287897
Dicoumarol
A cell-permeable quinone reductase inhibitor with anticoagulant properties.
Synonym(s):
Dicoumarol, 3,3ʹ-Methylenebis(4-hydroxycoumarin), Bishydroxycoumarin, Dicumarol
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About This Item
Empirical Formula (Hill Notation):
C19H12O6
CAS Number:
Molecular Weight:
336.29
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77
Quality Level
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
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.
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
Precautionary Statements
Hazard Classifications
Acute Tox. 3 Oral - Aquatic Chronic 2 - STOT RE 1 Oral
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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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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