287897

Dicoumarol

A cell-permeable quinone reductase inhibitor with anticoagulant properties.

• Sinonimo/i: Dicoumarol, 3,3ʹ-Methylenebis(4-hydroxycoumarin), Bishydroxycoumarin, Dicumarol
• Formula empirica (notazione di Hill): C₁₉H₁₂O₆
• Numero CAS: 66-76-2
• Peso molecolare: 336.29
• Numero MDL: MFCD00006857
• Codice UNSPSC: 12352200
• NACRES: NA.77

Proprietà

• Livello qualitativo: 100
• Descrizione: Merck USA index - 14, 3090
• Saggio: ≥98% (titration)
• Stato: solid
• Produttore/marchio commerciale: Calbiochem^®
• Condizioni di stoccaggio: OK to freeze; protect from light
• Colore: white
• Solubilità: 0.1 M NaOH: 15 mg/mL; pyridine: 50 mg/mL
• Condizioni di spedizione: ambient
• Temperatura di conservazione: 2-8°C
• Stringa SMILE: [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; DOBMPNYZJYQDGZ-UHFFFAOYSA-N

Descrizione

Descrizione generale

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).

Azioni biochim/fisiol

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

Confezionamento

Packaged under inert gas

Attenzione

Toxicity: Toxic & Carcinogenic / Teratogenic (G)

Ricostituzione

Unstable in solution; reconstitute just prior to use.

Altre note

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.

Note legali

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

Informazioni sulla sicurezza

• Pittogrammi: GHS06,GHS08,GHS09
• Avvertenze: Danger
• Indicazioni di pericolo: H301,H372,H411
• Consigli di prudenza: P260 - P264 - P273 - P301 + P310 - P314 - P391
• Classi di pericolo: Acute Tox. 3 Oral - Aquatic Chronic 2 - STOT RE 1 Oral
• Codice della classe di stoccaggio: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable