2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITRO-
2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITRO- Basic information
- Product Name:
- 2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITRO-
- Synonyms:
-
- 2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITRO-
- N6-[ 2-[4-(2,4-DICHLORO-PHENYL)-5-IMIDAZOL-1-YL-PYRIMIDIN-2-YLAMINO]-ETHYL]-3-NITRO-PYRIDINE-2,6-DIAMINE
- CHIR98014(CT98014)
- N2-(2-((4-(2,4-dichlorophenyl)-5-(1H-iMidazol-1-yl)pyriMidin-2-yl)aMino)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
- 2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-
- N6-[2-[[4-(2,4-dichlorophenyl)-5-(1H-imidazol-1-yl)-2-pyrimidinyl]amino]ethyl]-3-nitro-2,6-Pyridinediamine CHIR98014
- CHIR-98014;CHIR 98014;CT98014
- CAS:
- 252935-94-7
- MF:
- C20H17Cl2N9O2
- MW:
- 486.31
- Product Categories:
-
- Akt
- mTOR
- PI3K/Akt/mTOR
- Inhibitors
- PI3K
- Mol File:
- 252935-94-7.mol
2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITRO- Chemical Properties
- Density
- 1.62
- storage temp.
- -20°C
- solubility
- insoluble in H2O; insoluble in EtOH; ≥8.1 mg/mL in DMSO with gentle warming
- form
- powder
- color
- white to brown
2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITRO- Usage And Synthesis
Uses
CHIR 98014 has been used for the generation of small molecules neural progenitor cells and differentiation towards motor neurons. It has also been used as a Wnt/β-catenin pharmacological agonist in the cell-conditioned medium to perform chromatin immunoprecipitation (ChIP) studies in HT22 neurons.
Definition
ChEBI: CHIR-98014 is a member of the class of aminopyrimidines that is pyrimidine substituted by {2-[(6-amino-5-nitropyridin-2-yl)amino]ethyl}amino, 2,4-dichlorophenyl, and 1H-imidazol-1-yl groups at positions 2, 4 and 5, respectively. It is a potent ATP-competitive inhibitor of GSK3alpha and GSK3beta (IC50 values of 0.65 and 0.58 nM, respectively). It has a role as an EC 2.7.11.26 (tau-protein kinase) inhibitor, an apoptosis inducer, an antineoplastic agent, a hypoglycemic agent, a Wnt signalling activator and a tau aggregation inhibitor. It is a secondary amino compound, a dichlorobenzene, a member of imidazoles, a diaminopyridine, an aminopyrimidine and a C-nitro compound.
Biological Activity
chir-98014 is a potent inhibitor of gsk-3α and gsk-3β with ic50 values of 0.65 nm and 0.58 nm, respectively [1]gsk-3 (glycogen synthase kinase 3) is a serine/threonine protein kinase and plays a pivotal role in a number of central intracellular signaling pathways, including cellular proliferation, migration, inflammation and immune responses, glucose regulation, and apoptosis. recently, it has been reported that gsk-3 abnormally expressed in a variety of diseases, including type ii diabetes, alzheimer's disease, inflammation, cancer, and bipolar disorder [2, 3].chir-98014 is a potent gsk-3α and gsk-3β inhibitor. when tested with insulin receptor-expressing cho-ir cells or primary rat hepatocytes, chir-98014 stimulated the gs activity ratio as high as two- to three fold compared with basal in a dose dependent manner. similarly, in isolated type 1 skeletal muscle from insulin-sensitive lean zucker and from insulin-resistant zdf rats, administration of chir-98014 activated gs activity ratio [1]. in mouse es-d3 cells, chir-98014 treatment (48 and 72 hours later) resulted in a significant activation of the wnt/beta-catenin pathway via inhibiting gsk-3 [4].in markedly diabetic and insulin-resistant db/db mice model, oral administration of chir-98014 (30mg/kg) significantly reduced fasting hyperglycemia within 4 hours and improved glucose disposal during an ipgtt [1].
Biochem/physiol Actions
CHIR 98014 is a glycogen synthase kinase-3 (GSK-3) inhibitor with IC50 values of 0.65 nM and 0.58 nM for GSK3α and GSK3β, respectively. CHIR98014 is 500-fold to >10,000-fold selectivity for GSK-3 versus 20 other protein kinases tested, including closest homologs Cdc2 and ERK2.
target
GSK-3β
storage
Store at -20°C
References
[1]. ring, d.b., et al., selective glycogen synthase kinase 3 inhibitors potentiate insulin activation of glucose transport and utilization in vitro and in vivo. diabetes, 2003. 52(3): p. 588-95.
[2]. pan wa, et al. the rna recognition motif of nifk is required for rrna maturation during cell cycle progression. rna biol. 2015. 12(3):255-67.
[3]. mccubrey ja, et al. gsk-3 as potential target for therapeutic intervention in cancer. oncotarget. 2014. 5(10):2881-911.
[4]. naujok o, et al. cytotoxicity and activation of the wnt/beta-catenin pathway in mouse embryonic stem cells treated with four gsk3 inhibitors. bmc res notes. 2014. 7(1):273-281.
2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITRO-Supplier
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2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITRO-(252935-94-7)Related Product Information
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