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Merck

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:
75483-04-4
Molecular Weight:
265.69
UNSPSC Code:
12352200
NACRES:
NA.51
MDL number:
MFCD00634787
Assay:
≥97% (HPLC)
Form:
solid
Quality level:
100
Storage condition:
OK to freeze, desiccated, protect from light

Key Documents

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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

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

Quality Level

100

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
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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Wooyoung Hur et al.
Chemistry & biology, 17(5), 537-547 (2010-06-11)
Eukaryotic cells counteract oxidative and other environmental stress through the activation of Nrf2, the transcription factor that controls the expression of a host of protective enzymes by binding to the antioxidant response element (ARE). The electrophilic molecules that are able

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