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General description
A cell-permeable (aryl,indole) maleimide compound that acts as a potent, selective, ATP-competitive inhibitor of GSK-3 activity (Ki = 9.1 nM for GSK-3α). At 10 µM concentration, does not significantly inhibit a panel of 24 other protein kinases tested. Reported to stimulate glycogen synthesis in Chang human liver cells (EC50 = 3.6 µM) and induce transcription of β-catenin-LEF/TCF (lymphoid enhancer factor/T cell factor) regulated reporter gene in HEK293 human embryonic kidney cell lines. Offers protection against polyglutamine-induced death in SK-N-SH and COS-7 cells and attenuates hypoxia-induced apoptosis in VSMC and COS-7 cells. Shown to reduce phosphoenolpyruvate carboxykinase (PEPCK) and glucose-6-phosphatase (G6Pase) expression in hepatoma cells. Promotes the survival of CLL lymphocytes via Wnt/β-catenin-mediated transcription activation. Exhibits delayed cardioprotection in vivo in a rat model via a KATP (ATP-sensitive potassium channels) and MPTP (mitochondrial permeability transition pore)-dependent mechanism at reperfusion.
Preparation Note
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Other Notes
Gross, E., et al. 2008. Am. J. Phy. Heart Circ Physiol.294, H1497.
Bain, J., et al. 2007. Biochem. J.408, 297.
Lu, D., et al. 2004. PNAS.101, 3118.
Carmichael, J., et al. 2002. J. Biol. Chem.277, 33791.
Culbert, A.A., et al. 2001. FEBS Lett.507, 288.
Lochhead, P.A., et al. 2001. Diabetes50, 937.
Cross, D.A., et al. 2001. J. Neurochem.77, 94.
Coghlan, M.P., et al. 2000. Chem. Biol.7, 793.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Irritant (B)
| assay | ≥98% (HPLC) |
| Quality Segment | 100 |
| form | solid |
| manufacturer/tradename | Calbiochem® |
| storage condition | OK to freeze |
| color | orange |
| solubility | DMSO: 50 mg/mL |
| shipped in | ambient |
| storage temp. | 2-8°C |
| SMILES string | Clc1c(ccc(c1)Cl)C2=C(C(=O)NC2=O)c3c4c([n](c3)C)cccc4 |
| InChI | 1S/C19H12Cl2N2O2/c1-23-9-13(11-4-2-3-5-15(11)23)17-16(18(24)22-19(17)25)12-7-6-10(20)8-14(12)21/h2-9H,1H3,(H,22,24,25) |
| InChI key | JCSGFHVFHSKIJH-UHFFFAOYSA-N |
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¥ 2622.09
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¥ 2290.21
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¥ 1779.22
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¥ 5887.85
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¥ 2151.46
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¥ 1509.00
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