5.04377

AMPK Signaling Activator XIII, ZLN005

• Synonym(s): AMPK Signaling Activator XIII, ZLN005, 2-(4- tert-Butylphenyl)-1H-benzo[d]imidazole, 2-(4-(2-Methyl-2-propanyl)phenyl)-1H-benzimidazole, Luciferase Inhibitor IV, 2-(4-tert-Butylphenyl)-1H-benzo[d]imidazole, 2-(4-(2-Methyl-2-propanyl)phenyl)-1H-benzimidazole, Luciferase Inhibitor IV
• Empirical Formula (Hill Notation): C₁₇H₁₈N₂
• CAS Number: 4529-96-8
• Molecular Weight: 250.34
• MDL number: MFCD01560221
• UNSPSC Code: 12352200
• NACRES: NA.77
• Assay: ≥99% (HPLC)
• Form: powder
• Storage condition: OK to freeze, protect from light

Properties

• assay: ≥99% (HPLC)
• Quality Segment: 100
• form: powder
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: pink-white
• solubility: DMSO: 50 mg/mL
• storage temp.: 2-8°C
• SMILES string: [nH]1c2c(nc1c3ccc(cc3)C(C)(C)C)cccc2
• InChI: 1S/C17H18N2/c1-17(2,3)13-10-8-12(9-11-13)16-18-14-6-4-5-7-15(14)19-16/h4-11H,1-3H3,(H,18,19)
• InChI key: LQUNNCQSFFKSSK-UHFFFAOYSA-N

Description

General description

A cell-permeable benzimidazole that, in addition to its inhibitory potency against luciferase activity (IC₅₀<10 nM), is reported to activate AMPK signaling by increasing cellular ADP/ATP ratio via mitochondria respiration uncoupling in a cell type-specific manner, effectively activating AMPK & PGC-1α in muscle, but not liver, cell types both in cultures (5-20 µM & 1-24 h in rat L6 myotubes; no effect in primary rat hepatocytes) in vitro and in db/db mice (gastrocnemius/calf muscle, but not liver tissue; 15 mg/kg/day via p.o. for 6 wks) in vivo. ZLN005 is orally available in mice (plasma C_max & T_max = 3.7 µM & 15 min, respectively, following single 15 mg/kg oral dosage to db/db mice) and is efficacious in improving glucose (1.5 g/kg i.p.) tolerance among 4-wk-treated and insulin (1 unit/kg) tolerance among 5-wk treated db/db mice (by 14% and 18%, respectively; 15 mg/kg/day via p.o.) in vivo without any apparent effects on body weight or food intake among db/db or non-diabetic controls.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
increases cellular ADP/ATP ratio via mitochondria respiration uncoupling

Secondary Target
luciferase activity inhibitor

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.

Other Notes

Zhang, L.N., et al. 2013. Diabetes.62, 1297.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3