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BioAssay: AID 458180

Agonist activity at aryl hydrocarbon receptor in human MCF7 cells after 24 hrs CYP1A1-dependent EROD assay

The physiological role of aryl hydrocarbon receptor (AhR) is not yet fully understood, and investigation is hampered by the limited solubility of reported AhR ligands in aqueous media. To achieve improved solubility, we focused on our previous finding that planarity-disruption of molecules leads to less efficient crystal packing and greater aqueous solubility. Here, we describe chemical more ..
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 Tested Compounds
 Tested Compounds
All(9)
 
 
Active(7)
 
 
Unspecified(2)
 
 
 Tested Substances
 Tested Substances
All(9)
 
 
Active(7)
 
 
Unspecified(2)
 
 
 Related BioAssays
 Related BioAssays
AID: 458180
Data Source: ChEMBL (609238)
Depositor Category: Literature, Extracted
BioAssay Version:
Deposit Date: 2010-07-30
Modify Date: 2013-11-16

Data Table ( Complete ):           Active    All
Target
Sequence: RecName: Full=Aryl hydrocarbon receptor; Short=Ah receptor; Short=AhR; AltName: Full=Class E basic helix-loop-helix protein 76; Short=bHLHe76; Flags: Precursor
Description ..   
Protein Family: PAS
Comment ..   

Gene:AHR     Related Protein 3D Structures     More BioActivity Data..
BioActive Compounds: 7
Description:
Title: beta-Naphthoflavone analogs as potent and soluble aryl hydrocarbon receptor agonists: improvement of solubility by disruption of molecular planarity.

Abstract: The physiological role of aryl hydrocarbon receptor (AhR) is not yet fully understood, and investigation is hampered by the limited solubility of reported AhR ligands in aqueous media. To achieve improved solubility, we focused on our previous finding that planarity-disruption of molecules leads to less efficient crystal packing and greater aqueous solubility. Here, we describe chemical modification of an AhR agonist, beta-naphthoflavone, focusing on planarity-disruption. As expected, introduction of substituents at the ortho-positions of the phenyl group resulted in greater solubility. Among the compounds prepared, the fluoro analog showed more potent AhR agonistic activity and greater solubility than did beta-naphthoflavone. Our results indicate that this strategy to improve aqueous solubility, that is, introduction of substituent(s) that disrupt planarity, may be generally applicable to bicyclic molecules.
(PMID: 20060304)
Comment
Compounds with activity <= 50uM or explicitly reported as active by ChEMBL are flagged as active in this PubChem assay presentation.

Categorized Comment
ChEMBL Assay Type: Functional

ChEMBL Assay Data Source: Scientific Literature

ChEMBL Assay Cell Type: MCF7

ChEMBL Target ID: 10694

ChEMBL Target Type: Target is a single protein chain

Result Definitions
TIDNameDescriptionHistogramTypeUnit
OutcomeThe BioAssay activity outcomeOutcome
1EC50*EC50 PubChem standard valueFloatμM
2EC50 activity commentEC50 activity commentString
3EC50 standard flagEC50 standard flagInteger
4EC50 qualifierEC50 qualifierString
5EC50 published valueEC50 published valueFloatμM
6EC50 standard valueEC50 standard valueFloatnM

* Activity Concentration.

Data Table (Concise)
Classification
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