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AB291107

CHIR99021, Sterile-Filtered

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CHIR99021, Sterile-Filtered (ab291107) is a potent, highly selective aminopyrimidine GSK-3 inhibitor (IC50= values are 6.7 and 10 nM at GSK-3β and GSK-3α, respectively).

- Exhibits >500-fold selectivity for GSK3 against 20 closely related protein kinases and >800-fold selectivity for 23 additional enzymes and 22 receptors
- Promotes self-renewal of mouse and human ESC due to β-catenin and c-Myc protein level stabilization
- Already pre-dissolved to a concentration of 10 mM

View Alternative Names

1,8-cineole 2-exo-monooxygenase, AI327312, Albendazole monooxygenase, Albendazole sulfoxidase, CCNB, CCNB1_HUMAN, CCNB2_HUMAN, CDC28A, CDK1_HUMAN, CDKN1, CELL CYCLE CONTROLLER CDC2, CP33, CP34, CP3A4_HUMAN, CYCB3, CYP3, CYP3A, CYP3A3, CYP3A4, CYPIIIA3, CYPIIIA4, Catabolin, Cdc 2, Cell Divsion Cycle 2 Protein, Cell cycle regulated protein kinase, Cell division control protein 2, Cell division control protein 2 homolog, Cell division cycle 2 G1 to S and G2 to M, Cell division protein kinase 1, CycB2, Cyclin B1, Cyclin B2, Cyclin-dependent kinase 1, Cytochrome P450 3A3, Cytochrome P450 3A4, Cytochrome P450 HLp, Cytochrome P450 NF-25, Cytochrome P450 family 3 subfamily A polypeptide 4, Cytochrome P450 subfamily IIIA polypeptide 4, Cytochrome P450-PCN1, DKFZp686D0638, DKFZp686L20222, ERK-2, ERT1, Extracellular signal-regulated kinase 2, G2 mitotic specific cyclin B1, G2 mitotic specific cyclin B2, G2/mitotic specific cyclin B3, G2/mitotic-specific cyclin-B1, G2/mitotic-specific cyclin-B2, GSK-3 alpha, GSK-3 beta, GSK3A_HUMAN, GSK3B_HUMAN, GSK3beta isoform, Glucocorticoid inducible P450, Glycogen synthase kinase-3 alpha, Glycogen synthase kinase-3 beta, H1, HLP, HPK 38, HsT17299, IFN beta inducing factor, IL 1, IL-1 beta, IL1B_HUMAN, IL1F2, Interleukin 1 beta precursor, Interleukin-1 beta, KIAA0175, Likely ortholog of maternal embryonic leucine zipper kinase, MAP kinase 1, MAP kinase 2, MAP kinase isoform p42, MAPK 1, MELK_HUMAN, MGC108931, MGC111195, MGC126680, MGC140694, MK01_HUMAN, MPK38, Maternal embryonic leucine zipper kinase, Mitogen-activated protein kinase 1, Mitogen-activated protein kinase 2, NF 25, Nifedipine oxidase, OAF, OTTHUMP00000021377, OTTHUMP00000046113, OTTHUMP00000162031, Osteoclast activating factor, P34CDC2, P38, P41, P450 III steroid inducible, P450 PCN1, P450, family III, P450C3, PLK, PLK1_HUMAN, PRKM 2, PRKM1, Polo-like kinase 1, Preinterleukin 1 beta, Preinterleukin beta, Pro interleukin 1 beta, Protein kinase Eg3, Protein kinase PK38, Quinine 3-monooxygenase, RP23 382O11.1, STPK 13, Serine/threonine protein kinase GSK3A, Serine/threonine-protein kinase 13, Serine/threonine-protein kinase GSK3B, Serine/threonine-protein kinase PLK1, Taurochenodeoxycholate 6-alpha-hydroxylase, Tyrosine protein kinase MELK, cytochrome P450, subfamily IIIA (niphedipine oxidase), polypeptide 3, cytochrome P450, subfamily IIIA (niphedipine oxidase), polypeptide 4, hMELK, mKIAA0175, p34 Cdk1, p34 protein kinase, p42-MAPK, pEg3 kinase, protein kinase, mitogen-activated, 1, protein kinase, mitogen-activated, 2, protein tyrosine kinase ERK2

Key facts

CAS number

252917-06-9

Purity

>95%

Form

Liquid

form

Molecular weight

465.3 Da

Molecular formula

C<sub>2</sub><sub>2</sub>H<sub>1</sub><sub>8</sub>Cl<sub>2</sub>N<sub>8</sub>

PubChem

9956119

Nature

Synthetic

Biochemical name

6-((2-((4-(2,4-Dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)pyrimidin-2-yl)amino)ethyl)amino)nicotinonitrile

Biological description

Potent, highly selective aminopyrimidine GSK3 inhibitor (IC50 values are 6.7 and 10 nM at GSK3β and GSK3α, respectively). Exhibits >500-fold selectivity for GSK3 against 20 closely related protein kinases and >800-fold selectivity for 23 additional enzymes and 22 receptors. Promotes self-renewal of mouse and human ESC due to β-catenin and c-Myc protein level stabilization. Commonly used in multiple stages of organoid generation.

Canonical smiles

CC1=CN=C(N1)C2=CN=C(N=C2C3=C(C=C(C=C3)Cl)Cl)NCCNC4=NC=C(C=C4)C#N

InChi

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)

InChiKey

AQGNHMOJWBZFQQ-UHFFFAOYSA-N

IUPAC Name

6-[2-[[4-(2,4-dichlorophenyl)-5-(5-methyl-1H-imidazol-2-yl)pyrimidin-2-yl]amino]ethylamino]pyridine-3-carbonitrile

Product details

CHIR99021 can be used in assays related to Cell Signalling, Apoptosis, Cancer Growth Inhibitors and Tyrosine Kinase Inhibitors.
The molecular weight of CHIR99021, Sterile-Filtered (ab291107) is 465.3 g/mol.

CHIR99021, Sterile-Filtered ab291107, (previously known as EZSolution CHIR99021, Sterile-Filtered, 1991) is a 10 mM (4.65 mg in 1 ml), sterile-filtered solution of the GSK-3β inhibitor CHIR99021 in anhydrous DMSO.

Properties and storage information

Shipped at conditions
Blue Ice
Appropriate short-term storage conditions
-20°C
Appropriate long-term storage conditions
-20°C
Storage information
It is important to note that this is air sensitive and impurities can occur as a result of air oxidation|Store under desiccating conditions

Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

Glycogen synthase kinase 3 beta or GSK3 beta is a serine/threonine protein kinase that regulates various cellular processes. It is also referred to as GSK3B and has a molecular weight of approximately 47 kilodaltons (kDa). This enzyme is widely expressed in many tissues with notably high expression levels in the brain. Mechanically GSK3 beta phosphorylates target proteins affecting their activity stability and interactions with other proteins.
Biological function summary

As an important regulatory protein GSK3 beta plays a role in multiple cellular functions including metabolism cell cycle and cell signaling. It often interacts with components in signaling complexes and modulates the activity of these complexes involving phosphorylation. It is involved in the regulation of transcription factors such as c-Myc and β-catenin influencing cell fate and survival. This ability to modulate diverse functions highlights GSK3 beta's importance in cellular regulation.

Pathways

GSK3 beta participates in significant signaling pathways such as the Wnt/β-catenin and insulin signaling pathways. In the Wnt pathway GSK3 beta phosphorylates β-catenin marking it for degradation which regulates gene transcription. In insulin signaling it interacts with proteins like AKT to mediate glycogen synthesis. These interactions highlight its role in maintaining cellular homeostasis and energy balance.

GSK3 beta has implications in Alzheimer's disease and type 2 diabetes. It is associated with tau protein hyperphosphorylation and neurofibrillary tangles in Alzheimer's disease. In diabetes its role in insulin signaling impacts glucose metabolism. Further GSK3 beta's dysfunction relates to disrupted signaling related to these conditions positioning it as a potential therapeutic target.

Product protocols

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