SB 415286

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Description: Potent, selective GSK-3 inhibitor
Chemical Name: 3-[(3-Chloro-4-hydroxyphenyl)amino]-4-(2-nitrophenyl)-1H-pyrrole-2,5-dione
Purity: ≥99% (HPLC)
Citations (27)
Literature (4)
Pathways (1)

Biological Activity for SB 415286

SB 415286 is a potent and selective glycogen synthase kinase-3 (GSK-3) inhibitor (Ki = 31 nM for GSK-3α); competes with ATP. Has minimal activity against 24 other protein kinases (IC50 > 10 μ M). Stimulates glycogen synthesis, gene transcription and is neuroprotective.

Licensing Information

Sold for research purposes under agreement from GlaxoSmithKline

Technical Data for SB 415286

M. Wt 359.73
Formula C16H10ClN3O5
Storage Store at RT
Purity ≥99% (HPLC)
CAS Number 264218-23-7
PubChem ID 4210951
Smiles OC1=C(Cl)C=C(NC2=C(C(=O)NC2=O)C2=C(C=CC=C2)[N+]([O-])=O)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 415286

Solvent Max Conc. mg/mL Max Conc. mM
ethanol 8.99 25
DMSO 17.99 50

Preparing Stock Solutions for SB 415286

The following data is based on the product molecular weight 359.73. 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.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.5 mM 5.56 mL 27.8 mL 55.6 mL
2.5 mM 1.11 mL 5.56 mL 11.12 mL
5 mM 0.56 mL 2.78 mL 5.56 mL
25 mM 0.11 mL 0.56 mL 1.11 mL

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Product Datasheets for SB 415286

Certificate of Analysis / Product Datasheet
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References for SB 415286

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

Liang and Chuang (2006) Regulation and function of glycogen synthase kinase-3 isoforms in neuronal survival. J.Biol.Chem. 282 3904 PMID: 17148450

If you know of a relevant reference for SB 415286, please let us know.

View Related Products by Product Action

View all Glycogen Synthase Kinase 3 Inhibitors

Keywords: SB 415286, SB 415286 supplier, Potent, selective, GSK-3, inhibitors, inhibits, Glycogen, Synthase, Kinases, 3, Carbohydrate, Metabolism, SB415286, GlaxoSmithKline, GSK, Kinase, 1617, Tocris Bioscience

27 Citations for SB 415286

Citations are publications that use Tocris products. Selected citations for SB 415286 include:

Liddell et al (2016) Pyrrolidine dithiocarbamate activates the Nrf2 pathway in astrocytes. J Neuroinflammation 13 49 PMID: 26920699

Severson et al (2010) Glycogen Synthase Kinase 3 (GSK-3) influences epithelial barrier function by regulating occludin, claudin-1 and E-cadherin expression. Neuro Oncol 397 592 PMID: 20617560

Yang et al (2011) Glycogen synthase kinase 3β inhibition enhances repair of DNA double-strand breaks in irradiated hippocampal neurons. Nature 13 459 PMID: 21398658

Napolitano et al (2018) mTOR-dependent phosphorylation controls TFEB nuclear export. Nat Commun 9 3312 PMID: 30120233

Westhoff et al (2014) Sequential dosing in chemosensitization: targeting the PI3K/Akt/mTOR pathway in neuroblastoma. PLoS One 8 e83128 PMID: 24391739

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

Noh et al (2015) Resveratrol regulates naïve CD 8+ T-cell proliferation by upregulating IFN-γ-induced tryptophanyl-tRNA synthetase expression. BMB Rep 48 283 PMID: 25248565

Wang et al (2015) Pharmacologically blocking p53-dependent apoptosis protects intestinal stem cells and mice from radiation. Sci Rep 5 8566 PMID: 25858503

Cuesto et al (2015) GSK3β Inhibition Promotes Synaptogenesis in Drosophila and Mammalian Neurons. PLoS One 10 e0118475 PMID: 25764078

Acevedo et al (2014) Phosphorylation of amyloid precursor protein at threonine 668 is essential for its copper-responsive trafficking in SH-SY5Y neuroblastoma cells. Hum Mol Genet 289 11007 PMID: 24610780

Ray et al (2013) Tristetraprolin mediates radiation-induced TNF-α production in lung macrophages. PLoS One 8 e57290 PMID: 23468959

Dickey et al (2011) GSK-3β inhibition promotes cell death, apoptosis, and in vivo tumor growth delay in neuroblastoma Neuro-2A cell line. J Neurooncol 104 145 PMID: 21161565

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

Chen et al (2013) Anti-dengue virus nonstructural protein 1 antibodies cause NO-mediated endothelial cell apoptosis via ceramide-regulated glycogen synthase kinase-3β and NF-κB activation. J Immunol 191 1744 PMID: 23851680

Thotala et al (2010) A new class of molecular targeted radioprotectors: GSK-3beta inhibitors. Int J Radiat Oncol Biol Phys 76 557 PMID: 20117291

Vossel et al (2015) Tau reduction prevents Aβ-induced axonal transport deficits by blocking activation of GSK3β. Biochem J 209 419 PMID: 25963821

Stretton et al (2015) GSK3-mediated raptor phosphorylation supports amino-acid-dependent mTORC1-directed signalling. J Biol Chem 470 207 PMID: 26348909

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

Sharma et al (2012) Sidestream smoke exposure increases the susceptibility of airway epithelia to adenoviral infection. PLoS One 7 e49930 PMID: 23166798

Tsai et al (2010) The mood stabilizers valproic acid and Li enhance mesenchymal stem cell migration via distinct mechanisms. Neuropsychopharmacology 35 2225 PMID: 20613717

Nyati et al (2010) Molecular imaging of glycogen synthase kinase-3beta and casein kinase-1alpha kinases. Anal Biochem 405 246 PMID: 20561505

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

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

Ishola et al (2007) Phosphatidylinositol 3-kinase regulation of gastrin-releasing peptide-induced cell cycle progression in neuroblastoma cells. Biochem Biophys Res Commun 1770 927 PMID: 17379415

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

Garvalov et al (2007) Cdc42 regulates cofilin during the establishment of neuronal polarity. J Neurosci 27 13117 PMID: 18045906

Witte et al (2008) Microtubule stabilization specifies initial neuronal polarization. J Cell Biol 180 619 PMID: 18268107

Do you know of a great paper that uses SB 415286 from Tocris? Please let us know.

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Literature in this Area

Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!

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Pathways for SB 415286

Wnt Signaling Pathway

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The Wnt pathway is involved in cellular differentiation and proliferation in adult tissues and also during embryogenesis. Disturbances within the pathway may lead to the formation of tumors and promote metastasis.