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Submit ReviewGW 6471
Description: PPARα antagonist
Chemical Name: N-((2S)-2-(((1Z)-1-Methyl-3-oxo-3-(4-(trifluoromethyl)phenyl)prop-1-enyl)amino)-3-(4-(2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy)phenyl)propyl)propanamide
Purity: ≥98% (HPLC)
Biological Activity for GW 6471
GW 6471 is a PPARα antagonist (IC50 = 0.24 μM). GW 6471 enhances the binding affinity of the PPARα ligand-binding domain to the co-repressor proteins SMRT and NCoR. GW 6471 blocks SARS-CoV-2 infection in airway organoids (EC50 = 2.1 μM) by blocking and downregulating the hypoxia inducible factor 1 subunit alpha (HIF1α) and HIF1 pathway; also reduces viral RNA. GW 6471 induces apoptosis and cell cycle arrest in kidney cancer cells.
Licensing Information
Sold with the permission of GlaxoSmithKline.
Compound Libraries for GW 6471
GW 6471 is also offered as part of the Tocriscreen 2.0 Max. Find out more about compound libraries available from Tocris.
Technical Data for GW 6471
| M. Wt | 619.67 |
| Formula | C35H36F3N3O4 |
| Storage | Store at +4°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 880635-03-0 |
| PubChem ID | 446738 |
| InChI Key | TYEFSRMOUXWTDN-DYQICHDWSA-N |
| Smiles | CC2=C(N=C(C4=CC=CC=C4)O2)CCOC(C=C1)=CC=C1C[C@@H](CNC(CC)=O)N/C(C)=C\C(C3=CC=C(C(F)(F)F)C=C3)=O |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for GW 6471
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 46.48 | 75 | |
| ethanol | 6.2 | 10 |
Preparing Stock Solutions for GW 6471
The following data is based on the product molecular weight 619.67. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 0.75 mM | 2.15 mL | 10.76 mL | 21.52 mL |
| 3.75 mM | 0.43 mL | 2.15 mL | 4.3 mL |
| 7.5 mM | 0.22 mL | 1.08 mL | 2.15 mL |
| 37.5 mM | 0.04 mL | 0.22 mL | 0.43 mL |
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Product Datasheets for GW 6471
References for GW 6471
References are publications that support the biological activity of the product.
Xu et al (2002) Structural basis for antagonist-mediated recruitment of nuclear co-repressors by PPARα. Nature 415 813 PMID: 11845213
Muller et al (2009) An innovative method to study target protein-drug interactions by mass spectrometry. J.Med.Chem. 52 2875 PMID: 19379014
Duan et al (2021) An airway organoid-based screen identifies a role for the HIF1α-glycolysis axis in SARS-CoV-2 infection. Cell Rep. 37 PMID: 34731648
Aboud et al (2013) Inhibition of PPARα induces cell cycle arrest and apoptosis, and synergizes with glycolysis inhibition in kidney cancer cells. PLoS One 8 PMID: 23951092
If you know of a relevant reference for GW 6471, please let us know.
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Keywords: GW 6471, GW 6471 supplier, GW6471, PPAR, PPARa, PPARalpha, PPARα, peroxisome, proliferator-activated, receptor, alpha, antagonists, GlaxoSmithKline, gsk, Receptors, Coronavirus, COVID-19, 4618, Tocris Bioscience
38 Citations for GW 6471
Citations are publications that use Tocris products. Selected citations for GW 6471 include:
Smith et al (2019) Identification and characterization of a novel anti-inflammatory lipid isolated from Mycobacterium vaccae, a soil-derived bacterium with immunoregulatory and stress resilience properties. Psychopharmacology (Berl) PMID: 31119329
David A et al (2021) Inhibition of phosphodiesterase type 9 reduces obesity and cardiometabolic syndrome in mice. J Clin Invest 131 PMID: 34618683
Peter et al (2021) High-fat diet-activated fatty acid oxidation mediates intestinal stemness and tumorigenicity. Cell Rep 35 109212 PMID: 34107251
Charles et al (2021) Regulation of PPARα by APP in Alzheimer disease affects the pharmacological modulation of synaptic activity. JCI Insight 6 PMID: 34228639
Redlich et al (2014) Palmitoylethanolamide stimulates phagocytosis of Escherichia coli K1 by macrophages and increases the resistance of mice against infections. Int J Mol Sci 11 108 PMID: 24927796
Kok et al (2013) Differential regulation of the expressions of the PGC-1α splice variants, lipins, and PPARα in heart compared to liver. J Lipid Res 54 1662 PMID: 23505321
Crane et al (2013) Lipids derived from virulent Francisella tularensis broadly inhibit pulmonary inflammation via toll-like receptor 2 and peroxisome proliferator-activated receptor α. Clin Vaccine Immunol 20 1531 PMID: 23925884
Carracedo et al (2012) A metabolic prosurvival role for PML in breast cancer. J Clin Invest 122 3088 PMID: 22886304
Neuhaus et al (2017) Multifaceted Mechanisms of WY-14643 to Stabilize the Blood-Brain Barrier in a Model of Traumatic Brain Injury. Front Mol Neurosci 10 149 PMID: 28603485
Yamaguchi et al (2018) Diurnal Variation in PDK4 Expression Is Associated With Plasma Free Fatty Acid Availability in People. J Clin Endocrinol Metab 103 1068 PMID: 29294006
Helmy et al (2015) Additive Renoprotection by pioglit. and fenofi. against Inflammatory, Oxidative and Apoptotic Manifestations of cisp. Nephrotoxicity: Modulation by PPARs. PLoS One 10 e0142303 PMID: 26536032
Bumpus and Johnson (2011) 5-Aminoimidazole-4-carboxyamide-ribonucleoside (AICAR)-stimulated hepatic expression of Cyp4a10, Cyp4a14, Cyp4a31, and other peroxisome proliferator-activated receptor α-responsive mouse genes is AICAR 5'-monophosphate-dependent and AMP-activated Br J Pharmacol 339 886 PMID: 21896918
Hamtiaux et al (2011) Increasing antiproliferative properties of endocannabinoids in N1E-115 neuroblastoma cells through inhibition of their metabolism. PLoS One 6 e26823 PMID: 22046372
Arun et al (2022) Downregulation of PTEN Promotes Autophagy via Concurrent Reduction in Apoptosis in Cardiac Hypertrophy in PPAR α-/- Mice. Front Cardiovasc Med 9 798639 PMID: 35224041
Marc K et al (2019) An ANGPTL4-ceramide-protein kinase Cζ axis mediates chronic glucocorticoid exposure-induced hepatic steatosis and hypertriglyceridemia in mice. J Biol Chem 294 9213-9224 PMID: 31053639
Min et al (2019) Phytanic acid activates PPARα to promote beige adipogenic differentiation of preadipocytes. J Nutr Biochem 67 201-211 PMID: 30951974
Lin et al (2015) Palmitoylethanolamide inhibits glutamate release in rat cerebrocortical nerve terminals. J Appl Toxicol 16 5555 PMID: 25768340
Midgett et al (2015) In vitro evaluation of the effects of perfluorooctanesulfonic acid (PFOS) and perfluorooctanoic acid (PFOA) on IL-2 production in human T-cells. J Pharmacol Exp Ther 35 459 PMID: 25056757
Borrelli et al (2015) Palmitoylethanolamide, a naturally occurring lipid, is an orally effective intestinal anti-inflammatory agent. Lipids Health Dis 172 142 PMID: 25205418
Lin et al (2020) Exposure of female mice to perfluorooctanoic acid suppresses hypothalamic kisspeptin-reproductive endocrine system through enhanced hepatic fibroblast growth factor 21 synthesis, leading to ovulation failure and prolonged dioestrus. J Neuroendocrinol 32 e12848 PMID: 32307816
Carine et al (2020) TGFβ2-induced formation of lipid droplets supports acidosis-driven EMT and the metastatic spreading of cancer cells. Nat Commun 11 454 PMID: 31974393
Mark et al (2015) PPARα inhibition modulates multiple reprogrammed metabolic pathways in kidney cancer and attenuates tumor growth. Am J Physiol Cell Physiol 308 C890-8 PMID: 25810260
Oruqaj et al (2015) Compromised peroxisomes in idiopathic pulmonary fibrosis, a vicious cycle inducing a higher fibrotic response via TGF-β signaling. Proc Natl Acad Sci U S A 112 E2048 PMID: 25848047
Qian et al (2015) Peroxisomes in Different Skeletal Cell Types during Intramembranous and Endochondral Ossification and Their Regulation during Osteoblast Differentiation by Distinct Peroxisome Proliferator-Activated Receptors. PLoS One 10 e0143439 PMID: 26630504
Paul N et al (2012) The synthetic cannabinoid R(+)WIN55,212-2 augments interferon-β expression via peroxisome proliferator-activated receptor-α. J Biol Chem 287 25440-53 PMID: 22654113
Ning et al (2023) Nuclear receptor modulators inhibit osteosarcoma cell proliferation and tumour growth by regulating the mTOR signaling pathway. Cell Death Dis 14 51 PMID: 36681687
Ambrosino et al (2013) Activation and desensitization of TRPV1 channels in sensory neurons by the PPARα agonist palmitoylethanolamide. Br J Pharmacol 168 1430 PMID: 23083124
El-Sisi et al (2013) Effects of three different fibrates on intrahepatic cholestasis experimentally induced in rats. J Neuroinflammation 2013 781348 PMID: 23997763
Hamtiaux et al (2012) The association of N-palmitoylethanolamine with the FAAH inhibitor URB597 impairs melanoma growth through a supra-additive action. BMC Cancer 12 92 PMID: 22429826
Mottillo et al (2012) Lipolytic products activate peroxisome proliferator-activated receptor (PPAR) α and δ in brown adipocytes to match fatty acid oxidation with supply. J Neuroinflammation 287 25038 PMID: 22685301
Kong et al (2012) Activation of peroxisome proliferator activated receptor α ameliorates ethanol induced steatohepatitis in mice. PPAR Res 10 246 PMID: 22208561
Poleni et al (2010) Activation of PPARs α, β/δ, and γ Impairs TGF-β1-Induced Collagens' Production and Modulates the TIMP-1/MMPs Balance in Three-Dimensional Cultured Chondrocytes. PPAR Res 2010 635912 PMID: 20981144
Guo et al (2018) Antagonism of PPAR-γ signaling expands human hematopoietic stem and progenitor cells by enhancing glycolysis. Nat Med 24 360 PMID: 29377004
Capasso et al (2014) Palmitoylethanolamide normalizes intestinal motility in a model of post-inflammatory accelerated transit: involvement of CB? receptors and TRPV1 channels. Br J Pharmacol 171 4026 PMID: 24818658
Shih et al (2014) Antiplatelet activity of nifed. is mediated by inhibition of NF-κB activation caused by enhancement of PPAR-β/-γ activity. Br J Pharmacol 171 1490 PMID: 24730061
Kim et al (2014) An endoplasmic reticulum stress-initiated sphingolipid metabolite, ceramide-1-phosphate, regulates epithelial innate immunity by stimulating β-defensin production. Mol Cell Biol 34 4368 PMID: 25312644
Okine et al (2014) A role for PPARα in the medial prefrontal cortex in formalin-evoked nociceptive responding in rats. Br J Pharmacol 171 1462 PMID: 24303983
Li et al (2014) Fenofibrate induces apoptosis of triple-negative breast cancer cells via activation of NF-κB pathway. BMC Cancer 14 96 PMID: 24529079
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