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SML1046

Sigma-Aldrich

CHIR99021

≥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:
Molecular Weight:
465.34
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

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Product Name

CHIR99021, ≥98% (HPLC)

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
SML1094C9873361559
assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥97% (HPLC)

form

powder

form

powder

form

powder

form

solid

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

200

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

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

color

white to light brown

color

white to brown

color

white to beige

color

light beige

General description

CHIR99021 is an aminopyrimidine derivative.[1] 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.[2] CHIR99021 promotes self-renewal of ESCs by modulating transforming growth factor β (TGF-β), Notch and mitogen-activated protein kinases (MAPK) signaling pathways.[1] 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.[3]

Application

CHIR99021 has been used as a Wnt signaling agonist to study its effects on the differentiation of human pluripotent stem cell-derived cardiomyocytes (hPSCs).[4][5]
CHIR99021 has been used:
  • in cocktail with small molecules to convert human lung fibroblast cells into neurons[6]
  • as a culture medium supplement in potassium supplemented simplex optimization medium (KSOM) for the culture of blastocysts[7]
  • for chronic inhibition of GSK-3 to investigate its role in corticogenesis[8]

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.

related product

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

No data available

flash_point_c

No data available


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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)
Enterochromaffin Cells Are Gut Chemosensors that
Couple to Sensory Neural Pathways
Bellono NW
Cell, 170, 185-198 (2017)
Chemical conversion of human lung fibroblasts into neuronal cells
Wan XY, et al.
International Journal of Molecular Medicine, 41(3), 1463-1468 (2018)

Articles

Naive pluripotent stem cells cultured in vitro using specialized media and inhibitors mimic "ground-state" cells from blastocysts.

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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.

Questions

1–3 of 3 Questions  
  1. Is CHIR99021 light sensitive?

    1 answer
    1. This material is not reported as being light sensitive.

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  2. What is the solubility of Product SML1046?

    1 answer
    1. The solubility of Product SML1046 has been tested in DMSO at 2 mg/ml when warmed. Although testing in water has not been conducted, it is expected to be less than 1 mg/ml at 25°C, similar to its solubility in saline. Additionally, solubility testing in ethanol has also shown a solubility of less than 1 mg/ml at 25°C.

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  3. How is Product SML1046, CHIR99021, to be dissolved? And once dissolved, is the solution stable?

    1 answer
    1. This product is soluble in DMSO (warmed) at 2-5 mg/mL. Solubility in polar solvents such as water, saline, or ethanol, is expected to be <1 mg/ml at 25° C. Following reconstitution, aliquot and freeze at -20°C. Stock solutions are stable for up to 6 months at -20°C. Avoid repeated freeze/thaw cycles and protect from light.

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