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U120

Sigma-Aldrich

U0126 ethanolate

≥98% (HPLC), powder

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Synonym(s):
1,4-Diamino-2,3-dicyano-1,4-bis(o-aminophenylmercapto)butadiene ethanolate
Empirical Formula (Hill Notation):
C18H16N6S2 · C2H5OH
Molecular Weight:
426.56
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

white to off-white

solubility

DMSO: >10 mg/mL (Stock solutions in DMSO should be used within a month. Acidic solutions exhibit weaker inhibition)

storage temp.

2-8°C

SMILES string

N#CC(C(C#N)=C(N)SC1=C(N)C=CC=C1)=C(N)SC2=C(N)C=CC=C2.CCO

InChI

1S/C18H16N6S2.C2H6O/c19-9-11(17(23)25-15-7-3-1-5-13(15)21)12(10-20)18(24)26-16-8-4-2-6-14(16)22;1-2-3/h1-8H,21-24H2;3H,2H2,1H3

InChI key

CFQULUVMLGZVAF-UHFFFAOYSA-N

Gene Information

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This Item
662005662006SML1268
vibrant-m

U120

U0126 ethanolate

vibrant-m

662005

U0126

vibrant-m

662006

U0124

vibrant-m

SML1268

BQU57

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

form

powder

form

solid

form

solid

form

powder

color

white to off-white

color

white

color

white

color

white to beige

solubility

DMSO: >10 mg/mL (Stock solutions in DMSO should be used within a month. Acidic solutions exhibit weaker inhibition)

solubility

DMSO: 200 mg/mL

solubility

DMSO: 100 mg/mL

solubility

DMSO: 25 mg/mL, clear

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

Application

U0126 ethanolate has been used as an MEK inhibitor in mononucleated myogenic cells derived from breast muscles of chicken embryos. U0126 has also been used to study ERK2 function in amyloid precursor protein (APP) knockout (KO) mice neurons.

Biochem/physiol Actions

U0126, 1,4-diamino-2,3-dicyano-1,4-bis[2-aminophenylthio] butadiene, is a highly selective inhibitor of both MEK1 and MEK2. U0126 was found to functionally antagonize AP-1 transcriptional activity via noncompetitive inhibition of the dual specificity kinase MEK with IC50 of 72 nM for MEK1 and 58 nM for MEK2. U0126 inhibited anchorage-independent growth of Ki-ras-transformed rat fibroblasts by simultaneously blocking both extracellular signal-regulated kinase (ERK) and mammalian target of rapamycin (mTOR)-p70(S6K) pathways. The effects of U0126 on the growth of eight human breast cancer cell lines shown that U0126 selectively repressed anchorage-independent growth of MDA-MB231 and HBC4 cells, two lines with constitutively activated ERK. Loss of contact with substratum triggers apoptosis in many normal cell types, a phenomenon termed anoikis. U0126 sensitized MDA-MB231 and HBC4 to anoikis, i.e., upon treatment with U0126, cells deprived of anchorage entered apoptosis.

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.

Caution

photosensitive

Preparation Note

U0126 ethanolate is soluble in DMSO at a concentration >10 mg/ml. Stock solutions of the product in DMSO should be used within a month. Acidic solutions of the product exhibit weaker MEK inhibitory functions.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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