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Key Documents

5.05987

Sigma-Aldrich

Keap1-Nrf2 Interaction Probe, ML334

Synonym(s):

Keap1-Nrf2 Interaction Probe, ML334, (1S,2R)-2-((S)-1-((1,3-dioxoisoindolin-2-yl)methyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)cyclohexanecarboxylic acid, (SRS)-LH601, Nrf Activator VI

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About This Item

Empirical Formula (Hill Notation):
C26H26N2O5
CAS Number:
1432500-66-7
Molecular Weight:
446.50
MDL number:
MFCD30290156
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

Quality Level

100

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

cream

solubility

DMSO: 100 mg/mL

storage temp.

−20°C

SMILES string

N4(C(=O)c5c(cccc5)C4=O)C[C@H]1N(CCc3c1cccc3)C(=O)[C@H]2[C@H](CCCC2)C(=O)O

InChI

1S/C26H26N2O5/c29-23(20-11-5-6-12-21(20)26(32)33)27-14-13-16-7-1-2-8-17(16)22(27)15-28-24(30)18-9-3-4-10-19(18)25(28)31/h1-4,7-10,20-22H,5-6,11-15H2,(H,32,33)/t20-,21+,22-/m1/s1

InChI key

LNENLABLFGGAFF-BHIFYINESA-N

General description

A cell-permeable tetrahydroisoquinoline derivative that acts as a direct, non-covalent inhibitor of Keap1 - Nrf2 (Kelch-like ECH-associated protein 1 - nuclear factor erythroid 2-related factor 2) protein - protein interaction (Kd = 1 µM) that causes the dissociation of Nrf2 from keap1 in the cytosol. Exhibits ARE-inducing activity (EC50 = 18 µM in U2OS Keap1-Nrf2 functional assay) and promotes Nrf2 translocation to the nucleus (EC50 = 12 µM). Has good solubility in aqueous buffers (>100 µM in phosphate buffered saline).

Please note that the molecular weight for this compound is batch-specific due to variable water content.

Biochem/physiol Actions

Primary Target
Keap1–Nrf2
Reversible: yes

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Hu, L., et al, 2013, Bioorg. Med. Chem. Lett.23, 3039.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Global Trade Item Number

SKUGTIN
5.05987.000104055977262599

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