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Submit ReviewSB 415286
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)
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 |
| InChI Key | PQCXVIPXISBFPN-UHFFFAOYSA-N |
| 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 | |
|---|---|---|---|
| Solubility | |||
| 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.
| 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
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.
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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:
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
Sharma et al (2012) Sidestream smoke exposure increases the susceptibility of airway epithelia to adenoviral infection. PLoS One 7 e49930 PMID: 23166798
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
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
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
Cuesto et al (2015) GSK3β Inhibition Promotes Synaptogenesis in Drosophila and Mammalian Neurons. PLoS One 10 e0118475 PMID: 25764078
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
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
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
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
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
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
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