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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All Photos(3)

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

Product Name

CHIR99021, ≥98% (HPLC)

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

assay

≥98% (HPLC)

form

powder

color

white to light brown

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

−20°C

Quality Level

100

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Biochem/physiol Actions

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

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.

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

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.

pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

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)

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)

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)

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)

View All Related Papers

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