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SML1046

CHIR99021

Name: CHIR99021
Brand: SIGMA

≥98% (HPLC), powder, GSK-3 inhibitor

Synonym(s):

6-[[2-[[4-(2,4-Dichlorophenyl)-5-(5-methyl-1H-imidazol-2-yl)-2-pyrimidinyl]amino]ethyl]amino]-3-pyridinecarbonitrile, CT99021

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About This Item

Empirical Formula (Hill Notation):

C₂₂H₁₈Cl₂N₈

CAS Number:

252917-06-9

Molecular Weight:

465.34

UNSPSC Code:

12352200

PubChem Substance ID:

329825639

NACRES:

NA.77

MDL number:

MFCD11846251

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

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Properties

Product Name

CHIR99021, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to light brown

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

ClC(C=C1Cl)=CC=C1C2=NC(NCCNC(N=C3)=CC=C3C#N)=NC=C2C4=NC(C)=CN4

InChI

1S/C22H18Cl2N8/c1-13-10-29-21(31-13)17-12-30-22(32-20(17)16-4-3-15(23)8-18(16)24)27-7-6-26-19-5-2-14(9-25)11-28-19/h2-5,8,10-12H,6-7H2,1H3,(H,26,28)(H,29,31)(H,27,30,32)

InChI key

AQGNHMOJWBZFQQ-UHFFFAOYSA-N

Description

General description

CHIR99021 is an aminopyrimidine derivative. CHIR99021 promotes self-renewal potential of embryonic stem cells (ESCs) of mice by inhibiting glycogen synthase kinase-3 (GSK-3) activity and potentiates the upregulation of β-catenin and c-Myc functions. CHIR99021 promotes self-renewal of ESCs by modulating transforming growth factor β (TGF-β), Notch and mitogen-activated protein kinases (MAPK) signaling pathways. CHIR99021 is an agonist of wingless/integrated (wnt) signalling, upregulates cyclinA expression and promotes cell proliferation in non-small-cell lung cancer (NSCLC) cell lines.

Application

CHIR99021 has been used:

in cocktail with small molecules to convert human lung fibroblast cells into neurons
as a culture medium supplement in potassium supplemented simplex optimization medium (KSOM) for the culture of blastocysts
for chronic inhibition of GSK-3 to investigate its role in corticogenesis

CHIR99021 has been used as a Wnt signaling agonist to study its effects on the differentiation of human pluripotent stem cell-derived cardiomyocytes (hPSCs).

Biochem/physiol Actions

CHIR99021 is a very potent inhibitor of Glycogen synthase kinase 3 (GSK3, IC₅₀ values for GSK3α and GSK3β = 10 and 6.7 nM, respectively). There is no cross-reactivity against CDKs. CHIR99201 potentiates self-renewal of human and mouse embryonic stem cells, and enhances reprogramming of somatic cells into stem cells.

CHIR99021 is a very potent inhibitor of Glycogen synthase kinase 3.