287897

Dicoumarol

A cell-permeable quinone reductase inhibitor with anticoagulant properties.

• Synonym(s): Dicoumarol, 3,3ʹ-Methylenebis(4-hydroxycoumarin), Bishydroxycoumarin, Dicumarol
• Empirical Formula (Hill Notation): C₁₉H₁₂O₆
• CAS Number: 66-76-2
• Molecular Weight: 336.29
• MDL number: MFCD00006857
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥98% (titration)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: white
• solubility: 0.1 M NaOH: 15 mg/mL; pyridine: 50 mg/mL
• shipped in: ambient
• storage temp.: 2-8°C
• 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
• InChI key: DOBMPNYZJYQDGZ-UHFFFAOYSA-N

Description

General description

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).

Biochem/physiol Actions

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

Packaging

Packaged under inert gas

Warning

Toxicity: Toxic & Carcinogenic / Teratogenic (G)

Reconstitution

Unstable in solution; reconstitute just prior to use.

Other Notes

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.

Legal Information

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

Safety Information

• Pictograms: GHS06,GHS08,GHS09
• Signal Word: Danger
• Hazard Statements: H301,H372,H411
• Precautionary Statements: P260 - P264 - P273 - P301 + P310 - P314 - P391
• Hazard Classifications: Acute Tox. 3 Oral - Aquatic Chronic 2 - STOT RE 1 Oral
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable