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287897
Sigma-AldrichDicoumarol - CAS 66-76-2 - Calbiochem
A cell-permeable quinone reductase inhibitor with anticoagulant properties.
More>>A cell-permeable quinone reductase inhibitor with anticoagulant properties. Less<<
Dicoumarol - CAS 66-76-2 - Calbiochem MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.
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Description
Overview
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).
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.
Blocks brefeldin A-dependent mono-ADP-ribosylation in vitro
Primary Target IC<sub>50</sub>
180 µM and 150 µM in blocking brefeldin A-dependent mono-ADP-ribosylation in vitro and Golgi disassembly in living cells, respectively
Purity
≥98% by titration
Physicochemical Information
Cell permeable
Y
Dimensions
Materials Information
Toxicological Information
Safety Information according to GHS
RTECS
GN7875000
Safety Information
R Phrase
R: 22-48/25-51/53
Harmful if swallowed. Toxic: danger of serious damage to health by prolonged exposure if swallowed. Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
S Phrase
S: 37-45-61
Wear suitable gloves. In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). Avoid release to the environment. Refer to special instructions/safety data sheet.
Product Usage Statements
Storage and Shipping Information
Ship Code
Ambient Temperature Only
Toxicity
Toxic & Carcinogenic / Teratogenic
Hazardous Materials Attention:
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.
Storage
+2°C to +8°C
Protect from Light
Protect from light
Do not freeze
Ok to freeze
Special Instructions
Unstable in solution; reconstitute just prior to use.
Dicoumarol - CAS 66-76-2 - Calbiochem Certificates of Analysis
Title
Lot Number
287897
References
Reference overview
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.
Data Sheet
Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.
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).
Form
White solid
Intert gas (Yes/No)
Packaged under inert gas
CAS number
66-76-2
RTECS
GN7875000
Chemical formula
C₁₉H₁₂O₆
Structure formula
Purity
≥98% by titration
Solubility
0.1 N NaOH (15 mg/ml) or Pyridine (50 mg/ml)
Storage
Protect from light +2°C to +8°C
Do Not Freeze
Ok to freeze
Special Instructions
Unstable in solution; reconstitute just prior to use.
Toxicity
Toxic & Carcinogenic / Teratogenic
Merck USA index
14, 3090
References
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.
