Skip to main content

The Utility of Fluorescent Estrogens for Receptor Imaging

  • Chapter
Estrogens, Progestins, and Their Antagonists

Part of the book series: Hormones in Health and Disease ((HHD))

  • 179 Accesses

Abstract

Recent refinements in instrumentation for fluorescence microscopy and continuing progress in the development of fluorescent probes have progressively expanded the horizons for the microscopic analysis of cellular structure. An important factor that continues to limit the usefulness of fluorescence microscopy, particularly for studies in viable cells, is the availability of appropriate imaging probes. When suitable probes are available, fluorescence microscopy has enormous potential for deciphering the complex organization of even rare macromolecules within the living cell, since techniques are now available for detecting very low intensities of fluorescence emission.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Anstead GM, Altenbach RJ, Wilson SR, and Katzenellenbogen JA (1988). 2,3-Diarylindenes and 2,3-diarylindenones: Synthesis, molecular structure, photochemistry, estrogen receptor binding affinity, and comparisons with related triarylethylenes. J. Med. Chem. 31:1316–1326.

    Article  Google Scholar 

  • Anstead GM, Hwang K-J, and Katzenellenbogen JA (1993). Characterization of the spectroscopic properties of a tetrahydrochrysene system containing a rigidified hydroxynitrostilbene chromophore: An inherently fluorescent ligand designed for the estrogen receptor. Photochem. Photobiol. 57:616–628.

    Article  PubMed  CAS  Google Scholar 

  • Aubin JE (1979). Autofluorescence of viable cultured mammalian cells. J. Histochem. Cytochem. 27:36–43.

    Article  PubMed  CAS  Google Scholar 

  • Baker ME, Sklar DH, Terry LS, and Hedges MR (1985) Diethyl pyrocarbonate, a histidine selective reagent, inhibits estrogen binding to receptor protein in rat uterus cytosol. Biochem. International 11:233–238.

    CAS  Google Scholar 

  • Barrows GH, Stroupe SB, and Rhiem JD (1980). Nuclear uptake of a 17b-estradiol-fluorescein derivative as a marker of estrogen dependence. Am. J. Clin. Pathol. 73:330–339.

    PubMed  CAS  Google Scholar 

  • Beisker W, Dolbeare F, and Gray JW (1987). An improved immunocytochemical procedure for high-sensitivity detection of incorporated bromodeoxyuridine. Cytometry 8:235–239.

    Article  PubMed  CAS  Google Scholar 

  • Berns EMJJ, Mulder E, Rommerts FFG, Blankenstein RA, de Graf E, and van der Molen HJ (1984). Fluorescent ligands, used in histochemistry, do not discriminate between estrogen-receptor-positive and receptor-negative human tumor cell lines. Breast Cancer Res. Treat. 4:195–204.

    Article  PubMed  CAS  Google Scholar 

  • Bickoff EM, Booth AN, Lyman RL, Livingston AL, Thompson CR, and De Eds F (1957). Coumestrol, a new estrogen isolated from forage crops. Science 126:969–970.

    Article  PubMed  CAS  Google Scholar 

  • Bindal RD and Katzenellenbogen JA (1986). l,2-bis(4-Hydroxyphenyl)-3,4-dihy-dro-6-napthalene, a photofluorogenic ligand for the estrogen receptor. Photochem. Photobiol. 43:121–126.

    Article  PubMed  CAS  Google Scholar 

  • Burroughs CD, Bern HA, and Stokstad EL (1985). Prolonged vaginal cornification and other changes in mice treated neonatally with coumestrol, a plant estrogen. J. Tox. Environ. Health 15:51–61.

    Article  CAS  Google Scholar 

  • Burroughs CD, Mills KT, and Bern HA (1990). Long term genital tract changes in female mice treated neonatally with coumestrol. Reprod. Toxicol. 4:127–135.

    Article  PubMed  CAS  Google Scholar 

  • Carlson KE, Coppey M, Magdelenat H, and Katzenellenbogen JA (1989). Receptor binding of NBD-labeled fluorescent estrogens and progestins in whole cells and cell-free preparations. J. Steroid Biochem. 32:345–355.

    Article  PubMed  CAS  Google Scholar 

  • Chamness GC and McGuire WL (1982). Questions about histochemical methods for steroid receptors. Arch. Pathol. Lab. Med. 106:53–54.

    PubMed  CAS  Google Scholar 

  • Chamness GC, Mercer WD, and McGuire WL (1980). Are histochemical methods for estrogen receptor valid? J. Histochem. Cytochem. 28:792–798.

    Article  PubMed  CAS  Google Scholar 

  • Clark JH, Hardin JW, Upchurch S, and Eriksson H (1978). Heterogeneity of estrogen binding sites in the cytosol of the rat uterus. J. Biol. Chem. 253:7630–7634.

    PubMed  CAS  Google Scholar 

  • Dandliker WB, Brawn RJ, Hsu M-L, Brawn PN, Levin J, Meyers CY, and Kolb VM (1978). Investigation of hormone-receptor interactions by means of fluorescence labeling. Cancer Res. 38:4212–4224.

    PubMed  CAS  Google Scholar 

  • Erber S, Birnbock H, and von Angerer E (1990). Synthesis and biological properties of a l-(6-aziridinylhexyl)-2-phenylindole, a potential fluorescence label for estrogen receptors. Arch. Pharm. Weinheim 323:459–463.

    Article  PubMed  CAS  Google Scholar 

  • Farnsworth NR, Bingel AS, Cordell GA, Crane FA, and Fong HHS (1975). Potential value of plants as antifertility agents, part II. J. Pharm. Sci. 64:717–754.

    Article  PubMed  CAS  Google Scholar 

  • Faulstich H, Zobeley S, Rinnerthaler G, and Small JV (1988). Fluorescent phallotox-ins as probes for filamentous actin. J. Muscle Res. & Cell Motil. 9:370–383.

    Article  CAS  Google Scholar 

  • Fevig TL, Lloyd JE, Zablocki JA, and Katzenellenbogen JA (1987). Preparation, receptor binding, and fluorescence properties of hexestrol-fluorophore conjugates: Evaluation of site of attachment, fluorophore structure, and fluorophore-ligand spacing. J. Med. Chem. 30:156–165.

    Article  PubMed  CAS  Google Scholar 

  • French AN, Wilson SR, Welch MJ, and Katzenellenbogen JA (1993). A synthesis of 7α-substituted estradiols: Synthesis and biological evaluation of a 7α-pen-tyl-substituted BODIPY fluorescent conjugate and a fluorine-18-labeled 7α-pentylestradiol analog. Steroids 58:157–169.

    Article  PubMed  CAS  Google Scholar 

  • Green S, Walter P, Kumar V, Krust A, Bornert J-M, Argos P, and Chambon P (1986). Human estrogen receptor cDNA: Sequence, expression and homology to v-erbA. Nature 320:134–139.

    Article  PubMed  CAS  Google Scholar 

  • Greene GL, Nolan C, Engler JP, and Jensen EV (1980). Monoclonal antibodies to human estrogen receptor. Proc. Natl. Acad. Sci., USA 77:5115–5119.

    Article  PubMed  CAS  Google Scholar 

  • Hwang K-J, Carlson KE, Anstead GM, and Katzenellenbogen JA (1992a). Donor-acceptor tetrahydrochrysenes, inherently fluorescent, high-affinity ligands for the estrogen receptor: binding and fluorescence characteristics and fluorometric assay of receptor. Biochemistry 31:11536–11545.

    Article  PubMed  CAS  Google Scholar 

  • Hwang K-J, O’Neil JP, and Katzenellenbogen JA (1992b). 5,6,11,12-Tetrahydro-chrysenes: Synthesis of rigid stilbene systems designed to be fluorescent ligands for the estrogen receptor. J. Org. Chem. 57:1262–1271.

    Article  CAS  Google Scholar 

  • Jensen EV, Suzuki T, Kawashima T, Stumpf WE, Jungblut PW, and DeSombre ER (1968). A two step mechanism for the interaction of estradiol with rat uterus. Proc Natl. Acad. Sci., USA 59:632–638.

    Article  PubMed  CAS  Google Scholar 

  • Joyce BG, Nicholson RI, Morton MS, and Griffiths K (1982). Studies with steroid-fluorescein conjugates on oestrogen target tissues. Eur. J. Cancer Clin. Oncol. 18:1147–1152.

    Article  PubMed  CAS  Google Scholar 

  • Katzenellenbogen JA, Carlson KE, Bindal RD, Neeley RL, Martin PM, and Magdelenat HP (1986). Fluorescence-based assay of estrogen receptor using 12-Oxo-9(ll)-dehydroestradiol-17p. Anal Biochem 159:336–348.

    Article  PubMed  CAS  Google Scholar 

  • King WJ and Greene GL (1984). Monoclonal antibodies localize oestrogen receptor to the nuclei of target cells. Nature (London) 307:745–747.

    Article  CAS  Google Scholar 

  • Lee SH (1981). The histochemistry of estrogen receptors. Histochem. 71:491–500.

    Article  CAS  Google Scholar 

  • Lee YJ, Notides AC, Tsay Y-G, and Kende A (1977). Coumestrol, NBD-norhexestrol, and dansyl-norhexestrol, fluorescent probes of estrogen binding proteins. Biochemistry 16:2896–2901.

    Article  PubMed  CAS  Google Scholar 

  • Lightfoot RJ (1974). Infertility in ewes caused by prolonged grazing on oestrogenic pastures: Oestrus, fertilization, and cervical mucus. Austr. J. Biol. Sci. 27:409–414.

    CAS  Google Scholar 

  • Markaverich BM, Roberts RR, Alejandro MA, Johnson GA, Middleditch BS, and Clark, JH (1988). Bioflavonoid interaction with rat uterine type II binding sites and cell growth inhibition. J. Steroid Biochem. 30:71–78.

    Article  PubMed  CAS  Google Scholar 

  • Martin PM, Horwitz KB, Ryan DS, and McGuire WL (1978). Phytoestrogen interaction with estrogen receptors in human breast cancer cells. Endocrinol. 103:1860–1867.

    Article  CAS  Google Scholar 

  • Martin PM, Magdelenat HP, Benyahia B, Rigaud O, and Katzenellenbogen JA (1983). New approach for visualizing estrogen receptors in target cells using inherently fluorescent ligands and image intensification. Cancer Res 43:4956–4965.

    PubMed  CAS  Google Scholar 

  • McCarty KS Jr, Reintgen DS, Seigler HF, and McCarty KS Sr (1982). Cytochemistry of sex steroid receptors: a critique. Breast Cancer Res Treat. 1:315–325.

    Article  Google Scholar 

  • McCarty KS Jr, Woodward BH, Nichols DE, Wilkinson W, and McCarty KS Sr (1980). Comparison of biochemical and histochemical techniques for estrogen receptor analyses in mammary carcinoma. Cancer 46:2842–2845.

    Article  PubMed  Google Scholar 

  • Miksicek RJ (1993). In situ localization of the estrogen receptor in living cells with the fluorescent phytoestrogen coumestrol. J. Histochem. Cytochem. 41:801–810.

    Article  PubMed  CAS  Google Scholar 

  • Miksicek RJ (1994). Interaction of naturally occurring nonsteroidal estrogens with expressed recombinant human estrogen receptor. J. Ster. Biochem. Mol. Biol. 49:153–160.

    Article  CAS  Google Scholar 

  • Miksicek RJ (1995). Estrogenic flavonoids: Structural requirements for biological activity. Proc. Soc. Exp. Biol. Med. 208:44–50.

    PubMed  CAS  Google Scholar 

  • Miksicek RJ, Carlson KE, Hwang K-J, and Katzenellenbogen JA (1995). Studies using fluorescent tetrahydrochrysene estrogens for in situ visualization of the estrogen receptor in living cells. Mol. Endocrinol 9:592–604.

    Article  PubMed  CAS  Google Scholar 

  • Nelson K, Pavlik EJ, van Nagell JR Jr, Hanson MB, Donaldson ES, and Flanigan RC (1984). Estrogenicity of coumestrol in the mouse: Fluorescence detection of interaction with estrogen receptors. Biochemistry 23:2565–2572.

    Article  PubMed  CAS  Google Scholar 

  • Nenci I, Beccati MD, Piffanelli A, and Lanza G (1976). Detection and dynamic localization of estradiol-receptor complexes in intact target cells by immunofluorescence technique. J. Steroid Biochem. 7:505–510.

    Article  PubMed  CAS  Google Scholar 

  • Nenci I, Dandliker WB, Meyers CY, Marchetti E, Marzola A, and Fabris G (1980). Estrogen receptor cytochemistry by fluorescent estrogen. J. Histochem. Cytochem. 28:1081–1088.

    Article  PubMed  CAS  Google Scholar 

  • Nomura Y, Miura S, Koyama H, Enomoto K, Kasumi F, Yamamoto H, Kimura M, Tominaga T, Iion H, Morimoto T, and Tashira H (1992). Relative effect of steroid hormone receptors on the prognosis of patients with operable breast cancer. Cancer 69:153–157.

    Article  PubMed  CAS  Google Scholar 

  • Panko WB, Mattioli CS, and Wheeler TM (1982). Lack of correlation of a histo-chemical method for estrogen receptor analysis with the biochemical assay results. Cancer 49:2148–2152.

    Article  PubMed  CAS  Google Scholar 

  • Pertschuk LP, Gaetjens E, and Eisenberg KB (1981). Steroid hormone receptor proteins—Histochemical markers of potential hormone-dependence. Meth. Achiev. Exp. Pathol 10:162–189.

    CAS  Google Scholar 

  • Pertschuk LP, Tobin EH, Brigati DJ, Kim DS, Bloom ND, Gaetjens E, Berman PJ, Carter AC, and Degensheim GA (1978). Immunofluorescent detection of estrogen receptors in breast cancer: Comparison with dextran-coated charcoal and sucrose gradient assays. Cancer 41:907–911.

    Article  PubMed  CAS  Google Scholar 

  • Pertschuk LP, Tobin EH, Carter AC, Eisenberg KB, Leo VC, Gaetjens E, and Bloom ND (1982) Immunohistologic and histochemical methods for detection of steroid binding in breast cancer: a reappraisal. Breast Cancer Res. Treat. 1:297–314.

    Article  Google Scholar 

  • Pertschuk LP, Tobin EH, Gaetjens E, Carter AC, Degenshein GA, Bloom ND, and Brigati DJ (1980b). Histochemical assay of estrogen and progesterone receptors in breast cancer: Correlation with biochemical assay and patients’ response to endocrine therapies. Cancer 46:2896–2901.

    Article  PubMed  CAS  Google Scholar 

  • Pertschuk LP, Tobin EH, Tanapat P, Gaetjens E, Carter AC, Bloom ND, Macchia RJ, and Eisenberg KB (1980a). Histochemical analysis of steroid hormone receptors in breast and prostatic carcinoma. J. Histochem. Cytochem. 28:799–810.

    Article  PubMed  CAS  Google Scholar 

  • Press MF, Xu S, and Greene GL (1989). Subcellular distribution of estrogen and progesterone receptor with and without specific ligand. Am. J. Pathol. 135:857–864.

    Google Scholar 

  • Rao BR, Fry CG, Hunt S, Kuhnel R, and Dandliker WB (1980). A fluorescent probe for rapid detection of estrogen receptors. Cancer 46:2902–2906.

    Article  PubMed  CAS  Google Scholar 

  • Roederer M and Murphy RF (1986). Cell-by-cell autofluorescence correction for low signal-to-noise systems: application to epidermal growth factor endocytosis by 3T3 fibroblasts. Cytometry 7:558–565.

    Article  PubMed  CAS  Google Scholar 

  • Salman M, Reddy BR, Delgado P, Stotter PL, Fulcher LC, and Chamness GC (1991). 17α-substituted analogs of estradiol for the development of fluorescent estrogen receptor ligands. Steroids 56:375–387.

    Article  PubMed  CAS  Google Scholar 

  • Scarlata S and Miksicek R (1995). Binding properties of coumestrol to expressed human estrogen receptor. Mol. Cell Endocrinol 115:65–72.

    Article  PubMed  CAS  Google Scholar 

  • Schutt DA (1976). The effects of plant estrogens on animal reproduction. Endeavor (Oxford) 35:110–113.

    Google Scholar 

  • Underwood JCE, Sher E, Reed M, Eisman JA, and Martin TJ (1982). Biochemical assessment of histochemical methods for oestrogen receptor localization. J. Clin. Pathol. 35:401–406.

    Article  PubMed  CAS  Google Scholar 

  • Verdeal K, Brown RR, Richardson T, and Ryan DS (1980). Affinity of phytoestrogens for estradiol-binding proteins and effect of coumestrol of growth of 7,12-dimethylbenz[a]-anthracene-induced rat mammary tumors. J. Natl. Cancer Inst. 64:285–290.

    PubMed  CAS  Google Scholar 

  • Wang Y and Miksicek RJ (1994). Characterization of estrogen receptor cDNAs from human uterus: identification of a novel Pvu II polymorphism. Mol. Cell. Endocrinol. 101:101–110.

    Article  PubMed  CAS  Google Scholar 

  • Welshon WV, Krummel BM, and Gorski J (1984). Nuclear localization of unoccupied oestrogen receptors. Nature (London) 307:747–749.

    Article  Google Scholar 

  • Whitten PL and Naftolin F (1992). Effects of a phytoestrogen diet on estrogen-dependent reproductive processes in immature female rats. Steroids 57:56–61.

    Article  PubMed  CAS  Google Scholar 

  • Wolfbeis OS and Schaffner K (1980). Solvent and acidity dependence of the absorption and fluorescence of coumestrol. Photochem. Photobiol. 32:143–148.

    Article  CAS  Google Scholar 

  • Ylikomi T, Bocquel MT, Berry M, and Chambon P (1992). Cooperation of proto-signals for nuclear accumulation of estrogen and progesterone receptors. EMBO J. 11:3681–3694.

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1997 Birkhäuser Boston

About this chapter

Cite this chapter

Miksicek, R.J. (1997). The Utility of Fluorescent Estrogens for Receptor Imaging. In: Pavlik, E.J. (eds) Estrogens, Progestins, and Their Antagonists. Hormones in Health and Disease. Birkhäuser Boston. https://doi.org/10.1007/978-1-4612-4096-9_9

Download citation

  • DOI: https://doi.org/10.1007/978-1-4612-4096-9_9

  • Publisher Name: Birkhäuser Boston

  • Print ISBN: 978-1-4612-8650-9

  • Online ISBN: 978-1-4612-4096-9

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics