfamate. Biochemistry 1995;34:11508-14
  • Abbate F, Winum J-Y, Potter BVL, Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with EMATE, a dual inhibitor of carbonic anhydrases and steroid sulfatase. Bioorg Med Chem Lett 2004;14:231-4
  • Elger W, Schwarz S, Hedden A, Sulfamates of various estrogens are prodrugs with increased systemic and reduced hepatic estrogenicity at oral application. J Steroid Biochem Mol Biol 1995;55:395-403
  • Jenapharm. WO0006175; 2000
  • Sterix. US7067503; 2006
  • SRI International. US6046186; 2000
  • Duquesne University of the Holy Ghost; Kyowa Hakko Kogyo Co. US6376687; 2002
  • Duquesne University of the Holy Ghost. US6288050; 2001
  • Ishida H, Nakata T, Suzuki M, A novel steroidal selective steroid sulfatase inhibitor KW-2581 inhibits sulfated-estrogen dependent growth of breast cancer cells in vitro and in animal models. Breast Cancer Res Treat 2007;106:215-27
  • Ishida H, Sato N, Hosogi J, Inactivation of recombinant human steroid sulfatase by KW-2581. J Steroid Biochem Mol Biol 2008;108:17-22
  • Ishida H, Nakata T, Sato N, 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 Res Treat 2007;104:211-19
  • Imperial College of Science Technology and Medicine. WO9824802; 1998
  • Woo LWL, Leblond B, Purohit A, Potter BVL. Synthesis and evaluation of analogues of estrone-3-O-sulfamate as potent steroid sulfatase inhibitors. Bioorg Med Chem 2012;20:2506-19
  • Sterix. US6011024; 2000
  • Sterix. US20090221841; 2009
  • Teikoku Hormone Mfg. EP0934949; 1999
  • Imperial College of Science Technology and Medicine; University of Bath. WO9927935; 1999
  • Hejaz HA, Purohit A, Mahon MF, Synthesis and biological activity of the superestrogen (E)-17-oximino-3-O-sulfamoyl-1,3,5(10)-estratriene: X-ray crystal structure of (E)-17-oximino-3-hydroxy-1,3,5(10)-estratriene. J Med Chem 1999;42:3188-92
  • Sterix. WO0232409; 2002
  • Sterix. WO03033518; 2003
  • Sterix. WO2007099304; 2007
  • Sterix. US20090182000; 2009
  • Fischer DS, Woo LWL, Mahon MF, D-ring modified estrone derivatives as novel potent inhibitors of steroid sulfatase. Bioorg Med Chem 2003;11:1685-700
  • Fischer DS, Chander SK, Woo LW, Novel D-ring modified steroid derivatives as potent, non-estrogenic, steroid sulfatase inhibitors with in vivo activity. J Steroid Biochem Mol Biol 2003;84:343-9
  • Foster PA, Chander SK, Parsons MFC, Efficacy of three potent steroid sulfatase inhibitors: pre-clinical investigations for their use in the treatment of hormone-dependent breast cancer. Breast Cancer Res Treat 2008;111:129-38
  • Numazawa M, Tominaga T, Watari Y, Tada Y. Inhibition of estrone sulfatase by aromatase inhibitor-based estrogen 3-sulfamates. Steroids 2006;71:371-9
  • Schering. WO2004074307; 2004
  • Schering. US6583130; 2003
  • Jenapharm. US5705495; 1998
  • Woo LWL, Purohit A, Reed MJ, Potter BVL. Oestrone 3-O-(N-acetyl)sulphamate, a potential molecular probe of the active site of oestrone sulphatase. Bioorg Med Chem Lett 1997;7:3075-80
  • Organon. WO0053620; 2000
  • Ciobanu LC, Boivin RP, Luu-The V, Potent inhibition of steroid sulfatase activity by 3-O-sulfamate 17alpha-benzyl(or 4'-tert-butylbenzyl)estra-1,3,5(10)-trienes: combination of two substituents at positions C3 and c17alpha of estradiol. J Med Chem 1999;42:2280-6
  • Ciobanu LC, Luu-The V, Martel C, Inhibition of estrone sulfate-induced uterine growth by potent nonestrogenic steroidal inhibitors of steroid sulfatase. Cancer Res 2003;63:6442-6
  • Poirier D, Boivin RP. 17 alpha-alkyl- or 17 alpha-substituted benzyl-17 beta-estradiols: a new family of estrone-sulfatase inhibitors. Bioorg Med Chem Lett 1998;8:1891-6
  • Sterix. WO0216393; 2002
  • Sterix. WO0216394; 2002
  • Leese MP, Leblond B, Newman SP, Anti-cancer activities of novel D-ring modified 2-substituted estrogen-3-O-sulfamates. J Steroid Biochem Mol Biol 2005;94:239-51
  • ID Pharma. US6339079; 2002
  • SRI International. WO9832763; 1998
  • SRI International. US5763432; 1998
  • SRI International. US5861388; 1999
  • Hanson SR, Whalen LJ, Wong C-H. Synthesis and evaluation of general mechanism-based inhibitors of sulfatases based on (difluoro)methyl phenyl sulfate and cyclic phenyl sulfamate motifs. Bioorg Med Chem 2006;14:8386-95
  • Duquesne University of the Holy Ghost. US5567831; 1996
  • Chu GH, Milano S, Kluth L, Structure-activity relationship studies of the amide functionality in (p-O-sulfamoyl)-N-alkanoyl tyramines as estrone sulfatase inhibitors. Steroids 1997;62:530-5
  • Kolli A, Chu GH, Rhodes ME, Development of (p-O-sulfamoyl)-N-alkanoyl-phenylalkyl amines as non-steroidal estrone sulfatase inhibitors. J Steroid Biochem Mol Biol 1999;68:31-40
  • Selcer KW, Kabler H, Sarap J, Inhibition of steryl sulfatase activity in LNCaP human prostate cancer cells. Steroids 2002;67:821-6
  • Woo LWL, Purohit A, Reed MJ, Potter BVL. Active site directed inhibition of estrone sulfatase by nonsteroidal coumarin sulfamates. J Med Chem 1996;39:1349-51
  • Purohit A, Woo LW, Singh A, In vivo activity of 4-methylcoumarin-7-O-sulfamate, a nonsteroidal, nonestrogenic steroid sulfatase inhibitor. Cancer Res 1996;56:4950-5
  • Imperial College of Science Technology and Medicine; University of Bath. WO9732872; 1997
  • Imperial College of Science Technology and Medicine; University of Bath. WO9730041; 1997
  • Woo LWL, Purohit A, Malini B, Potent active site-directed inhibition of steroid sulphatase by tricyclic coumarin-based sulphamates. Chem Biol 2000;7:773-91
  • Woo LWL, Ganeshapillai D, Thomas MP, Structure–activity relationship for the first-in-class clinical steroid sulfatase inhibitor irosustat (STX64, BN83495). ChemMedChem 2011;6:2019-34
  • Ventura V, Sola J, Celma C, In vitro metabolism of irosustat, a novel steroid sulfatase inhibitor: interspecies comparison, metabolite identification, and metabolic enzyme identification. Drug Metab Dispos 2011;39:1235-46
  • Coombes R, Schmid P, Isambert N, A phase I dose escalation study of steroid sulfatase inhibitor BN83495/STX64 in postmenopausal women with ER positive breast cancer. Cancer Res 2009;69:abstract 4097
  • Stanway SJ, Purohit A, Woo LWL, Phase I study of STX 64 (667Coumate) in breast cancer patients: the first study of a steroid sulfatase inhibitor. Clin Cancer Res 2006;12:1585-92
  • Novartis. WO9952890; 1999
  • Nussbaumer P, Lehr P, Billich A. 2-Substituted 4-(thio)chromenone 6-O-sulfamates: potent inhibitors of human steroid sulfatase. J Med Chem 2002;45:4310-20
  • Nussbaumer P, Winiski AP, Billich A. Estrogenic potential of 2-alkyl-4-(thio)chromenone 6-O-sulfamates: potent inhibitors of human steroid sulfatase. J Med Chem 2003;46:5091-4
  • Novartis. WO0136398; 2001
  • Schreiner EP, Wolff B, Winiski AP, Billich A. 6-(2-adamantan-2-ylidene-hydroxybenzoxazole)-O-sulfamate: a potent non-steroidal irreversible inhibitor of human steroid sulfatase. Bioorg Med Chem Lett 2003;13:4313-16
  • Billich A, Meingassner JG, Nussbaumer P, 6-[2-(adamantylidene)-hydroxybenzoxazole]-O-sulfamate, a steroid sulfatase inhibitor for the treatment of androgen- and estrogen-dependent diseases. J Steroid Biochem Mol Biol 2004;92:29-37
  • Hans-Knoll-Institut. DE19701664; 1998
  • Jutten P, Schumann W, Hartl A, A novel type of nonsteroidal estrone sulfatase inhibitors. Bioorg Med Chem Lett 2002;12:1339-42
  • Jutten P, Schumann W, Hartl A, Thiosemicarbazones of formyl benzoic acids as novel potent inhibitors of estrone sulfatase. J Med Chem 2007;50:3661-6
  • Novartis. WO03031397; 2003
  • Nussbaumer P, Geyl D, Horvath A, Nortropinyl-arylsulfonylureas as novel, reversible inhibitors of human steroid sulfatase. Bioorg Med Chem Lett 2003;13:3673-7
  • Lehr P, Billich A, Wolff B, N-Acyl arylsulfonamides as novel, reversible inhibitors of human steroid sulfatase. Bioorg Med Chem Lett 2005;15:1235-8
  • Lee W, DeRome M, DeBear J, Aryl piperazines: a new class of steroid sulfatase inhibitors for the treatment of hormone-dependent breast cancer. Abstr Pap Am Chem Soc 2003;226:MEDI-301
  • Solvay Pharmaceuticals. US20060281710; 2006
  • Chu GH, Peters A, Selcer KW, Li PK. Synthesis and sulfatase inhibitory activities of (E)- and (Z)-4-hydroxytamoxifen sulfamates. Bioorg Med Chem Lett 1999;9:141-4
  • Duquesne University of the Holy Ghost; Kyowa Hakko Kogyo Co. US6288107; 2001
  • Rasmussen LM, Zaveri NT, Stenvang J, A novel dual-target steroid sulfatase inhibitor and antiestrogen: SR 16157, a promising agent for the therapy of breast cancer. Breast Cancer Res Treat 2007;106:191-203
  • SRI International. US6054446; 2000
  • Rausch L, Green C, Steinmetz K, Preclinical pharmacokinetic, toxicological and biomarker evaluation of SR16157, a novel dual-acting steroid sulfatase inhibitor and selective estrogen receptor modulator. Cancer Chemother Pharmacol 2011;67:1341-52
  • Sterix. US6506792; 2003
  • Woo LW, Sutcliffe OB, Bubert C, First dual aromatase-steroid sulfatase inhibitors. J Med Chem 2003;46:3193-6
  • Sterix. WO03045925; 2003
  • Sterix. US20070213383; 2007
  • Laboratoire Thermomex. US20070112009; 2007
  • Wood PM, Woo LW, Humphreys A, A letrozole-based dual aromatase-sulphatase inhibitor with in vivo activity. J Steroid Biochem Mol Biol 2005;94:123-30
  • Jackson T, Woo LW, Trusselle MN, Dual aromatase-sulfatase inhibitors based on the anastrozole template: synthesis, in vitro SAR, molecular modelling and in vivo activity. Org Biomol Chem 2007;5:2940-52
  • Sterix. WO2005118560; 2005
  • Jackson T, Woo LW, Trusselle MN, Non-steroidal aromatase inhibitors based on a biphenyl scaffold: synthesis, in vitro SAR, and molecular modelling. ChemMedChem 2008;3:603-18
  • Woo LW, Jackson T, Putey A, Highly potent first examples of dual aromatase-steroid sulfatase inhibitors based on a biphenyl template. J Med Chem 2010;53:2155-70
  • Sterix. WO2007068905; 2007
  • Sterix. US20080319037; 2008
  • Sterix. US20100173963; 2010
  • Leese MP, Newman SP, Purohit A, 2-Alkylsulfanyl estrogen derivatives: synthesis of a novel class of multi-targeted anti-tumour agents. Bioorg Med Chem Lett 2004;14:3135-8
  • Leese MP, Hejaz HAM, Mahon MF, A-ring-substituted estrogen-3-O-sulfamates: potent multitargeted anticancer agents. J Med Chem 2005;48:5243-56
  • Sterix. US20040127473; 2004
  • Purohit A, Vernon KA, Wagenaar Hummelinck AE, 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;64:269-75
  • Purohit A, Hejaz HAM, Walden L, The effect of 2-methoxyoestrone-3-O-sulphamate on the growth of breast cancer cells and induced mammary tumours. Int J Cancer 2000;85:584-9
  • MacCarthy-Morrogh L, Townsend PA, Purohit A, Differential effects of estrone and estrone-3-O-sulfamate derivatives on mitotic. Arrest, apoptosis, and microtubule assembly in human breast cancer cells. Cancer Res 2000;60:5441-50
  • Sterix. US20070225256; 2007
  • Sterix. US20040009959; 2004
  • Jourdan F, Leese MP, Dohle W, Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate. J Med Chem 2010;53:2942-51
  • Sterix. US8030296; 2011
  • Leese MP, Leblond B, Smith A, 2-Substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity. J Med Chem 2006;49:7683-96
  • Foster PA, Newman SP, Leese MP, A new micronized formulation of 2-methoxyestradiol-bis-sulfamate (STX140) is therapeutically potent against breast cancer. Anticancer Res 2008;28:577-81
  • Foster PA, Ho YT, Newman SP, STX140 and STX641 cause apoptosis via the intrinsic mitochondrial pathway and down-regulate survivin and XIAP expression in ovarian and prostate cancer cells. Anticancer Res 2009;29:3751-7
  • Sterix. WO2008117061; 2008
  • Leese MP, Jourdan F, Kimberley MR, Chimeric microtubule disruptors. Chem Commun 2010;46:2907-9
  • Leese MP, Jourdan F, Dohle W, Steroidomimetic tetrahydroisoquinolines for the design of new microtubule disruptors. ACS Med Chem Lett 2012;3:5-9
  • Parenti G. Treating lysosomal storage diseases with pharmacological chaperones: from concept to clinics. EMBO Mol Med 2009;1:268-79
  • Amicus Therapeutics. 2008
  • Children, Youth and Women's Health Service, Australia. WO2010022461; 2010
  • Frobe C, Simone A, Charig A, Eigen E. Axillary malodour production: a new mechanism. J Soc Cosmet Chem 1990;41:173-85
  • Colgate-Palmolive. US5643559; 1997
  • Colgate-Palmolive. US5676937; 1997
  • Charig A, Froebe C, Simone A, Eigen E. Inhibitor of odor-producing axillary bacterial exozymes. J Soc Cosmet Chem 1991;42:133-45
  • Henkel AG & Co. EP1393518; 2001
  • Palmieri C, Januszewski A, Stanway S, Coombes RC. Irosustat: a first-generation steroid sulfatase inhibitor in breast cancer. Expert Rev Anticancer Ther 2011;11:179-83

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.