Home / GSK-3 Inhibitors / CHIR 99021

CHIR 99021

4423 90 Citations 4 Reviews Datasheet / COA / SDS
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4423/50
GSK-3 Inhibitors Small Molecule
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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%

Product Details
Citations (90)
Reviews (4)
Biological Activity Technical Data Background Product Datasheets Calculators

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.

Technical Data

M.Wt:
465.34
Formula:
C22H18Cl2N8
Solubility:
Soluble to 20 mM in DMSO
Purity:
≥98%
Storage:
Store at -20°C
CAS No:
252917-06-9

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.

Background References

  1. The generation of kidney organoids by differentiation of human pluripotent cells to ureteric bud progenitor-like cells.
    Xia Y, Sancho-Martinez I, Nivet E et al.
    Nat Protoc.
  2. 3D mouse embryonic stem cell culture for generating inner ear organoids.
    Koehler KR, Hashino E.
    Nat Protoc
  3. AKT kinase activity is required for Li to modulate mood-related behaviors in mice.
    Pan et al.
    Neuropsychopharmacology, 2011;36:1397
  4. Selective glycogen synthase kinase 3 inhibitors potentiate Ins activation of glucose transport and utilization in vitro and in vivo.
    Ring et al.
    Diabetes, 2003;52:588
  5. Pleiotropy of glycogen synthase kinase-3 inhibition by CHIR99021 promotes self-renewal of embyronic stem cells from refractory mouse strains.
    Ye et al.
    PLoS One, 2012;7:e35892
  6. Generation of human-induced pluripotent stem cells in the absence of exogenous Sox2.
    Li et al.
    Stem Cells, 2009;27:2992
  7. Derivation of pluripotent stem cells with in vivo embryonic and extraembryonic potency.
    Yang et al.
    Cell., 2017;169:243
  8. In vitro expansion of human gastric epithelial stem cells and their responses to bacterial infection.
    Bartfeld et al.
    Gastroenterology, 2015;148:126
  9. SnapShot: Growing Organoids from Stem Cells.
    Sato et al.
    Cell, 2015;161:1700
  10. Establishment of gastrointestinal epithelial organoids
    Mahe et al.
    Curr.Protoc. Mouse Biol., 2014;3:217
  11. In vitro generation of human pluripotent stem cell derived lung organoids.
    Dye et al.
    Elife, 2015;
  12. Human blood vessel organoids as a model of diabetic vasculopathy.
    Wimmer et al.
    Nature, 2019;565:505
  13. 3D Printing of Personalized Thick and Perfusable Cardiac Patches and Hearts.
    Noor et al.
    Adv.Sci.(Weinh), 2019;6:1900344
  14. Generation of spatial-patterned early-developing cardiac organoids using human pluripotent stem cells.
    Hoang et al.
    Nat.Protoc., 2018;13:723

Product Datasheets

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Citations for CHIR 99021

The citations listed below are publications that use Tocris products. Selected citations for CHIR 99021 include:

90 Citations: Showing 1 - 10

  1. Quantification of human neuromuscular function through optogenetics.
    Authors: Vila Et al.
    Theranostics  2019;9:1232
  2. Human blood vessel organoids as a model of diabetic vasculopathy.
    Authors: Wimmer Et al.
    Nature  2019;565:505
  3. A C/EBPα-Wnt connection in gut homeostasis and carcinogenesis.
    Authors: Heuberger Et al.
    Life Sci Alliance  2019;2:e201800173
  4. In Vivo Generation of Post-infarct Human Cardiac Muscle by Laminin-Promoted Cardiovascular Progenitors.
    Authors: Yap Et al.
    Cell Rep  2019;26:3231
  5. Single-Cell Sequencing of iPSC-DA Neurons Reconstructs Disease Progression and Identifies HDAC4 as a Regulator of Parkinson Cell Phenotypes.
    Authors: Lang Et al.
    Cell Stem Cell  2019;24:93
  6. Establishment of porcine and human expanded potential stem cells.
    Authors: Gao Et al.
    Nat Cell Biol  2019;21:687
  7. Fine Tuning of Hepatocyte Differentiation from Human Embryonic Stem Cells: Growth Factor vs. Small Molecule-Based Approaches.
    Authors: Varghese Et al.
    Stem Cells Int  2019;2019:5968236
  8. Chemical conversion of human fetal astrocytes into neurons through modulation of multiple signaling pathways.
    Authors: Yin Et al.
    Stem Cell Reports  2019;12:488
  9. Implantation initiation of self-assembled embryo-like structures generated using three types of mouse blastocyst-derived stem cells.
    Authors: Zhang Et al.
    Nat Commun  2019;10:496
  10. Dual stem cell therapy synergistically improves cardiac function and vascular regeneration following myocardial infarction.
    Authors: Park Et al.
    Nat Commun  2019;10:3123
  11. ETV1 activates a rapid conduction transcriptional program in rodent and human cardiomyocytes.
    Authors: Shekhar Et al.
    Sci Rep  2018;8:9944
  12. Shared effects of DISC1 disruption and elevated WNT signaling in human cerebral organoids.
    Authors: Srikanth Et al.
    Transl Psychiatry  2018;8:77
  13. Stage-specific Effects of Bioactive Lipids on Human iPSC Cardiac Differentiation and Cardiomyocyte Proliferation.
    Authors: Sharma Et al.
    Sci Rep  2018;8:6618
  14. Expansion of Airway Basal Cells and Generation of Polarized Epithelium.
    Authors: Levardon Et al.
    Bio Protoc  2018;8
  15. Functional comparison of distinct Brachyury+ states in a renal differentiation assay.
    Authors: Zhou Et al.
    Biol Open  2018;7
  16. Human-Induced Pluripotent Stem Cells Manufactured Using a Current Good Manufacturing Practice-Compliant Process Differentiate Into Clinically Relevant Cells From Three Germ Layers.
    Authors: Shafa Et al.
    Front Med (Lausanne)  2018;5:69
  17. Paneth Cells Respond to Inflammation and Contribute to Tissue Regeneration by Acquiring Stem-like Features through SCF/c-Kit Signaling.
    Authors: Schmitt Et al.
    Cell Rep  2018;24:2312
  18. Th17 lymphocytes induce neuronal cell death in a human iPSC-based model of Parkinson's disease.
    Authors: Sommer Et al.
    Cell Stem Cell  2018;23:123
  19. Myoepithelial Cells of Submucosal Glands Can Function as Reserve Stem Cells to Regenerate Airways after Injury.
    Authors: Tata Et al.
    Cell Stem Cell  2018;22:668
  20. CRISPR-based chromatin remodeling of the endogenous Oct4 or Sox2 locus enables reprogramming to pluripotency.
    Authors: Liu Et al.
    Cell Stem Cell.  2018;22:252
  21. Highly efficient transfection of human induced pluripotent stem cells using magnetic nanoparticles.
    Authors: Yamoah Et al.
    Int J Nanomedicine  2018;13:6073
  22. The COPII cargo adapter SEC24C is essential for neuronal homeostasis.
    Authors: Wang Et al.
    J Clin Invest  2018;128:3319
  23. Generation of functioning nephrons by implanting human pluripotent stem cell-derived kidney progenitors.
    Authors: Bantounas Et al.
    Stem Cell Reports  2018;10:766
  24. Direct reprogramming of mouse fibroblasts into functional skeletal muscle progenitors.
    Authors: Bar-Nur Et al.
    Stem Cell Reports  2018;10:1505
  25. Notch and Aryl Hydrocarbon Receptor Signaling Impact Definitive Hematopoiesis from Human Pluripotent Stem Cells.
    Authors: Leung Et al.
    Stem Cells  2018;
  26. Rapid generation of gene-targeted EPS-derived mouse models through tetraploid complementation.
    Authors: Li Et al.
    Protein Cell  2018;
  27. Cocktail of chemical compounds robustly promoting cell reprogramming protects liver against acute injury.
    Authors: Tang and Cheng
    Protein Cell  2017;8:273
  28. 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.
    Authors: Lin Et al.
    Front Endocrinol (Lausanne)  2017;8:253
  29. Mutual reinforcement between telomere capping and canonical Wnt signalling in the intestinalstem cell niche.
    Authors: Yang
    Nat Commun  2017;8:14766
  30. A pluripotent stem cell-based model for post-implantation human amniotic sac development.
    Authors: Shao
    Nat Commun  2017;8(1):208
  31. Biomaterial-Free Three-Dimensional Bioprinting of Cardiac Tissue using Human Induced Pluripotent Stem Cell Derived Cardiomyocytes.
    Authors: Ong Et al.
    Sci Rep  2017;7:4566
  32. Core Transcription Factors, MicroRNAs, and Small Molecules Drive Transdifferentiation of Human Fibroblasts Towards The Cardiac Cell Lineage.
    Authors: Christoforou Et al.
    Sci Rep  2017;7:40285
  33. Establishment of mouse expanded potential stem cells.
    Authors: Yang Et al.
    Nature  2017;550:393
  34. Guided self-organization and cortical plate formation in human brain organoids.
    Authors: Lancaster Et al.
    Nat Biotechnol  2017;35:659
  35. Efficient differentiation of TBX18(+)/WT1(+) epicardial-like cells from human pluripotent stem cells using small molecular compounds.
    Authors: Zhao Et al.
    Stem Cells Dev  2017;26:528
  36. Defined Culture Conditions Accelerate Small-molecule-assisted Neural Induction for the Production of Neural Progenitors from Human-induced Pluripotent Stem Cells.
    Authors: Walsh Et al.
    Cell Transplant  2017;26:1890
  37. Induced Pluripotent Stem Cell-Derived Dopaminergic Neurons from Adult Common Marmoset Fibroblasts.
    Authors: Vermilyea Et al.
    Stem Cells Dev  2017;26:1225
  38. Differentiation of human pluripotent stem cells into functional lung alveolar epithelial cells.
    Authors: Kotton Et al.
    Cell Stem Cell.  2017;21:472
  39. A modular platform for differentiation of human PSCs into all major ectodermal lineages.
    Authors: Tchieu Et al.
    Cell Stem Cell.  2017;21:399
  40. Live imaging reveals that the first division of differentiating human embryonic stem cells often yields asymmetric fates.
    Authors: Brown
    Cell Rep  2017;21(2):301
  41. Efficient Derivation of Functional Human Airway Epithelium from Pluripotent Stem Cells via Temporal Regulation of Wnt Signaling.
    Authors: McCauley Et al.
    Cell Stem Cell  2017;20:844
  42. In Vivo Human Somitogenesis Guides Somite Development from hPSCs.
    Authors: Xi
    Cell Rep.  2017;18(6):1573
  43. Anatomically and Functionally Distinct Lung Mesenchymal Populations Marked by Lgr5 and Lgr6.
    Authors: Lee Et al.
    Cell  2017;170:1149
  44. Derivation of pluripotent stem cells with in vivo embryonic and extraembryonic potency.
    Authors: Yang Et al.
    Cell.  2017;169:243
  45. Correction of Hirschsprung-Associated Mutations in Human Induced Pluripotent Stem Cells Via Clustered Regularly Interspaced Short Palindromic Repeats/Cas9, Restores Neural Crest Cell Function.
    Authors: Lai Et al.
    Gastroenterology  2017;153:139
  46. Directed differentiation of human induced pluripotent stem cells into functional cholangiocyte-like cells.
    Authors: Sampaziotis Et al.
    Nat Protoc  2017;12:814
  47. Generation of nephron progenitor cells and kidney organoids from human pluripotent stem cells.
    Authors: Morizane and Bonventre
    Nat Protoc  2017;12:195
  48. Dynamic regulation of Nanog and stem cell-signaling pathways by Hoxa1 during early neuro-ectodermal differentiation of ES cells.
    Authors: Kumar Et al.
    Proc Natl Acad Sci U S A  2017;114:5838
  49. Integrin signalling regulates the expansion of neuroepithelial progenitors and neurogenesis via Wnt7a and Decorin.
    Authors: Long Et al.
    Nat Biotechnol  2016;7:10354
  50. Generating trunk neural crest from human pluripotent stem cells.
    Authors: Huang Et al.
    PLoS One  2016;6:19727
  51. Deriving human ENS lineages for cell therapy and drug discovery in Hirschsprung disease.
    Authors: Fattahi Et al.
    Nature  2016;531:105
  52. Generation of serotonin neurons from human pluripotent stem cells.
    Authors: Lu Et al.
    Nat Biotechnol  2016;34:89
  53. Regulation of WNT Signaling by VSX2 During Optic Vesicle Patterning in Human Induced Pluripotent Stem Cells.
    Authors: Capowski Et al.
    Stem Cells  2016;34:2625
  54. Enhancing a Wnt-Telomere Feedback Loop Restores Intestinal Stem Cell Function in a Human Organotypic Model of Dyskeratosis Congenita
    Authors: Woo Et al.
    Cell Stem Cell  2016;19:397
  55. Dual SMAD Signaling Inhibition Enables Long-Term Expansion of Diverse Epithelial Basal Cells
    Authors: Mou Et al.
    Cell: Stem Cell  2016;19:217
  56. Pharmacological reprogramming of fibroblasts into neural stem cells by signaling-directed transcriptional activation.
    Authors: Zhang Et al.
    Cell Stem Cell  2016;18:653
  57. Human Enteroids as a Model of Upper Small Intestinal Ion Transport Physiology and Pathophysiology.
    Authors: Foulke-Abel Et al.
    Nat Commun  2016;150:638
  58. Tankyrase inhibition promotes a stable human na�ve pluripotent state with improved functionality.
    Authors: Zimmerlin Et al.
    Development  2016;143:4368
  59. WNT/β-catenin signaling mediates human neural crest induction via a pre-neural border intermediate.
    Authors: Leung Et al.
    Development  2016;143:398
  60. Allelic Imbalance in Regulation of ANRIL through Chromatin Interaction at 9p21 Endometriosis Risk Locus.
    Authors: Nakaoka Et al.
    PLoS Genet  2016;12:e1005893
  61. Generation of human muscle fibers and satellite-like cells from human pluripotent stem cells in vitro.
    Authors: Chal Et al.
    Nat.Protoc.  2016;11:1833
  62. Generation of kidney organoids from human pluripotent stem cells.
    Authors: Takasato Et al.
    Nature Protocols  2016;11:1681
  63. GH is permissive for neoplastic colon growth.
    Authors: Chesnokova Et al.
    Proc Natl Acad Sci U S A  2016;113:E3250
  64. HP Promotes Cardiac Differentiation of Human Pluripotent Stem Cells in Chemically Defined Albumin-Free Medium, Enabling Consistent Manufacture of Cardiomyocytes.
    Authors: Lin Et al.
    Stem Cells Transl Med  2016;
  65. Human pluripotent stem cell derived midbrain PITX3(eGFP/w) neurons: a versatile tool for pharmacological screening and neurodegenerative modeling.
    Authors: Watmuff Et al.
    Front Cell Neurosci  2015;9:104
  66. Enolase 1 (ENO1) and protein disulfide-isomerase associated 3 (PDIA3) regulate Wnt/β-catenin-driven trans-differentiation of murine alveolar epithelial cells.
    Authors: Mutze Et al.
    Cell Rep  2015;8:877
  67. Plasticity of Hopx(+) type I alveolar cells to regenerate type II cells in the lung.
    Authors: Jain Et al.
    Nat Commun  2015;6:6727
  68. Generation and expansion of highly pure motor neuron progenitors from human pluripotent stem cells.
    Authors: Du Et al.
    Nat.Commun.  2015;6:6626
  69. Inhibition of Excessive Monoamine Oxidase A/B Activity Protects Against Stress-induced Neuronal Death in Huntington Disease.
    Authors: Ooi Et al.
    Nat Chem Biol  2015;52:1850
  70. Efficient generation of NKX6-1+ pancreatic progenitors from multiple human pluripotent stem cell lines.
    Authors: Nostro Et al.
    Eur J Immunol  2015;4:591
  71. The lymph node as a new site for kidney organogenesis.
    Authors: Francipane and Lagasse
    Stem Cells Transl Med  2015;4:295
  72. Glycogen synthase kinase-3 controls IL-10 expression in CD4(+) effector T-cell subsets through epigenetic modification of the IL-10 promoter.
    Authors: Hill Et al.
    Mol Neurobiol  2015;45:1103
  73. Nephron organoids derived from human pluripotent stem cells model kidney development and injury.
    Authors: Morizane Et al.
    Stem Cell Reports  2015;33:1193
  74. Phosphorylation and SCF-mediated degradation regulate CREB-H transcription of metabolic targets.
    Authors: Barbosa Et al.
    Stem Cell Reports  2015;26:2939
  75. Automated Video-Based Analysis of Contractility and Calcium Flux in Human-Induced Pluripotent Stem Cell-Derived Cardiomyocytes Cultured over Different Spatial Scales.
    Authors: Huebsch Et al.
    Tissue Eng Part C Methods  2015;21:467
  76. Small Molecules Efficiently Reprogram Human Astroglial Cells into Functional Neurons.
    Authors: Zhang Et al.
    Cell Stem Cell  2015;17:735
  77. Non-genomic and Immune Evolution of Melanoma Acquiring MAPKi Resistance.
    Authors: Hugo Et al.
    Cell  2015;162:1271
  78. GSK3β-Dzip1-Rab8 cascade regulates ciliogenesis after mitosis.
    Authors: Zhang Et al.
    PLoS Biol  2015;13:e1002129
  79. Functional annotation of native enhancers with a Cas9-histone demethylase fusion.
    Authors: Kearns Et al.
    Nat Methods  2015;12:401
  80. Genomic DISC1 Disruption in hiPSCs Alters Wnt Signaling and Neural Cell Fate.
    Authors: Srikanth Et al.
    Sci Rep  2015;12:1414
  81. The bimodally expressed microRNA miR-142 gates exit from pluripotency.
    Authors: Sladitschek and Neveu
    J Biol Chem  2015;11:850
  82. GSK-3 modulates cellular responses to a broad spectrum of kinase inhibitors.
    Authors: Thorne Et al.
    Mol Biol Cell  2015;11:58
  83. Manganese Superoxide Dismutase Gene Expression Is Induced by Nanog and Oct4, Essential Pluripotent Stem Cells' Transcription Factors.
    Authors: Solari Et al.
    Mol Syst Biol  2015;10:e0144336
  84. Cytotoxicity and activation of the Wnt/beta-catenin pathway in mouse embryonic stem cells treated with four GSK3 inhibitors.
    Authors: Naujok Et al.
    BMC Res Notes  2014;7:273
  85. Mouse liver repopulation with hepatocytes generated from human fibroblasts.
    Authors: Zhu Et al.
    Nature  2014;508:93
  86. Derivation and expansion of PAX7-positive muscle progenitors from human and mouse embryonic stem cells.
    Authors: Shelton Et al.
    Dis Model Mech  2014;3:516
  87. A method to identify and isolate pluripotent human stem cells and mouse epiblast stem cells using lipid body-associated retinyl ester fluorescence.
    Authors: Muthusamy Et al.
    Stem Cell Reports  2014;3:169
  88. Functionality of endothelial cells and pericytes from human pluripotent stem cells demonstrated in cultured vascular plexus and zebrafish xenografts.
    Authors: Orlova Et al.
    Arterioscler Thromb Vasc Biol  2014;34:177
  89. A novel suppressive effect of alcohol dehydrogenase 5 in neuronal differentiation.
    Authors: Wu Et al.
    Stem Cell Res  2014;289:20193
  90. SIRPA, VCAM1 and CD34 identify discrete lineages during early human cardiovascular development.
    Authors: Skelton Et al.
    J Cachexia Sarcopenia Muscle  2014;13:172

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Reviews for CHIR 99021

Average Rating: 4.8 (Based on 4 Reviews)

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works great for Wnt activation
By avinash waghray on 08/08/2019
Species: Human

In Tissue culture for growing basal cells

PMID: 27320041
Check the maintenance of naive pluripotency in 2i
By Megha PB on 07/18/2018
Species: Mouse

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.

reliable product
By Pinyuan Tian on 07/05/2018
Species: Human

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.

cells treatment
By Anonymous on 12/04/2017
Species: Human

Treating cells

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