492040

Nrf2 Activator

The Nrf2 Activator modulates the biological activity of Nrf2. This small molecule/inhibitor is primarily used for Phosphorylation & Dephosphorylation applications.

• Synonym(s): Nrf2 Activator, (E)-1-(2-Methoxyphenyl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one, Nuclear factor-erythroid 2 p45-related factor 2 Activator, 2-Trifluoromethyl-2ʹ-methoxychalone, Antioxidant Response Element Activator II, ARE Activator II, Antioxidant Response Element Activator II, ARE Activator II, (E)-1-(2-Methoxyphenyl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one, Nuclear factor-erythroid 2 p45-related factor 2 Activator, 2-Trifluoromethyl-2ʹ-methoxychalone
• Empirical Formula (Hill Notation): C₁₇H₁₃F₃O₂
• CAS Number: 1309371-03-6
• Molecular Weight: 306.28
• MDL number: MFCD30186783
• UNSPSC Code: 12352200

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: syrup
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: yellow
• solubility: DMSO: 100 mg/mL; ethanol: 100 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: O=C(/C=C/C1=C(C=CC=C1)C(F)(F)F)C2=C(OC)C=CC=C2

Description

General description

A cell-permeable chalcone that effectively activates NQO1 (NADPH-/quinone oxidoreductase 1) ARE- (antioxidant response element) mediated reporter transcription in human bronchial epithelial Beas-2B cells (7.0-fold of control; 20 µM compound) and induces Nrf2- (Nuclear factor erythroid 2 p45-related factor 2) regulated antioxidants and cytoprotective genes transcription, including GCLM (glutamate-cysteine ligase modifier subunit), NQO1, and HO1 (heme oxygenase-1), both in cultures ([compound] = 10 to 20 µM) in vitro and in mice (50 mg/kg p.o.) in vivo.

A cell-permeable chalcone that is shown to effectively activate NQO1 (NADPH/quinine oxidoreductase 1) ARE- (antioxidant response element) mediated reporter transcription in human bronchial epithelial Beas-2B cells (6.3- and 7.0-fold of control, respectively, with 10 and 20 µM compound) and induce Nrf2- (Nuclear factor erythroid 2 p45-related factor 2) regulated antioxidants and cytoprotective genes transcription, including GCLM (glutamate-cysteine ligase modifier subunit), NQO1, and HO1 (heme oxygenase-1), both in Beas-2B cultures (4-, 6.7-, and 178-fold, respectively, of basal NQO1/24 h, GCLM/6 h, and HO1/6 h mRNA level; [compound ] = 10 µM) in vitro and in mice (6- and 10-fold, respectively, of control GCLM and NQO1 mRNA level in small intestine 24 h after single p.o. dosage of 50 mg/kg) in vivo. The drug′s cellular target(s) and mechanism of action is unknown, but likely involves covalent thio modification of the target(s) by the compound′s electrophilic enone moiety.

Packaging

Packaged under inert gas

Warning

Toxicity: Regulatory Review (Z)

Other Notes

Kumar, V., et al. 2011. J. Med. Chem.54, 4147.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 2