S8307
SB 203580
≥98% (HPLC), solid, p38 MAPK inhibitor
Synonym(s):
4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)-1H-imidazole
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About This Item
Empirical Formula (Hill Notation):
C21H16FN3OS
CAS Number:
Molecular Weight:
377.43
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
SB 203580, solid, ≥98% (HPLC)
SMILES string
CS(=O)c1ccc(cc1)-c2nc(-c3ccc(F)cc3)c([nH]2)-c4ccncc4
InChI key
CDMGBJANTYXAIV-UHFFFAOYSA-N
InChI
1S/C21H16FN3OS/c1-27(26)18-8-4-16(5-9-18)21-24-19(14-2-6-17(22)7-3-14)20(25-21)15-10-12-23-13-11-15/h2-13H,1H3,(H,24,25)
assay
≥98% (HPLC)
form
solid
color
white to off-white
solubility
DMSO: ≥20 mg/mL
storage temp.
−20°C
Quality Level
Gene Information
Application
MDCK cells were treated with SB 203580 to study the role of MAPK signaling in inducing hypertonicity of cell membrane and potassium depletion.16 It was used to inhibit MAPK signaling in mouse cortical neurons17 and human hepatocellular carcinoma cell lines.18
Biochem/physiol Actions
SB 203580 is a pyridinyl imidazole that suppresses the activation of MAPKAP kinase-2 and inhibits the phosphorylation of heat shock protein (HSP) 27 in response to IL-1, cellular stresses and bacterial endotoxin in vivo. It does not inhibit JNK or p42 MAP kinase and therefore, is useful for studying the physiological roles and targets of p38 MAPK and MAPKAP kinase-2. It has been shown to induce the activation of the serine/threonine kinase Raf-1 and has been reported to inhibit cytokine production.
Features and Benefits
This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the MAPKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Harini Lakshminarasimhan et al.
Scientific reports, 7(1), 4533-4533 (2017-07-05)
Doxorubicin (DOX), a common chemotherapeutic agent, impairs synaptic plasticity. DOX also causes a persistent increase in basal neuronal excitability, which occludes serotonin-induced enhanced excitability. Therefore, we sought to characterize and reverse DOX-induced physiological changes and modulation of molecules implicated in
S Hashimoto et al.
Biochemical and biophysical research communications, 258(2), 443-447 (1999-05-18)
We examined the regulatory role of a reduction/oxidation (redox) control protein, thioredoxin (TRX), in tumor necrosis factor-alpha (TNF-alpha)-induced p38 MAP kinase activation and p38 MAP kinase-mediated cytokine expression utilizing TRX-transfected murine L929 cells (TRX14). The results showed that TNF-alpha-induced p38
C A Hall-Jackson et al.
Oncogene, 18(12), 2047-2054 (1999-05-13)
The inhibition of SAPK2a/p38 (a mitogen activated protein (MAP) kinase family member) by SB 203580 depends on the presence of threonine at residue 106. Nearly all other protein kinases are insensitive to this drug because a more bulky residue occupies
Camille Robinet et al.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism, 30(2), 286-298 (2009-10-02)
MCT2 is the predominant neuronal monocarboxylate transporter allowing lactate use as an alternative energy substrate. It is suggested that MCT2 is upregulated to meet enhanced energy demands after modifications in synaptic transmission. Brain-derived neurotrophic factor (BDNF), a promoter of synaptic
Ying Yang et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 42(5), 2130-2143 (2017-08-16)
C1q and tumour necrosis factor-related protein 1 (CTRP1) possesses anti-atherogenic and anti-inflammatory effects. This study investigated whether the CTRP1 levels in the plasma and epicardial adipose tissue (EAT) were associated with congestive heart failure (CHF) and to disclose possible molecular
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