Name | 4-HYDROXY-2-[(1E)-[4-(1-METHYLETHYL)PHENYL]METHYLENE]HYDRAZIDE |
Synonyms | CS-1084 GSK 4716 4-hydroxy-N'-(4-isopropylbenzylidene)benzohydrazide (E)-4-hydroxy-N'-(4-isopropylbenzylidene)benzohydrazide 4-HYDROXY-2-[(1E)-[4-(1-METHYLETHYL)PHENYL]METHYLENE]HYDRAZIDE 2-[[4-(1-Methylethyl)phenyl]methylene]hydrazide 4-hydroxybenzoic acid 4-Hydroxybenzoic acid 2-[[4-(1-methylethyl)phenyl]methylene]hydrazide Benzoic acid, 4-hydroxy-, 2-[[4-(1-methylethyl)phenyl]methylene]hydrazide |
CAS | 101574-65-6 |
Molecular Formula | C17H18N2O2 |
Molar Mass | 282.34 |
Density | 1.12 |
Solubility | DMSO: >10mg/mL |
Appearance | powder |
Color | white to off-white |
pKa | 8.48±0.15(Predicted) |
Storage Condition | Inert atmosphere,2-8°C |
In vitro study | Treatment of differentiated C2C12 cells with the ERRβ/γ agonist (relative to vehicle) over a 2 to 4 h time period reveals a reproducible and robust increase in the immunoreactivity of the GRα-D isoform. It is observed that MAO-A mRNA expression is significantly increased by treatment with the ERRβ/γ agonist, GSK4716. Furthermore, it is observed that GSK4716 induces the expression of the mRNAs encoding peroxisome proliferator-activated receptor-γcoactivator 1α (PGC-1α) and PGC-1β (key regulator of many metabolic genes) identified as direct coactivators for the ERR family. GSK4716 induces the expression of PGC-1 and genes involved in fatty acid oxidation in concordance with the characterized role of ERRγ in cardiac metabolism. Treatment of primary mouse myotubes with GSK4716, an ERRβ/γ agonist, results in a concerted increase in the expression levels of Ppargc1a , Ppargc1b , and the Esrr genes. Furthermore, Cpt1b , Atp5b , and Idh3 , genes in key mitochondrial pathways, are also induced by GSK4716. Additionally, GSK4716 increases citrate synthase activity and cytochrome c protein levels. |
Risk Codes | R43 - May cause sensitization by skin contact R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
Safety Description | S36/37 - Wear suitable protective clothing and gloves. S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
UN IDs | UN 3077 9 / PGIII |
WGK Germany | 3 |
Hazard Class | 9 |
1mg | 5mg | 10mg | |
---|---|---|---|
1 mM | 3.542 ml | 17.709 ml | 35.418 ml |
5 mM | 0.708 ml | 3.542 ml | 7.084 ml |
10 mM | 0.354 ml | 1.771 ml | 3.542 ml |
5 mM | 0.071 ml | 0.354 ml | 0.708 ml |
Introduction | estrogen-related receptors (ERR) are orphan nuclear receptors that are homologous to the estrogen receptor family, expressed in tissues with high metabolic requirements. Peroxisome proliferator-activated receptor gamma-coactivator 1α (PGC-1α) is known to enhance ERR activity by binding to such receptors. GSK4716 is an ERR β/γ agonist (IC50=2 μm) that activates the receptor with a potency similar to that of the protein ligand PGC-1α. It binds more than 50-fold selectivity to ERRβ/γ compared to the estrogen receptor. This compound has been used to demonstrate the contribution of ERR receptor activity to the regulation of mitochondrial activity in skeletal muscle during exercise. |
biological activity | GSK-4716 is a selective ERR beta/gamma agonist. |
Target | ERR β/γ |