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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
Molecular Weight:
465.34
MDL Number:
MFCD11846251
MOL File:
252917-06-9.mol
MSDS File:
SDS
Last updated:2023-09-08 17:00:39

CHIR-99021 Properties

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
FDA UNII 234CMT4GK4

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H300-H315-H319-H335
Precautionary statements  P261-P264-P301+P310-P305+P351+P338
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
NFPA 704
0
4 0

CHIR-99021 price More Price(66)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 361571 InSolution? GSK-3 Inhibitor XVI, CHIR99021 252917-06-9 5mg $318 2024-03-01 Buy
Sigma-Aldrich 361559 GSK-3 Inhibitor XVI 252917-06-9 5mg $309 2024-03-01 Buy
TCI Chemical C2943 CHIR 99021 252917-06-9 25MG $241 2024-03-01 Buy
TCI Chemical C2943 CHIR 99021 252917-06-9 100MG $658 2024-03-01 Buy
Cayman Chemical 13122 CHIR 99021 ≥95% 252917-06-9 1mg $32 2024-03-01 Buy
Product number Packaging Price Buy
361571 5mg $318 Buy
361559 5mg $309 Buy
C2943 25MG $241 Buy
C2943 100MG $658 Buy
13122 1mg $32 Buy

CHIR-99021 Chemical Properties,Uses,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

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

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.

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

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.

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

Global( 236)Suppliers
Supplier Tel Email Country ProdList Advantage
Anhui Ruihan Technology Co., Ltd
+8617756083858 daisy@anhuiruihan.com China 994 58
Capot Chemical Co.,Ltd.
571-85586718 +8613336195806 sales@capotchem.com China 29797 60
Hangzhou FandaChem Co.,Ltd.
008657128800458; +8615858145714 fandachem@gmail.com China 9359 55
ATK CHEMICAL COMPANY LIMITED
+undefined-21-51877795 ivan@atkchemical.com China 32480 60
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29919 58
Biochempartner
0086-13720134139 candy@biochempartner.com CHINA 967 58
Hubei Jusheng Technology Co.,Ltd.
18871490254 linda@hubeijusheng.com CHINA 28180 58
BOC Sciences
+1-631-485-4226 inquiry@bocsci.com United States 19553 58
Chongqing Chemdad Co., Ltd
+86-023-61398051 +8613650506873 sales@chemdad.com China 39916 58
CONIER CHEM AND PHARMA LIMITED
+8618523575427 sales@conier.com China 47464 58

View Lastest Price from CHIR-99021 manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
CHIR-99021 pictures 2023-09-08 CHIR-99021
252917-06-9
US $30.00 / kg 1kg 99% 1000t/year Anhui Ruihan Technology Co., Ltd
6-[2-[4-(2,4-Dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)pyrimidin-2-ylamino]ethylamino]pyridine-3-carbonitrile pictures 2021-10-12 6-[2-[4-(2,4-Dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)pyrimidin-2-ylamino]ethylamino]pyridine-3-carbonitrile
252917-06-9
US $1.10 / g 1g 99.00% 100 Tons Min Dideu Industries Group Limited
6-[2-[4-(2,4-Dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)pyrimidin-2-ylamino]ethylamino]pyridine-3-carbonitrile pictures 2019-07-06 6-[2-[4-(2,4-Dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)pyrimidin-2-ylamino]ethylamino]pyridine-3-carbonitrile
252917-06-9
US $2.00 / kg 1kg 99% 100kg Career Henan Chemical Co
  • CHIR-99021 pictures
  • CHIR-99021
    252917-06-9
  • US $30.00 / kg
  • 99%
  • Anhui Ruihan Technology Co., Ltd
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 GSK-3 Inhibitor XVI 3-Pyridinecarbonitrile, 6-[[2-[[4-(2,4-dichlorophenyl)-5-(5-methyl-1H-imidazol-2-yl)-2-pyrimidinyl]amino]ethyl]amino] 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 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 CT99021;CHIR99021;CHIR 99021;CT-99021 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 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 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