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BioAssay: AID 262965

Binding affinity to human ERalpha relative to estradiol by radiometric binding assay

In a search for estrogen receptor (ER) ligands to be radiolabeled with fluorine-18 for imaging of ER-positive breast tumors with positron emission tomography (PET), we investigated cyclofenil analogues substituted at the C3 or C4 position of the cyclohexyl group. McMurry coupling of 4,4'-dihydroxybenzophenone with various ketones produced key cyclofenil intermediates, from which C3 and C4 more ..
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 Tested Compounds
 Tested Compounds
All(24)
 
 
Unspecified(24)
 
 
 Tested Substances
 Tested Substances
All(24)
 
 
Unspecified(24)
 
 
 Related BioAssays
 Related BioAssays
AID: 262965
Data Source: ChEMBL (343764)
Depositor Category: Literature, Extracted
BioAssay Version:
Deposit Date: 2010-05-24
Modify Date: 2014-05-21

Data Table ( Complete ):           All
Target
Sequence: RecName: Full=Steroid hormone receptor ERR1; AltName: Full=Estrogen receptor-like 1; AltName: Full=Estrogen-related receptor alpha; Short=ERR-alpha; AltName: Full=Nuclear receptor subfamily 3 group B member 1
Description ..   
Protein Family: The ligand binding domain of estrogen receptor-related nuclear receptors
Comment ..   

Gene:ESRRA     Related Protein 3D Structures     More BioActivity Data..
Tested Compounds:
Description:
Title: Fluorine-substituted cyclofenil derivatives as estrogen receptor ligands: synthesis and structure-affinity relationship study of potential positron emission tomography agents for imaging estrogen receptors in breast cancer.

Abstract: In a search for estrogen receptor (ER) ligands to be radiolabeled with fluorine-18 for imaging of ER-positive breast tumors with positron emission tomography (PET), we investigated cyclofenil analogues substituted at the C3 or C4 position of the cyclohexyl group. McMurry coupling of 4,4'-dihydroxybenzophenone with various ketones produced key cyclofenil intermediates, from which C3 and C4 substituents containing alkyl and various oxygen or fluorine-substituted alkyl groups were elaborated. Binding assays to both ERalpha and ERbeta revealed that the C3 site is more tolerant of steric bulk and polar groups than the C4 site, consistent with a computational model of the ERalpha ligand binding pocket. Fluorine substitution is tolerated very well at some sites, giving some compounds having affinities comparable to or higher than that of estradiol. These fluoro and fluoroalkyl cyclofenils merit further consideration as fluorine-18 labeled ER ligands for PET imaging of ERs in breast tumors.
(PMID: 16610793)
Categorized Comment
Assay Type: Binding

Assay Data Source: Scientific Literature

BAO: Assay Format: biochemical format

Target Type: Target is a single protein chain

Result Definitions
TIDNameDescriptionHistogramTypeUnit
OutcomeThe BioAssay activity outcomeOutcome
1RBA activity commentRBA activity commentString
2RBA standard flagRBA standard flagInteger
3RBA qualifierRBA qualifierString
4RBA published valueRBA published valueFloat
5RBA standard valueRBA standard valueFloat

Data Table (Concise)
Classification
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