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Review

Steroid sulfatase inhibitors

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Pages 605-625 | Published online: 02 Mar 2005

Bibliography

  • PARENTI G, MERONI G, BALLABIO A: The sulfatase gene family. Carr: Opin. Genet. Develop. (1997) 7:386–391.
  • ROY AB: The hydrolysis of sulfate esters. In: The Enzymes Boyer PD (Ed.), Academic Press, New York (1971):2–19.
  • DIBBELT L, KUSS E: Human placental sterylsulfatase. Biol. Chem. Hoppe-Seyler (1991) 372:173–185.
  • KOLODNY EH, FLUHARTY AL: Metachromic leukodystrophy and multiple sulfatase deficiency: sulfate lipidosis. In: The Metabolic and Molecular Bases of Inherited Disease. Scriver CR, Beaudet AL, Sly WS, Valle D (Eds), McGraw-Hill, New York, USA (1995):2693–2741.
  • MATALON R, ARBOGAST B, DORFMAN A: Deficiency of chondroitin sulfate N'-hacetylgalactosamine 4-sulfate sulfatase in Maoteaux-Lamy syndrome. Biochem. Biophy. Res. Commun. (1974) 61:1450–1457.
  • O'BRIEN JF, CANTZ M, SPRANGIER J: Maroteaux-Lamy disease (mucopoly-saccharidosis VI), subtype A: deficiency of N-acetylgalactosamine 4-sulfate. Biochem. Biophy. Res. Commun. (1974) 60:1170–1177.
  • CHANG PL, MUELLER OT, LAFRENIE RM et al.: The human arylsulfatase-C isoenzymes: two distinct genes that escape from X inactivation. Am. J Hum. Genet. (1990) 46:729–737.
  • FRANCO B, MERONI G, PARENTI G et al: A cluster of genes of sulfatase genes on Xq22.3: mutations in chondrodysplasia punctata (CDPX) and implications for warfarin embryopathy. Cell (1995) 81:15–25.
  • PUCA AA, ZOLLO M, REPETTO M et al.: Identification by shotgun sequencing, genomic organization, and functional analysis of a fourth arylsulfatase gene (ARSF) from the Xp22.3 region. Genomics (1997) 42:192–199.
  • STEIN CH, HILLE A, SEIDEL J et al: Cloning and expression of human steroid-sulfatase. Bia Chem. (1989) 264:13865–13872.
  • WILLEMSEN R, KROOS M, HOOGEVEEN AT et al.: Ultrastructural localization of steroid sulphatase in cultured human fibrobalsts by immunocytchemistry. A comparative study with lysosomal enzymes and the mannose 6-phosphate receptor. Histochem. (1988) 20:41–51.
  • GNIOT-SZULZYCKA J, DRY WA A: A 'soluble' form of sterol suphate suphohydrolase from cell nuclei of human placenta tissue - examinations with oestrone sulphate as substrate. Steroid Biochem. MM. Biol. (1994) 49:195–201.
  • MARTEL C, MELNER MH, GAGNE D, SIMARD J, LABRIE E Widespread tissue distribution of steroid sulfatase, 313-hydroxysteroid dehydrogenase/A5-44 isomerase (313-HSD), 173-HSD, 5a-reductase and aromatase activities in the rhesus monkey. Mol Cell. Endocrinol (1994) 104:103–111.
  • HERNANDEZ-GUZMAN FG, HIGASHIYAMA T, OSAWA Y, GHOSH D: Purification, characterization and crystallization of human placental estrone/dehydroepiandrosterone sulfatase, a membrane-bound enzyme of the endoplasmic reticulum. Steroid Biochem. Ma Biol. (2001) 78:441–450.
  • HOWARTH NM, PUROHIT A, ROBINSON JJ, VICKER N, REED MJ, POTTER BV: Estrone 3-sulfate mimics, inhibitors of estrone sulfatase activity: homology model construction and docking studies. Biochemistry (2002) 41:14801–14814.
  • SCHMIDT B, SELMER T,INGENDOH A, VON FIGURA K: A novel amino acid modification in sulfatases that is defective in multiple sulfatase deficiency. Cell (1995) 82:271–278.
  • DIERKS T, SCHMIDT B, VON K: Conversion of cysteine to formylglycine: a protein modification in the endoplasmatic reticulum. Proc. Nati Acad. Sci. USA (1997) 94:11963–11968.
  • LUKATELA G, KRAUSS N, THREIS K et al.: 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) 37:3564–3664.
  • BOND SC, CLEMENTS PR, ASHBY SJ et al: Structure of a human lysosomal sulfatase. Structure (1997) 5:277–289.
  • RECKSIEK M, SELMER T, DIERKS T, SCHMIDT B, VON FIGURA K: Sulfatases, trapping of the sulfated enzyme intermediate by substituting the active site formylglycine.. Chem. (1998) 273:6096–6103.
  • VON BOLOW R, SCHMIDT B, DIERKS T, VON FIGURA K, USON I: Crystal structure of an enzyme-substrate complex provides insight into the interaction between human arylsulfatase A and its substrates during catalysis. J. Ma Biol. (2001) 305:269–277.
  • WALDOW A, SCHMIDT B, DIERKS T, VON BOLOW R, VON FIGURA K: Amino acid residues forming the active site of arylsulfatase A. Biol. Chem. (1999) 274:12284–12288.
  • UHLHORN-DIERKS G, KOLTER T, SANDHOFF K: How does nature cleave sulfuric acid esters? A novel posttranslational modification of sulfatases Angew. Chem. (Int. Ed.) (1998) 37:2453–2455.
  • PUROHIT A, WILLIAMS GJ, HOWARTH NM, POTTER BVL, MJ: Inactivation of steroid sulfatase by an active site directed inhibitor, estrone 3-0-sulfamate. Biochemistry (1995) 34:11508–11514.
  • BALLABIO A, SHAPIRO LJ: Steroid sulfatase deficiency and X-linked ichthyosis. In: The Metabolic and Molecular Bases of Inherited Disease. Scriver CR, Beaudet AL, Sly WS, Valle D (Eds), McGraw-Hill, New York, USA (1995):2999–3022.
  • HERNANDEZ-MARTIN A, GONZALEZ-SARMIENTO R DE UNAMUNO P: X-linked ichthyosis. Br. Dermatol (1999) 141:617–627.
  • WILLIAMS ML, ELIAS PM: Stratum corneum lipids in disorders of cornification. Gin. Invest. (1981) 68:1404–1410.
  • MARANO RPC, ORTIZ MA, 0, UXO M, IGLESIAS E: Ocular findings associated with congenital X-linked ichthyosis. Ann. Ophthalmol (1991) 23:167–173.
  • PASQUALINI JR, GELLY C, BL, VELLA C: Importance of estrogen sulfates in breast cancer.' Steroid Biochem. (1989) 34:155–163.
  • REED MJ, PUROHIT A: Sulphatase inhibitors: the rationale for the development of a new endocrine therapy. Rev Endocrine Related Cancer (1993) 45:51–62.
  • REED MJ, PUROHIT A, HOWARTH NM, POTTER BVL: Steroid sulphatase inhibitors: a new endocrine therapy. Drugs of the Future (1994) 19:673–680.
  • PAYNE AH, LAWRENCE CC, DL, JAFFE RB: Intranuclear binding of 173-estradiol and estrone in female ovine pituitaries following incubation with estrone sulfate. J. Biol. Chem. (1973) 248:1598–1602.
  • UTSUMI T, YOSHIMURA N, S, MARUTA M, MAEDA K, HARADA N: Elevated steroid sulfatase expression in breast cancers. Steroid Biochem. Ma Biol. (2000) 73:141–145.
  • UTSUMI T, YOSHIMURA N, TAKEUCHI S et al.: Steroid sulfatase expression is an independent predictor of recurrence in human breast cancer. Cancer Res. (1999) 59:377–381.
  • SELCER KW, JAGANNATHAN S, RHODES ME, LI PK: Inhibition of placental estrone sulfatase activity and MCF-7 breast cancer cell proliferation by estrone-3-amino derivatives. Steroid Biochem. MM. Biol. (1996) 59:83–91.
  • SELCER KW, HEDGE PV, LI PK: Inhibition of estrone sulfatase and proliferation of human breast cancer cells by nonsteroidal (p- asulfamoy1)-N-alkanoyl tyramines. Cancer Res. (1997) 57:702–707.
  • BILLICH A, NUSSBAUMER P, LEHR P: Stimulation of MCF-7 breast cancer cell proliferation by estrone sulfate and dehydroepiandrosterone sulfate: inhibition by novel non-steroidal steroid sulfatase inhibitors. " Steroid. Biochem. Mol. Biol (2000) 73:225–235.
  • •DHEAS can stimulate breast cancer cell growth in an aromatase-independent pathway.
  • PUROHIT A, WILLIAMS GJ, CJ, POTTER BVL, REED MJ: hi vivo inhibition of oestrone sulphatase and dehydroepiandrosterone suphatase by oestrone-3-0-sulphamate. Int. .1. Cancer (1995) 63:106–111.
  • PUROHIT A, WOO LW, POTTER By, REED MJ: In vivo inhibition of estrone sulfatase activity and growth of nitrosomethylurea-induced mammary tumors by 667COUMATE. Cancer Res. (2000) 60:3394–3396.
  • •In vivo confirmation of antiturnour activity by a non-oestrogenic STS inhibitor.
  • PETERS RH, CHAO WR, SATO B, SHIGENO K, ZAVERI NT, TANABE M: Steroidal oxathiazine inhibitors of estrone sulfatase. Steroids (2003) 68:97–110.
  • LE BAIL JC, ALLEN K, NICOLAS JC, HABRIOUX G: Dehydroepiandrosterone sulfate estrogenic action at its physiological plasma concentration in human breast cancer cell lines. Anti-Cancer Res. (1998) 18:1683–1688.
  • SELCER KW, KABLER H, SARAP J, XIAO Z, LI PK: Inhibition of Aeryl sulfatase activity in LNCaP human prostate cancer cells. Steroids (2002) 67:821–826.
  • FAREDIN I, KOKAI K, 10TH I, FAZEKAS AG, JULESZ M: The metabolism of [14q-dehydroepiandrosterone by human skin M vitro. Acta Med. Acad. Sci. Hung. (1970) 27:95–102.
  • VOIGT W, SAWAYA ME, HSIA SL, AMTHOR C: Cutaneous production of potent androgens from dehydroepiandrosterone in adult women. IRSC Med. Sci. (1982) 10:529–530.
  • HOFFMANN R, HAPPLE R: Current understanding of androgenic alopecia. Part I: etiopathogenesis. Eur. DermatoL (2000) 10:319–327.
  • HOFFMANN R, ROT A, NIIYAMA S, BILLICH A: Steroid sulfatase in the human hair follicle concentrates in the dermal papilla. Invest. Dermatol (2001) 117:1342–1348.
  • BILLICH A, ROT A, LAM C, SCHMIDT JB, SCHUSTER I: Immunohistochemical localization of steroid sulfatase in acne lesions: implications for the contribution of dehydroepiandrosterone sulfate to the pathogenesis of acne. Harm. Res. (2000) 532: 92–103.
  • ••Evidence for involvement of STS in thepathogenesis of acne.
  • CHEN W THIBOUTOT D, ZOUBOULIS CC: Cutaneous androgen metabolism: basic research and clinical perspectives.' Invest. Dermal& (2002) 119:992–1007.
  • WOLF OT, KIRSCHBAUM C: Actions of dehydroepiandrosterone and its sulfate in central nervous system: effects on cognition and emotion in animals and humans. Brain Res. Rev (1999) 30:264–288.
  • LI PK, RHODES ME, JAGANNATHAN S, JOHNSON DA: Reversal of scopolamine induced amnesia in rats by the steroids sulfatase inhbitor estrone-3- asulfamate. Cognitive Brain Res. (1995) 2:251–254.
  • LI PK, RHODES ME, BURKE AM, JOHNSON DA: Memory enhancement mediated by the steroid sulfatase inhibitor (p- 0-sulfamoy1)-N-tetradecanoyl tyramine. Life Sci. (1996) 60:45–51.
  • RHODES ME, LI PK, BURKE AM, JOHNSON DA: Enhanced plasma DHEAS, brain acetylcholine and memory mediated by steroid sulfatase inhibition. Brain Res. (1997) 773:28–32.
  • JOHNSON DA, WU T, LI P, MAHER TJ: The effect of steroid sulfatase inhibition on learning and spatial memory. Brain Res. (2000) 865.286–290.
  • FLOOD JF, FARR SA, JOHNSON DA, LI PK, MORLEY JE: Peripheral steroid sulfatase inhibition potentiates improvement of memory retention for hippocampally administered dehydroepiandrosterone sulfate but not pregnenolone sulfate. Psychoneumendocrinology (1999) 24:799–811.
  • NICOLAS LB, PINOTEAU W, PAPOT S, ROUTIER S, GUILLAUMET G, MORTAUD S: Aggressive behavior induced by the steroid sulfatase inhibitor COUMATE and by DHEAS in CBA/H mice. Brain Res. (2001) 922:216–222.
  • DAYNES RA, ARANEO BA, TA, HUANG K, DUDLEY D: Regulation of murine lymphokine production in vivo. III. The lymphoid tissue microenvironment exerts regulatory influences over T helper cell function.' Exp. Med. (1990) 171:979–996.
  • SUITTERS AJ, SHAW S, WALES MR et al.: Immune enhancing effects of dehydroepiandrosterone and dehydroepiandrosterone sulphate and the role of steroid sulphatase. Immunology(1997) 91:314–321.
  • FOULKES R, SHAW S, SUITTERS A: Immunological consequences of inhibiting dehydroepiandrosterone (DHEA) sulfatase in vivo. In: Steroid hormones and the T cell cytokine profile. Rook GAW, Lightman S (Eds), Springer, Berlin (1998):135–162.
  • 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. Steroid Biochem. MM. Biol. (1995) 55:395–403.
  • SHANKARAN R, AMEEN M, WL, DAVIDSON RG, PL: Characterization of arylsulfatase isoenzymes from human liver and placenta. Biochim. Biophys. Acta (1991) 1078:251–257.
  • SUZUKI T, HIRATO K, YANAIHARA T et al.: Purification and properties of steroid sulfatase from human placenta. Endocrinol fpn. (1992) 39:93–101.
  • NUSSBAUMER P, BILBAN M, BILLICH A: 4,4'-Benzophenone- 0, U-disulfamate: a potent inhibitor of steroid sulfatase. Bioorg. Med. Chem. Lett. (2002) 12:2093–2095.
  • NUSSBAUMER P, LEHR P, BILLICH A:2-Substituted 4- (thio)chromenone 6-0-sulfamates: potent inhibitors of human steroid sulfatase. J.Med.Chem. (2002) 45:4310–4320.
  • •Paper on highly potent STS inhibitors.
  • CIOBANU LC, BOIVIN RP, LUU-THE V, D: Synthesis and steroid sulphatase inhibitory activity of C-19- and C-21-steroidal derivatives bearing a benzyl-inhibiting group. Eur: j Med. Chem. (2001) 36:659–671.
  • BILBAN M, BILLICH A, AUER M, NUSSBAUMER P: New fluorogenic substrate for the first continuous steroid sulfatase assay. Bioorg. Med. Chem. Lett. (2000) 10:967–969.
  • WOO LL, PUROHIT A, MALINI, B, REED MJ, POTTER BV: Potent active site-directed inhibition of steroid sulphatase by tricyclic coumarin-based sulphamates. Chem. Biol. (2000) 7:773–791.
  • SAJI S, TOI M: Aromatase inhibitors and other novel agents in breast cancer treatment. Expert Opin. Emerging Drugs. (2002) 7:301–317.
  • HOWARTH NM, COOPER G, PUROHIT A, DUNCAN L, REED MJ, POTTER BVL: 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.
  • DUNCAN L, PUROHIT A, NM, POTTER BVL, REED MJ: Inhibition of estrone sulfatase activity by estrone-3-methylthiophosphonate: a potential therapeutic agent in breast cancer. Cancer Res. (1993) 53:298–303.
  • POIRIER D, BOIVIN RP: 17a-Alkyl- or 17a-substituted benzy1-1713-estradiols: a new family of estrone-sulfatase inhibitors. Bioorg. Med. Chem. Lett. (1998) 8:1891–1896.
  • CIOBANU LC, BOIVIN RP, LUU-THE V, LABRIE F, POIRIER D: Potent inhibition of steroid sulfatase activity by 3-0-sulfamate 17a-benzyl (or 4- teributylbenzyflestra-1,3,5(10)-trienes: combination of two substituents at positions C-3 and 17a of estradiol. J. Med. Chem. (1999) 42:2280–2286.
  • ••Paper on potent reversible and highly potentirreversible STS inhibitors. Also presented at Proceedings of the 216th ACS National Meeting, Boston, USA(August 23–27 1998) Abst. 280.
  • BOIVIN RP, LABRIE F, POIRIER D: 17a-alkan (or alkyn) amide derivatives of estradiol as inhibitors of steroid-sulfatase activity. Steroids (1999) 64:825–833.
  • BOIVIN RP, LUU-THE V, LACHANCE R, LABRIE F, POIRIER D: Structure-activity relationships of 17a-derivatives of estradiol as inhibitors of steroid sulfatase. J. Med. Chem. (2000) 43:4465–4478.
  • JOTTEN P, SCHUMANN W, HARTL A et al.: A novel type of non-steroidal estrone sulfatase inhibitors. Bioorg. Med. Chem. Lett. (2002) 12:1339–1342.
  • HOWARTH NM, PUROHIT A, REED MJ, POTTER BVL: Estrone sulfamates: potent inhibitors of estrone sulfatase with therapeutic potential. Med. Chem. (1994) 37:219–221.
  • WOO LWL, PUROHIT A, REED MJ, POTTER BVL: Active site directed inhibition of estrone sulfatase by non-steroidal coumarin sulfamates. Med. Chem. (1996) 39:1349–1351.
  • WOO LWL, HOWARTH NM, PUROHIT A, HEJAZ HAM, REED MJ, POTTER BVL: Steroidal and non-steroidal sulfamates as potent inhibitors of steroid sulfatase. J. Med. Chem. (1998) 41:1068–1083.
  • LI PK, MILANO S, KLUTH L, ME: Synthesis and sulfatase inhibitory activities of non-steroidal estrone sulfatase inhibitors. J. Steroid Biochem. MoL Biol. (1996) 59:41–48.
  • PUROHIT A, WOO LWL, SINGH A, WINTERBORN CJ, POTTER BVL, REED MJ: In vivo actvity of 4-methylcoumarin-7-0-sulfamate, a non-steroidal non-estrogenic steroid sulfatase inhibitor. Cancer Res. (1996) 56.4950–4955.
  • LI PK, CHU GH, GUO JP, PETERS A, SELCER KW: Development of potent non-estrogenic estrone sulfatase inhbitors. Steroids (1998) 63:425–432.
  • PUROHIT A, VERNON KA, AE et al: The development of A-ring modified analogues of oestrone-3- a sulphamate as potent steroid sulphatase inhibitors with reduced oestrogenicity. Biochem. Mol Biol. (1998) 64:269–275.
  • KOLLI A, CHU HH, RHODES ME, INOUE K, SELCER KW, LI PK: Development of (p- Osulfamoy1)-N-alkanoyl-phenylalkyl amines as non-steroidal estrone sulfatase inhibitors. I Steroid Biochem. Molec. Biol. (1999) 68:31–40.
  • MALINI B, PUROHIT A, GANESHAPILLAI D, WOO LW, POTTER BV, REED MJ: Inhibition of steroid sulphatase activity by tricyclic coumarin sulphamates. J. Steroid Biochem. Ma Biol. (2000) 75:253–258.
  • SAHM UG, WILLIAMS GJ, PUROHIT A et al.: Development of an oral formulation for oestrone 3-0-sulphamate, a potent sulphatase inhibitor. Pharm. Sci. (1996) 2:17–20.
  • POIRIER D, CIOBANU LC, MALTAIS R: Steroid sulfatase inhibitors. Expert Opin. Titer. Patents (1999) 9:1083–1099.
  • ••Good review on STS inhibitors.
  • SMITH HJ, NICHOLLS PJ, SIMONS C, LE LAIN R: Inhibitors of steroidogenesis as agents for the treatment of hormone-dependent cancers. Exp. Opin. Titer: Patents (2001) 11:789–824.
  • •Good review on inhibitors of, including STS inhibitors.
  • CUSHMAN M, HE H-M, JA, LIN CM, HAMEL E: Synthesis, antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methoxyestradiol, an endogenous mammalian metabolite of estradiol that inhibits tubulin polymerization by binding to the colchicines binding site. J. Med. Chem. (1995) 38:2041–2049.
  • HOOGENBOOM LAP, DE HAAN L, HOOIJERINK D et al.: Estrogenic activity of estradiol and its metabolites in the ER-CALUX assay with human T47D breast cells. APMIS (2001) 109:101–107.
  • FOTSIS T, ZHANG Y, PEPPER MS et al.:The endogenous estrogen metabolite 2-methoxyestradiol inhibits angiogenesis and suppresses tumor growth. Nature (1994) 368:237–239.
  • PUROHIT A, HEJAZ HAM, WALDEN L et al.: The effect of 2-methoxyoestrone-3-0-sulfamate on the growth of breast cancer cells and induced mammary tumours. Int. J. Cancer (2000) 85:584–589.
  • •In vivo confirmation of antiturnour and non-oestrogenic activity by a potent STS inhibitor.
  • HEJAZ HAM, PUROHIT A, ME REED MJ, POTTER BVL: Synthesis and biological activity of the superestrogen (. -10-sulfamoy1-1,3,5(10)-estratriene: X-ray crystal structure of (L)-17-oximino-3-hydroxy-1, 3, 5 (10)-estratriene. J. Med. Chem. (1999) 42:3188–3192.
  • CIOBANU LC, LUU-THE V, POIRIER D:Non-steroidal compounds designed to mimic potent steroid sulfatase inhibitors. J. Steroid Biochem. Ma Biol. (2002) 80:339–353.
  • •Very potent monoarylsulfarnate-type STS inhibitors.
  • AHMED S, JAMES K, OWEN CP, PATEL CK, PATEL M: Novel inhibitors of the enzyme estrone sulfatase (ES). Bioorg. Med. Chem. Lett. (2001) 11:841–844.
  • AHMED S, JAMES K, OWEN CP, PATEL CK, PATEL M: Hydrophobicity, a physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES). Bioorg. Med. Chem. Lett. (2001) 11:2525–2528.
  • AHMED S, JAMES K, OWEN CP, PATEL CK: Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES). J. Steroid Biochem. MM. Biol. (2002) 80:419–427.
  • AHMED S, JAMES K, OWEN CP, PATEL CK: 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.
  • CHU G-H, PETERS A, SELCER KW, LI PK: Synthesis and sulfatase inhibitory activities of (E)- and (Z)-4-hydroxytamoxifen sulfamates. Bioorg. Med. Chem. Lett. (1999) 9:141–144.

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