S8307

SB 203580

Name: SB 203580
Brand: SIGMA
Price: 245 USD
Availability: InStock

≥98% (HPLC), solid, p38 MAPK inhibitor

Synonym(s):

4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)-1H-imidazole

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1 MG

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About This Item

Empirical Formula (Hill Notation):

C₂₁H₁₆FN₃OS

CAS Number:

152121-47-6

Molecular Weight:

377.43

MDL number:

MFCD00922198

UNSPSC Code:

12352200

PubChem Substance ID:

24899788

NACRES:

NA.77

Key Documents

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Product Name

SB 203580, solid, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

DMSO: ≥20 mg/mL

storage temp.

−20°C

SMILES string

CS(=O)c1ccc(cc1)-c2nc(-c3ccc(F)cc3)c([nH]2)-c4ccncc4

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)

InChI key

CDMGBJANTYXAIV-UHFFFAOYSA-N

Gene Information

human ... CYP1A2(1544), CYP2C19(1557), CYP2C9(1559), CYP2D6(1565), CYP3A4(1576), IL1B(3553), MAPK14(1432), MAPK8IP2(23542), RAF1(5894), TNF(7124)

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Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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This Item	S7067	S8822	559389
Sigma-Aldrich S8307 SB 203580	Sigma-Aldrich S7067 SB 202190	Sigma-Aldrich S8822 SB-525334	Sigma-Aldrich 559389 SB 203580
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)
form solid	form powder	form solid	form film (Thin)
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. −20°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. −20°C
solubility DMSO: ≥20 mg/mL	solubility DMSO: 10 mg/mL, clear	solubility DMSO: ≥20 mg/mL	solubility DMSO: 30 mg/mL
color white to off-white	color faintly yellow, to beige	color yellow	color -

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.

pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Thioredoxin negatively regulates p38 MAP kinase activation and IL-6 production by tumor necrosis factor-alpha.

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

Characterization and reversal of Doxorubicin-mediated biphasic activation of ERK and persistent excitability in sensory neurons of Aplysia californica.

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

Association Between C1q/TNF-Related Protein-1 Levels in Human Plasma and Epicardial Adipose Tissues and Congestive Heart Failure.

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

ASK1 Mediates Nur77 Expression in T-Cell Receptor Mediated Thymocyte Apoptosis.

Jianxin Huo et al.

Cells, 9(3) (2020-03-04)

: Apoptosis signal-regulating kinase 1 (ASK1) is a mitogen-activated protein kinase kinase kinase (MAPKKK) that activates downstream JNK and p38 mitogen-activated protein kinase (MAPK) to relay death signals into cells in response to various environmental stress. However, whether ASK1 plays

Internalization-Dependent Free Fatty Acid Receptor 2 Signaling Is Essential for Propionate-Induced Anorectic Gut Hormone Release.

Natarin Caengprasath et al.

iScience, 23(9), 101449-101449 (2020-08-28)

The ability of propionate, a short-chain fatty acid produced from the fermentation of non-digestible carbohydrates in the colon, to stimulate the release of anorectic gut hormones, such as glucagon like peptide-1 (GLP-1), is an attractive approach to enhance appetite regulation

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