GSK3787PPARβ/δ antagonist,novel and irreversible CAS# 188591-46-0 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 188591-46-0 | SDF | Download SDF |
| PubChem ID | 2800647 | Appearance | Powder |
| Formula | C15H12ClF3N2O3S | M.Wt | 392.78 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble to 100 mM in DMSO | ||
| Chemical Name | 4-chloro-N-[2-[5-(trifluoromethyl)pyridin-2-yl]sulfonylethyl]benzamide | ||
| SMILES | C1=CC(=CC=C1C(=O)NCCS(=O)(=O)C2=NC=C(C=C2)C(F)(F)F)Cl | ||
| Standard InChIKey | JFUIMTGOQCQTPF-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C15H12ClF3N2O3S/c16-12-4-1-10(2-5-12)14(22)20-7-8-25(23,24)13-6-3-11(9-21-13)15(17,18)19/h1-6,9H,7-8H2,(H,20,22) | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Potent and selective peroxisome proliferator-activated receptor δ (PPARδ) antagonist (pIC50 = 6.6). Displays no measurable affinity for PPARα or PPARγ in vitro (pIC50< 5). |
GSK3787 Dilution Calculator
GSK3787 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.546 mL | 12.7298 mL | 25.4595 mL | 50.9191 mL | 63.6489 mL |
| 5 mM | 0.5092 mL | 2.546 mL | 5.0919 mL | 10.1838 mL | 12.7298 mL |
| 10 mM | 0.2546 mL | 1.273 mL | 2.546 mL | 5.0919 mL | 6.3649 mL |
| 50 mM | 0.0509 mL | 0.2546 mL | 0.5092 mL | 1.0184 mL | 1.273 mL |
| 100 mM | 0.0255 mL | 0.1273 mL | 0.2546 mL | 0.5092 mL | 0.6365 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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GSK3787 is a novel and irreversible antagonist of the peroxisome proliferator-activated receptor-β/δ (PPAR-β/δ) that covalently binds to a cysteine residue in the ligand-binding domain of PPAR- β/δ. Although it responses to ligand activation to modulate the association of both PPAR-β/δ and PPAR-γ coregulator peptides, GSK3787 exhibits considerably higher antagonism of PPAR-β/δ than that of PPAR-γ. Results of recent studies have shown that oral administration of GSK3787 results in the antagonism of GW0742-induced overexpression of Angptl4 and Adrp mRNA in wild-type mouse colon, which is correlated with reduced promoter occupancy of PPAR-β/δ on the Angptl4 and Adrp genes.
Reference
Palkar PS, Borland MG, Naruhn S, Ferry CH, Lee C, Sk UH, Sharma AK, Amin S, Murray IA, Anderson CR, Perdew GH, Gonzalez FJ, Müller R, Peters JM. Cellular and pharmacological selectivity of the peroxisome proliferator-activated receptor-beta/delta antagonist GSK3787. Mol Pharmacol. 2010;78(3):419-430
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Cellular and pharmacological selectivity of the peroxisome proliferator-activated receptor-beta/delta antagonist GSK3787.[Pubmed:20516370]
Mol Pharmacol. 2010 Sep;78(3):419-30.
The availability of high-affinity agonists for peroxisome proliferator-activated receptor-beta/delta (PPARbeta/delta) has led to significant advances in our understanding of the functional role of PPARbeta/delta. In this study, a new PPARbeta/delta antagonist, 4-chloro-N-(2-{[5-trifluoromethyl)-2-pyridyl]sulfonyl}ethyl)benzamide (GSK3787), was characterized using in vivo and in vitro models. Orally administered GSK3787 caused antagonism of 4-[2-(3-fluoro-4-trifluoromethyl-phenyl)-4-methyl-thiazol-5-ylmethylsulfanyl]-2-m ethyl-phenoxy}-acetic acid (GW0742)-induced up-regulation of Angptl4 and Adrp mRNA expression in wild-type mouse colon but not in Pparbeta/delta-null mouse colon. Chromatin immunoprecipitation (ChIP) analysis indicates that this correlated with reduced promoter occupancy of PPARbeta/delta on the Angptl4 and Adrp genes. Reporter assays demonstrated antagonism of PPARbeta/delta activity and weak antagonism and agonism of PPARgamma activity but no effect on PPARalpha activity. Time-resolved fluorescence resonance energy transfer assays confirmed the ability of GSK3787 to modulate the association of both PPARbeta/delta and PPARgamma coregulator peptides in response to ligand activation, consistent with reporter assays. In vivo and in vitro analysis indicates that the efficacy of GSK3787 to modulate PPARgamma activity is markedly lower than the efficacy of GSK3787 to act as a PPARbeta/delta antagonist. GSK3787 antagonized GW0742-induced expression of Angptl4 in mouse fibroblasts, mouse keratinocytes, and human cancer cell lines. Cell proliferation was unchanged in response to either GW0742 or GSK3787 in human cancer cell lines. Results from these studies demonstrate that GSK3787 can antagonize PPARbeta/delta in vivo, thus providing a new strategy to delineate the functional role of a receptor with great potential as a therapeutic target for the treatment and prevention of disease.
Identification and characterization of 4-chloro-N-(2-{[5-trifluoromethyl)-2-pyridyl]sulfonyl}ethyl)benzamide (GSK3787), a selective and irreversible peroxisome proliferator-activated receptor delta (PPARdelta) antagonist.[Pubmed:20128594]
J Med Chem. 2010 Feb 25;53(4):1857-61.
4-Chloro-N-(2-{[5-trifluoromethyl)-2-pyridyl]sulfonyl}ethyl)benzamide 3 (GSK3787) was identified as a potent and selective ligand for PPARdelta with good pharmacokinetic properties. A detailed binding study using mass spectral analysis confirmed covalent binding to Cys249 within the PPARdelta binding pocket. Gene expression studies showed that pyridylsulfone 3 antagonized the transcriptional activity of PPARdelta and inhibited basal CPT1a gene transcription. Compound 3 is a PPARdelta antagonist with utility as a tool to elucidate PPARdelta cell biology and pharmacology.
