287897

Dicoumarol

A cell-permeable quinone reductase inhibitor with anticoagulant properties.

• Sinónimos: Dicoumarol, 3,3ʹ-Methylenebis(4-hydroxycoumarin), Bishydroxycoumarin, Dicumarol
• Fórmula empírica (notación de Hill): C₁₉H₁₂O₆
• Número de CAS: 66-76-2
• Peso molecular: 336.29
• Número MDL: MFCD00006857
• Código UNSPSC: 12352200
• NACRES: NA.77

Propiedades

• Nivel de calidad: 100
• Ensayo: ≥98% (titration)
• Formulario: solid
• fabricante / nombre comercial: Calbiochem^®
• condiciones de almacenamiento: OK to freeze; protect from light
• color: white
• solubilidad: 0.1 M NaOH: 15 mg/mL; pyridine: 50 mg/mL
• Condiciones de envío: ambient
• temp. de almacenamiento: 2-8°C
• cadena SMILES: [o]1c2c(c(c([c]1=O)Cc3[c]([o]c4c(c3O)cccc4)=O)O)cccc2
• InChI: 1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2
• Clave InChI: DOBMPNYZJYQDGZ-UHFFFAOYSA-N

Descripción

Descripción general

A cell-permeable quinone reductase inhibitor with anti-coagulant properties. Binds competitively with NADH or NADPH to inhibit NAD(P)H:quinone oxidoreductase (NQO1). Shown to inhibit IGF-I-, menadione-, and DMNQ-mediated activation of stress-activated protein kinase/c-jun NH2-terminal kinase (SAPK/JNK) and subsequent phosphorylation of c-Jun, as well as stress-induced activation (hypertonic sorbitol) of SAPK/JNK. Does not affect p38 phosphorylation or protein kinase B (AKT) activation. Also shown to induce apoptosis in MCF7 breast carcinoma cells. Inhibits glutathione-S transferase (GST) A1-1 enzyme (K_iu = 4.4 µM, K_ic = 3.6 µM) in vitro and in MCF7/VPα cells (a multidrug resistant derivative of MCF7 transfected with GST A1-1). Blocks brefeldin A-dependent mono-ADP-ribosylation in vitro and Golgi disassembly in living cells (IC₅₀ = 180 µM and 150 µM, respectively).

A cell-permeable quinone reductase inhibitor with anticoagulant properties. Potentiates apoptosis by simultaneously blocking SAPK/JNK and NF-κB pathways. Does not affect phosphorylation of p38 or activation of AKT. Blocks brefeldin A-dependent mono-ADP-ribosylation in vitro and Golgi disassembly in living cells (IC₅₀ = 180 µM and 150 µM, respectively).

Acciones bioquímicas o fisiológicas

Cell permeable: yes

Primary Target
Blocks brefeldin A-dependent mono-ADP-ribosylation in vitro

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 180 µM and 150 µM in blocking brefeldin A-dependent mono-ADP-ribosylation in vitro and Golgi disassembly in living cells, respectively

Envase

Packaged under inert gas

Advertencia

Toxicity: Toxic & Carcinogenic / Teratogenic (G)

Reconstitución

Unstable in solution; reconstitute just prior to use.

Otras notas

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.

Seanor, K.L., et al. 2003. Antioxid. Redox. Signal5, 103.
Krause, D., et al. 2001. J. Biol. Chem.276, 19244.
Pink, J.J., et al. 2000. J. Biol. Chem.275, 5416.
Cross, J.V., et al. 1999. J. Biol. Chem.274, 31150.
Morrow, C.S., et al. 1998. J. Biol. Chem.273, 20114.
Weigert, R., et al. 1997. J. Biol. Chem.272, 14200.

Información legal

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Información de seguridad

• Pictogramas: GHS06,GHS08,GHS09
• Palabra de señalización: Danger
• Frases de peligro: H301,H372,H411
• Consejos de prudencia: P260 - P264 - P273 - P301 + P310 - P314 - P391
• Clasificaciones de peligro: Acute Tox. 3 Oral - Aquatic Chronic 2 - STOT RE 1 Oral
• Código de clase de almacenamiento: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable