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A6355

3-(2-Aminoethyl)-5-((4-ethoxyphenyl)methylene)-2,4-thiazolidinedione hydrochloride

Name: 3-(2-Aminoethyl)-5-((4-ethoxyphenyl)methylene)-2,4-thiazolidinedione hydrochloride
Brand: SIGMA

powder, ≥98% (HPLC)

Synonym(s):

Erk Inhibitor

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About This Item

Empirical Formula (Hill Notation):

C₁₄H₁₆N₂O₃S · HCl

CAS Number:

294675-79-9

Molecular Weight:

328.81

MDL number:

MFCD09038681

UNSPSC Code:

12352202

PubChem Substance ID:

24891079

NACRES:

NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated
under inert gas

color

off-white

solubility

DMSO: ≥4 mg/mL

storage temp.

2-8°C

SMILES string

Cl[H].CCOc1ccc(cc1)C=C2SC(=O)N(CCN)C2=O

InChI

1S/C14H16N2O3S.ClH/c1-2-19-11-5-3-10(4-6-11)9-12-13(17)16(8-7-15)14(18)20-12;/h3-6,9H,2,7-8,15H2,1H3;1H/b12-9+;

InChI key

PQVLWVGMXJPJLG-NBYYMMLRSA-N

Application

3-(2-Aminoethyl)-5-((4-ethoxyphenyl)methylene)-2,4-thiazolidinedione is an extracellular signal-regulated kinase (ERK) docking domain inhibitor. ERK inhibitors have been used to study traumatic brain injuries.

Biochem/physiol Actions

3-(2-Aminoethyl)-5-((4-ethoxyphenyl)methylene)-2,4-thiazolidinedione is extracellular signal-regulated kinase (ERK) docking domain inhibitor. Inhibits ERK binding rather then ERK activity at the ATP domain. IC₅₀ = 25 μM in HeLa, A549, and SUM-159 tumor cells. Currently, no specific inhibitors of the ERK proteins exist. Preferentially binds to ERK2 with a Kd of ~5 μM and prevents its interaction with protein substrates. Shown to block ERK-mediated phosphorylation of ribosomal S6 kinase-1 (RSK-1) and ternary complex factor Elk-1, but exhibits little effect on ERK1/2 phosphorylation by MEK1/2.

Features and Benefits

This compound is featured on the MAPKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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MAPKs

The mitogen-activated protein kinase (MAPK) family consists of both stress activated (SAPK) and mitogen-activated (MAPK) protein kinases. They form a network of signal transduction cascades that mediate cellular responses to a diverse range of stimuli, including growth factors, chemical or osmotic stress, irradiation, bacterial infection and proinflammatory cytokines.

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