메뉴 건너뛰기




Volumn 59, Issue 1, 1996, Pages 103-117

Synthesis, structure and biological properties of Z-17α-(2-iodovinyl)-11β-chloromethyl estradiol-17β (Z-CMIV), a high affinity ligand for the characterization of estrogen receptor-positive tumors

Author keywords

[No Author keywords available]

Indexed keywords

11BETA CHLOROMETHYLESTRADIOL; ESTRADIOL; ESTROGEN; ESTROGEN RECEPTOR; IODINE 125; PROGESTERONE RECEPTOR;

EID: 0030236586     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-0760(96)00007-6     Document Type: Article
Times cited : (18)

References (54)
  • 3
    • 0020148458 scopus 로고
    • 125I] iodoestradiol for estrogen receptor containing breast cancer cells
    • 125I] iodoestradiol for estrogen receptor containing breast cancer cells. Endocrinology 110 (1982) 2177-2179.
    • (1982) Endocrinology , vol.110 , pp. 2177-2179
    • Bronzert, D.A.1    Hochberg, R.B.2    Lippman, M.E.3
  • 4
    • 0023759843 scopus 로고
    • Bromine-80 m radiotoxicity and the potential for estrogen receptor-directed therapy with auger electrons
    • 4. De Sombre E. R., Harper P. V., Hughes A., Mease R. C., Gatles S. J., De Jesus O. T. and Schwartz J. L.: Bromine-80 m radiotoxicity and the potential for estrogen receptor-directed therapy with Auger electrons. Cancer Res. 48 (1988) 5805-5809.
    • (1988) Cancer Res. , vol.48 , pp. 5805-5809
    • De Sombre, E.R.1    Harper, P.V.2    Hughes, A.3    Mease, R.C.4    Gatles, S.J.5    De Jesus, O.T.6    Schwartz, J.L.7
  • 5
    • 0011268653 scopus 로고
    • Z-11β-chloromethyl-17α-iodovinyl-estradiol, a potential agent for targeted radiotherapy of estrogen receptor positive tumors
    • 5. Zeicher M., Henrot P., Loos M., Strijckmans P. and Quivy J.: Z-11β-chloromethyl-17α-iodovinyl-estradiol, a potential agent for targeted radiotherapy of estrogen receptor positive tumors. Eur. J. Nucl. Med. 16, 7 (1990) 439.
    • (1990) Eur. J. Nucl. Med. , vol.16 , Issue.7 , pp. 439
    • Zeicher, M.1    Henrot, P.2    Loos, M.3    Strijckmans, P.4    Quivy, J.5
  • 6
    • 45549111588 scopus 로고
    • Fundamental considerations in the design of fluorine-18 labeled progestins and androgens as imaging agents for receptor-positive tumors of the breast and prostate
    • 6. Brandes S. J. and Katzenellenbogen J. A.: Fundamental considerations in the design of fluorine-18 labeled progestins and androgens as imaging agents for receptor-positive tumors of the breast and prostate. Nucl. Med. Biol. 15 (1988) 53-67.
    • (1988) Nucl. Med. Biol. , vol.15 , pp. 53-67
    • Brandes, S.J.1    Katzenellenbogen, J.A.2
  • 7
    • 0011269545 scopus 로고
    • In vitro screening of cytotoxic estrogens of potential therapeutic activity
    • Edited by J. Raus, H. Martens and G. Leclercq. Academic Press, London
    • 7. Leclercq G., De Vleeschouwer N., Legros N. and Heuson, J. C.: In vitro screening of cytotoxic estrogens of potential therapeutic activity. In: Cytotoxic Estrogens in Hormone Receptive Tumors (Edited by J. Raus, H. Martens and G. Leclercq). Academic Press, London, (1980) pp. 165-181.
    • (1980) Cytotoxic Estrogens in Hormone Receptive Tumors , pp. 165-181
    • Leclercq, G.1    De Vleeschouwer, N.2    Legros, N.3    Heuson, J.C.4
  • 8
    • 0020518446 scopus 로고
    • Guide-lines for the design of new antisteroids and cytotoxic-linked estrogens for the treatment of breast cancer
    • 8. Leclercq G., De Vleeschouwer N. and Heuson J. C.: Guide-lines for the design of new antisteroids and cytotoxic-linked estrogens for the treatment of breast cancer. J. Steroid Biochem. 19 (1983) 75-78.
    • (1983) J. Steroid Biochem. , vol.19 , pp. 75-78
    • Leclercq, G.1    De Vleeschouwer, N.2    Heuson, J.C.3
  • 9
    • 0019638247 scopus 로고
    • The synthesis and study of some potential affinity labelling reagents for estrogen receptors
    • 9. Ratajczak T., Sheppard P. N., Capon R. J. and Hahnel R.: The synthesis and study of some potential affinity labelling reagents for estrogen receptors. Steroids 38 (1981) 537-555.
    • (1981) Steroids , vol.38 , pp. 537-555
    • Ratajczak, T.1    Sheppard, P.N.2    Capon, R.J.3    Hahnel, R.4
  • 11
    • 0021254578 scopus 로고
    • Biological activity and receptor binding of a strongly interacting estrogen in human breast cancer cells
    • 11. Reiner G. A., Katzenellenbogen B. S., Bindal R. D. and Katzenellenbogen J. A.: Biological activity and receptor binding of a strongly interacting estrogen in human breast cancer cells. Cancer Res. 44 (1984) 2302-2308.
    • (1984) Cancer Res. , vol.44 , pp. 2302-2308
    • Reiner, G.A.1    Katzenellenbogen, B.S.2    Bindal, R.D.3    Katzenellenbogen, J.A.4
  • 14
    • 0021224089 scopus 로고
    • 125i]iodovinyl-11β-methoxyestradiol as a highly selective radioligand for tissues containing estrogen receptors: Concise communication
    • 125I]iodovinyl-11β-methoxyestradiol as a highly selective radioligand for tissues containing estrogen receptors: concise communication. J. Nucl. Med. 25 (1984) 998-1002.
    • (1984) J. Nucl. Med. , vol.25 , pp. 998-1002
    • Hanson, R.N.1    Franke, L.A.2
  • 15
    • 0011347533 scopus 로고
    • Radiolabeled ligands specific for estrogen and progesterone receptor and their use as diagnostic and radiotherapeutic agents and in determination of the receptors
    • French Patent FR 8813737 (Oct. 19 1988), Eur. Patent 0,365,421 (1992) U.S. Patent 5,002,753 (1991)
    • 15. Zeicher M. and Quivy J.: Radiolabeled ligands specific for estrogen and progesterone receptor and their use as diagnostic and radiotherapeutic agents and in determination of the receptors. French Patent FR 8813737 (Oct. 19 1988), Eur. Patent 0,365,421 (1992) U.S. Patent 5,002,753 (1991). Chem. Abstr. 114 (1991) 139123h.
    • (1991) Chem. Abstr. , vol.114
    • Zeicher, M.1    Quivy, J.2
  • 19
    • 33947332509 scopus 로고
    • A synthesis of 11β-hydroxyestrone and related 16-and 17-hydroxyestratrien
    • 19. Baran J. S.: A synthesis of 11β-hydroxyestrone and related 16-and 17-hydroxyestratrien. J. Med. Chem. 10 (1967) 1188-1190.
    • (1967) J. Med. Chem. , vol.10 , pp. 1188-1190
    • Baran, J.S.1
  • 20
    • 0011344036 scopus 로고
    • University Chemical Laboratory, Cambridge
    • 20. Motherwell S.: PLUTO plotting. University Chemical Laboratory, Cambridge, (1978).
    • (1978) PLUTO Plotting
    • Motherwell, S.1
  • 21
    • 0011347015 scopus 로고
    • Vercauteren, D.P. KEMIT program
    • Department of Chemistry, Facultés N.-D. de la Paix, Namur
    • 21. Vanderveken, D. J.: Vercauteren, D.P. KEMIT program. Scientific Computer Facilities, Department of Chemistry, Facultés N.-D. de la Paix, Namur, (1992).
    • (1992) Scientific Computer Facilities
    • Vanderveken, D.J.1
  • 22
    • 0018886213 scopus 로고
    • Devis R. Nonsteroidal compounds which bind epididymal androgen-binding protein but not the androgen receptor
    • 22. Rousseau G. C., Quivy J. I., Kirchhoff J. and Bui X. H.: Devis R. Nonsteroidal compounds which bind epididymal androgen-binding protein but not the androgen receptor. Nature 284 (1980) 458-459.
    • (1980) Nature , vol.284 , pp. 458-459
    • Rousseau, G.C.1    Quivy, J.I.2    Kirchhoff, J.3    Bui, X.H.4
  • 23
    • 84969001783 scopus 로고
    • The attractions of proteins for small molecules and ions
    • 23. Scatchard G.: The attractions of proteins for small molecules and ions. Ann. N.Y. Acad. Sci. 51 (1994) 660-672.
    • (1994) Ann. N.Y. Acad. Sci. , vol.51 , pp. 660-672
    • Scatchard, G.1
  • 24
    • 0025925251 scopus 로고
    • Effect of estrogenic and antioestrogenic triphenylethylene derivatives on progesterone and estrogen receptors levels of MCF-7 cells
    • 24. Legros N., Leclercq G. and McCague R.: Effect of estrogenic and antioestrogenic triphenylethylene derivatives on progesterone and estrogen receptors levels of MCF-7 cells. Biochem. Pharmacol. 42 (1991) 1837-1841.
    • (1991) Biochem. Pharmacol. , vol.42 , pp. 1837-1841
    • Legros, N.1    Leclercq, G.2    McCague, R.3
  • 25
    • 0019083094 scopus 로고
    • Revision of the standard for the assessment of hormone receptors in human breast cancer
    • 25. EORTC Breast Cancer Cooperative Group: Revision of the standard for the assessment of hormone receptors in human breast cancer. Eur. J. Cancer 16 (1980) 1513-1515.
    • (1980) Eur. J. Cancer , vol.16 , pp. 1513-1515
  • 27
    • 4944230527 scopus 로고
    • Tri-n-butyltin hybrid as reagent in organic synthesis
    • 27. Neuman W. P,: Tri-n-butyltin hybrid as reagent in organic synthesis. Synthesis (1987) 665-683.
    • (1987) Synthesis , pp. 665-683
    • Neuman, W.P.1
  • 28
    • 0027230247 scopus 로고
    • Radiolabeled steroidal estrogens in cancer research
    • 28. Cummins C. H.: Radiolabeled steroidal estrogens in cancer research. Steroids 58 (1993) 245-257.
    • (1993) Steroids , vol.58 , pp. 245-257
    • Cummins, C.H.1
  • 29
    • 0001496637 scopus 로고
    • Structure cristalline et moléculaire de l'oestradiol hémihydrate
    • 29. Busetta B. and Hospital M.: Structure cristalline et moléculaire de l'oestradiol hémihydrate. Acta Crust. B28 (1972) 560-567.
    • (1972) Acta Crust. , vol.B28 , pp. 560-567
    • Busetta, B.1    Hospital, M.2
  • 30
    • 4244018437 scopus 로고
    • Structure cristalline et moléculaire du methoxy-11β oestradiol
    • 30. Courseille C., Busetta B., Precigoux G. and Hospital M.: Structure cristalline et moléculaire du methoxy-11β oestradiol. Acta Cryst. B29 (1973) 2462-2465.
    • (1973) Acta Cryst. , vol.B29 , pp. 2462-2465
    • Courseille, C.1    Busetta, B.2    Precigoux, G.3    Hospital, M.4
  • 31
    • 0022647460 scopus 로고
    • Analysis of monomeric-dimeric states of the estrogen receptor with monoclonal antiestrophilins
    • 31. Lindstedt A., West N. B. and Brenner R. M.: Analysis of monomeric-dimeric states of the estrogen receptor with monoclonal antiestrophilins. J. Steroid Biochem. 24 (1985) 677-686.
    • (1985) J. Steroid Biochem. , vol.24 , pp. 677-686
    • Lindstedt, A.1    West, N.B.2    Brenner, R.M.3
  • 32
    • 0025228653 scopus 로고
    • Interaction of three monoclonal antibodies with the nonactivated and activated forms of estrogen receptor
    • 32. Giambiagi N. and Pasqualini J. R.: Interaction of three monoclonal antibodies with the nonactivated and activated forms of estrogen receptor. Endocrinology 126 (1990) 1403-1409.
    • (1990) Endocrinology , vol.126 , pp. 1403-1409
    • Giambiagi, N.1    Pasqualini, J.R.2
  • 33
    • 0023708107 scopus 로고
    • Quantitative determination of nuclear estrogen receptors by an enzyme immunoassay: Applicability and caveats
    • 33. Kral L. G., Doherty L. M. and Brooks S. C.: Quantitative determination of nuclear estrogen receptors by an enzyme immunoassay: applicability and caveats. J. Steroid Biochem 31 (1988) 459-466.
    • (1988) J. Steroid Biochem , vol.31 , pp. 459-466
    • Kral, L.G.1    Doherty, L.M.2    Brooks, S.C.3
  • 34
    • 0025678887 scopus 로고
    • Discrepancies between antibody (EIA) and saturation analysis of estrogen receptor content in breast tumor samples
    • 34. Marsigliante S., Puddefoot J. R., Barker S., Gledhill J. and Vinson G. P.: Discrepancies between antibody (EIA) and saturation analysis of estrogen receptor content in breast tumor samples. J. Steroid. Biochem. Molec. Biol. 37 (1990) 643-648.
    • (1990) J. Steroid. Biochem. Molec. Biol. , vol.37 , pp. 643-648
    • Marsigliante, S.1    Puddefoot, J.R.2    Barker, S.3    Gledhill, J.4    Vinson, G.P.5
  • 35
    • 0020047139 scopus 로고
    • Effects of estrogen and antiestrogens on estrogen receptor dynamics and the induction of progesterone receptor in MCF-7 human breast cancer cells
    • 35. Eckert R. L. and Katzenellenbogen B. S.: Effects of estrogen and antiestrogens on estrogen receptor dynamics and the induction of progesterone receptor in MCF-7 human breast cancer cells. Cancer Res. 42 (1982) 139-144.
    • (1982) Cancer Res. , vol.42 , pp. 139-144
    • Eckert, R.L.1    Katzenellenbogen, B.S.2
  • 37
    • 0027389803 scopus 로고
    • Synthesis, radiolabeling and tissue distribution of 11β-Fluoroalkyl-and 11β-Fluoroalkoxy-substituted estrogens: Target tissue uptake selectivity and defluorination of a homologous series of Fluorine-18-labeled estrogens
    • 37. French A. N., Napolitano E., Vanbrocklin H. F., Hanson R. N., Welch M. J. and Katzenellenbogen J. A.: Synthesis, radiolabeling and tissue distribution of 11β-Fluoroalkyl-and 11β-Fluoroalkoxy-substituted estrogens: Target tissue uptake selectivity and defluorination of a homologous series of Fluorine-18-labeled estrogens. Nucl. Med. Biol. 20 (1993) 31-47.
    • (1993) Nucl. Med. Biol. , vol.20 , pp. 31-47
    • French, A.N.1    Napolitano, E.2    Vanbrocklin, H.F.3    Hanson, R.N.4    Welch, M.J.5    Katzenellenbogen, J.A.6
  • 38
    • 0001431216 scopus 로고
    • Steroid hormone receptors
    • Edited by J. C. Emmett. Pergamon Press, Oxford
    • 38. Ojasoo T., Raynaud J. P. and Mornon J. P.: Steroid hormone receptors. In: Comprehensive Medicinal Chemistry, (Edited by J. C. Emmett). Pergamon Press, Oxford, Vol. 3 (1990) pp. 1175-1226.
    • (1990) Comprehensive Medicinal Chemistry , vol.3 , pp. 1175-1226
    • Ojasoo, T.1    Raynaud, J.P.2    Mornon, J.P.3
  • 41
    • 0011844673 scopus 로고
    • An analysis of the steroid binding domain of receptors and of ligand structure and binding affinity
    • Edited by J. Carlstedt-Duke, H. Eriksson and J.Å. Gustafsson. Birkhauser Verlag AG, Basel
    • 41. Raynaud J. P., Bissery V., Gaboriaud C., Ojasoo T., Teutsch G. and Mornon J. P.: An analysis of the steroid binding domain of receptors and of ligand structure and binding affinity. In The Steroid/Thyroid Hormone Receptor Family and Gene Regulation, Life Sciences, Vol. 4 (Edited by J. Carlstedt-Duke, H. Eriksson and J.Å. Gustafsson). Birkhauser Verlag AG, Basel (1994) pp. 337-366.
    • (1994) The Steroid/Thyroid Hormone Receptor Family and Gene Regulation, Life Sciences , vol.4 , pp. 337-366
    • Raynaud, J.P.1    Bissery, V.2    Gaboriaud, C.3    Ojasoo, T.4    Teutsch, G.5    Mornon, J.P.6
  • 42
    • 85052202935 scopus 로고
    • Two approaches to structure-activity relationships in the field of sex-steroids and their analogs
    • Edited by M. Bohl and W. L. Duax. CRC Press, Boca Raton
    • 42. Ojasoo T, Doré J. C., Mornon J. P. and Raynaud J. P.: Two approaches to structure-activity relationships in the field of sex-steroids and their analogs. In Molecular Structure and Biological Activity of Steroids (Edited by M. Bohl and W. L. Duax). CRC Press, Boca Raton (1992) pp. 157-207.
    • (1992) Molecular Structure and Biological Activity of Steroids , pp. 157-207
    • Ojasoo, T.1    Doré, J.C.2    Mornon, J.P.3    Raynaud, J.P.4
  • 44
    • 0028843084 scopus 로고
    • Molecular modeling of the human estrogen receptor and ligand interactions based on site-directed mutagenesis amino acid sequence homology
    • 44. Lewis D. F. V., Parker M. G. and King R. J. B.: Molecular modeling of the human estrogen receptor and ligand interactions based on site-directed mutagenesis amino acid sequence homology. J. Steroid Biochem. Molec. Biol. 52 (1995) 55-65.
    • (1995) J. Steroid Biochem. Molec. Biol. , vol.52 , pp. 55-65
    • Lewis, D.F.V.1    Parker, M.G.2    King, R.J.B.3
  • 45
    • 0029012163 scopus 로고
    • Crystal structure of the ligand-binding domain of the human nuclear receptor RXR-a
    • 45. Bourguet W., Ruff M., Chambon P., Gronemeyer H. and Moras D.: Crystal structure of the ligand-binding domain of the human nuclear receptor RXR-a. Nature 375 (1995) 377-382.
    • (1995) Nature , vol.375 , pp. 377-382
    • Bourguet, W.1    Ruff, M.2    Chambon, P.3    Gronemeyer, H.4    Moras, D.5
  • 46
    • 0018140998 scopus 로고
    • Unique steroid congeners for receptor studies
    • 46. Ojasoo T. and Raynaud J. P.: Unique steroid congeners for receptor studies. Cancer Res. 38 (1978) 4186-4198.
    • (1978) Cancer Res. , vol.38 , pp. 4186-4198
    • Ojasoo, T.1    Raynaud, J.P.2
  • 47
    • 0027337615 scopus 로고
    • Crystallographic analysis of the catalytic mechanism of haloalkane dehydrogenase
    • 47. Verschueren K. H. G., Seljée F., Rozeboom H. J., Kalk K. H. and Dijkstra B. A.: Crystallographic analysis of the catalytic mechanism of haloalkane dehydrogenase. Nature 363 (1993) 693-698.
    • (1993) Nature , vol.363 , pp. 693-698
    • Verschueren, K.H.G.1    Seljée, F.2    Rozeboom, H.J.3    Kalk, K.H.4    Dijkstra, B.A.5
  • 48
    • 0022634647 scopus 로고
    • Hemoglobin as a receptor of drugs and peptides: X-ray studies of the stereochemistry of binding
    • 48. Perutz M. F., Fermi G., Abraham D. J., Poyart C. and Bursaux E.: Hemoglobin as a receptor of drugs and peptides: X-ray studies of the stereochemistry of binding. J. Am. Chem. Soc. 108 (1986) 1064-1078.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 1064-1078
    • Perutz, M.F.1    Fermi, G.2    Abraham, D.J.3    Poyart, C.4    Bursaux, E.5
  • 49
    • 0029030873 scopus 로고
    • 11β-substituted estradiol derivatives, potential high-affinity carbon-11-labeled probes for the estrogen receptor: A structure-affinity relationship study
    • 49. Napolitano E., Fiaschi R., Carlson K. A. and Katzenellenbogen J. A.: 11β-substituted estradiol derivatives, potential high-affinity carbon-11-labeled probes for the estrogen receptor: a structure-affinity relationship study. J. Med. Chem. 38 (1995) 429-434.
    • (1995) J. Med. Chem. , vol.38 , pp. 429-434
    • Napolitano, E.1    Fiaschi, R.2    Carlson, K.A.3    Katzenellenbogen, J.A.4
  • 52
    • 0026058740 scopus 로고
    • Comparison between tritiated estradiol and tamoxifen aziridine for measuring estrogen receptors in human breast cancer cytosols
    • 52. Piccart M., Muquardt C., Pirotte P., Veenstra S., Grillo F. and Leclercq G.: Comparison between tritiated estradiol and tamoxifen aziridine for measuring estrogen receptors in human breast cancer cytosols. J. Natl. Cancer Inst. 83 (1991) 1553-1559.
    • (1991) J. Natl. Cancer Inst. , vol.83 , pp. 1553-1559
    • Piccart, M.1    Muquardt, C.2    Pirotte, P.3    Veenstra, S.4    Grillo, F.5    Leclercq, G.6
  • 53
    • 0027532108 scopus 로고
    • Transcriptional activation of the estrogen receptor
    • 53. Wei L. L.: Transcriptional activation of the estrogen receptor. Clin. Chem. 39 (1993) 341-345.
    • (1993) Clin. Chem. , vol.39 , pp. 341-345
    • Wei, L.L.1
  • 54
    • 0026622048 scopus 로고
    • Role of estrogen receptorvariants in the development of hormone resistance in breast cancer
    • 54. Sluyser M.: Role of estrogen receptorvariants in the development of hormone resistance in breast cancer. Clin. Biochem. 25 (1992) 407-414.
    • (1992) Clin. Biochem. , vol.25 , pp. 407-414
    • Sluyser, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.