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SML1094

Sigma-Aldrich

CHIR 98014

≥98% (HPLC), powder, GSK-3 inhibitor

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Synonym(s):
N-6-[2-[[4-(2,4-Dichlorophenyl)-5-(1H-imidazol-1-yl)-2-pyrimidinyl]amino]ethyl]-3-nitro-2,6-pyridinediamine, CHIR-98014
Empirical Formula (Hill Notation):
C20H17Cl2N9O2
CAS Number:
252935-94-7
Molecular Weight:
486.31
MDL number:
MFCD10565922
UNSPSC Code:
12352200
PubChem Substance ID:
329825471
NACRES:
NA.77

Quality Level

200

Assay

≥98% (HPLC)

form

powder

color

white to brown

solubility

DMSO: 0.5 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

NC1=C(C=CC(NCCNC2=NC(C3=C(Cl)C=C(Cl)C=C3)=C(N4C=CN=C4)C=N2)=N1)[N+]([O-])=O

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

Application

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.

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Synaptic abnormalities have been described in individuals with autism spectrum disorders (ASD). The cell-adhesion molecule Neuroligin-3 (Nlgn3) has an essential role in the function and maturation of synapses and NLGN3 ASD-associated mutations disrupt hippocampal and cortical function. Here we show
Diana Gumber et al.
eLife, 9 (2020-12-18)
WNT proteins are secreted symmetry breaking signals that interact with cell surface receptors of the FZD family to regulate a multitude of developmental processes. Studying selectivity between WNTs and FZDs has been hampered by the paucity of purified WNT proteins
Paola Rusmini et al.
Autophagy, 15(4), 631-651 (2018-10-20)
Macroautophagy/autophagy, a defense mechanism against aberrant stresses, in neurons counteracts aggregate-prone misfolded protein toxicity. Autophagy induction might be beneficial in neurodegenerative diseases (NDs). The natural compound trehalose promotes autophagy via TFEB (transcription factor EB), ameliorating disease phenotype in multiple ND

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