Facile synthesis of high affinity styrylpyridine systems as inherently fluorescent ligands for the estrogen receptor

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 24, 1998, Pages 3589-3594

  Meyers, Marvin J ^a   Carlson, Kathryn E ^a   Katzenellenbogen, John A ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTROGEN RECEPTOR; PYRIDINE DERIVATIVE; STYRYLPYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL BINDING; FLUORESCENCE; HORMONE RECEPTOR INTERACTION; HYDROGEN BOND; MOLECULAR MODEL; RECEPTOR BINDING; SIGNAL DETECTION; SPECTROSCOPY;

FLUORESCENT DYES; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN BINDING; PYRIDINES; RECEPTORS, ESTROGEN; SPECTROMETRY, FLUORESCENCE;

EID: 0032535588     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00652-0     Document Type: Article

References (17)

1. 1. Van, N. T.; Raber, M.; Barrows, G. H.; Barlogie, B. Science 1984, 224, 876.
2. 2. Nenci, I. Cancer Res. 1978, 38, 4204.
3. 3. Hwang, K.-J.; Carlson, K. E.; Anstead, G. M.; Katzenellenbogen, J. A. Biochemistry 1992, 31, 11536.
4. 4. Martin, P. M.; Magdelenat, H. P.; Benyahia, B.; Rigaud, O.; Katzenellenbogen, J. A. Cancer Res. 1983, 43, 4956.
5. 5. Miksicek, R. J.; Carlson, K. E.; Hwang, K.-J.; Katzenellenbogen, J. A. Mol. Endo. 1995, 9, 592.
6. 6. Haroutounian, S. A.; Katzenellenbogen, J. A. Photochem. Photobiol. 1988, 47, 503.
7. 7. Haroutounian, S. A.; Scribner, A. W.; Katzenellenbogen, J. A. Steroids 1995, 60, 636.
8. 8. Bong, P.-H.; Kim, H. J.; Chae, K. H.; Shim, S. C.; Nakashima, N.; Yoshihara, K. J. Am. Chem. Soc. 1986, 108, 1006.
9. 9. Stevens, A. C.; Frutos, R. P.; Harvey, D. F.; Brian, A. A. Bioconj. Chem. 1993, 4, 19.
10. 10. For a similar series of weakly estrogenic structural analogs (6), see Schwarz, W.; Hartmann, R.; Schoenenberger, H. Arch. Pharm. 1991, 324, 223, 231.
11. 11. Potter, G. A.; McCague, R. J. Org. Chem. 1990, 55, 6184.
12. 12. Katzenellenbogen, J. A.; Johnson, H. J., Jr.; Myers, H. N. Biochemistry 1973, 12, 4085.
13. 13. Payne, D. W.; Katzenellenbogen, J. A. Endocrinology 1979, 105, 743.
14. 14. Brzozowski, A.; Pike, A.; Dauter, Z.; Hubbard, R.; Bonn, T.; Engstrom, O.; Ohman, L.; Greene, G.; Gustafsson, J.; Carlquist, M. Nature 1997, 389, 753.
15. 15. Kaftory, M.; Biali, S.; Rappoport, Z. J. Am. Chem. Soc. 1985, 107, 1701.
16. 16. Background fluorescence for the buffer solution and for the ER in buffer were subtracted from fluorescence results.
17. 17. Tilford, C. H.; Van Campen, M. G., Jr. J. Am. Chem. Soc. 1954, 76, 2431,