SB 216763

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Cat.No. 1616 - SB 216763 | C19H12Cl2N2O2 | CAS No. 280744-09-4
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)
Datasheet
Citations (50)
Reviews
Literature

Biological Activity

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

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.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 27.84 75
ethanol 0.48 1.3

Preparing Stock Solutions

The following data is based on the product molecular weight 371.22. 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 2.69 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

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

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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View all Glycogen Synthase Kinase 3 Inhibitors

Keywords: SB 216763, supplier, Potent, selective, GSK-3, inhibitors, inhibits, Glycogen, Synthase, Kinases, 3, Carbohydrate, Metabolism, SB216763, GlaxoSmithKline, GSK, Glycogen, Synthase, Kinase, 3, Glycogen, Synthase, Kinase, Stem, Cell, Proliferation, Glycogen, Synthase, Kinase, 3, Tocris Bioscience

50 Citations for SB 216763

Citations are publications that use Tocris products. Selected citations for SB 216763 include:

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

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

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

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 insulin-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

Lee et al (2014) Inhibiting glycogen synthase kinase-3 mitigates the hematopoietic acute radiation syndrome in mice. Radiat Res 181 445 PMID: 24720754

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

Kuo et al (2014) Repression of glucocorticoid-stimulated angiopoietin-like 4 gene transcription by insulin. J Lipid Res 55 919 PMID: 24565756

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

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

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

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

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

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

Anichtchik et al (2008) Loss of PINK1 function affects development and results in neurodegeneration in zebrafish. J Neurosci 28 8199 PMID: 18701682

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

Sarkar et al (2008) A rational mechanism for combination treatment of Huntington's disease using lithium 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

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

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

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

Sarkar et al (2005) Lithium induces autophagy by inhibiting inositol monophosphatase. EMBO J 170 1101 PMID: 16186256

Kahn et al (2015) Effects of kinesin-5 inhibition on dendritic architecture and microtubule organization. Mol Biol Cell 26 66 PMID: 25355946

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

Khattabi and Sharma (2013) Preventing p38 MAPK-mediated MafA degradation ameliorates β-cell dysfunction under oxidative stress. Hum Mol Genet 27 1078 PMID: 23660596

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

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

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

Enman and Unterwald (2012) Inhibition of GSK3 attenuates amphetamine-induced hyperactivity and sensitization in the mouse. Neuro Oncol 231 217 PMID: 22649795

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

Shen et al (2011) Inhibition of adipocytogenesis by canonical WNT signaling in human mesenchymal stem cells. Exp Cell Res 317 1796 PMID: 21640723

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


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