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
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00006857
• Assay: ≥98% (titration)
• Form: solid
• Storage condition: OK to freeze, protect from light

Properties

• Quality Segment: 100
• description: Merck USA index - 14, 3090
• 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
• SMILES string: [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
• 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).

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

Preparation Note

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

Disclaimer

Toxicity: Toxic & Carcinogenic / Teratogenic (G)

Safety Information

• pictograms: GHS06,GHS08,GHS09
• signalword: Danger
• hcodes: H301,H372,H411
• pcodes: P260 - P264 - P273 - P301 + P310 - P314 - P391
• Hazard Classifications: Acute Tox. 3 Oral - Aquatic Chronic 2 - STOT RE 1 Oral
• Storage Class: 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