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SML1046

Sigma-Aldrich

CHIR99021

≥98% (HPLC), powder, GSK-3 inhibitor

Synonyma:

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

Empirický vzorec (Hillův zápis):
C22H18Cl2N8
Číslo CAS:
252917-06-9
Molekulová hmotnost:
465.34
MDL number:
MFCD11846251
UNSPSC Code:
12352200
PubChem Substance ID:
329825639
NACRES:
NA.77

product name

CHIR99021, ≥98% (HPLC)

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

Č. produktu
Popis
Stanovení ceny

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

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

Osvědčení o analýze (COA)

Vyhledejte osvědčení Osvědčení o analýze (COA) zadáním čísla šarže/dávky těchto produktů. Čísla šarže a dávky lze nalézt na štítku produktu za slovy „Lot“ nebo „Batch“.

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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)
Chemical conversion of human lung fibroblasts into neuronal cells
Wan XY, et al.
International Journal of Molecular Medicine, 41(3), 1463-1468 (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)
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