GW501516
| Code | Size | Price |
|---|
| AG-CR1-3641-M001 | 1 mg | £35.00 |
Quantity:
| AG-CR1-3641-M005 | 5 mg | £75.00 |
Quantity:
| AG-CR1-3641-M025 | 25 mg | £270.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
-20°C
Storage:
Short Term: 4°C Long Term: -20°C
Documents
Further Information
Alternate Names/Synonyms:
GSK-516; GW1516; Endurobol; 2-[2-Methyl-4-[[[4-methyl-2-[4-(trifluoromethyl)phenyl]-5-thiazolyl]methyl]thio]phenoxy]acetic acid
Appearance:
White to off-white solid.
CAS:
317318-70-0
EClass:
32160000
Form (Short):
liquid
Handling Advice:
Keep cool and dry.
InChi:
InChI=1S/C21H18F3NO3S2/c1-12-9-16(7-8-17(12)28-10-19(26)27)29-11-18-13(2)25-20(30-18)14-3-5-15(6-4-14)21(22,23)24/h3-9H,10-11H2,1-2H3,(H,26,27)
InChiKey:
YDBLKRPLXZNVNB-UHFFFAOYSA-N
Long Description:
Chemical. CAS: 317318-70-0. Formula: C21H18F3NO3S2. MW: 453.5. Potent and selective peroxisome proliferator-activated receptor (PPAR) delta agonist/activator with high affinity (Ki=1nM) and potency (EC50=1nM) for PPARdelta and >1000 fold selectivity over PPARalpha and PPARgamma. The peroxisome proliferator-activated receptor delta (PPAR delta) has emerged as an important regulator of lipid homeostasis and inflammatory signaling. Recent in vitro, in vivo and human clinical studies have highlighted a role for PPARdelta activation in the prevention and treatment of insulin resistance and atherosclerosis. Antidiabetic compound. Shown to activate pathways initiated through exercise and was investigated as a potential treatment for obesity, diabetes, dyslipidemia and cardiovascular disease. Off-target high doses lead to tumor progression in rodents. Increases ABC A1 transporter expression and induces apolipoprotein A1-mediated cholesterol efflux in vitro. Increase serum HDL cholesterol and lowers small-dense LDL levels in obesity in vivo models. Reduces plasma triglyceride concentration. Increases expression of genes involved in lipid utilization, beta-oxidation, cholesterol efflux and energy uncoupling, as well as apolipoprotein-A1 specific efflux of intracellular cholesterol, indicating the muscle tissue is an important target. Model compound for a new type of obesity therapeutic, as well as a selective pharmacological tool for understanding lipid metabolism.
MDL:
MFCD09033000
Molecular Formula:
C21H18F3NO3S2
Molecular Weight:
453.5
Package Type:
Vial
Product Description:
Potent and selective peroxisome proliferator-activated receptor (PPAR) delta agonist/activator with high affinity (Ki=1nM) and potency (EC50=1nM) for PPARdelta and >1000 fold selectivity over PPARalpha and PPARgamma. The peroxisome proliferator-activated receptor delta (PPAR delta) has emerged as an important regulator of lipid homeostasis and inflammatory signaling. Recent in vitro, in vivo and human clinical studies have highlighted a role for PPARdelta activation in the prevention and treatment of insulin resistance and atherosclerosis. Antidiabetic compound. Shown to activate pathways initiated through exercise and was investigated as a potential treatment for obesity, diabetes, dyslipidemia and cardiovascular disease. Off-target high doses lead to tumor progression in rodents. Increases ABC A1 transporter expression and induces apolipoprotein A1-mediated cholesterol efflux in vitro. Increase serum HDL cholesterol and lowers small-dense LDL levels in obesity in vivo models. Reduces plasma triglyceride concentration. Increases expression of genes involved in lipid utilization, beta-oxidation, cholesterol efflux and energy uncoupling, as well as apolipoprotein-A1 specific efflux of intracellular cholesterol, indicating the muscle tissue is an important target. Model compound for a new type of obesity therapeutic, as well as a selective pharmacological tool for understanding lipid metabolism.
Purity:
>98% (NMR)
SMILES:
CC1=CC(SCC2=C(C)N=C(C3=CC=C(C(F)(F)F)C=C3)S2)=CC=C1OCC(O)=O
Solubility Chemicals:
Soluble in DMSO (30mg/ml), dimethylformamide (30mg/ml), ethanol (10mg/ml) or methanol (30mg/ml). Sparingly soluble in water.
Transportation:
Non-hazardous
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
A selective peroxisome proliferator-activated receptor delta agonist promotes reverse cholesterol transport: W.R. Oliver, et al.; PNAS 98, 5306 (2001) | Novel selective small molecule agonists for peroxisome proliferator-activated receptor delta (PPARdelta)-synthesis and biological activity: M.L. Sznaidman, et al.; Bioorg. Med. Chem. Lett. 13, 1517 (2003) | The peroxisome proliferator-activated receptor beta/delta agonist, GW501516, regulates the expression of genes involved in lipid catabolism and energy uncoupling in skeletal muscle cells: U. Dressel, et al.; Mol. Endocrinol. 17, 2477 (2003) | Activation of peroxisome proliferator-activated receptor delta induces fatty acid beta-oxidation in skeletal muscle and attenuates metabolic syndrome: T. Tanaka, et al.; PNAS 100, 15924 (2003) | Peroxisome proliferator-activated receptor delta and gamma agonists differentially alter tumor differentiation and progression during mammary carcinogenesis: Y. Yin, et al.; Cancer Res. 65, 3950 (2005) | Activation of PPARbeta/delta induces endothelial cell proliferation and angiogenesis: L. Piqueras, et al.; Arterioscler. Thromb. Vasc. Biol. 27, 63 (2007) | AMPK and PPARdelta agonists are exercise mimetics: V.A. Narkar, et al.; Cell 134, 405 (2008) | Peroxisome proliferator-activated receptor delta agonists inhibit T helper type 1 (Th1) and Th17 responses in experimental allergic encephalomyelitis: S. Kanakasabai, et al.; Immunol. 130, 572 (2010) | Activation of PPARdelta promotes mitochondrial energy metabolism and decreases basal insulin secretion in palmitate-treated beta-cells: L. Jiang, et al.; Mol. Cell Biochem. 343, 249 (2010) | Activation of peroxisome proliferator-activated receptor-{delta} by GW501516 prevents fatty acid-induced nuclear factor-{kappa}B activation and insulin resistance in skeletal muscle cells: T. Coll, et al.; Endocrinol. 151, 1560 (2010) | The role played by the peroxisome proliferator-activated receptor-beta/delta (PPARbeta/delta) activator, GW501516, in control of fatty acid metabolism: a new potential therapeutic target for treating metabolic syndrome: J. Lee & W.Y. Chung; Endocrinol. 152, 1742 (2011) | Peroxisome proliferator-activated receptor delta: a multifaceted metabolic player: L.A. Bojic & M.W. Huff; Curr. Opin. Lipidol. 24, 171 (2013) (Review) | Harnessing the benefits of PPARbeta/delta agonists: L.S. Mackenzie & L. Lione; Life Sci. 93, 963 (2013) (Review) | Short-term administration of GW501516 improves inflammatory state in white adipose tissue and liver damage in high-fructose-fed mice through modulation of the renin-angiotensin system: D.C. Magliano, et al.; Endocrine 50, 355 (2015) | Unraveling the Effects of PPARbeta/delta on Insulin Resistance and Cardiovascular Disease: M. Vazquez-Carrera; Trends Endocrinol. Metab. 27, 319 (2016) (Review) | Remodeling of metabolism and inflammation by exercise ameliorates tumor-associated anemia: R. Furrer, et al.; Sci. Adv. Immunol. 7, 37 (2021)
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