SB 202190

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Cat.No. 1264 - SB 202190 | C20H14N3OF | CAS No. 152121-30-7
Description: Potent, selective inhibitor of p38 MAPK
Chemical Name: 4-[4-(4-Fluorophenyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]phenol
Purity: ≥99% (HPLC)
Datasheet
Citations (36)
Reviews (3)
Literature (4)
Pathways (1)

Biological Activity

A highly selective, potent and cell-permeable inhibitor of p38 MAP kinase. Binds within the ATP pocket of the active kinase (Kd = 38 nM, as measured in recombinant human p38), and selectively inhibits the p38α and β isoforms (IC50 = 50 and 100 nM at SAPK2a/p38 and SAPK2b/p38β2 respectively). Promotes stability of naive human pluripotent stem cells in culture. Also available as part of the MAPK Inhibitor Tocriset™.

Licensing Information

Sold with the permission of GlaxoSmithKline

Compound Libraries

SB 202190 is also offered as part of the Tocriscreen Plus and Tocriscreen Kinase Inhibitor Toolbox I. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 331.35
Formula C20H14N3OF
Storage Store at -20°C
Purity ≥99% (HPLC)
CAS Number 152121-30-7
PubChem ID 16759148
InChI Key YKRNPHOBDOUQTG-UHFFFAOYSA-N
Smiles OC1=CC=C(C=C1)C1=NC(=C(N1)C1=CC=NC=C1)C1=CC=C(F)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

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 33.13 100

Preparing Stock Solutions

The following data is based on the product molecular weight 331.35. 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 3.02 mL 15.09 mL 30.18 mL
5 mM 0.6 mL 3.02 mL 6.04 mL
10 mM 0.3 mL 1.51 mL 3.02 mL
50 mM 0.06 mL 0.3 mL 0.6 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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References

References are publications that support the biological activity of the product.

Davies et al (2000) Specificity and mechanism of action of some commonly used protein kinase inhibitors. Biochem.J. 351 95 PMID: 10998351

Frantz et al (1998) The activation of p38 mitogen-activated protein kinase determines the efficiency of ATP competition for pyridinylimidazole inhibitor binding. Biochemistry 37 13846 PMID: 9753474

Jiang et al (1996) Characterization of the structure and function of a new mitogen-activated protein kinase (p38β). J.Biol.Chem. 271 17920 PMID: 8663524

Nemoto et al (1998) Induction of apoptosis by SB 202190 through inhibition of p38β mitogen-activated protein kinase. J.Biol.Chem. 273 16415 PMID: 9632706

Gafni et al (2013) Derivation of novel human ground state naive pluripotent stem cells. Nature 504 282 PMID: 24172903

Sato et al (2015) SnapShot: Growing Organoids from Stem Cells. Cell 161 1700 PMID: 26091044

Mahe et al (2014) Establishment of gastrointestinal epithelial organoids Curr.Protoc. Mouse Biol. 3 217 PMID: 25105065

Bartfeld et al (2015) In vitro expansion of human gastric epithelial stem cells and their responses to bacterial infection. Gastroenterology 148 126 PMID: 25307862

Karthaus et al (2014) Identification of multipotent luminal progenitor cells in human prostate organoid cultures. Cell 159 163 PMID: 25201529


If you know of a relevant reference for SB 202190, please let us know.

View Related Products by Product Action

View all p38 MAPK Inhibitors

Keywords: SB 202190, SB 202190 supplier, Potent, selective, inhibitors, inhibits, p38, MAPK, Signaling, Signalling, Mitogen-Activated, Protein, Kinases, SB202190, GlaxoSmithKline, GSK, organoids, Stem, Cell, Proliferation, Organoids, 1264, Tocris Bioscience

36 Citations for SB 202190

Citations are publications that use Tocris products. Selected citations for SB 202190 include:

Zhang et al (2015) Excess salt exacerbates blood-brain barrier disruption via a p38/MAPK/SGK1-dependent pathway in permanent cerebral ischemia. PLoS One 5 16548 PMID: 26549644

Oliveira et al (2015) The role of Na+/K+-ATPase during chick skeletal myogenesis. J Neurosci 10 e0120940 PMID: 25775465

Morse et al (2013) Label-free integrative pharmacology on-target of opioid ligands at the opioid receptor family. BMC Pharmacol Toxicol 14 17 PMID: 23497702

Guillemot and Citi (2006) Cingulin regulates claudin-2 expression and cell proliferation through the small GTPase RhoA. Mol Biol Cell 17 3569 PMID: 16723500

Rajnicek et al (2006) Temporally and spatially coordinated roles for Rho, Rac, Cdc42 and their effectors in growth cone guidance by a physiological electric field. J Cell Sci 119 1723 PMID: 16595546

Bellik et al (2005) Intracellular pathways triggered by the selective FLT-1-agonist placental growth factor in vascular smooth muscle cells exposed to hypoxia. Br J Pharmacol 146 568 PMID: 16086034

Kang et al (2018) Improving Cell Survival in Injected Embryos Allows Primed Pluripotent Stem Cells to Generate Chimeric Cynomolgus Monkeys. Cell Rep 25 2563 PMID: 30485820

Shaw and Lloyd (2012) Post-transcriptional regulation of placenta growth factor mRNA by hydrogen peroxide. Nature 84 155 PMID: 22683469

Wong et al (2010) Bone morphogenic protein-4 impairs endothelial function through oxidative stress-dependent cyclooxygenase-2 upregulation: implications on hypertension. Circ Res 107 984 PMID: 20724703

Ma et al (2005) Oxygen-sensitive {δ}-opioid receptor-regulated survival and death signals: novel insights into neuronal preconditioning and protection. Mediators Inflamm 280 16208 PMID: 15687501

Gallagher et al (2004) Extracellular signal-regulated protein kinase activation is required for metabotropic glutamate receptor-dependent long-term depression in hippocampal area CA1. Biochem J 24 4859 PMID: 15152046

Montero et al (2004) Calcineurin-independent inhibition of mitochondrial Ca2+ uptake by cyclosporin A. Br J Pharmacol 141 263 PMID: 14691054

Schiff et al (2019) P38 inhibition reverses TGFβ1 and TNFα-induced contraction in a model of proliferative vitreoretinopathy. Commun Biol 2 162 PMID: 31069271

Pervolaraki et al (2017) Type I and Type III IF.s Display Different Dependency on Mitogen-Activated Protein Kinases to Mount an Antiviral State in the Human Gut. Front Immunol 8 459 PMID: 28484457

Wong et al (2016) Andrographolide induces Nrf2 and heme oxygenase 1 in astrocytes by activating p38 MAPK and ERK. J Neuroinflammation 13 251 PMID: 27663973

Page et al (2015) Matrix rigidity regulates the transition of tumor cells to a bone-destructive phenotype through integrin β3 and TGF-β receptor type II. Biomaterials 64 33 PMID: 26115412

Tichet et al (2015) Tumour-derived SPARC drives vascular permeability and extravasation through endothelial VCAM1 signalling to promote metastasis. Nat Commun 6 6993 PMID: 25925867

Doulatov et al (2009) PLZF is a regulator of homeostatic and cytokine-induced myeloid development. Genes Dev 23 2076 PMID: 19723763

Atherton et al (2003) IL-13-induced changes in the goblet cell density of human bronchial epithelial cell cultures: MAP kinase and phosphatidylinositol 3-kinase regulation. Am J Physiol Lung Cell Mol Physiol 285 L730 PMID: 12794003

Ranganathan et al (2019) Evaluating Shigella flexneri Pathogenesis in the Human Enteroid Model. Infect Immun 87 PMID: 30642900

Nadeem (2017) IL-17A causes depression-like symptoms via NFκB and p38MAPK signaling pathways in mice: Implications for psoriasis associated depression. Cytokine 97 14 PMID: 28570931

Zhou (2017) TNFα induces tolerant production of CXC chemokines in colorectal cancer HCT116 cells via A20 inhibition of ERK signaling. Int Immunopharmacol 54 PMID: 29175508

Nicastro et al (2013) 3,3'-diindolylmethane rapidly and selectively inhibits hepatocyte growth factor/c-Met signaling in breast cancer cells. J Nutr Biochem 24 1882 PMID: 23968581

Xia et al (2013) Identification of repurposed small molecule drugs for chordoma therapy. Cancer Biol Ther 14 638 PMID: 23792643

Makhortova et al (2011) A screen for regulators of survival of motor neuron protein levels. Nat Chem Biol 7 544 PMID: 21685895

Morse et al (2011) Ligand-directed functional selectivity at the mu opioid receptor revealed by label-free integrative pharmacology on-target. PLoS One 6 e25643 PMID: 22003401

Riedl et al (2009) Proteomic analysis uncovers novel actions of the neurosecretory protein VGF in nociceptive processing. Nat Commun 29 13377 PMID: 19846725

Molina et al (2017) p38 MAPK as an essential regulator of dorsal-ventral axis specification and skeletogenesis during sea urchin development: a re-evaluation. Development 144 2270 PMID: 28507001

Babu et al (2014) TGFβ-mediated suppression of CD248 in non-cancer cells via canonical Smad-dependent signaling pathways is uncoupled in cancer cells. BMC Cancer 14 113 PMID: 24555435

Toutounchian et al (2014) Modulation of radiation injury response in retinal endothelial cells by quinic acid derivative KZ-41 involves p38 MAPK. PLoS One 9 e100210 PMID: 24956278

Kleinewietfeld et al (2013) Sodium chloride drives autoimmune disease by the induction of pathogenic TH17 cells. Sci Rep 496 518 PMID: 23467095

Akhmetshina et al (2012) Activation of canonical Wnt signalling is required for TGF-β-mediated fibrosis. J Biol Chem 3 735 PMID: 22415826

Zhu et al (2012) BlyS is up-regulated by hypoxia and promotes migration of human breast cancer cells. Am J Physiol Lung Cell Mol Physiol 31 31 PMID: 22463935

Ye et al (2011) Dermatophagoides pteronyssinus 2 regulates nerve growth factor release to induce airway inflammation via a reactive oxygen species-dependent pathway. Am J Physiol Regul Integr Comp Physiol 300 L216 PMID: 21097523

Medici et al (2011) Transforming growth factor-β2 promotes Snail-mediated endothelial-mesenchymal transition through convergence of Smad-dependent and Smad-independent signalling. J Exp Clin Cancer Res 437 515 PMID: 21585337

Turpeinen et al (2011) Dual specificity phosphatase 1 regulates human inducible nitric oxide synthase expression by p38 MAP kinase. J Neurosci 2011 127587 PMID: 21547253


Do you know of a great paper that uses SB 202190 from Tocris? Please let us know.

Reviews for SB 202190

Average Rating: 3.3 (Based on 3 Reviews.)

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Easy to store and use.
By Anonymous on 02/07/2019
Assay Type: Ex Vivo
Species: Human

I used this to test the potency of this to kill of COLO 205 cells with the addition of TNF in a dose dependent manner.


Works, but don't store 6 months greater.
By Scott Scarneo on 02/06/2019
Assay Type: Ex Vivo
Species: Human
Cell Line/Tissue: MDA-231

Stored ok, seemed to lose potency over time at -20 aliquots.

review image

Good inhibitor for cell studies.
By Anonymous on 12/26/2018
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: MDA-MB-231

I compared this inhibitor to a TAK1 inhibitor to compared effects on cell death.


Literature in this Area

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*Please note that Tocris will only send literature to established scientific business / institute addresses.


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MAPK Signaling Scientific Review

MAP kinase signaling is integral to the regulation of numerous cellular processes such as proliferation and differentiation, and as a result is an important focus of cancer and immunology research. Updated for 2016, this review discusses the regulation of the MAPK pathway and properties of MAPK cascades. Compounds available from Tocris are listed.

Pathways for SB 202190

MAPK

MAPK Signaling Pathway

The mitogen-activated protein kinase pathway evokes an intracellular signaling cascade in response to extracellular stimuli such as heat and stress. It can influence cell division, metabolism and survival.