Synonym: 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
Linear Formula: C18H16N6S2 · C2H5OH
Product Type: Chemical
| assay |
≥98% (HPLC) |
| color |
white to off-white |
| form |
powder |
| 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 |
| Quality Level |
100  |
| SMILES string |
N#CC(C(C#N)=C(N)SC1=C(N)C=CC=C1)=C(N)SC2=C(N)C=CC=C2.CCO |
| solubility |
DMSO: >10 mg/mL (Stock solutions in DMSO should be used within a month. Acidic solutions exhibit weaker inhibition) |
| storage condition |
protect from light |
| 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. |
| Caution: |
photosensitive |
| 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 . |
| 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 . |
| Packaging: |
1, 5 mg in glass bottle |
| 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. |
| RIDADR |
NONH for all modes of transport |
| WGK Germany |
WGK 3 |
| Flash Point(F) |
Not applicable |
| Flash Point(C) |
Not applicable |
| Purity |
≥98% (HPLC) |
| Storage Temp. |
2-8°C |
| UNSPSC |
12352200 |
