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Volumn 88, Issue 4-5, 2004, Pages 409-420

2-Phenylindole sulfamates: Inhibitors of steroid sulfatase with antiproliferative activity in MCF-7 breast cancer cells

Author keywords

Breast cancer; Enzyme inhibition; Phenylindole sulfamate; Steroid sulfatase

Indexed keywords

2 PHENYLINDOLE SULFAMATE; ENZYME INHIBITOR; ESTRONE SULFATE; INDOLE DERIVATIVE; STERYL SULFATASE; UNCLASSIFIED DRUG;

EID: 2442563905     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2003.12.012     Document Type: Article
Times cited : (40)

References (47)
  • 1
    • 0034016224 scopus 로고    scopus 로고
    • Comparison of estrogen concentrations, estrone sulfatase and aromatase activities in normal, and in cancerous, human breast tissues
    • Chetrite G.S., Cortes-Prieto J., Philippe J.C., Wright F., Pasqualini J.R. Comparison of estrogen concentrations, estrone sulfatase and aromatase activities in normal, and in cancerous, human breast tissues. J. Steroid Biochem. Mol. Biol. 72:2000;23-27
    • (2000) J. Steroid Biochem. Mol. Biol. , vol.72 , pp. 23-27
    • Chetrite, G.S.1    Cortes-Prieto, J.2    Philippe, J.C.3    Wright, F.4    Pasqualini, J.R.5
  • 2
    • 0029872530 scopus 로고    scopus 로고
    • Concentrations of estrone, estradiol, and estrone sulfate and evaluation of sulfatase and aromatase activities in pre- and postmenopausal breast cancer patients
    • Pasqualini J.R., Chetrite G., Blacker C., Feinstein M.C., Delalonde L., Talbi M., Maloche C. Concentrations of estrone, estradiol, and estrone sulfate and evaluation of sulfatase and aromatase activities in pre- and postmenopausal breast cancer patients. J. Clin. Endocrinol. Metab. 81:1996;1460-1464
    • (1996) J. Clin. Endocrinol. Metab. , vol.81 , pp. 1460-1464
    • Pasqualini, J.R.1    Chetrite, G.2    Blacker, C.3    Feinstein, M.C.4    Delalonde, L.5    Talbi, M.6    Maloche, C.7
  • 4
    • 0029045633 scopus 로고
    • 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
    • Pasqualini J.R., Chetrite G., Nguyen B.L., Maloche C., Delalonde L., Talbi M., Feinstein M.C., Blacker C., Botella J., 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. 53:1995;407-412
    • (1995) J. Steroid Biochem. Mol. Biol. , vol.53 , pp. 407-412
    • Pasqualini, J.R.1    Chetrite, G.2    Nguyen, B.L.3    Maloche, C.4    Delalonde, L.5    Talbi, M.6    Feinstein, M.C.7    Blacker, C.8    Botella, J.9    Paris, J.10
  • 5
    • 0034993363 scopus 로고    scopus 로고
    • Analysis and characteristics of multiple types of human 17β-hydroxysteroid dehydrogenase
    • Luu-The V. Analysis and characteristics of multiple types of human 17β-hydroxysteroid dehydrogenase. J. Steroid Biochem. Mol. Biol. 76:2001;143-151
    • (2001) J. Steroid Biochem. Mol. Biol. , vol.76 , pp. 143-151
    • Luu-The, V.1
  • 6
    • 0035931123 scopus 로고    scopus 로고
    • 17β-Hydroxysteroid dehydrogenase type 7- an ancient 3-ketosteroid reductase of cholesterogenesis
    • Breitling R., Krazeisen A., Moller G., Adamski J. 17β-Hydroxysteroid dehydrogenase type 7- an ancient 3-ketosteroid reductase of cholesterogenesis. Mol. Cell Endocrinol. 171:2001;199-204
    • (2001) Mol. Cell Endocrinol. , vol.171 , pp. 199-204
    • Breitling, R.1    Krazeisen, A.2    Moller, G.3    Adamski, J.4
  • 8
    • 0035529054 scopus 로고    scopus 로고
    • Abnormal expression of 17β-hydroxysteroid dehydrogenases in breast cancer predicts late recurrence
    • Gunnarsson C., Olsson B.M., Stal O. Abnormal expression of 17β-hydroxysteroid dehydrogenases in breast cancer predicts late recurrence. Cancer Res. 61:2001;8448-8451
    • (2001) Cancer Res. , vol.61 , pp. 8448-8451
    • Gunnarsson, C.1    Olsson, B.M.2    Stal, O.3
  • 9
    • 0034982135 scopus 로고    scopus 로고
    • The selective estrogen enzyme modulator (SEEM) in breast cancer
    • Chetrite G.S., Pasqualini J.R. The selective estrogen enzyme modulator (SEEM) in breast cancer. J. Steroid Biochem. Mol. Biol. 76:2001;95-104
    • (2001) J. Steroid Biochem. Mol. Biol. , vol.76 , pp. 95-104
    • Chetrite, G.S.1    Pasqualini, J.R.2
  • 11
    • 0038175996 scopus 로고    scopus 로고
    • High expression of steroid sulfatase mRNA predicts poor prognosis in patients with estrogen receptor-positive breast cancer
    • Miyoshi Y., Ando A., Hasegawa S., Ishitobi M., Taguchi T., Tamaki Y., Noguchi S. High expression of steroid sulfatase mRNA predicts poor prognosis in patients with estrogen receptor-positive breast cancer. Clin. Cancer Res. 9:2003;2288-2293
    • (2003) Clin. Cancer Res. , vol.9 , pp. 2288-2293
    • Miyoshi, Y.1    Ando, A.2    Hasegawa, S.3    Ishitobi, M.4    Taguchi, T.5    Tamaki, Y.6    Noguchi, S.7
  • 12
    • 0030236696 scopus 로고    scopus 로고
    • Inhibition of placental estrone sulfatase activity and MCF-7 breast cancer cell proliferation by estrone-3-amino derivatives
    • Selcer K.W., Jagannathan S., Rhodes M.E., Li P.K. Inhibition of placental estrone sulfatase activity and MCF-7 breast cancer cell proliferation by estrone-3-amino derivatives. J. Steroid Biochem. Mol. Biol. 59:1996;83-91
    • (1996) J. Steroid Biochem. Mol. Biol. , vol.59 , pp. 83-91
    • Selcer, K.W.1    Jagannathan, S.2    Rhodes, M.E.3    Li, P.K.4
  • 13
    • 0028948089 scopus 로고
    • Estrone sulfate analogs as estrone sulfatase inhibitors
    • Li P.K., Pillai R., Dibbelt L. Estrone sulfate analogs as estrone sulfatase inhibitors. Steroids. 60:1995;299-306
    • (1995) Steroids , vol.60 , pp. 299-306
    • Li, P.K.1    Pillai, R.2    Dibbelt, L.3
  • 14
    • 0028009821 scopus 로고
    • Estrone sulfamates: Potent inhibitors of estrone sulfatase with therapeutic potential
    • Howarth N.M., Purohit A., Reed M.J., Potter B.V. Estrone sulfamates: potent inhibitors of estrone sulfatase with therapeutic potential. J. Med. Chem. 37:1994;219-221
    • (1994) J. Med. Chem. , vol.37 , pp. 219-221
    • Howarth, N.M.1    Purohit, A.2    Reed, M.J.3    Potter, B.V.4
  • 15
    • 0029620774 scopus 로고
    • Sulfamates of various estrogens are prodrugs with increased systemic and reduced hepatic estrogenicity at oral application
    • Elger W., Schwarz S., Hedden A., Reddersen G., Schneider B. Sulfamates of various estrogens are prodrugs with increased systemic and reduced hepatic estrogenicity at oral application. J. Steroid Biochem. Mol. Biol. 55:1995;395-403
    • (1995) J. Steroid Biochem. Mol. Biol. , vol.55 , pp. 395-403
    • Elger, W.1    Schwarz, S.2    Hedden, A.3    Reddersen, G.4    Schneider, B.5
  • 16
    • 0031947952 scopus 로고    scopus 로고
    • The development of A-ring modified analogues of oestrone-3-O-sulphamate as potent steroid sulphatase inhibitors with reduced oestrogenicity
    • Purohit A., Vernon K.A., Hummelinck A.E., Woo L.W., Hejaz H.A., Potter B.V., 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. 64:1998;269-275
    • (1998) J. Steroid Biochem. Mol. Biol. , vol.64 , pp. 269-275
    • Purohit, A.1    Vernon, K.A.2    Hummelinck, A.E.3    Woo, L.W.4    Hejaz, H.A.5    Potter, B.V.6    Reed, M.J.7
  • 17
    • 0033578075 scopus 로고    scopus 로고
    • Potent inhibition of steroid sulfatase activity by 3-O-sulfamate 17α-benzyl(or 4′-tert-butylbenzyl)estra-1,3,5(10)-trienes: Combination of two substituents at positions C3 and C17α of estradiol
    • Ciobanu L.C., Boivin R.P., Luu T.V., Labrie F., Poirier D. Potent inhibition of steroid sulfatase activity by 3-O-sulfamate 17α-benzyl(or 4′-tert-butylbenzyl)estra-1, 3, 5(10)-trienes: combination of two substituents at positions C3 and C17α of estradiol. J. Med. Chem. 42:1999;2280-2286
    • (1999) J. Med. Chem. , vol.42 , pp. 2280-2286
    • Ciobanu, L.C.1    Boivin, R.P.2    Luu, T.V.3    Labrie, F.4    Poirier, D.5
  • 21
    • 0037321793 scopus 로고    scopus 로고
    • Inhibition of MCF-7 breast cancer cell proliferation and in vivo steroid sulphatase activity by 2-methoxyoestradiol-bis-sulphamate
    • Raobaikady B., Purohit A., Chander S.K., Woo L.W., Leese M.P., Potter B.V., Reed M.J. Inhibition of MCF-7 breast cancer cell proliferation and in vivo steroid sulphatase activity by 2-methoxyoestradiol-bis-sulphamate. J. Steroid Biochem. Mol. Biol. 84:2003;351-358
    • (2003) J. Steroid Biochem. Mol. Biol. , vol.84 , pp. 351-358
    • Raobaikady, B.1    Purohit, A.2    Chander, S.K.3    Woo, L.W.4    Leese, M.P.5    Potter, B.V.6    Reed, M.J.7
  • 22
    • 0033780686 scopus 로고    scopus 로고
    • Potent active site-directed inhibition of steroid sulphatase by tricyclic coumarin-based sulphamates
    • Woo L.L., Purohit A., Malini B., Reed M.J., Potter B.V. Potent active site-directed inhibition of steroid sulphatase by tricyclic coumarin-based sulphamates. Chem. Biol. 7:2000;773-791
    • (2000) Chem. Biol. , vol.7 , pp. 773-791
    • Woo, L.L.1    Purohit, A.2    Malini, B.3    Reed, M.J.4    Potter, B.V.5
  • 23
    • 0037068475 scopus 로고    scopus 로고
    • 2-Substituted 4-(thio)chromenone 6-O-sulfamates: Potent inhibitors of human steroid sulfatase
    • Nussbaumer P., Lehr P., Billich A. 2-Substituted 4-(thio)chromenone 6-O-sulfamates: potent inhibitors of human steroid sulfatase. J. Med. Chem. 45:2002;4310-4320
    • (2002) J. Med. Chem. , vol.45 , pp. 4310-4320
    • Nussbaumer, P.1    Lehr, P.2    Billich, A.3
  • 24
    • 0036229620 scopus 로고    scopus 로고
    • Nonsteroidal compounds designed to mimic potent steroid sulfatase inhibitors
    • Ciobanu L.C., Luu-The V., Poirier D. Nonsteroidal compounds designed to mimic potent steroid sulfatase inhibitors. J. Steroid Biochem. Mol. Biol. 80:2002;339-353
    • (2002) J. Steroid Biochem. Mol. Biol. , vol.80 , pp. 339-353
    • Ciobanu, L.C.1    Luu-The, V.2    Poirier, D.3
  • 25
    • 0036225438 scopus 로고    scopus 로고
    • Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES)
    • Ahmed S., James K., Owen C.P., Patel C.K. Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES). J. Steroid Biochem. Mol. Biol. 80:2002;419-427
    • (2002) J. Steroid Biochem. Mol. Biol. , vol.80 , pp. 419-427
    • Ahmed, S.1    James, K.2    Owen, C.P.3    Patel, C.K.4
  • 26
    • 0036979174 scopus 로고    scopus 로고
    • Sulfamoyloxy-substituted 2-phenylindoles: Antiestrogen-based inhibitors of the steroid sulfatase in human breast cancer cells
    • Golob T., Liebl R., von Angerer E. Sulfamoyloxy-substituted 2-phenylindoles: antiestrogen-based inhibitors of the steroid sulfatase in human breast cancer cells. Bioorg. Med. Chem. 10:2002;3941-3953
    • (2002) Bioorg. Med. Chem. , vol.10 , pp. 3941-3953
    • Golob, T.1    Liebl, R.2    Von Angerer, E.3
  • 27
    • 0032589988 scopus 로고    scopus 로고
    • 17α-Alkan (or alkyn) amide derivatives of estradiol as inhibitors of steroid-sulfatase activity
    • Boivin R.P., Labrie F., Poirier D. 17α-Alkan (or alkyn) amide derivatives of estradiol as inhibitors of steroid-sulfatase activity. Steroids. 64:1999;825-833
    • (1999) Steroids , vol.64 , pp. 825-833
    • Boivin, R.P.1    Labrie, F.2    Poirier, D.3
  • 28
    • 0034676325 scopus 로고    scopus 로고
    • Structure-activity relationships of 17α-derivatives of estradiol as inhibitors of steroid sulfatase
    • Boivin R.P., Luu-The V., Lachance R., Labrie F., Poirier D. Structure-activity relationships of 17α-derivatives of estradiol as inhibitors of steroid sulfatase. J. Med. Chem. 43:2000;4465-4478
    • (2000) J. Med. Chem. , vol.43 , pp. 4465-4478
    • Boivin, R.P.1    Luu-The, V.2    Lachance, R.3    Labrie, F.4    Poirier, D.5
  • 29
    • 0030764441 scopus 로고    scopus 로고
    • Structure-activity relationship studies of the amide functionality in (p-O-sulfamoyl)-N-alkanoyl tyramines as estrone sulfatase inhibitors
    • Chu G.H., Milano S., Kluth L., Rhodes M., Boni R., Johnson D.A., Li P.K. Structure-activity relationship studies of the amide functionality in (p-O-sulfamoyl)-N-alkanoyl tyramines as estrone sulfatase inhibitors. Steroids. 62:1997;530-535
    • (1997) Steroids , vol.62 , pp. 530-535
    • Chu, G.H.1    Milano, S.2    Kluth, L.3    Rhodes, M.4    Boni, R.5    Johnson, D.A.6    Li, P.K.7
  • 30
    • 0033062017 scopus 로고    scopus 로고
    • Development of (p-O-sulfamoyl)-N-alkanoyl-phenylalkyl amines as non-steroidal estrone sulfatase inhibitors
    • Kolli A., Chu G.H., Rhodes M.E., Inoue K., Selcer K.W., Li P.K. Development of (p-O-sulfamoyl)-N-alkanoyl-phenylalkyl amines as non-steroidal estrone sulfatase inhibitors. J. Steroid Biochem. Mol. Biol. 68:1999;31-40
    • (1999) J. Steroid Biochem. Mol. Biol. , vol.68 , pp. 31-40
    • Kolli, A.1    Chu, G.H.2    Rhodes, M.E.3    Inoue, K.4    Selcer, K.W.5    Li, P.K.6
  • 31
    • 0026701699 scopus 로고
    • ICI 182,780, a new antioestrogen with clinical potential
    • Wakeling A.E., Bowler J. ICI 182, 780, a new antioestrogen with clinical potential. J. Steroid Biochem. Mol. Biol. 43:1992;173-177
    • (1992) J. Steroid Biochem. Mol. Biol. , vol.43 , pp. 173-177
    • Wakeling, A.E.1    Bowler, J.2
  • 32
    • 0030130570 scopus 로고    scopus 로고
    • 2-Phenylindoles with sulfur containing side chains. Estrogen receptor affinity, antiestrogenic potency, and antitumor activity
    • Biberger C., von Angerer E. 2-Phenylindoles with sulfur containing side chains. Estrogen receptor affinity, antiestrogenic potency, and antitumor activity. J. Steroid Biochem. Mol. Biol. 58:1996;31-43
    • (1996) J. Steroid Biochem. Mol. Biol. , vol.58 , pp. 31-43
    • Biberger, C.1    Von Angerer, E.2
  • 33
    • 0021738560 scopus 로고
    • 2-Phenylindoles. Relationship between structure, estrogen receptor affinity, and mammary tumor inhibiting activity in the rat
    • von Angerer E., Prekajac J., Strohmeier J. 2-Phenylindoles. Relationship between structure, estrogen receptor affinity, and mammary tumor inhibiting activity in the rat. J. Med. Chem. 27:1984;1439-1447
    • (1984) J. Med. Chem. , vol.27 , pp. 1439-1447
    • Von Angerer, E.1    Prekajac, J.2    Strohmeier, J.3
  • 34
    • 0030476245 scopus 로고    scopus 로고
    • Synthesis of estrogen sulfamates: Compounds with a novel endocrinological profile
    • Schwarz S., Thieme I., Richter M., Undeutsch B., Henkel H., Elger W. Synthesis of estrogen sulfamates: compounds with a novel endocrinological profile. Steroids. 61:1996;710-717
    • (1996) Steroids , vol.61 , pp. 710-717
    • Schwarz, S.1    Thieme, I.2    Richter, M.3    Undeutsch, B.4    Henkel, H.5    Elger, W.6
  • 36
    • 0017184389 scopus 로고
    • A rapid and sensitive method for quantification of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford M.M. A rapid and sensitive method for quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72:1976;248-248
    • (1976) Anal. Biochem. , vol.72 , pp. 248-248
    • Bradford, M.M.1
  • 37
    • 0027234663 scopus 로고
    • Detection of breast cancer-associated estrone sulfatase in breast cancer biopsies and cell lines using polymerase chain reaction
    • Evans T.R., Rowlands M.G., Luqmani Y.A., Chander S.K., Coombes R.C. Detection of breast cancer-associated estrone sulfatase in breast cancer biopsies and cell lines using polymerase chain reaction. J. Steroid Biochem. Mol. Biol. 46:1993;195-201
    • (1993) J. Steroid Biochem. Mol. Biol. , vol.46 , pp. 195-201
    • Evans, T.R.1    Rowlands, M.G.2    Luqmani, Y.A.3    Chander, S.K.4    Coombes, R.C.5
  • 38
  • 40
    • 0031045478 scopus 로고    scopus 로고
    • Inhibition of estrone sulfatase and proliferation of human breast cancer cells by nonsteroidal (p-O-sulfamoyl)-N-alkanoyl tyramines
    • Selcer K.W., Hegde P.V., Li P.K. Inhibition of estrone sulfatase and proliferation of human breast cancer cells by nonsteroidal (p-O-sulfamoyl)-N- alkanoyl tyramines. Cancer Res. 57:1997;702-707
    • (1997) Cancer Res. , vol.57 , pp. 702-707
    • Selcer, K.W.1    Hegde, P.V.2    Li, P.K.3
  • 41
    • 0035660223 scopus 로고    scopus 로고
    • Purification, characterization and crystallization of human placental estrone/dehydroepiandrosterone sulfatase, a membrane-bound enzyme of the endoplasmic reticulum
    • Hernandez-Guzman F.G., Higashiyama T., Osawa Y., Ghosh D. Purification, characterization and crystallization of human placental estrone/ dehydroepiandrosterone sulfatase, a membrane-bound enzyme of the endoplasmic reticulum. J. Steroid Biochem. Mol. Biol. 78:2001;441-450
    • (2001) J. Steroid Biochem. Mol. Biol. , vol.78 , pp. 441-450
    • Hernandez-Guzman, F.G.1    Higashiyama, T.2    Osawa, Y.3    Ghosh, D.4
  • 42
    • 0038265006 scopus 로고    scopus 로고
    • Structure of human estrone sulfatase suggests functional roles of membrane association
    • Hernandez-Guzman F.G., Higashiyama T., Pangborn W., Osawa Y., Ghosh D. Structure of human estrone sulfatase suggests functional roles of membrane association. J. Biol. Chem. 278:2003;22989-22997
    • (2003) J. Biol. Chem. , vol.278 , pp. 22989-22997
    • Hernandez-Guzman, F.G.1    Higashiyama, T.2    Pangborn, W.3    Osawa, Y.4    Ghosh, D.5
  • 43
    • 0029114308 scopus 로고
    • Inactivation of steroid sulfatase by an active site-directed inhibitor, estrone-3-O-sulfamate
    • Purohit A., Williams G.J., Howarth N.M., Potter B.V., Reed M.J. Inactivation of steroid sulfatase by an active site-directed inhibitor, estrone-3-O-sulfamate. Biochemistry. 34:1995;11508-11514
    • (1995) Biochemistry , vol.34 , pp. 11508-11514
    • Purohit, A.1    Williams, G.J.2    Howarth, N.M.3    Potter, B.V.4    Reed, M.J.5
  • 44
    • 0033734846 scopus 로고    scopus 로고
    • Stimulation of MCF-7 breast cancer cell proliferation by estrone sulfate and dehydroepiandrosterone sulfate: Inhibition by novel non-steroidal steroid sulfatase inhibitors
    • 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. J. Steroid Biochem. Mol. Biol. 73:2000;225-235
    • (2000) J. Steroid Biochem. Mol. Biol. , vol.73 , pp. 225-235
    • Billich, A.1    Nussbaumer, P.2    Lehr, P.3
  • 45
  • 47
    • 0025374703 scopus 로고
    • Sulfate derivatives of 2-phenylindoles as novel steroid sulfatase inhibitors: An in vitro study on structure-activity relationship
    • Birnböck H., von Angerer E. Sulfate derivatives of 2-phenylindoles as novel steroid sulfatase inhibitors: an in vitro study on structure-activity relationship. Biochem. Pharmacol. 39:1990;1709-1713
    • (1990) Biochem. Pharmacol. , vol.39 , pp. 1709-1713
    • Birnböck, H.1    Von Angerer, E.2


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