TY - JOUR
T1 - Derivatives of 4-styrylpyridines
T2 - Synthesis, estrogen receptor binding affinity, and photophysical properties
AU - Haroutounian, Serkos A.
AU - Scribner, Andrew W.
AU - Katzenellenbogen, John A.
N1 - Funding Information:
Support of this research through a grant from the National Institutes of Health (PHS 5R37 DK15556) is gratefully acknowledged. We thank Kathryn E. Carlson for helpful comments on the manuscript and for her help and that of Karen Avenatti in receptor binding assays and fluorescence measurements. Dr. Yuichi Sugano provided assistance with molecular modeling. NMR spectra at 300 and 400 MHz were obtained on instruments supported by a grant from the National Institutes of Health (PHS lSl0 RR02299) and the National Science Foundation (CHE 90001438 EQ), respectively; mass spectra were obtained on instruments supported by a grant from the National Institutes of Health (GM27029).
PY - 1995/9
Y1 - 1995/9
N2 - In order to develop novel ligands for the estrogen receptor (ER) that might have high binding affinity and fluorescence properties suitable for assaying ER levels in cells, we have prepared a series of substituted 4′-hydroxyl-styrylpyridines and phenylethylpyridines and studied their optical spectroscopy and receptor binding properties. Several derivatives that contain alkyl substituents on the internal ethene or ethane carbons were prepared. While most of these compounds have only modest affinity for ER, one fluorescent analog, (E-l-(4-hydroxyphenyl)-l-phenyl-2-(4-pyridinyl)ethene (13), has reasonably good binding affinity for ER and shows long wavelength fluorescence emission that is sensitive to solvent polarity and pH. This compound may prove to be a useful probe for detecting ER in cells.
AB - In order to develop novel ligands for the estrogen receptor (ER) that might have high binding affinity and fluorescence properties suitable for assaying ER levels in cells, we have prepared a series of substituted 4′-hydroxyl-styrylpyridines and phenylethylpyridines and studied their optical spectroscopy and receptor binding properties. Several derivatives that contain alkyl substituents on the internal ethene or ethane carbons were prepared. While most of these compounds have only modest affinity for ER, one fluorescent analog, (E-l-(4-hydroxyphenyl)-l-phenyl-2-(4-pyridinyl)ethene (13), has reasonably good binding affinity for ER and shows long wavelength fluorescence emission that is sensitive to solvent polarity and pH. This compound may prove to be a useful probe for detecting ER in cells.
KW - estrogen receptor binding
KW - fluorescent estrogens
KW - non-steroidal estrogens
KW - styrylpyridines
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U2 - 10.1016/0039-128X(95)00072-X
DO - 10.1016/0039-128X(95)00072-X
M3 - Article
C2 - 8545854
AN - SCOPUS:0029160131
SN - 0039-128X
VL - 60
SP - 636
EP - 645
JO - Steroids
JF - Steroids
IS - 9
ER -