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CHIR 99021

Cat. No. 4423 89 Citations 3 Reviews Submit a Review Datasheet / COA / SDS
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Cat.No. 4423 - CHIR 99021 | C22H18Cl2N8 | CAS No. 252917-06-9
Description: Highly selective GSK-3 inhibitor
Chemical Name: 6-[[2-[[4-(2,4-Dichlorophenyl)-5-(5-methyl-1H-imidazol-2-yl)-2-pyrimidinyl]amino]ethyl]amino]-3-pyridinecarbonitrile
Purity: ≥98% (HPLC)
Datasheet
Citations (89)
Reviews (3)
Protocols (8)
Literature
Biological Activity Technical Data Solubility Calculators Datasheets References

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.

CHIR 99021 synthesized to cGMP guidelines also available.

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=C1Cl)=CC=C1C2=NC(NCCNC3=CC=C(C#N)C=N3)=NC=C2C4=NC=C(C)N4

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

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 the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.2 mM 10.74 mL 53.72 mL 107.45 mL
1 mM 2.15 mL 10.74 mL 21.49 mL
2 mM 1.07 mL 5.37 mL 10.74 mL
10 mM 0.21 mL 1.07 mL 2.15 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the biological activity of the product.

Pan et al (2011) AKT kinase activity is required for Li to modulate mood-related behaviors in mice. Neuropsychopharmacology 36 1397 PMID: 21389981

Ring et al (2003) Selective glycogen synthase kinase 3 inhibitors potentiate Ins 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

Sato et al (2015) SnapShot: Growing Organoids from Stem Cells. Cell 161 1700 PMID: 26091044

Mahe et al (2014) Establishment of gastrointestinal epithelial organoids Curr.Protoc. Mouse Biol. 3 217 PMID: 25105065

Bartfeld et al (2015) In vitro expansion of human gastric epithelial stem cells and their responses to bacterial infection. Gastroenterology 148 126 PMID: 25307862

Xia et al (2014) The generation of kidney organoids by differentiation of human pluripotent cells to ureteric bud progenitor-like cells. Nat. Protoc. 9 2693 PMID: 25340442

Dye et al (2015) In vitro generation of human pluripotent stem cell derived lung organoids. Elife PMID: 25803487

Koehler et al (2014) 3D mouse embryonic stem cell culture for generating inner ear organoids. Nat.Protoc. 9 1229 PMID: 24784820

Wimmer et al (2019) Human blood vessel organoids as a model of diabetic vasculopathy. Nature 565 505 PMID: 30651639

Noor et al (2019) 3D Printing of Personalized Thick and Perfusable Cardiac Patches and Hearts. Adv.Sci.(Weinh) 6 1900344 PMID: 31179230

Hoang et al (2018) Generation of spatial-patterned early-developing cardiac organoids using human pluripotent stem cells. Nat.Protoc. 13 723 PMID: 29543795

If you know of a relevant reference for CHIR 99021, please let us know.

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Keywords: CHIR 99021, CHIR 99021 supplier, 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, Reprogramming, Organoids, 4423, Tocris Bioscience

89 Citations for CHIR 99021

Citations are publications that use Tocris products. Selected citations for CHIR 99021 include:

Yin et al (2019) Chemical conversion of human fetal astrocytes into neurons through modulation of multiple signaling pathways. Stem Cell Reports 12 488 PMID: 30745031

Wimmer et al (2019) Human blood vessel organoids as a model of diabetic vasculopathy. Nature 565 505 PMID: 30651639

Lang et al (2019) Single-Cell Sequencing of iPSC-DA Neurons Reconstructs Disease Progression and Identifies HDAC4 as a Regulator of Parkinson Cell Phenotypes. Cell Stem Cell 24 93 PMID: 30503143

Zhang et al (2019) Implantation initiation of self-assembled embryo-like structures generated using three types of mouse blastocyst-derived stem cells. Nat Commun 10 496 PMID: 30700702

Varghese et al (2019) Fine Tuning of Hepatocyte Differentiation from Human Embryonic Stem Cells: Growth Factor vs. Small Molecule-Based Approaches. Stem Cells Int 2019 5968236 PMID: 30805010

Vila et al (2019) Quantification of human neuromuscular function through optogenetics. Theranostics 9 1232 PMID: 30867827

Yap et al (2019) In Vivo Generation of Post-infarct Human Cardiac Muscle by Laminin-Promoted Cardiovascular Progenitors. Cell Rep 26 3231 PMID: 30893597

Heuberger et al (2019) A C/EBPα-Wnt connection in gut homeostasis and carcinogenesis. Life Sci Alliance 2 e201800173 PMID: 30599048

Gao et al (2019) Establishment of porcine and human expanded potential stem cells. Nat Cell Biol 21 687 PMID: 31160711

Yang et al (2017) Establishment of mouse expanded potential stem cells. Nature 550 393 PMID: 29019987

Vermilyea et al (2017) Induced Pluripotent Stem Cell-Derived Dopaminergic Neurons from Adult Common Marmoset Fibroblasts. Stem Cells Dev 26 1225 PMID: 28635509

Sampaziotis et al (2017) Directed differentiation of human induced pluripotent stem cells into functional cholangiocyte-like cells. Nat Protoc 12 814 PMID: 28333915

McCauley et al (2017) Efficient Derivation of Functional Human Airway Epithelium from Pluripotent Stem Cells via Temporal Regulation of Wnt Signaling. Cell Stem Cell 20 844 PMID: 28366587

Lancaster et al (2017) Guided self-organization and cortical plate formation in human brain organoids. Nat Biotechnol 35 659 PMID: 28562594

Morizane and Bonventre (2017) Generation of nephron progenitor cells and kidney organoids from human pluripotent stem cells. Nat Protoc 12 195 PMID: 28005067

Ong et al (2017) Biomaterial-Free Three-Dimensional Bioprinting of Cardiac Tissue using Human Induced Pluripotent Stem Cell Derived Cardiomyocytes. Sci Rep 7 4566 PMID: 28676704

Kumar et al (2017) Dynamic regulation of Nanog and stem cell-signaling pathways by Hoxa1 during early neuro-ectodermal differentiation of ES cells. Proc Natl Acad Sci U S A 114 5838 PMID: 28584089

Lai et al (2017) Correction of Hirschsprung-Associated Mutations in Human Induced Pluripotent Stem Cells Via Clustered Regularly Interspaced Short Palindromic Repeats/Cas9, Restores Neural Crest Cell Function. Gastroenterology 153 139 PMID: 28342760

Lee et al (2017) Anatomically and Functionally Distinct Lung Mesenchymal Populations Marked by Lgr5 and Lgr6. Cell 170 1149 PMID: 28886383

Lin et al (2017) Culture in Glucose-Depleted Medium Supplemented with Fatty Acid and 3,3',5-Triiodo-l-Thyronine Facilitates Purification and Maturation of Human Pluripotent Stem Cell-Derived Cardiomyocytes. Front Endocrinol (Lausanne) 8 253 PMID: 29067001

Tang and Cheng (2017) Cocktail of chemical compounds robustly promoting cell reprogramming protects liver against acute injury. Protein Cell 8 273 PMID: 28190217

Walsh et al (2017) Defined Culture Conditions Accelerate Small-molecule-assisted Neural Induction for the Production of Neural Progenitors from Human-induced Pluripotent Stem Cells. Cell Transplant 26 1890 PMID: 29390875

Schmitt et al (2018) Paneth Cells Respond to Inflammation and Contribute to Tissue Regeneration by Acquiring Stem-like Features through SCF/c-Kit Signaling. Cell Rep 24 2312 PMID: 30157426

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

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

Tata et al (2018) Myoepithelial Cells of Submucosal Glands Can Function as Reserve Stem Cells to Regenerate Airways after Injury. Cell Stem Cell 22 668 PMID: 29656943

Zhou et al (2018) Functional comparison of distinct Brachyury+ states in a renal differentiation assay. Biol Open 7 PMID: 29666052

Li et al (2018) Rapid generation of gene-targeted EPS-derived mouse models through tetraploid complementation. Protein Cell PMID: 29948855

Srikanth et al (2018) Shared effects of DISC1 disruption and elevated WNT signaling in human cerebral organoids. Transl Psychiatry 8 77 PMID: 29643329

Sharma et al (2018) Stage-specific Effects of Bioactive Lipids on Human iPSC Cardiac Differentiation and Cardiomyocyte Proliferation. Sci Rep 8 6618 PMID: 29700394

Yamoah et al (2018) Highly efficient transfection of human induced pluripotent stem cells using magnetic nanoparticles. Int J Nanomedicine 13 6073 PMID: 30323594

Levardon et al (2018) Expansion of Airway Basal Cells and Generation of Polarized Epithelium. Bio Protoc 8 PMID: 30009215

Shekhar et al (2018) ETV1 activates a rapid conduction transcriptional program in rodent and human cardiomyocytes. Sci Rep 8 9944 PMID: 29967479

Leung et al (2018) Notch and Aryl Hydrocarbon Receptor Signaling Impact Definitive Hematopoiesis from Human Pluripotent Stem Cells. Stem Cells PMID: 29569827

Wang et al (2018) The COPII cargo adapter SEC24C is essential for neuronal homeostasis. J Clin Invest 128 3319 PMID: 29939162

Shafa et al (2018) Human-Induced Pluripotent Stem Cells Manufactured Using a Current Good Manufacturing Practice-Compliant Process Differentiate Into Clinically Relevant Cells From Three Germ Layers. Front Med (Lausanne) 5 69 PMID: 29600249

Capowski et al (2016) Regulation of WNT Signaling by VSX2 During Optic Vesicle Patterning in Human Induced Pluripotent Stem Cells. Stem Cells 34 2625 PMID: 27301076

Zimmerlin et al (2016) Tankyrase inhibition promotes a stable human naïve pluripotent state with improved functionality. Development 143 4368 PMID: 27660325

Lin et al (2016) HP Promotes Cardiac Differentiation of Human Pluripotent Stem Cells in Chemically Defined Albumin-Free Medium, Enabling Consistent Manufacture of Cardiomyocytes. Stem Cells Transl Med PMID: 27591141

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

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

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

Orlova et al (2014) Functionality of endothelial cells and pericytes from human pluripotent stem cells demonstrated in cultured vascular plexus and zebrafish xenografts. Arterioscler Thromb Vasc Biol 34 177 PMID: 24158517

Naujok et al (2014) Cytotoxicity and activation of the Wnt/beta-catenin pathway in mouse embryonic stem cells treated with four GSK3 inhibitors. BMC Res Notes 7 273 PMID: 24779365

Sommer et al (2018) Th17 lymphocytes induce neuronal cell death in a human iPSC-based model of Parkinson's disease. Cell Stem Cell 23 123 PMID: 29979986

Liu et al (2018) CRISPR-based chromatin remodeling of the endogenous Oct4 or Sox2 locus enables reprogramming to pluripotency. Cell Stem Cell. 22 252 PMID: 29358044

Bantounas et al (2018) Generation of functioning nephrons by implanting human pluripotent stem cell-derived kidney progenitors. Stem Cell Reports 10 766 PMID: 29429961

Bar-Nur et al (2018) Direct reprogramming of mouse fibroblasts into functional skeletal muscle progenitors. Stem Cell Reports 10 1505 PMID: 29742392

Leung et al (2016) WNT/β-catenin signaling mediates human neural crest induction via a pre-neural border intermediate. Development 143 398 PMID: 26839343

Chesnokova et al (2016) GH is permissive for neoplastic colon growth. Proc Natl Acad Sci U S A 113 E3250 PMID: 27226307

Nakaoka et al (2016) Allelic Imbalance in Regulation of ANRIL through Chromatin Interaction at 9p21 Endometriosis Risk Locus. PLoS Genet 12 e1005893 PMID: 27055116

Fattahi et al (2016) Deriving human ENS lineages for cell therapy and drug discovery in Hirschsprung disease. Nature 531 105 PMID: 26863197

Christoforou et al (2017) Core Transcription Factors, MicroRNAs, and Small Molecules Drive Transdifferentiation of Human Fibroblasts Towards The Cardiac Cell Lineage. Sci Rep 7 40285 PMID: 28071742

Zhao et al (2017) Efficient differentiation of TBX18(+)/WT1(+) epicardial-like cells from human pluripotent stem cells using small molecular compounds. Stem Cells Dev 26 528 PMID: 27927069

Yang (2017) Mutual reinforcement between telomere capping and canonical Wnt signalling in the intestinalstem cell niche. Nat Commun 8 14766 PMID: 28303901

Zhang et al (2015) Small Molecules Efficiently Reprogram Human Astroglial Cells into Functional Neurons. Cell Stem Cell 17 735 PMID: 26481520

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

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

Kearns et al (2015) Functional annotation of native enhancers with a Cas9-histone demethylase fusion. Nat Methods 12 401 PMID: 25775043

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

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

Kotton et al (2017) Differentiation of human pluripotent stem cells into functional lung alveolar epithelial cells. Cell Stem Cell. 21 472 PMID: 28965766

Tchieu et al (2017) A modular platform for differentiation of human PSCs into all major ectodermal lineages. Cell Stem Cell. 21 399 PMID: 28886367

Shao (2017) A pluripotent stem cell-based model for post-implantation human amniotic sac development. Nat Commun 8 208 PMID: 28785084

Brown (2017) Live imaging reveals that the first division of differentiating human embryonic stem cells often yields asymmetric fates. Cell Rep 21 301 PMID: 29020617

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

Du et al (2015) Generation and expansion of highly pure motor neuron progenitors from human pluripotent stem cells. Nat.Commun. 6 6626 PMID: 25806427

Sladitschek and Neveu (2015) The bimodally expressed microRNA miR-142 gates exit from pluripotency. J Biol Chem 11 850 PMID: 26690966

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

Hugo et al (2015) Non-genomic and Immune Evolution of Melanoma Acquiring MAPKi Resistance. Cell 162 1271 PMID: 26359985

Do you know of a great paper that uses CHIR 99021 from Tocris? Please let us know.

Reviews for CHIR 99021

Average Rating: 4.7 (Based on 3 Reviews.)

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Check the maintenance of naive pluripotency in 2i.
By Megha PB on 07/18/2018
Assay Type: In Vitro
Species: Mouse
Cell Line/Tissue: E14TG2a

Culture mouse ES cells in 2i media and without 2i to assess differentiation. Only the cells in 2i are pluripotent while mES cells cultured in -2i for 48 hours exit naive pluripotency.

review image
reliable product.
By Pinyuan Tian on 07/05/2018
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: pluripotent stem cells

For directed differentiation of pluripotent stem cells to kidney organoids, cells are treated with GSK-3 inhibitor, CHIR99021 to induce canonical WNT signaling. CHIR99021 concentration and differentiation time period are the key factors for this protocol. I found this product gave me reproducible results.

Although the datasheet says store at -20°C, it's better to aliquot and keep it at -80°C for long term storage.

review image
cells treatment.
By Anonymous on 12/04/2017
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: Neuroblastoma

Treating cells

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