Biomaterial Database

Derivatives of 4-styrylpyridines: synthesis, estrogen receptor binding affinity, and photophysical properties. 1995

S A Haroutounian, and A W Scribner, and J A Katzenellenbogen

Chemistry Laboratory, Agricultural University of Athens, Greece.

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)-1-(4-hydroxyphenyl)-1-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.

UI	MeSH Term	Description	Entries
D010636	Phenols	Benzene derivatives that include one or more hydroxyl groups attached to the ring structure.
D011725	Pyridines	Compounds with a six membered aromatic ring containing NITROGEN. The saturated version is PIPERIDINES.
D011960	Receptors, Estrogen	Cytoplasmic proteins that bind estrogens and migrate to the nucleus where they regulate DNA transcription. Evaluation of the state of estrogen receptors in breast cancer patients has become clinically important.	Estrogen Receptor,Estrogen Receptors,Estrogen Nuclear Receptor,Estrogen Receptor Type I,Estrogen Receptor Type II,Estrogen Receptors Type I,Estrogen Receptors Type II,Receptor, Estrogen Nuclear,Receptors, Estrogen, Type I,Receptors, Estrogen, Type II,Nuclear Receptor, Estrogen,Receptor, Estrogen
D005453	Fluorescence	The property of emitting radiation while being irradiated. The radiation emitted is usually of longer wavelength than that incident or absorbed, e.g., a substance can be irradiated with invisible radiation and emit visible light. X-ray fluorescence is used in diagnosis.
D000042	Absorption	The physical or physiological processes by which substances, tissue, cells, etc. take up or take in other substances or energy.
D001667	Binding, Competitive	The interaction of two or more substrates or ligands with the same binding site. The displacement of one by the other is used in quantitative and selective affinity measurements.	Competitive Binding
D013329	Structure-Activity Relationship	The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups.	Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D013343	Styrenes	Derivatives and polymers of styrene. They are used in the manufacturing of synthetic rubber, plastics, and resins. Some of the polymers form the skeletal structures for ion exchange resin beads.
D015394	Molecular Structure	The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds.	Structure, Molecular,Molecular Structures,Structures, Molecular