5.31167
GSK-3 Inhibitor XXIX, CHIR98014
别名:
GSK-3 Inhibitor XXIX, CHIR98014, N²-(2-(4-(2,4-Dichlorophenyl)-5-(1H-imidazol-1-yl)pyrimidin-2-ylamino)ethyl)-5-nitropyridine-2,6-diamine, N⁶-(2-((4-(2,4-Dichlorophenyl)-5-(1H-imidazol-1-yl)-2-pyrimidinyl)amino}ethyl)-3-nitro-2,6-pyridinediamine, CHIR-98014, CT-98014
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关于此项目
经验公式（希尔记法）:
C20H17Cl2N9O2
化学文摘社编号:
分子量:
486.31
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
Assay:
≥95% (HPLC)
Form:
powder
Storage condition:
OK to freeze, protect from light
assay
≥95% (HPLC)
Quality Segment
form
powder
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze, protect from light
color
yellow
solubility
DMSO: 25 mg/mL
storage temp.
2-8°C
SMILES string
Clc1c(ccc(c1)Cl)c2nc(ncc2[n]4cncc4)NCCNc3nc(c(cc3)[N+](=O)[O-])N
InChI
1S/C20H17Cl2N9O2/c21-12-1-2-13(14(22)9-12)18-16(30-8-7-24-11-30)10-27-20(29-18)26-6-5-25-17-4-3-15(31(32)33)19(23)28-17/h1-4,7-11H,5-6H2,(H3,23,25,28)(H,26,27,29)
InChI key
MDZCSIDIPDZWKL-UHFFFAOYSA-N
General description
A cell-permeable, highly potent, ATP-competitive, reversible inhibitor of both GSK-3α and β (IC₅₀ = 650 and 580 pM, respectively).
A cell-permeable, brain permeant aminopyrimidine compound that acts as a potent, ATP-competitive and reversible inhibitor of both GSK-3α and β (IC50 = 650 and 580 pM, respectively; Ki = 870 pM for human GSK-3β) and significantly affects downstream effects of GSK-3. Displays excellent selectivity over closely related Cdc2 and Erk2 (IC50 = 3.7 µM & >10 µM, respectively). Does not affect the activity of several other protein kinases studied. Acutely sensitizes glycogen synthase activity in isolated skeletal muscle from insulin-sensitive lean Zucker and insulin-resistant Zucker diabetic fatty (ZDF) rats and can also augment insulin-stimulated glucose uptake in ZDF rats. However, it does not affect the basal glucose uptake rate. Induces a significant reduction in fasting hyperglycemia in diabetic and insulin-resistant db/db mice (~30 mg/kg, s.c.). Reduces Tau phosphorylation (Ser396) in the cortex and hippocampus of postnatal rats. Also shown to activate Wnt/β-catenin signaling and direct the differentiation of human pluripotent stem cells into cardiomyocytes.
Biochem/physiol Actions
Cell permeable: yes
Primary Target
GSK-3 α & β
GSK-3 α & β
Target IC50: 650 and 580 pM for GSK-3&alpha
Target Ki: 870 pM for human GSK-3&beta
Preparation Note
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Other Notes
Grigoryan, T., et al. 2013. Proc. Natl. Acad. Sci. USA110, 18174.
Lian, X., et al. 2012. Proc. Natl. Acad. Sci. USA109, E1848.
Selenica, M.L., et al. 2007. Br. J. Pharmacol.152, 959.
Ring, D.B., et al. 2003. Diabetes.52, 588.
Nikoulina, S.E., et al. 2002. Diabetes.51, 2190.
Lian, X., et al. 2012. Proc. Natl. Acad. Sci. USA109, E1848.
Selenica, M.L., et al. 2007. Br. J. Pharmacol.152, 959.
Ring, D.B., et al. 2003. Diabetes.52, 588.
Nikoulina, S.E., et al. 2002. Diabetes.51, 2190.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Standard Handling (A)
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable