SB 203580

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Cat.No. 1202 - SB 203580 | C21H16FN3OS | CAS No. 152121-47-6
Description: Selective inhibitor of p38 MAPK
Chemical Name: 4-[5-(4-Fluorophenyl)-2-[4-(methylsulfonyl)phenyl]-1H-imidazol-4-yl]pyridine
Purity: ≥98% (HPLC)
Datasheet
Citations (86)
Reviews
Literature
Pathways

Biological Activity

Selective inhibitor of p38 MAPK (IC50 values are 50 and 500 nM for SAPK2a/p38 and SAPK2b/p38β2 respectively). Displays 100-500-fold selectivity over LCK, GSK-3β and PKBα. Shown to inhibit IL-2-induced T cell proliferation, cyclooxygenase-1 and -2, and thromboxane synthase. Enhances clonal growth of skin epithelial progenitor cells; stimulates neural stem cell (NSC) proliferation. Essential component of medium for maintaining stem cells in naive pluripotent state.

Available as part of the MAPK Cascade Inhibitor Tocriset™ and MAPK Inhibitor Tocriset™. Water-soluble Salt also available.

Licensing Information

Sold with the permission of GlaxoSmithKline

Compound Libraries

SB 203580 is also offered as part of the Tocriscreen Plus and Tocriscreen Stem Cell Toolbox. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 377.44
Formula C21H16FN3OS
Storage Desiccate at +4°C
Purity ≥98% (HPLC)
CAS Number 152121-47-6
PubChem ID 176155
InChI Key CDMGBJANTYXAIV-UHFFFAOYSA-N
Smiles CS(=O)C1=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.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 9.44 25
1eq. HCl 37.74 100

Preparing Stock Solutions

The following data is based on the product molecular weight 377.44. 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 2.65 mL 13.25 mL 26.49 mL
5 mM 0.53 mL 2.65 mL 5.3 mL
10 mM 0.26 mL 1.32 mL 2.65 mL
50 mM 0.05 mL 0.26 mL 0.53 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 biological activity of the product.

Borsch-Haubold et al (1998) Direct inhibition of cyclooxygenase-1 and -2 by the kinase inhibitors SB 203580 and PD 98059. J.Biol.Chem. 273 28766 PMID: 9786874

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

Saklatvala et al (1996) Role for p38 mitogen-activated protein kinase in platelet aggregation caused by collagen on a thromboxane analogue. J.Biol.Chem. 271 6586 PMID: 8636072

Sato et al (2008) Inhibitors of p38 mitogen-activated protein kinase enhance proliferation of mouse neural stem cells. J.Neurosci.Res. 86 2179 PMID: 18338804

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


If you know of a relevant reference for SB 203580, please let us know.

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Keywords: SB 203580, SB 203580 supplier, Selective, inhibitors, inhibits, p38, MAPK, Mitogen-Activated, Protein, Kinases, Signaling, Signalling, SB203580, GlaxoSmithKline, GSK, Stem, Cell, Proliferation, 1202, Tocris Bioscience

86 Citations for SB 203580

Citations are publications that use Tocris products. Selected citations for SB 203580 include:

Lourenco et al (2015) Macrophage migration inhibitory factor-CXCR4 is the dominant chemotactic axis in human mesenchymal stem cell recruitment to tumors. J Immunol 194 3463 PMID: 25712213

Yang et al (2015) 1α,25-Dihydroxyvitamin D3 Induces Neutrophil Apoptosis through the p38 MAPK Signaling Pathway in Chronic Obstructive Pulmonary Disease Patients. PLoS One 10 e0120515 PMID: 25905635

Tang et al (2015) P2X7 Receptor Regulates Internalization of Antimicrobial Peptide LL-37 by Human Macrophages That Promotes Intracellular Pathogen Clearance. J Immunol 195 1191 PMID: 26116509

Wan et al (2014) Cathelicidin LL-37 induces time-resolved release of LTB4 and TXA2 by human macrophages and triggers eicosanoid generation in vivo. FASEB J 28 3456 PMID: 24736410

Yu et al (2014) Differential effects of the Toll-like receptor 2 agonists, PGN and Pam3CSK4 on anti-IgE induced human mast cell activation. PLoS One 9 e112989 PMID: 25398056

Kim et al (2014) AMP-activated protein kinase determines apoptotic sensitivity of cancer cells to ginsenoside-Rh2. J Ginseng Res 38 16 PMID: 24558305

Kim et al (2014) Decrease of PKB/Akt Phosphorylation is Partially Mediated by SAPK/JNK Activation in Serum-free L6 Myoblasts Starved with Low Glucose. J Phys Ther Sci 26 1757 PMID: 25435694

Gonsalves et al (2014) Angiogenic growth factors augment K-Cl cotransporter expression in erythroid cells via hypoxia-inducible factor-1α. Am J Hematol 89 273 PMID: 24227191

Bae et al (2014) Activation of pattern recognition receptors in brown adipocytes induces inflammation and suppresses uncoupling protein 1 expression and mitochondrial respiration. Am J Physiol Cell Physiol 306 C918 PMID: 24627558

Caldwell et al (2014) Network dynamics determine the autocrine and paracrine signaling functions of TNF. Genes Dev 28 2120 PMID: 25274725

Choi et al (2013) EI24 regulates epithelial-to-mesenchymal transition and tumor progression by suppressing TRAF2-mediated NF-κB activity. PLoS One 4 2383 PMID: 24280371

Jensen et al (2013) An ERK-p38 subnetwork coordinates host cell apoptosis and necrosis during coxsackievirus B3 infection. J Neurosci 13 67 PMID: 23332156

Enomoto et al (2013) Transcriptional regulation of an insulin-sensitizing adipokine adipolin/CTRP12 in adipocytes by Krüppel-like factor 15. Mol Med 8 e83183 PMID: 24358263

Sethi et al (2013) Gremlin utilizes canonical and non-canonical TGFβ signaling to induce lysyl oxidase (LOX) genes in human trabecular meshwork cells. J Neuroinflammation 113 117 PMID: 23748100

Kang et al (2011) MUC5AC expression through bidirectional communication of Notch and epidermal growth factor receptor pathways. J Immunol 187 222 PMID: 21622856

Suh et al (2011) Induction of steroid sulfatase expression by tumor necrosis factor-α through phosphatidylinositol 3-kinase/Akt signaling pathway in PC-3 human prostate cancer cells. Exp Mol Med 43 646 PMID: 21904110

Jung et al (2008) Reactive oxygen species stabilize hypoxia-inducible factor-1 alpha protein and stimulate transcriptional activity via AMP-activated protein kinase in DU145 human prostate cancer cells. Carcinogenesis 29 713 PMID: 18258605

Wu (2017) TRIB3 downregulation enhances doxorubicin-induced cytotoxicity in gastric cancer cells. Arch Biochem Biophys 622 26 PMID: 28442401

Han (2017) Cannabinoid receptor 1 contributes to sprouted innervation in endometrial ectopic growth through mitogen-activated protein kinase activation. Brain Res 1663 132 PMID: 28322749

Sethi et al (2011) Role of TGFβ/Smad signaling in gremlin induction of human trabecular meshwork extracellular matrix proteins. PLoS One 52 5251 PMID: 21642622

Hecker et al (2011) Reversible differentiation of myofibroblasts by MyoD. J Neurosci 317 1914 PMID: 21440539

Kim et al (2011) Thrombin-induced Migration and Matrix Metalloproteinase-9 Expression Are Regulated by MAPK and PI3K Pathways in C6 Glioma Cells. Mol Cancer 15 211 PMID: 21994479

Kovac et al (2011) Brain microvascular pericytes are immunoactive in culture: cytokine, chemokine, nitric oxide, and LRP-1 expression in response to lipopolysaccharide. J Biol Chem 8 139 PMID: 21995440

Wei et al (2008) Mitogen-activated protein kinases mediate upregulation of hypothalamic angiotensin II type 1 receptors in heart failure rats. Hypertension 52 679 PMID: 18768402

Coba et al (2008) Kinase networks integrate profiles of N-methyl-D-aspartate receptor-mediated gene expression in hippocampus. J Biol Chem 283 34101 PMID: 18815127

Schlee et al (2007) Induction of human beta-defensin 2 by the probiotic Escherichia coli Nissle 1917 is mediated through flagellin. Infect Immun 75 2399 PMID: 17283097

Toyoda et al (2007) Requirement of extracellular signal-regulated kinase/mitogen-activated protein kinase for long-term potentiation in adult mouse anterior cingulate cortex. Mol Pain 3 36 PMID: 18053155

Yang et al (2016) The PDGF-BB-SOX7 axis-modulated IL-33 in pericytes and stromal cells promotes metastasis through tumour-associated macrophages. Cardiorenal Med 7 11385 PMID: 27150562

Wei et al (2014) Central SDF-1/CXCL12 expression and its cardiovascular and sympathetic effects: the role of angiotensin II, TNF-α, and MAP kinase signaling. Am J Physiol Heart Circ Physiol 307 H1643 PMID: 25260613

Heckler et al (2014) ERK/MAPK regulates ERRγ expression, transcriptional activity and receptor-mediated tamoxifen resistance in ER+ breast cancer. FEBS J 281 2431 PMID: 24684682

Ju et al (2012) Inhibition of α-SMA by the ectodomain of FGFR2c attenuates lung fibrosis. Diabetologia 18 992 PMID: 22451267

Cai et al (2012) Rit GTPase regulates a p38 MAPK-dependent neuronal survival pathway. J Cell Mol Med 531 125 PMID: 23123784

Chen et al (2012) Cyclic AMP increases COX-2 expression via mitogen-activated kinase in human myometrial cells. PLoS One 16 1447 PMID: 21854542

Pera et al (2010) Cigarette smoke and lipopolysaccharide induce a proliferative airway smooth muscle phenotype. Exp Cell Res 11 48 PMID: 20429916

Novoyatleva et al (2010) TWEAK is a positive regulator of cardiomyocyte proliferation. Toxins (Basel) 85 681 PMID: 19887380

Katiyar et al (2007) Somatic excision demonstrates that c-Jun induces cellular migration and invasion through induction of stem cell factor. Mol Cell Biol 27 1356 PMID: 17145782

Zhou et al (2007) Delayed and persistent ERK1/2 activation is required for 4-hydroxytamoxifen-induced cell death. Invest Ophthalmol Vis Sci 72 765 PMID: 17714751

Rahman et al (2016) 18α-glycyrrhetinic acid lethality for neuroblastoma cells via de-regulating the Beclin-1/Bcl-2 complex and inducing apoptosis. Biochemical Pharmacology 117 97 PMID: 27520483

Gardoni et al (2012) The neuropeptide PACAP38 induces dendritic spine remodeling through ADAM10-N-cadherin signaling pathway. J Cell Sci 125 1401 PMID: 22328515

Trendelenburg et al (2012) TAK-1/p38/nNFκB signaling inhibits myoblast differentiation by increasing levels of Activin A. Skelet Muscle 2 3 PMID: 22313861

Meotti et al (2012) Inflammatory muscle pain is dependent on the activation of kinin B1 and B2 receptors and intracellular kinase pathways. Br J Pharmacol 166 1127 PMID: 22220695

Khuituan et al (2012) Fibroblast growth factor-23 abolishes 1,25-dihydroxyvitamin D3-enhanced duodenal calcium transport in male mice. Am J Physiol Endocrinol Metab 302 E903 PMID: 22275752

Zhou et al (2010) miR-155 and its star-form partner miR-155* cooperatively regulate type I interferon production by human plasmacytoid dendritic cells. Blood 116 5885 PMID: 20852130

Yoo et al (2010) Redox Factor-1 Inhibits Cyclooxygenase-2 Expression via Inhibiting of p38 MAPK in the A549 Cells. Korean J Physiol Pharmacol 14 139 PMID: 20631885

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. Steroids 5 40 PMID: 17018141

O'Riordan et al (2006) Regulation of nuclear factor κB in the hippocampus by group I metabotropic glutamate receptors. Cell Host Microbe 26 4870 PMID: 16672661

Aiston et al (2006) The role of protein kinase B/Akt in insulin-induced inactivation of phosphorylase in rat hepatocytes. Cardiovasc Res 49 174 PMID: 16341839

Kauppinen et al (2006) Direct phosphorylation and regulation of poly(ADP-ribose) polymerase-1 by extracellular signal-regulated kinases 1/2. Proc Natl Acad Sci U S A 103 7136 PMID: 16627622

Sunters et al (2006) Paclitaxel-induced nuclear translocation of FOXO3a in breast cancer cells is mediated by c-Jun NH2-terminal kinase and Akt. Cancer Res 66 212 PMID: 16397234

Chang et al (2016) Derivation of Patient Specific Pluripotent Stem Cells Using Clinically Discarded Cumulus Cells. PLoS One 11 e0165715 PMID: 27802323

Liu et al (2015) Hyperphosphate-Induced Myocardial Hypertrophy through the GATA-4/NFAT-3 Signaling Pathway Is Attenuated by ERK Inhibitor Treatment. Biogerontology 5 79 PMID: 25999956

Davis et al (2015) Nijmegen breakage syndrome fibroblasts expressing the C-terminal truncated NBN(p70) protein undergo p38/MK2-dependent premature senescence. Exp Hematol Oncol 16 43 PMID: 25214013

Koerber et al (2015) Analysis of the anti-proliferative and the pro-apoptotic efficacy of Syk inhibition in multiple myeloma. Mol Vis 4 21 PMID: 26251761

Brosig et al (2015) Gene expression regulation in retinal pigment epithelial cells induced by viral RNA and viral/bacterial DNA. Immunol Cell Biol 21 1000 PMID: 26330750

Okada et al (2015) STAT3 signaling contributes to the high effector activities of interleukin-15-derived dendritic cells. Int J Mol Med 93 461 PMID: 25582338

Aziz et al (2015) MFG-E8 inhibits neutrophil migration through αvβ3-integrin-dependent MAP kinase activation. Elife 36 18 PMID: 25936372

Zebrowski et al (2015) Developmental alterations in centrosome integrity contribute to the post-mitotic state of mammalian cardiomyocytes. Mol Vis 4 PMID: 26247711

Hollborn et al (2015) Regulation of the hyperosmotic induction of aquaporin 5 and VEGF in retinal pigment epithelial cells: involvement of NFAT5. Oncotarget 21 360 PMID: 25878490

Koeglsperger et al (2013) Impaired glutamate recycling and GluN2B-mediated neuronal calcium overload in mice lacking TGF-β1 in the CNS. Glia 61 985 PMID: 23536313

Kook et al (2013) Fibroblast growth factor-4 enhances proliferation of mouse embryonic stem cells via activation of c-Jun signaling. PLoS One 8 e71641 PMID: 23967228

Tyszkiewicz and Yan (2005) beta-Amyloid peptides impair PKC-dependent functions of metabotropic glutamate receptors in prefrontal cortical neurons. J Neurophysiol 93 3102 PMID: 15659527

Yun et al (2005) Glucose deprivation increases mRNA stability of vascular endothelial growth factor through activation of AMP-activated protein kinase in DU145 prostate carcinoma. Nat Commun 280 9963 PMID: 15640157

Suk et al (2013) A Taiwanese Propolis Derivative Induces Apoptosis through Inducing Endoplasmic Reticular Stress and Activating Transcription Factor-3 in Human Hepatoma Cells. Evid Based Complement Alternat Med 2013 658370 PMID: 24222778

Marlow et al (2013) A novel model of dormancy for bone metastatic breast cancer cells. Cancer Res 73 6886 PMID: 24145351

Lang et al (2013) Effect of thioridazine on erythrocytes. Toxins (Basel) 5 1918 PMID: 24152992

Yi et al (2012) TLR signaling paralyzes monocyte chemotaxis through synergized effects of p38 MAPK and global Rap-1 activation. PLoS One 7 e30404 PMID: 22347375

Santos et al (2012) Distinct regulatory functions of calpain 1 and 2 during neural stem cell self-renewal and differentiation. PLoS One 7 e33468 PMID: 22432027

Sutcliffe et al (2009) Transcriptional regulation of monocyte chemotactic protein-1 release by endothelin-1 in human airway smooth muscle cells involves NF-kappaB and AP-1. Br J Pharmacol 157 436 PMID: 19371341

Davis and Kipling (2009) Assessing the role of stress signalling via p38 MAP kinase in the premature senescence of ataxia telangiectasia and Werner syndrome fibroblasts. Biogerontology 10 253 PMID: 18830681

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

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

Cervigni et al (2015) JNK2 controls fragmentation of the Golgi complex and the G2/M transition through phosphorylation of GRASP65. J Cell Sci 128 2249 PMID: 25948586

Li et al (2015) MAPK signaling downstream to TLR4 contributes to paclitaxel-induced peripheral neuropathy. Brain Behav.Immun. 49 255 PMID: 26065826

Siegl (2012) Using the one-lung method to link p38 to pro-inflammatory gene expression during overventilation in C57BL/6 and BALB/c mice. PLoS One 7 e41464 PMID: 22848503

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

Steubesand et al (2009) The expression of the beta-defensins hBD-2 and hBD-3 is differentially regulated by NF-kappaB and MAPK/AP-1 pathways in an in vitro model of Candida esophagitis. BMC Immunol 10 36 PMID: 19523197

Yeligar et al (2009) Ethanol augments RANTES/CCL5 expression in rat liver sinusoidal endothelial cells and human endothelial cells via activation of NF-kappa B, HIF-1 alpha, and AP-1. J Immunol 183 5964 PMID: 19828633

Liang et al (2014) δ-Opioid receptors up-regulate excitatory amino acid transporters in mouse astrocytes. Exp Eye Res 171 5417 PMID: 25052197

Bernet et al (2014) p38 MAPK signaling underlies a cell-autonomous loss of stem cell self-renewal in skeletal muscle of aged mice. Korean J Physiol Pharmacol 20 265 PMID: 24531379

Beermann et al (2014) Distinct signalling pathways of murine histamine H1- and H4-receptors expressed at comparable levels in HEK293 cells. Respir Res 9 e107481 PMID: 25243776

Keasey et al (2013) Inhibition of a novel specific neuroglial integrin signaling pathway increases STAT3-mediated CNTF expression. Cell Commun Signal 11 35 PMID: 23693126

Kim et al (2013) Epigallocatechin gallate (EGCG) stimulates autophagy in vascular endothelial cells: a potential role for reducing lipid accumulation. J Biol Chem 288 22693 PMID: 23754277

Katholnig et al (2013) p38α senses environmental stress to control innate immune responses via mechanistic target of rapamycin. J Immunol 190 1519 PMID: 23315073

Tsai et al (2011) Carnosic acid induces the NAD(P)H: quinone oxidoreductase 1 expression in rat clone 9 cells through the p38/nuclear factor erythroid-2 related factor 2 pathway. J Nutr 141 2119 PMID: 22031657

Isfort et al (2011) Real-time imaging reveals that P2Y2 and P2Y12 receptor agonists are not chemoattractants and macrophage chemotaxis to complement C5a is phosphatidylinositol 3-kinase (PI3K)- and p38 mitogen-activated protein kinase (MAPK)-independent. J Biol Chem 286 44776 PMID: 22057273

Zhou and Too (2011) Mitochondrial localized STAT3 is involved in NGF induced neurite outgrowth. Nat Med 6 e21680 PMID: 21738764


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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 203580

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.