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BioAssay: AID 695939

Transactivation of human PPARalpha expressed in human HEK293 cells after 16 to 20 hrs by dual luciferase beta-galactosidase reporter gene assay

We previously demonstrated that the alpha-benzylphenylpropanoic acid-type PPARgamma-selective agonist 6 exhibited a reversed stereochemistry-activity relationship, that is, the (R)-enantiomer is a more potent PPARgamma agonist than the (S)-enantiomer, compared with structurally similar alpha-ethylphenylpropanoic acid-type PPAR agonists. Here, we designed, synthesized and evaluated the optically more ..
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 Tested Compounds
 Tested Compounds
All(4)
 
 
Active(4)
 
 
 Tested Substances
 Tested Substances
All(4)
 
 
Active(4)
 
 
AID: 695939
Data Source: ChEMBL (856683)
BioAssay Type: Confirmatory, Concentration-Response Relationship Observed
Depositor Category: Literature, Extracted
BioAssay Version:
Deposit Date: 2013-06-29
Modify Date: 2014-08-23

Data Table ( Complete ):           View Active Data    View All Data
Target
Sequence: RecName: Full=Peroxisome proliferator-activated receptor alpha; Short=PPAR-alpha; AltName: Full=Nuclear receptor subfamily 1 group C member 1
Description ..   
Protein Family: The ligand binding domain of peroxisome proliferator-activated receptors
Comment ..   

Gene:PPARA     Related Protein 3D Structures     More BioActivity Data..
BioActive Compounds: 4
Description:
Title: Design, synthesis and in vitro evaluation of a series of alpha-substituted phenylpropanoic acid PPARgamma agonists to further investigate the stereochemistry-activity relationship.

Abstract: We previously demonstrated that the alpha-benzylphenylpropanoic acid-type PPARgamma-selective agonist 6 exhibited a reversed stereochemistry-activity relationship, that is, the (R)-enantiomer is a more potent PPARgamma agonist than the (S)-enantiomer, compared with structurally similar alpha-ethylphenylpropanoic acid-type PPAR agonists. Here, we designed, synthesized and evaluated the optically active alpha-cyclohexylmethylphenylpropanoic acid derivatives 7 and alpha-phenethylphenylpropanoic acid derivatives 8, respectively. Interestingly, alpha-cyclohexylmethyl derivatives showed reversal of the stereochemistry-activity relationship [i.e., (R) more potent than (S)], like alpha-benzyl derivatives, whereas alpha-phenethyl derivatives showed the 'normal' relationship [(S) more potent than (R)]. These results suggested that the presence of a branched carbon atom at the beta-position with respect to the carboxyl group is a critical determinant of the reversed stereochemistry-activity relationship.
(PMID: 23022278)
Comment
Compounds with activity <= 50uM or explicitly reported as active by ChEMBL are flagged as active in this PubChem assay presentation.
Categorized Comment - additional comments and annotations
From BioAssay Depositor:
Assay Type: Binding
Target Type: Target is a single protein chain
Assay Data Source: Scientific Literature
BAO: Assay Format: cell-based format
Assay Cell Type: HEK293
Result Definitions
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TIDNameDescriptionHistogramTypeUnit
OutcomeThe BioAssay activity outcomeOutcome
1EC50*EC50 PubChem standard valueFloatμM
3BEIBinding Efficiency Index(nM)Float
2SEISurface Efficiency Index(nM)Float
4LELigand EfficiencyFloat
5LLELipophilic Ligand EfficiencyFloat
6EC50 activity commentEC50 activity commentString
7EC50 standard flagEC50 standard flagInteger
8EC50 qualifierEC50 qualifierString
9EC50 published valueEC50 published valueFloatnM
10EC50 standard valueEC50 standard valueFloatnM
11EC50 binding domainsEC50 binding domainsString

* Activity Concentration.

Data Table (Concise)
Data Table ( Complete ):     View Active Data    View All Data
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