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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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5 MG
₩199,651
25 MG
₩801,444

₩199,651


Estimated to ship onJanuary 27, 2025Details


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5 MG
₩199,651
25 MG
₩801,444

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

₩199,651


Estimated to ship onJanuary 27, 2025Details


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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

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.

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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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Enterochromaffin Cells Are Gut Chemosensors that
Couple to Sensory Neural Pathways
Bellono NW
Cell, 170, 185-198 (2017)
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)
Chemical conversion of human lung fibroblasts into neuronal cells
Wan XY, et al.
International Journal of Molecular Medicine, 41(3), 1463-1468 (2018)
Longitudinal dissection in brain organoids at single cell resolution uncovers the developmental role of GSK3 in human corticogenesis
Tobon AL, et al.
bioRxiv (2018)
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)

Articles

Human pancreatic cancer organoid biobank (PDAC organoids) with various KRAS mutations to aide in 3D cell culture and cancer research applications.

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

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

1–2 of 2 Questions  
  1. 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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  2. 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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