287897

Dicoumarol

A cell-permeable quinone reductase inhibitor with anticoagulant properties.

• Synonim(y): Dicoumarol, 3,3ʹ-Methylenebis(4-hydroxycoumarin), Bishydroxycoumarin, Dicumarol
• Wzór empiryczny (zapis Hilla): C₁₉H₁₂O₆
• Numer CAS: 66-76-2
• Masa cząsteczkowa: 336.29
• Numer MDL: MFCD00006857
• Kod UNSPSC: 12352200
• NACRES: NA.77

Właściwości

• Poziom jakości: 100
• opis: Merck USA index - 14, 3090
• Próba: ≥98% (titration)
• Formularz: solid
• producent / nazwa handlowa: Calbiochem^®
• warunki przechowywania: OK to freeze; protect from light
• kolor: white
• rozpuszczalność: 0.1 M NaOH: 15 mg/mL; pyridine: 50 mg/mL
• Warunki transportu: ambient
• temp. przechowywania: 2-8°C
• ciąg SMILES: [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
• Klucz InChI: DOBMPNYZJYQDGZ-UHFFFAOYSA-N

Opis

Opis ogólny

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).

Działania biochem./fizjol.

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

Opakowanie

Packaged under inert gas

Ostrzeżenie

Toxicity: Toxic & Carcinogenic / Teratogenic (G)

Rekonstytucja

Unstable in solution; reconstitute just prior to use.

Inne uwagi

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.

Informacje prawne

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

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Informacja o środkach bezpieczeństwa

• Piktogramy: GHS06,GHS08,GHS09
• Hasło ostrzegawcze: Danger
• Zwroty wskazujące rodzaj zagrożenia: H301,H372,H411
• Zwroty wskazujące środki ostrożności: P260 - P264 - P273 - P301 + P310 - P314 - P391
• Klasyfikacja zagrożeń: Acute Tox. 3 Oral - Aquatic Chronic 2 - STOT RE 1 Oral
• Kod klasy składowania: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Klasa zagrożenia wodnego (WGK): WGK 3
• Temperatura zapłonu (°F): Not applicable
• Temperatura zapłonu (°C): Not applicable