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SML1046

Sigma-Aldrich

CHIR99021

≥98% (HPLC)

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Synonym(s):
6-[[2-[[4-(2,4-Dichlorophenyl)-5-(5-methyl-1H-imidazol-2-yl)-2-pyrimidinyl]amino]ethyl]amino]-3-pyridinecarbonitrile, CT99021
Empirical Formula (Hill Notation):
C22H18Cl2N8
CAS Number:
Molecular Weight:
465.34
MDL number:
PubChem Substance ID:

Quality Level

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

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This Item
SML1094C9873G5045
CHIR99021 ≥98% (HPLC)

Sigma-Aldrich

SML1046

CHIR99021

CHIR 98014 ≥98% (HPLC)

Sigma-Aldrich

SML1094

CHIR 98014

CPTH2 ≥98% (HPLC), powder

Sigma-Aldrich

C9873

CPTH2

GW6471 ≥98% (HPLC)

Sigma-Aldrich

G5045

GW6471

form

powder

form

powder

form

powder

form

powder

color

white to light brown

color

white to brown

color

white to beige

color

white to beige

solubility

DMSO: 2 mg/mL, clear (warmed)

solubility

DMSO: 0.5 mg/mL, clear (warmed)

solubility

DMSO: >10 mg/mL

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

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

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.

also commonly purchased with this product

Product No.
Description
Pricing

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

No data available

Flash Point(C)

No data available


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25G
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  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

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The roles of Notch3 on the cell proliferation and apoptosis induced by CHIR99021 in NSCLC cell lines: a functional link between Wnt and Notch signaling pathways
Li C, et al.
PLoS ONE, 8(12), e84659-e84659 (2013)
CHIR99021 promotes self-renewal of mouse embryonic stem cells by modulation of protein-encoding gene and long intergenic non-coding RNA expression
Wu Y, et al.
Experimental Cell Research, 319(17), 2684-2699 (2013)
Co-incident insertion enables high efficiency genome engineering in mouse embryonic stem cells
Shy BR
Nucleic Acids Research, 44, 7997-8010 (2016)
Longitudinal dissection in brain organoids at single cell resolution uncovers the developmental role of GSK3 in human corticogenesis
Tobon AL, et al.
bioRxiv (2018)
Pleiotropy of glycogen synthase kinase-3 inhibition by CHIR99021 promotes self-renewal of embryonic stem cells from refractory mouse strains
Ye S, et al.
PLoS ONE, 7(4), e35892-e35892 (2012)

Articles

Naive pluripotent stem cells are located within the epiblast of mature blastocysts. These primitive “ground-state” cells may be cultured in vitro using specialized media and small molecule inhibitors.

Organoid culture products to generate tissue and stem cell derived 3D brain, intestinal, gut, lung and cancer tumor organoid models.

Protocols

Step-by-step culture protocols for neural stem cell culture including NSC isolation, expansion, differentiation and characterization.

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