109511-58-2

Basic information

• Product Name: U0126
• Synonyms: U0126;1,4-DIAMINO-2,3-DICYANO-1,4-BIS(2-AMINOPHENYLTHIO)BUTADIENE;1,4-DIAMINO-2,3-DICYANO-1,4-BIS(2-AMINOPHYNYLTIO)BUTADIENE;1,4-DIAMINO-2,3-DICYANO-1,4-BIS(O-AMINOPHENYLMERCAPTO)BUTADIENE;1,4-DIAMINO-2,3-DICYANO-1;UO 126;U0126 >99%;2,3-Bis[amino[(2-aminophenyl)thio]methylene]butanedinitrile
• CAS NO: 109511-58-2
• Molecular Formula: C₁₈H₁₆N₆S₂
• Molecular Weight: 380.49
• Product Categories: Protein Kinase;Signalling;Inhibitor
• Mol File: 109511-58-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: approximate 154℃(dec.)
• Boiling Point: 565.1 ºC at 760 mmHg
• Flash Point: 295.6 ºC
• Appearance: White solid
• Density: 1.44
• Vapor Pressure: 8.59E-13mmHg at 25°C
• Refractive Index: 1.762
• Storage Temp.: Desiccate at +4°C
• Solubility: Soluble in DMSO (up to 200 mg/ml).
• PKA: 2.11±0.10(Predicted)
• Water Solubility: Soluble in DMSO. Poorly soluble in ethanol and water
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• CAS DataBase Reference: U0126(CAS DataBase Reference)
• NIST Chemistry Reference: U0126(109511-58-2)
• EPA Substance Registry System: U0126(109511-58-2)

Safety Data

• RTECS: EJ9710000
• Hazardous Substances Data: 109511-58-2(Hazardous Substances Data)

Usage

Description

U0126, also known as a MEK inhibitor, is a chemical compound that acts as a potent and specific inhibitor of MEK1 and MEK2 with IC50 values of 72 nM and 58 nM, respectively. It is a non-competitive inhibitor with respect to ATP and ERK, showing minimal effects on other kinases. U0126 has been shown to block doxazosin-induced osteoblastic differentiation and acts as an immunosuppressant by effectively blocking IL-2 synthesis and T cell proliferation without affecting the long-term outcomes of either T cell activation or tolerance.

Uses

Used in Pharmaceutical Industry:
U0126 is used as a MEK inhibitor for its potent and specific inhibition of MEK1 and MEK2, making it a valuable tool in the development of targeted therapies for various diseases, including cancer.
Used in Research Applications:
U0126 is used as a research tool for studying the role of MEK1 and MEK2 in cellular signaling pathways, as well as their involvement in various diseases. Its specificity and potency make it an ideal compound for investigating the effects of MEK inhibition on cell proliferation, differentiation, and apoptosis.
Used in Immunosuppressive Applications:
U0126 is used as an immunosuppressant for its ability to effectively block IL-2 synthesis and T cell proliferation, making it a potential candidate for the development of therapies targeting autoimmune diseases and transplant rejection.
Used in Drug Delivery Systems:
U0126 can be employed in the development of novel drug delivery systems to enhance its applications and efficacy against specific diseases, such as cancer. Various organic and metallic nanoparticles can be used as carriers for U0126 delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes.

Biological Activity

Potent and selective non-competitive inhibitor of MAP kinase kinase. Inhibits MEK-1 and MEK-2 (IC 50 values of 0.07 and 0.06 μ M respectively) with little or no effect on the activities of PKC, Abl, Raf, MEKK, ERK, JNK, MKK-3, MKK-4/SEK, MKK-6, Cdk2 or Cdk4. Centrally active following systemic administration in vivo . Also available as part of the MAPK Cascade Inhibitor Tocriset? and MAPK Inhibitor Tocriset? .

Biochem/physiol Actions

Primary TargetMEK1 and MEK2

References

1) Favata et al. (1998), Identification of a novel inhibitor of mitogen activated protein kinase kinase; J. Biol. Chem., 273 8623 2) Miyoshi et al. (2012), Antitumor activity of MEK and PI3K inhibitors against malignant pleural mesothelioma cells in vitro and in vivo; Int. J. Oncol., 41 449 3) Pricola et al. (2009), Interleukin-6 Maintains Bone Marrow-Derived Mesenchymal Stem Cell Stemness by an ERK1/2-Dependent Mechanism; J. Cell Biochem., 108 577

InChI:InChI=1/C18H16N6S2/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/h1-8H,21-24H2/b17-11+,18-12+

Upstream product

• 14778-29-1 1,1,2,2,-tetracyanoethane 
• 137-07-5 2-amino-benzenethiol 

Related news

Using U0126 (cas 109511-58-2) to dissect the role of the extracellular signal-regulated kinase 1/2 (ERK1/2) cascade in the regulation of gene expression by endothelin-1 in cardiac myocytes07/27/2019

The hypertrophic agonist endothelin-1 rapidly but transiently activates the extracellular signal-regulated kinase 1/2 (ERK1/2) cascade (and other signalling pathways) in cardiac myocytes, but the events linking this to hypertrophy are not understood. Using Affymetrix rat U34A microarrays, we ide...detailed

Non-specific effects of the MEK inhibitors PD098,059 and U0126 (cas 109511-58-2) on glutamate release from hippocampal synaptosomes07/26/2019

In order to investigate a role for the extracellular-signal-regulated kinases 1 and 2 (ERK1/2) on hippocampal neurotransmitter release, we studied the effect of commonly used MEK (mitogen-activated protein kinase [MAPK]/ERK kinase) inhibitors, PD098,059 and U0126, on depolarization-induced gluta...detailed

Effects of MEK-Specific Inhibitor U0126 (cas 109511-58-2) on the Conidial Germination, Appressorium Production, and Pathogenicity of Setosphaeria turcica07/23/2019

Systemic studies on the effects of mitogen-activated protein kinase (MAPK) signal transduction pathway on the growth and development of Setosphaeria turcica is helpful not only in understanding the molecular mechanism of pathogenhost interaction but also in the effective control of the diseases ...detailed

Quantitative NMR analysis of Erk activity and inhibition by U0126 (cas 109511-58-2) in a panel of patient-derived colorectal cancer cell lines07/22/2019

We comparatively analyzed the basal activity of extra-cellular signal-regulated kinase (Erk1/2) in lysates of 10 human colorectal cancer cell lines by semi-quantitative Western blotting and time-resolved NMR spectroscopy. Both methods revealed heterogeneous levels of endogenous Erk1/2 activities...detailed

Antiviral activity of the MEK-inhibitor U0126 (cas 109511-58-2) against pandemic H1N1v and highly pathogenic avian influenza virus in vitro and in vivo07/20/2019

The emergence of the 2009 H1N1 pandemic swine influenza A virus is a good example of how this viral infection can impact health systems around the world in a very short time. The continuous zoonotic circulation and reassortment potential of influenza A viruses (IAV) in nature represents an enorm...detailed

mTOR inhibitor temsirolimus and MEK1/2 inhibitor U0126 (cas 109511-58-2) promote chromosomal instability and cell type-dependent phenotype changes of glioblastoma cells07/21/2019

The phosphatidylinositol 3-kinase (PI3K)/AKT/mammalian target of rapamycin (mTOR) and the RAF/mitogen-activated and extracellular signal-regulated kinase kinase (MEK)/extracellular signal-regulated kinase (ERK) signaling pathways are frequently deregulated in cancer. Temsirolimus (TEM) and its p...detailed

U0126 (cas 109511-58-2) attenuates ischemia/reperfusion-induced apoptosis and autophagy in myocardium through MEK/ERK/EGR-1 pathway07/19/2019

Myocardial ischemia is one of the main causes of sudden cardiac death worldwide. Depending on the cell type and stimulus, ERK activity mediates different anti-proliferative events, such as apoptosis, autophagy, and senescence. The aim of this study was to determine the protective effect of 1,4-d...detailed

Relevant articles and documents

MEK inhibitors: The chemistry and biological activity of U0126, its analogs, and cyclization products

In search of antiinflammatory drugs with a new mechanism of action, U0126 was found to functionally antagonize AP-1 transcriptional activity via noncompetitive inhibition of the dual specificity kinase MEK with an IC50 of 0.07 μM for MEK 1 and 0.06 μM for MEK 2. U0126 can undergo isomerization and cyclization reactions to form a variety of products, both chemically and in vivo, all of which exhibit less affinity for MEK and lower inhibition of AP-1 activity than parent, U0126.