SB 203580

Cat. No. 1202

SB 203580 C21H16FN3OS [152121-47-6]

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Chemical Name: 4-[5-(4-Fluorophenyl)-2-[4-(methylsulfonyl)phenyl]-1H-imidazol-4-yl]pyridine

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. Part of the MAPK Cascade Inhibitor Tocriset™ and MAPK Inhibitor Tocriset™. Water-soluble salt SB 203580 hydrochloride (Cat. No. 1402) also available.

Licensing Information

Sold with the permission of GlaxoSmithKline

Technical Data

M.Wt:
377.44
Formula:
C21H16FN3OS
Solubility:
Soluble to 25 mM in DMSO and to 100 mM in 1eq. HCl
Purity:
>98 %
Storage:
Desiccate at +4°C
CAS No:
152121-47-6

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.

Certificate of Analysis / Safety Data Sheet

Certificate of Analysis: View current batch
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Safety Data Sheet: View Safety Data Sheet

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

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.

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

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.

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.

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

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

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.

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.

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.

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.

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.

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.

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.

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

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.

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

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.

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.

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

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.

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.

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.

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.

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.

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.

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.

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