SML1046

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
• Empirical Formula (Hill Notation): C₂₂H₁₈Cl₂N₈
• CAS Number: 252917-06-9
• Molecular Weight: 465.34
• MDL number: MFCD11846251
• UNSPSC Code: 12352200
• PubChem Substance ID: 329825639
• NACRES: NA.77

Properties

• 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

Description

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.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302
• pcodes: P264 - P270 - P301 + P312 - P501
• 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