ChemicalBook > CAS DataBase List > CHIR-99021

CHIR-99021

Product Name
CHIR-99021
CAS No.
252917-06-9
Chemical Name
CHIR-99021
Synonyms
CT99021;CHIR-99021 (CT99021) HCl;6-((2-((4-(2,4-Dichlorophenyl)-5-(5-methyl-1H-imidazol-2-yl)pyrimidin-2-yl)amino)ethyl)amino)nicotinonitrile;GSK 3IXV;CHIR CHIR;CHIR73911;CHIR-99021;CHIR-99012;CHIR 73911;CHIR-73911
CBNumber
CB11516097
Molecular Formula
C22H18Cl2N8
Formula Weight
465.34
MOL File
252917-06-9.mol
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CHIR-99021 Property

Boiling point:
784.1±70.0 °C(Predicted)
Density 
1.48
storage temp. 
-20°C
solubility 
DMSO: soluble2mg/mL, clear (warmed)
pka
11.92±0.10(Predicted)
form 
powder
color 
white to light brown
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
InChIKey
AQGNHMOJWBZFQQ-UHFFFAOYSA-N
CAS DataBase Reference
252917-06-9
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Safety

Hazard Codes 
T
Risk Statements 
25-36/37/38
Safety Statements 
26-36/37/39-45
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3
HS Code 
29335990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H300Fatal if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
361571
Product name
InSolution? GSK-3 Inhibitor XVI, CHIR99021
Packaging
5mg
Price
$318
Updated
2024/03/01
Sigma-Aldrich
Product number
361559
Product name
GSK-3 Inhibitor XVI
Packaging
5mg
Price
$309
Updated
2024/03/01
TCI Chemical
Product number
C2943
Product name
CHIR 99021
Packaging
25MG
Price
$241
Updated
2024/03/01
TCI Chemical
Product number
C2943
Product name
CHIR 99021
Packaging
100MG
Price
$658
Updated
2024/03/01
Cayman Chemical
Product number
13122
Product name
CHIR 99021
Purity
≥95%
Packaging
1mg
Price
$32
Updated
2024/03/01
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CHIR-99021 Chemical Properties,Usage,Production

Description

CHIR99021 is an aminopyrimidine derivative that is an extremely potent glycogen synthase kinase (GSK) 3 inhibitor, inhibiting both GSK3β (IC?? = 6.7 nM) and GSK3α (IC?? = 10 nM). GSK3 is a serine/threonine kinase that is a key inhibitor of the WNT pathway; therefore CHIR99021 functions as a WNT activator. It shows little activity against a large panel of kinases including CDK2 and other serine/threonine kinases such as MAPK and PKB (Bain et al.).
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.

Description

Glycogen synthase kinase 3 (GSK3) is a serine/threonine kinase that plays a key inhibitory role in both the insulin and Wnt signaling pathways. CHIR99021 is an aminopyrimidine derivative that inhibits GSK3α and GSK3β with IC50 values of 10 and 6.7 nM, respectively. When tested against twenty different protein kinases, this inhibitor shows greater than 500-fold selectivity for GSK3. CHIR99021 activates glycogen synthesis in CHO-IR cells (EC50 = 0.8 μM) and in isolated type 1 diabetic rat skeletal muscle. A single oral dose (30 mg/kg) of CHIR99021 enhances in vivo glucose metabolism in a rodent model of type 2 diabetes. CHIR99021 has also been shown to induce the reprogramming of murine and human somatic cells into stem cells.

Uses

Glycogen synthase kinase 3 (GSK3) is a serine/threonine kinase that plays a key inhibitory role in both the insulin and Wnt signaling pathways. CHIR99021 is an aminopyrimidine derivative that inhibits GSK3α and GSK3β with IC50 values of 10 and 6.7 nM, respectively. When tested against twenty different protein kinases, this inhibitor shows greater than 500-fold selectivity for GSK3. CHIR99021 activates glycogen synthesis in CHO-IR cells (EC50 = 0.8 μM) and in isolated type 1 diabetic rat skeletal muscle. A single oral dose (30 mg/kg) of CHIR99021 enhances in vivo glucose metabolism in a rodent model of type 2 diabetes. CHIR99021 has also been shown to induce the reprogramming of murine and human somatic cells into stem cells.

Uses

A specific GSK-3 inhibitor of GSK-3β and GSK-3α with IC50s of 5 nM and 10 nM, respectively.

Uses

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

Definition

ChEBI: A member of the class of aminopyrimidines that is 2-aminopyrimidine substituted at positions N2, 5 and 6 by (5-cyanopyridin-2-yl)ethyl, 4-methylimidazol-2-yl and 2,4-dichlorophenyl groups respectively.

Application

CHIR 99021 is an aminopyrimidine derivate that is a selective and potent inhibitor of glycogen synthase kinase 3 (GSK-3). It is used to maintain human and mouse stem cell lines and, in combination with other reagents, to chemically reprogram somatic cells into stem cells.
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.

Biological Activity

CHIR 99021 is a potent and highly selective inhibitor of glycogen synthase kinase 3 (GSK-3) (IC50 values are 6.7 and 10 nM for GSK-3β and GSK-3α respectively). Acts as Wnt activator. Exhibits >500-fold selectivity for GSK-3 over closely related kinases; also displays >800-fold selectivity against 45 additional enzymes and receptors. In combination with the irreversible inhibitor of LSD1 (Cat. No. 3852), CHIR 99021 enables reprogramming of mouse embryonic fibroblasts, transduced by Oct4 and Klf4 only, into iPSCs. CHIR 99021 enhances mouse and human ESC self-renewal when used in combination with PD 0325901 (Cat. No. 4192). CHIR 99021 allows formation of extended pluripotent stem (EPS) cells in combination with (S)-(+)-Dimethindene maleate (Cat.No. 1425), tetracycline antibiotic (Cat.No. 3268) and human leukemia inhibitory factor.

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.

storage

-20°C

References

1) Bennett et al. (2002), Regulation of Wnt signaling during adipogenesis; J. Biol. Chem., 277 30998 2) Bennett et al. (2005), Regulation of osteoblastogenesis and bone mass by Wnt10b; Proc. Natl. Acad. Sci. USA, 102 3324 3) Mussmann et al. (2007), Inhibition of GSK3 promotes replication and survival of pancreatic beta cells; J. Biol. Chem., 282 12030 4) Manceur et al. (2011), Inhibition of glycogen synthase kinase-3 enhances the differentiation and reduces the proliferation of adult human olfactory epithelium neural precursors; Exp. Cell. Res., 317 2086 5) Takaoka et al. (2016), Live imaging of transforming growth factor-β activated kinase 1 activation in Lewis Lung carcinoma 3LL cells implanted into syngeneic mice and treated with polyinosinic:polycytidylic acid; Cancer Sci., 107 644 [Focus Citation]

CHIR-99021 Preparation Products And Raw materials

Raw materials

Preparation Products

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CHIR-99021 Suppliers

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View Lastest Price from CHIR-99021 manufacturers

Anhui Ruihan Technology Co., Ltd
Product
CHIR-99021 252917-06-9
Price
US $30.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000t/year
Release date
2023-09-08
Career Henan Chemical Co
Product
6-[2-[4-(2,4-Dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)pyrimidin-2-ylamino]ethylamino]pyridine-3-carbonitrile 252917-06-9
Price
US $2.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100kg
Release date
2018-12-23

252917-06-9, CHIR-99021Related Search:

Carbon tetrachloride Dichloroethane CHLOROPHENYLSILANE 97 Phenylsilane Phenyltrichlorosilane Phenylphosphonic dichloride DICHLOROTRIPHENYLPHOSPHORANE PHENYLBORON DICHLORIDE PF 543 Valspodar ALK5 inhibitor II PF-543 (Citrate) Bortezomib Y27632 (hydrochloride) SB 431542 PD 0325901 Trametinib Olaparib

  • 6-[2-[4-(2,4-Dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)pyrimidin-2-ylamino]ethylamino]pyridine-3-carbonitrile
  • 6-{2-[4-(2,4-Dichloro-phenyl)-5-(4-methyl-1H-imidazol-2-yl)-pyrimidin-2-ylamino]-ethylamino}-nicotinonitrile
  • CHIR-99021
  • CT99021
  • GSK-3 Inhibitor XVI
  • 3-Pyridinecarbonitrile, 6-[[2-[[4-(2,4-dichlorophenyl)-5-(5-methyl-1H-imidazol-2-yl)-2-pyrimidinyl]amino]ethyl]amino]
  • CT99021;CHIR99021;CHIR 99021;CT-99021
  • CT 99021(CHIR 99021)
  • 6-[2-[4-(2,4-Dichlorophenyl)-5-(4-Methyl-1H-iMidazol-2-yl)pyriMidin-2-ylaMino]ethylaMino]pyridine-3-
  • CHIR 99021(CT 99021)
  • 6-(2-(4-(2,4-dichlorophenyl)-5-(4-Methyl-1H-iMidazol-2-yl)pyriMidin-2-ylaMino)ethylaMino)nicotinonitrile CHIR99021
  • CHIR-99021 (CT99021) HCl
  • CHIR 911, GSK-3 Inhibitor XVI
  • 6-(2-(4-(2,4-dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)pyrimidin-2-ylamino)ethylamino)nicotinonitrile hydrochloride
  • 6-[2-[4-(2,4-Dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)pyrimidin-2-ylamino]ethylamino]pyridine-3-carbonitrile CHIR-99021
  • CHIR-99021 GSK-3 Inhibitor XVI
  • 6-[[2-[[4-(2,4-Dichlorophenyl)-5-(5-methyl-1H-imidazol-2-yl)-2-pyrimidinyl]amino]ethyl]amino]-3-pyridinecarbonitrile
  • CHIR-99021, >=98%
  • CHIR-99021 HCL
  • 6-[2-[4-(2,4-Dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)pyrimidin-2-ylamino]ethylamino]pyrid
  • InSolution? GSK-3 Inhibitor XVI, CHIR99021
  • CHIR-99012
  • 6-[2-[[4-(2,4-dichlorophenyl)-5-(5-methyl-1H-imidazol-2-yl)pyrimidin-2-yl]amino]ethylamino]pyridine-3-carbonitrile
  • GSK-3 Inhibitor XVI - CAS 252917-06-9 - Calbiochem
  • InSolution GSK-3 Inhibitor XVI, CHIR99021 - CAS 252917-06-9 - Calbiochem
  • [2-[[4-(2,4-Dichlorophenyl)-5-(5-methyl-1H-imidazol-2-yl)-2-pyrimidinyl]amino]ethyl]amino]-3-pyridinecarbonitrile
  • CHIR 99021; CT 99021;CHIR99021;CT-99021
  • CHIR CHIR
  • 6-[2-[4-(2,4-Dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)pyrimidin-2-ylamino]ethylamino]pyridine-3-carbonitrile ISO 9001：2015 REACH
  • 6-((2-((4-(2,4-Dichlorophenyl)-5-(5-methyl-1H-imidazol-2-yl)pyrimidin-2-yl)amino)ethyl)amino)nicotinonitrile
  • CHIR99021 GSK3 inhibitor ab120890 CHIR-99021
  • GSK-3,Glycogen synthase kinase 3,CT 99021,CHIR 99021,β-catenin,inhibit,Autophagy,CT-99021,Beta catenin,CHIR99021,Wnt,Inhibitor,Glycogen synthase kinase-3
  • Laduviglusib
  • 6-[2-[[4-(2,4-Dichlorophenyl)-5-(5-methyl-2-imidazolyl)-2-pyrimidinyl]amino]ethylamino]-3-pyridinecarbonitrile
  • CHIR 73911
  • CHIR73911
  • CHIR-73911
  • GSK 3IXV
  • 252917-06-9
  • C22H18Cl2N8
  • C22H18Cl2N8HCl
  • C22H19Cl3N8
  • Inhibitors
  • Antineoplastic
  • Anti-cancer&immunity
  • PI3K/Akt/mTOR
  • Akt
  • mTOR
  • PI3K