U120

U0126 ethanolate

≥98% (HPLC), powder

• 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: MFCD25977152
• PubChem Substance ID: 24278770
• NACRES: NA.77

Properties

• Quality Level: 100
• 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: human ... MAP2K1(5604) , MAP2K2(5605)

Description

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

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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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves