CHIR 99021
Biological Activity
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). 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 tranylcypromine (Cat. No. 3852), enables reprogramming of mouse embryonic fibroblasts, transduced by Oct4 and Klf4 only, into iPSCs. Enhances mouse and human ESC self-renewal when used in combination with PD 0325901 (Cat. No. 4192). Allows formation of extended pluripotent stem (EPS) cells in combination with (S)-(+)-Dimethindene maleate (Cat.No. 1425), minocycline hydrochloride (Cat.No. 3268) and human leukemia inhibitory factor.
Compound Libraries
CHIR 99021 is also offered as part of the Tocriscreen Plus and Tocriscreen Stem Cell Toolbox. Find out more about compound libraries available from Tocris.
Technical Data
| M. Wt | 465.34 |
| Formula | C22H18Cl2N8 |
| Storage | Store at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 252917-06-9 |
| PubChem ID | 9956119 |
| InChI Key | AQGNHMOJWBZFQQ-UHFFFAOYSA-N |
| Smiles | ClC(C=C3Cl)=CC=C3C1=NC(NCCNC4=CC=C(C#N)C=N4)=NC=C1C2=NC(C)=CN2 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
All Tocris products are intended for laboratory research use only.
Solubility Data
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 9.31 | 20 |
Preparing Stock Solutions
The following data is based on the product molecular weight 465.34. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 2.15 mL | 10.74 mL | 21.49 mL |
| 5 mM | 0.43 mL | 2.15 mL | 4.3 mL |
| 10 mM | 0.21 mL | 1.07 mL | 2.15 mL |
| 50 mM | 0.04 mL | 0.21 mL | 0.43 mL |
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Product Datasheets
References
References are publications that support the products' biological activity.
Pan et al (2011) AKT kinase activity is required for lithium to modulate mood-related behaviors in mice. Neuropsychopharmacology 36 1397 PMID: 21389981
Ring et al (2003) Selective glycogen synthase kinase 3 inhibitors potentiate insulin activation of glucose transport and utilization in vitro and in vivo. Diabetes 52 588 PMID: 12606497
Li et al (2009) Generation of human-induced pluripotent stem cells in the absence of exogenous Sox2. Stem Cells 27 2992 PMID: 19839055
Ye et al (2012) Pleiotropy of glycogen synthase kinase-3 inhibition by CHIR99021 promotes self-renewal of embyronic stem cells from refractory mouse strains. PLoS One 7 e35892 PMID: 22540008
Yang et al (2017) Derivation of pluripotent stem cells with in vivo embryonic and extraembryonic potency. Cell. 169 243 PMID: 28388409
If you know of a relevant reference for CHIR 99021, please let us know.
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Keywords: CHIR99021 glycogen synthase kinase 3 gsk-3 gsk-3a gsk-3alpha gsk-3α gsk-3b gsk-3beta gsk-3β inhibitors inhibits highly selective potent organoids Glycogen Synthase Kinase 3
34 Citations for CHIR 99021
Citations are publications that use Tocris products. Selected citations for CHIR 99021 include:
Yang (2017) Mutual reinforcement between telomere capping and canonical Wnt signalling in the intestinalstem cell niche. Nat Commun 8 14766 PMID: 28303901
Yang et al (2017) Derivation of pluripotent stem cells with in vivo embryonic and extraembryonic potency. Cell. 169 243 PMID: 28388409
Xi (2017) In Vivo Human Somitogenesis Guides Somite Development from hPSCs. Cell Rep 18 1573 PMID: 28178531
Zhang et al (2016) Pharmacological reprogramming of fibroblasts into neural stem cells by signaling-directed transcriptional activation. Cell Stem Cell 18 653 PMID: 27133794
Mou et al (2016) Dual SMAD Signaling Inhibition Enables Long-Term Expansion of Diverse Epithelial Basal Cells Cell: Stem Cell 19 217 PMID: 27320041
Lu et al (2016) Generation of serotonin neurons from human pluripotent stem cells. Nat Biotechnol 34 89 PMID: 26655496
Foulke-Abel et al (2016) Human Enteroids as a Model of Upper Small Intestinal Ion Transport Physiology and Pathophysiology. Nat Commun 150 638 PMID: 26677983
Long et al (2016) Integrin signalling regulates the expansion of neuroepithelial progenitors and neurogenesis via Wnt7a and Decorin. Nat Biotechnol 7 10354 PMID: 26838601
Huang et al (2016) Generating trunk neural crest from human pluripotent stem cells. PLoS One 6 19727 PMID: 26812940
Woo et al (2016) Enhancing a Wnt-Telomere Feedback Loop Restores Intestinal Stem Cell Function in a Human Organotypic Model of Dyskeratosis Congenita Cell Stem Cell 19 397 PMID: 27545506
Takasato et al (2016) Generation of kidney organoids from human pluripotent stem cells. Nature Protocols 11 1681 PMID: 27560173
Chal et al (2016) Generation of human muscle fibers and satellite-like cells from human pluripotent stem cells in vitro. Nat.Protoc. 11 1833 PMID: 27583644
Solari et al (2015) Manganese Superoxide Dismutase Gene Expression Is Induced by Nanog and Oct4, Essential Pluripotent Stem Cells' Transcription Factors. Mol Syst Biol 10 e0144336 PMID: 26642061
Mutze et al (2015) Enolase 1 (ENO1) and protein disulfide-isomerase associated 3 (PDIA3) regulate Wnt/β-catenin-driven trans-differentiation of murine alveolar epithelial cells. Cell Rep 8 877 PMID: 26035385
Srikanth et al (2015) Genomic DISC1 Disruption in hiPSCs Alters Wnt Signaling and Neural Cell Fate. Sci Rep 12 1414 PMID: 26299970
Morizane et al (2015) Nephron organoids derived from human pluripotent stem cells model kidney development and injury. Stem Cell Reports 33 1193 PMID: 26458176
Nostro et al (2015) Efficient generation of NKX6-1+ pancreatic progenitors from multiple human pluripotent stem cell lines. Eur J Immunol 4 591 PMID: 25843049
Hill et al (2015) Glycogen synthase kinase-3 controls IL-10 expression in CD4(+) effector T-cell subsets through epigenetic modification of the IL-10 promoter. Mol Neurobiol 45 1103 PMID: 25627813
Ooi et al (2015) Inhibition of Excessive Monoamine Oxidase A/B Activity Protects Against Stress-induced Neuronal Death in Huntington Disease. Nat Chem Biol 52 1850 PMID: 25398695
Thorne et al (2015) GSK-3 modulates cellular responses to a broad spectrum of kinase inhibitors. Mol Biol Cell 11 58 PMID: 25402767
Barbosa et al (2015) Phosphorylation and SCF-mediated degradation regulate CREB-H transcription of metabolic targets. Stem Cell Reports 26 2939 PMID: 26108621
Watmuff et al (2015) Human pluripotent stem cell derived midbrain PITX3(eGFP/w) neurons: a versatile tool for pharmacological screening and neurodegenerative modeling. Front Cell Neurosci 9 104 PMID: 25873861
Kearns et al (2015) Functional annotation of native enhancers with a Cas9-histone demethylase fusion. Nat Methods 12 401 PMID: 25775043
Zhang et al (2015) GSK3β-Dzip1-Rab8 cascade regulates ciliogenesis after mitosis. PLoS Biol 13 e1002129 PMID: 25860027
Francipane and Lagasse (2015) The lymph node as a new site for kidney organogenesis. Stem Cells Transl Med 4 295 PMID: 25646529
Jain et al (2015) Plasticity of Hopx(+) type I alveolar cells to regenerate type II cells in the lung. Nat Commun 6 6727 PMID: 25865356
Huebsch et al (2015) Automated Video-Based Analysis of Contractility and Calcium Flux in Human-Induced Pluripotent Stem Cell-Derived Cardiomyocytes Cultured over Different Spatial Scales. Tissue Eng Part C Methods 21 467 PMID: 25333967
Sladitschek and Neveu (2015) The bimodally expressed microRNA miR-142 gates exit from pluripotency. J Biol Chem 11 850 PMID: 26690966
Du et al (2015) Generation and expansion of highly pure motor neuron progenitors from human pluripotent stem cells. Nat.Commun. 6 6626 PMID: 25806427
Muthusamy et al (2014) A method to identify and isolate pluripotent human stem cells and mouse epiblast stem cells using lipid body-associated retinyl ester fluorescence. Stem Cell Reports 3 169 PMID: 25068130
Zhu et al (2014) Mouse liver repopulation with hepatocytes generated from human fibroblasts. Nature 508 93 PMID: 24572354
Shelton et al (2014) Derivation and expansion of PAX7-positive muscle progenitors from human and mouse embryonic stem cells. Dis Model Mech 3 516 PMID: 25241748
Wu et al (2014) A novel suppressive effect of alcohol dehydrogenase 5 in neuronal differentiation. Stem Cell Res 289 20193 PMID: 24895131
Skelton et al (2014) SIRPA, VCAM1 and CD34 identify discrete lineages during early human cardiovascular development. J Cachexia Sarcopenia Muscle 13 172 PMID: 24968096
Do you know of a great paper that uses CHIR 99021 from Tocris? If so please let us know.