Synthesis and characterization of fluorescent 4-hydroxytamoxifen conjugates with unique antiestrogenic properties

Bioconjugate Chemistry

Volumn 21, Issue 5, 2010, Pages 903-910

  Rickert, Emily L ^b   Oriana, Sean ^b   Hartman Frey, Cori ^c   Long, Xinghua ^c   Webb, Timothy T ^c   Nephew, Kenneth P ^c   Weatherman, Ross V ^a  

^a ROSE HULMAN INSTITUTE OF TECHNOLOGY   (United States)

^b PURDUE UNIVERSITY   (United States)

^c INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CELL CULTURE; CELL MEMBRANES; DISEASES; FLUORESCENCE MICROSCOPY; LIGANDS; STEROID HORMONES;

ANTI-ESTROGENIC; BREAST CANCER CELLS; CANCER CELL LINES; CELL PERMEABILITY; ESTROGEN RECEPTOR; MEMBRANE RECEPTORS; PROPERTY; RECEPTOR LIGANDS; SYNTHESIS AND CHARACTERIZATIONS; TAMOXIFEN;

FLUORESCENCE;

1,6 HEXANEDIAMINE; 4 HYDROXYTAMOXIFEN; ESTRADIOL; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; STEROID HORMONE; TAMOXIFEN;

ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CELL MEMBRANE; CELL PERMEABILIZATION; CELL PROLIFERATION; CYTOPLASM; DRUG ACTIVITY; DRUG CONJUGATION; DRUG INHIBITION; DRUG MECHANISM; DRUG SYNTHESIS; ESTROGEN RESPONSIVE ELEMENT; FLUORESCENCE MICROSCOPY; HUMAN; HUMAN CELL; IN VITRO STUDY;

EID: 77952580350     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc900461h     Document Type: Article

References (42)

1. Katzenellenbogen, B. S., Tsai, T. S., Tatee, T., and Katzenellenbogen, J. A. (1979) Estrogen and antiestrogen action: studies in reproductive target tissues and tumors Adv. Exp. Med. Biol. 117, 111-32
2. Jordan, V. C. (2004) Selective estrogen receptor modulation: concept and consequences in cancer Cancer Cell 5, 207-13
3. Jordan, V. C. (2007) SERMs: meeting the promise of multifunctional medicines J. Natl. Cancer Inst. 99, 350-6
4. Jordan, V. C. (2007) Chemoprevention of breast cancer with selective oestrogen-receptor modulators Nat. Rev. Cancer 7, 46-53
5. Weatherman, R. V. (2008) Untangling the Estrogen Receptor Web: Tools to Selectively Study Estrogen binding Receptors, in Nuclear Receptors as Drug Targets (Ottow, E. and Weinmann, H., Eds.) pp 47 - 64, Wiley-VCH, Weinhem.
6. Hewitt, S. C., Harrell, J. C., and Korach, K. S. (2005) Lessons in estrogen biology from knockout and transgenic animals Annu. Rev. Physiol. 67, 285-308
7. Koehler, K. F., Helguero, L. A., Haldosen, L. A., Warner, M., and Gustafsson, J. A. (2005) Reflections on the discovery and significance of estrogen receptor beta Endocr. Rev. 26, 465-78
8. Prossnitz, E. R. and Maggiolini, M. (2009) Mechanisms of estrogen signaling and gene expression via GPR30 Mol. Cell. Endocrinol. 308, 32-8
9. Li, L., Haynes, M. P., and Bender, J. R. (2003) Plasma membrane localization and function of the estrogen receptor alpha variant (ER46) in human endothelial cells Proc. Natl. Acad. Sci. U.S.A. 100, 4807-12
10. Wehling, M. and Losel, R. (2006) Non-genomic steroid hormone effects: Membrane or intracellular receptors J. Steroid Biochem. Mol. Biol. 102, 180-3
11. Gigure, V., Yang, N., Segui, P., and Evans, R. (1988) Identification of a new class of steroid hormone receptors Nature 331, 91-4
12. Pietras, R. J. and Szego, C. M. (1977) Specific binding sites for oestrogen at the outer surfaces of isolated endometrial cells Nature 265, 69-72
13. Levin, E. R. (2009) Membrane ER{alpha} signaling to cell functions, J Physiol.
14. Jarman, M., Leung, O. T., Leclercq, G., Devleeschouwer, N., Stoessel, S., Coombes, R. C., and Skilton, R. A. (1986) Analogues of tamoxifen: the role of the basic side-chain. Applications of a whole-cell oestrogen-receptor binding assay to N-oxides and quaternary salts Anti-Cancer Drug Des. 1, 259-68
15. Revankar, C. M., Mitchell, H. D., Field, A. S., Burai, R., Corona, C., Ramesh, C., Sklar, L. A., Arterburn, J. B., and Prossnitz, E. R. (2007) Synthetic estrogen derivatives demonstrate the functionality of intracellular GPR30 ACS Chem. Biol. 2, 536-44
16. Berthois, Y., Pourreau-Schneider, N., Gandilhon, P., Mittre, H., Tubiana, N., and Martin, P. M. (1986) Estradiol membrane binding sites on human breast cancer cell lines. Use of a fluorescent estradiol conjugate to demonstrate plasma membrane binding systems J. Steroid Biochem. 25, 963-72
17. Jansson, S. E., Gripenberg, J., Karonen, S. L., Wasenius, V. M., Pantzar, P., Kontula, K., Karkkainen, J., and Adlercreutz, H. (1985) Cytochemical demonstration of estrogen binding sites in breast cancer by estradiol covalently linked to horseradish peroxidase Eur. J. Cancer Clin. Oncol. 21, 625-30
18. Stevis, P. E., Deecher, D. C., Suhadolnik, L., Mallis, L. M., and Frail, D. E. (1999) Differential effects of estradiol and estradiol-BSA conjugates Endocrinology 140, 5455-5458
19. Taguchi, Y., Koslowski, M., and Bodenner, D. L. (2004) Binding of estrogen receptor with estrogen conjugated to bovine serum albumin (BSA) Nucl. Recept. 2, 5
20. Carlson, K. E., Coppey, M., Magdelenat, H., and Katzenellenbogen, J. A. (1989) Receptor binding of NBD-labeled fluorescent estrogens and progestins in whole cells and cell-free preparations J. Steroid Biochem. 32, 345-55
21. Fisher, B., Gunduz, N., Zheng, S., and Saffer, E. A. (1982) Fluoresceinated estrone binding by human and mouse breast cancer cells Cancer Res. 42, 540-9
22. Revankar, C. M., Cimino, D. F., Sklar, L. A., Arterburn, J. B., and Prossnitz, E. R. (2005) A transmembrane intracellular estrogen receptor mediates rapid cell signaling Science 307, 1625-30
23. Weatherman, R. V., Carroll, D. C., and Scanlan, T. S. (2001) Activity of a tamoxifen-raloxifene hybrid ligand for estrogen receptors at an AP-1 site Bioorg. Med. Chem. Lett. 11, 3129-31
24. Weatherman, R. V., Clegg, N. J., and Scanlan, T. S. (2001) Differential SERM activation of the estrogen receptors (ERalpha and ERbeta) at AP-1 sites Chem. Biol. 8, 427-36
25. Rickert, E. L., Trebley, J. P., Peterson, A. C., Morrell, M. M., and Weatherman, R. V. (2007) Synthesis and characterization of bioactive tamoxifen-conjugated polymers Biomacromolecules 8, 3608-12
26. Fan, M., Yan, P. S., Hartman-Frey, C., Chen, L., Paik, H., Oyer, S. L., Salisbury, J. D., Cheng, A. S., Li, L., Abbosh, P. H., Huang, T. H., and Nephew, K. P. (2006) Diverse gene expression and DNA methylation profiles correlate with differential adaptation of breast cancer cells to the antiestrogens tamoxifen and fulvestrant Cancer Res. 66, 11954-66
27. Hwang, K. J., Carlson, K. E., Anstead, G. M., and Katzenellenbogen, J. A. (1992) Donor-acceptor tetrahydrochrysenes, inherently fluorescent, high-affinity ligands for the estrogen receptor: binding and fluorescence characteristics and fluorometric assay of receptor Biochemistry 31, 11536-45
28. de Medina, P., Favre, G., and Poirot, M. (2004) Multiple targeting by the antitumor drug tamoxifen: a structure-activity study Curr. Med. Chem. Anticancer Agents 4, 491-508
29. Trebley, J. P., Rickert, E. L., Reyes, P. T., and Weatherman, R. V. (2006) Tamoxifen-based probes for the study of estrogen receptor-mediated transcription Ernst Schering Res. Found Workshop 75-87
30. Katzenellenbogen, J. A., Carlson, K. E., and Katzenellenbogen, B. S. (1985) Facile geometric isomerization of phenolic non-steroidal estrogens and antiestrogens: limitations to the interpretation of experiments characterizing the activity of individual isomers J. Steroid Biochem. 22, 589-96
31. Robertson, D. W., Katzenellenbogen, J. A., Hayes, J. R., and Katzenellenbogen, B. S. (1982) Antiestrogen basicity - activity relationships: a comparison of the estrogen receptor binding and antiuterotrophic potencies of several analogues of (Z)-1,2-diphenyl-1-[4-[2-(dimethylamino)ethoxy]phenyl]-1- butene (tamoxifen, Nolvadex) having altered basicity J. Med. Chem. 25, 167-71
32. Shiau, A. K., Barstad, D., Loria, P. M., Cheng, L., Kushner, P. J., Agard, D. A., and Greene, G. L. (1998) The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen Cell 95, 927-937
33. Miksicek, R. J., Carlson, K. E., Hwang, K. J., and Katzenellenbogen, J. A. (1995) Studies using fluorescent tetrahydrochrysene estrogens for in situ visualization of the estrogen receptor in living cells Mol. Endocrinol. 9, 592-604
34. Long, X. and Nephew, K. P. (2006) Fulvestrant (ICI 182,780)-dependent interacting proteins mediate immobilization and degradation of estrogen receptor-alpha J. Biol. Chem. 281, 9607-15
35. Kawata, M., Matsuda, K., Nishi, M., Ogawa, H., and Ochiai, I. (2001) Intracellular dynamics of steroid hormone receptor Neurosci. Res. 40, 197-203
36. Leclercq, G., Lacroix, M., Laios, I., and Laurent, G. (2006) Estrogen receptor alpha: impact of ligands on intracellular shuttling and turnover rate in breast cancer cells Curr. Cancer Drug Targets 6, 39-64
37. Berry, N. B., Fan, M., and Nephew, K. P. (2008) Estrogen receptor alpha (ER{alpha}) hinge-region lysines 302 and 303 regulate receptor degradation by the proteasome, Mol. Endocrinol.
38. Fan, M., Rickert, E. L., Chen, L., Aftab, S. A., Nephew, K. P., and Weatherman, R. V. (2007) Characterization of molecular and structural determinants of selective estrogen receptor downregulators Breast Cancer Res. Treat. 103, 37-44
39. Harrington, W. R., Kim, S. H., Funk, C. C., Madak-Erdogan, Z., Schiff, R., Katzenellenbogen, J. A., and Katzenellenbogen, B. S. (2006) Estrogen dendrimer conjugates that preferentially activate extranuclear, nongenomic versus genomic pathways of estrogen action Mol. Endocrinol. 20, 491-502
40. Kim, S. H. and Katzenellenbogen, J. A. (2006) Hormone-PAMAM dendrimer conjugates: polymer dynamics and tether structure affect ligand access to receptors Angew. Chem., Int. Ed. Engl. 45, 7243-8
41. Engelk, M., Bojarski, P., Bloss, R., and Diehl, H. (2001) Tamoxifen perturbs lipid bilayer order and permeability: comparison of DSC, fluorescence anisotropy, laurdan generalized polarization and carboxyfluorescein leakage studies Biophys. Chem. 90, 157-73
42. Madak-Erdogan, Z., Kieser, K. J., Kim, S. H., Komm, B., Katzenellenbogen, J. A., and Katzenellenbogen, B. S. (2008) Nuclear and extranuclear pathway inputs in the regulation of global gene expression by estrogen receptors Mol. Endocrinol. 22, 2116-27