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Submit ReviewSB 216763
Description: Potent, selective GSK-3 inhibitor
Chemical Name: 3-(2,4-Dichlorophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione
Purity: ≥98% (HPLC)
Biological Activity for SB 216763
SB 216763 is a potent and selective, ATP-competitive glycogen synthase kinase-3 (GSK-3) inhibitor (IC50 = 34.3 nM for GSK-3α). Equally effective at inhibiting human GSK-3α and GSK-3β. Exhibits minimal activity against 24 other protein kinases (IC50 >10 μM). Stimulates glycogen synthesis in liver cells, and induces β-catenin-dependent gene transcription. Neuroprotective; also reduces pulmonary inflammation and fibrosis in a mouse model. Shown to maintain mouse embryonic stem cells in a pluripotent state.
Licensing Information
Sold for research purposes under agreement from GlaxoSmithKline
Technical Data for SB 216763
| M. Wt | 371.22 |
| Formula | C19H12Cl2N2O2 |
| Storage | Store at RT |
| Purity | ≥98% (HPLC) |
| CAS Number | 280744-09-4 |
| PubChem ID | 176158 |
| InChI Key | JCSGFHVFHSKIJH-UHFFFAOYSA-N |
| Smiles | CN1C=C(C2=CC=CC=C12)C1=C(C(=O)NC1=O)C1=C(Cl)C=C(Cl)C=C1 |
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 for SB 216763
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 37.12 | 100 |
Preparing Stock Solutions for SB 216763
The following data is based on the product molecular weight 371.22. 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 |
|---|---|---|---|
| 1 mM | 2.69 mL | 13.47 mL | 26.94 mL |
| 5 mM | 0.54 mL | 2.69 mL | 5.39 mL |
| 10 mM | 0.27 mL | 1.35 mL | 2.69 mL |
| 50 mM | 0.05 mL | 0.27 mL | 0.54 mL |
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Product Datasheets for SB 216763
References for SB 216763
References are publications that support the biological activity of the product.
Coghlan et al (2000) Selective small molecule inhibitors of glycogen synthase kinase-3 modulate glycogen metabolism and gene transcription. Chem.Biol. 7 793 PMID: 11033082
Cross et al (2001) Selective small-molecule inhibitors of glycogen synthase kinase-3 activity protect primary neurones from death. J.Neurochem. 77 94 PMID: 11279265
Gurrieri et al (2010) 3-(2,4-dichlorophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione (SB216763), a glycogen synthase kinase-3 inhibitor, displays therapeutic properties in a mouse model of pulmonary inflammation and fibrosis. J.Pharmacol.Exp.Ther. 332 785 PMID: 19959748
Liang and Chuang (2006) Regulation and function of glycogen synthase kinase-3 isoforms in neuronal survival. J.Biol.Chem. 282 3904 PMID: 17148450
Kirby et al (2012) Glycogen synthase kinase 3 (GSK3) inhibitor, SB-216763, promotes pluripotency in mouse embryonic stem cells. PLoS One 7 e39329 PMID: 22745733
If you know of a relevant reference for SB 216763, please let us know.
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Keywords: SB 216763, SB 216763 supplier, Potent, selective, GSK-3, inhibitors, inhibits, Glycogen, Synthase, Kinases, 3, Carbohydrate, Metabolism, SB216763, GlaxoSmithKline, GSK, Kinase, Stem, Cell, Proliferation, 1616, Tocris Bioscience
75 Citations for SB 216763
Citations are publications that use Tocris products. Selected citations for SB 216763 include:
Ranea-Robles et al (2018) Aberrant regulation of the GSK-3β/NRF2 axis unveils a novel therapy for adrenoleukodystrophy. EMBO Mol Med 10 PMID: 29997171
Lee et al (2014) Inhibiting glycogen synthase kinase-3 mitigates the hematopoietic acute radiation syndrome in mice. Radiat Res 181 445 PMID: 24720754
Kuo et al (2014) Repression of glucocorticoid-stimulated angiopoietin-like 4 gene transcription by Ins. J Lipid Res 55 919 PMID: 24565756
Gassowska et al (2014) Extracellular α-synuclein leads to microtubule destabilization via GSK-3β-dependent Tau phosphorylation in PC12 cells. PLoS One 9 e94259 PMID: 24722055
Robertson et al (2013) Sea urchin akt activity is Runx-dependent and required for post-cleavage stage cell division. Mol Cancer 2 472 PMID: 23789095
Kahn et al (2015) Effects of kinesin-5 inhibition on dendritic architecture and microtubule organization. Mol Biol Cell 26 66 PMID: 25355946
Wang et al (2011) The role of glycogen synthase kinase 3 in regulating IFN-β-mediated IL-10 production. J Immunol 186 675 PMID: 21160051
Wang et al (2011) Convergence of the mammalian target of rapamycin complex 1- and glycogen synthase kinase 3-β-signaling pathways regulates the innate inflammatory response. J Immunol 186 5217 PMID: 21422248
Baarsma et al (2011) Glycogen synthase kinase-3 regulates cigarette smoke extract- and IL-1β-induced cytokine secretion by airway smooth muscle. Am J Physiol Lung Cell Mol Physiol 300 L910 PMID: 21421749
Shen et al (2011) Inhibition of adipocytogenesis by canonical WNT signaling in human mesenchymal stem cells. Exp Cell Res 317 1796 PMID: 21640723
Dash et al (2011) Involvement of the glycogen synthase kinase-3 signaling pathway in TBI pathology and neurocognitive outcome. PLoS One 6 e24648 PMID: 21935433
Sarkar et al (2008) A rational mechanism for combination treatment of Huntington's disease using Li and rapamycin. Hum Mol Genet 17 170 PMID: 17921520
Cohen et al (2008) Acidosis, oxygen, and interference with mitochondrial permeability transition pore formation in the early minutes of reperfusion are critical to postconditioning's success. Behav Brain Res 103 464 PMID: 18626679
Alakoski et al (2019) Inhibition of cardiomyocyte Sprouty1 protects from cardiac ischemia-reperfusion injury. Basic Res Cardiol 114 7 PMID: 30635790
Acevedo et al (2014) Phosphorylation of amyloid precursor protein at threonine 668 is essential for its copper-responsive trafficking in SH-SY5Y neuroblastoma cells. Mol Endocrinol 289 11007 PMID: 24610780
Zhao et al (2014) β-arrestin2/miR-155/GSK3β regulates transition of 5'-azacytizine-induced Sca-1-positive cells to cardiomyocytes. J Cell Biol 18 1562 PMID: 24974728
Ray et al (2013) Tristetraprolin mediates radiation-induced TNF-α production in lung macrophages. PLoS One 8 e57290 PMID: 23468959
Zhu et al (2011) Li suppresses astrogliogenesis by neural stem and progenitor cells by inhibiting STAT3 pathway independently of glycogen synthase kinase 3 beta. PLoS One 6 e23341 PMID: 21931595
Hirabayashi et al (2009) Polycomb limits the neurogenic competence of neural precursor cells to promote astrogenic fate transition. Neuron 63 600 PMID: 19755104
Hu et al (2009) GSK3 inhibitors show benefits in an Alzheimer's disease (AD) model of neurodegeneration but adverse effects in control animals. Neurobiol Dis 33 193 PMID: 19038340
Rehani et al (2009) Toll-like receptor-mediated production of IL-1Ra is negatively regulated by GSK3 via the MAPK ERK1/2. J Immunol 182 547 PMID: 19109187
Kondo et al (2009) p38 MAPK is a major regulator of MafA protein stability under oxidative stress. Mol Endocrinol 23 1281 PMID: 19407223
Watanabe et al (2009) Phosphorylation of CLASP2 by GSK-3beta regulates its interaction with IQGAP1, EB1 and microtubules. J Cell Sci 122 2969 PMID: 19638411
Garcia et al (2009) c-jun controls the ability of IL-12 to induce IL-10 production from human memory CD4+ T cells. J Immunol 183 4475 PMID: 19734233
Noguerol et al (2019) Sexual dimorphism in PAR2-dependent regulation of primitive colonic cells. Biol Sex Differ 10 47 PMID: 31492202
Moloney et al (2017) Subcellular localization of the FLT3-ITD oncogene plays a significant role in the production of NOX- and p22(phox)-derived reactive oxygen species in acute myeloid leukemia. Leuk Res 52 34 PMID: 27870947
Abedini et al (2016) WNT5a is required for normal ovarian follicle development and antagonizes g.tropin responsiveness in granulosa cells by suppressing canonical WNT signaling. FASEB J 30 1534 PMID: 26667040
Khattabi and Sharma (2013) Preventing p38 MAPK-mediated MafA degradation ameliorates β-cell dysfunction under oxidative stress. Hum Mol Genet 27 1078 PMID: 23660596
Enman and Unterwald (2012) Inhibition of GSK3 attenuates amphetamine-induced hyperactivity and sensitization in the mouse. Neuro Oncol 231 217 PMID: 22649795
Thotala et al (2010) A new class of molecular targeted radioprotectors: GSK-3beta inhibitors. Int J Radiat Oncol Biol Phys 76 557 PMID: 20117291
Kitagawa et al (2010) GSK3 regulates the expressions of human and mouse c-Myb via different mechanisms. Cell Div 5 27 PMID: 21092141
Heyd (2010) Phosphorylation-dependent regulation of PSF by GSK3 controls CD45 alternative splicing. Mol Cell 40 126 PMID: 20932480
Kim et al (2009) DISC1 regulates new neuron development in the adult brain via modulation of AKT-mTOR signaling through KIAA1212. Neuron 63 761 PMID: 19778506
Creson et al (2009) Evidence for involvement of ERK, PI3K, and RSK in induction of Bcl-2 by valproate. J Mol Neurosci 37 123 PMID: 18677583
Korur et al (2009) GSK3beta regulates differentiation and growth arrest in glioblastoma. PLoS One 4 e7443 PMID: 19823589
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. Arch Med Sci 45 1103 PMID: 25627813
Yang et al (2015) Apelin-13 protects the heart against ischemia-reperfusion injury through the RISK-GSK-3β-mPTP pathway. Mol Biol Cell 11 1065 PMID: 26528352
Barbosa et al (2015) Phosphorylation and SCF-mediated degradation regulate CREB-H transcription of metabolic targets. Proc Natl Acad Sci U S A 26 2939 PMID: 26108621
Urs et al (2015) Targeting β-arrestin2 in the treatment of L-DOPA-induced dyskinesia in Parkinson's disease. Biochem J 112 E2517 PMID: 25918399
Stretton et al (2015) GSK3-mediated raptor phosphorylation supports amino-acid-dependent mTORC1-directed signalling. Biomed Res Int 470 207 PMID: 26348909
Small et al (2015) Morphine Reduces Myocardial Infarct Size via Heat Shock Protein 90 in Rodents. J Biol Chem 2015 129612 PMID: 26413502
Marchand et al (2015) Glycogen synthase kinase-3 (GSK3) inhibition induces prosurvival autophagic signals in human pancreatic cancer cells. Dev Cell 290 5592 PMID: 25561726
Thotala et al (2012) Glycogen synthase kinase 3β inhibitors protect hippocampal neurons from radiation-induced apoptosis by regulating MDM2-p53 pathway. Cell Death Differ 19 387 PMID: 21738215
Neumann et al (2010) Frizzled1 is a marker of inflammatory macrophages, and its ligand Wnt3a is involved in reprogramming Mycobacterium tuberculosis-infected macrophages. FASEB J 24 4599 PMID: 20667980
Fong et al (2010) Tumor-supportive and osteoclastogenic changes induced by breast cancer-derived factors are reversed by inhibition of {gamma}-secretase. J Biol Chem 285 31427 PMID: 20679341
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
Tam et al (2012) Death receptors DR6 and TROY regulate brain vascular development. Eur J Immunol 22 403 PMID: 22340501
Gärtner et al (2012) N-cadherin specifies first asymmetry in developing neurons. Mol Med 31 1893 PMID: 22354041
Adamowicz et al (2012) Inhibition of GSK3 abolishes bacterial-induced periodontal bone loss in mice. Mol Cell 18 1190 PMID: 22847803
Zhou et al (2011) GSK3β inactivation induces apoptosis of leukemia cells by repressing the function of c-Myb. J Cell Mol Med 22 3533 PMID: 21795403
Yang et al (2011) Glycogen synthase kinase 3β inhibition enhances repair of DNA double-strand breaks in irradiated hippocampal neurons. Diabetologia 13 459 PMID: 21398658
Gärtner et al (2006) Neuronal polarity is regulated by glycogen synthase kinase-3 (GSK-3beta) independently of Akt/PKB serine phosphorylation. J Cell Sci 119 3927 PMID: 16954147
Alao et al (2006) The cyclin D1 proto-oncogene is sequestered in the cytoplasm of mammalian cancer cell lines. Mol Cancer 5 7 PMID: 16503970
Alao et al (2006) Histone deacetylase inhibitor, trichostatin A induces ubiquitin-dependent cyclin D1 degradation in MCF-7 breast cancer cells. Mol Cancer 5 8 PMID: 16504004
Gross et al (2006) The JAK/STAT pathway is essential for opioid-induced cardioprotection: JAK2 as a mediator of STAT3, Akt, and GSK-3 beta. Am J Physiol Heart Circ Physiol 291 H827 PMID: 16517948
Ishola et al (2007) Phosphatidylinositol 3-kinase regulation of gastrin-releasing peptide-induced cell cycle progression in neuroblastoma cells. Biol Open 1770 927 PMID: 17379415
Lochhead et al (2006) A chaperone-dependent GSK3β transitional intermediate mediates activation-loop autophosphorylation. Basic Res Cardiol 24 627 PMID: 17188038
Aiston et al (2006) The role of protein kinase B/Akt in Ins-induced inactivation of phosphorylase in rat hepatocytes. Mol Biol Cell 49 174 PMID: 16341839
Streets et al (2006) Identification of an N-terminal glycogen synthase kinase 3 phosphorylation site which regulates the functional localization of polycystin-2 in vivo and in vitro. Biochim Biophys Acta 15 1465 PMID: 16551655
Alao et al (2006) Role of glycogen synthase kinase 3 β (GSK3β) in mediating the cytotoxic effects of the histone deacetylase inhibitor trichostatin A (TSA) in MCF-7 breast cancer cells. J Cell Biol 5 40 PMID: 17018141
Birkenfeld et al (2007) GEF-H1 modulates localized RhoA activation during cytokinesis under the control of mitotic kinases. Dev Cell 12 699 PMID: 17488622
Gross et al (2007) Diabetes abolishes morphine-induced cardioprotection via multiple pathways upstream of glycogen synthase kinase-3beta. Diabetes 56 127 PMID: 17192474
Zhu et al (2007) Activation of glycogen synthase kinase-3 inhibits long-term potentiation with synapse-associated impairments. J Neurosci 27 12211 PMID: 17989287
Chen et al (2007) Glycogen synthase kinase 3 regulates N-MthD.-aspartate receptor channel trafficking and function in cortical neurons. Mol Pharmacol 72 40 PMID: 17400762
Xu et al (2007) Polarity reveals intrinsic cell chirality. Proc Natl Acad Sci U S A 104 9296 PMID: 17517645
Lin et al (2007) GSK-3beta acts downstream of PP2A and the PI 3-kinase-Akt pathway, and upstream of caspase-2 in ceramide-induced mitochondrial apoptosis. J Cell Sci 120 2935 PMID: 17666435
Wang et al (2008) IFN-beta production by TLR4-stimulated innate immune cells is negatively regulated by GSK3-beta. J Immunol 181 6797 PMID: 18981097
Anichtchik et al (2008) Loss of PINK1 function affects development and results in neurodegeneration in zebrafish. J Neurosci 28 8199 PMID: 18701682
Garcia et al (2008) Antigenic experience dictates functional role of glycogen synthase kinase-3 in human CD4+ T cell responses. J Immunol 181 8363 PMID: 19050253
Clifford et al (2008) Novel regulation of vascular endothelial growth factor-A (VEGF-A) by transforming growth factor (beta)1: requirement for Smads, (beta)-CATENIN, AND GSK3(beta). J Biol Chem 283 35337 PMID: 18952601
Gross et al (2008) Delayed cardioprotection afforded by the glycogen synthase kinase 3 inhibitor SB-216763 occurs via a KATP- and MPTP-dependent mechanism at reperfusion. Am J Physiol Heart Circ Physiol 294 H1497 PMID: 18223186
Robertson et al (2008) Runx expression is mitogenic and mutually linked to Wnt activity in blastula-stage sea urchin embryos. PLoS One 3 e3770 PMID: 19020668
Gross et al (2004) Opioid-induced cardioprotection occurs via glycogen synthase kinase beta inhibition during reperfusion in intact rat hearts. Circ Res 94 960 PMID: 14976126
Beaulieu et al (2004) Li antagonizes DA-dependent behaviors mediated by an AKT/glycogen synthase kinase 3 signaling cascade. Proc Natl Acad Sci U S A 101 5099 PMID: 15044694
Sarkar et al (2005) Li induces autophagy by inhibiting inositol monophosphatase. EMBO J 170 1101 PMID: 16186256
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Pathways for SB 216763
