SB 415286

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Cat.No. 1617 - SB 415286 | C16H10ClN3O5 | CAS No. 264218-23-7
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)
Datasheet
Citations (20)
Literature

Biological Activity

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

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.

All Tocris products are intended for laboratory research use only.

Solubility Data

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

Preparing Stock Solutions

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

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.78 mL 13.9 mL 27.8 mL
5 mM 0.56 mL 2.78 mL 5.56 mL
10 mM 0.28 mL 1.39 mL 2.78 mL
50 mM 0.06 mL 0.28 mL 0.56 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

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

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20 Citations for SB 415286

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

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

Tsai et al (2010) The mood stabilizers valproic acid and lithium 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

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

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

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

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

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

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

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

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

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

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

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

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


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