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Sigma-Aldrich

Dicoumarol

A cell-permeable quinone reductase inhibitor with anticoagulant properties.

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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

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

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 (Kiu = 4.4 µM, Kic = 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

Signal Word

Danger

Hazard Statements

H301 - H372 - H411

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

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Tatiana A Giovannucci et al.
Cell death & disease, 12(10), 914-914 (2021-10-08)
Malignant cells display an increased sensitivity towards drugs that reduce the function of the ubiquitin-proteasome system (UPS), which is the primary proteolytic system for destruction of aberrant proteins. Here, we report on the discovery of the bioactivatable compound CBK77, which
Hong-Zhong Zhou et al.
Cell communication and signaling : CCS, 17(1), 168-168 (2019-12-18)
Our previous study has demonstrated that NAD(P)H: quinone oxidoreductase 1 (NQO1) is significantly upregulated in human liver cancer where it potentiates the apoptosis evasion of liver cancer cell. However, the underlying mechanisms of the oncogenic function of NQO1 in HCC

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