492041
Nrf2 Activator II, AI-1
The Nrf2 Activator II, AI-1, also referenced under CAS 75483-04-4, modulates the biological activity of Nrf2. This small molecule/inhibitor is primarily used for Biochemicals applications.
Synonym(s):
Nrf2 Activator II, AI-1, Ethyl-4-chloro-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate
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About This Item
Empirical Formula (Hill Notation):
C13H12ClNO3
CAS Number:
Molecular Weight:
265.69
UNSPSC Code:
12352200
NACRES:
NA.51
MDL number:
Assay:
≥97% (HPLC)
Form:
solid
Storage condition:
OK to freeze, desiccated, protect from light
Quality Segment
assay
≥97% (HPLC)
form
solid
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze, desiccated, protect from light
color
off-white
solubility
DMSO: 50 mg/mL
shipped in
ambient
storage temp.
2-8°C
SMILES string
Clc1c2c([n]([c](c1C(=O)OCC)=O)C)cccc2
InChI
1S/C13H12ClNO3/c1-3-18-13(17)10-11(14)8-6-4-5-7-9(8)15(2)12(10)16/h4-7H,3H2,1-2H3
InChI key
XUJQDJGGHFNYDY-UHFFFAOYSA-N
General description
A cell-permeable chloro-quinolinone compound that selectively and covalently modifies Kelch-like ECH-associated protein 1 (Keap1)-Cys151 and represses Keap1 function and reduces Nrf2 (Nuclear factor erythroid 2-related factor 2)-Keap1 interaction. Shown to stabilize Nrf2 by inhibiting the Keap1-driven ubiquitination of Nrf2 and thereby activating the Nrf2-ARE (antioxidant response element) pathway (EC50 = 2.7 µM in neuroblastoma IMR-32 cells). Offers protection against H2O2 induced oxidative stress, but unlike tert-butylhydroquinone. AI-1 does not act as a free radical scavenger. Its anti-oxidant effects are mediated via Nrf2 induced antioxidant response. Does not affect mutant ARE where GC are substituted with AT within the core ARE sequence.
Biochem/physiol Actions
Cell permeable: yes
Primary Target
Keap1
Keap1
Reversible: no
Packaging
Packaged under inert gas
Preparation Note
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Use only fresh DMSO for reconstitution.
Other Notes
Hur, W., et al. 2010. Chem. Biol.17, 537.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Standard Handling (A)
Storage Class
11 - Combustible Solids
wgk
WGK 3
Certificates of Analysis (COA)
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