287897 | Dicoumarol - CAS 66-76-2 - Calbiochem

287897
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      Overview

      Replacement Information

      Key Specifications Table

      Empirical FormulaCAS #
      C₁₉H₁₂O₆ 66-76-2

      Pricing & Availability

      Catalog NumberAvailability Packaging Qty/Pack Price Quantity
      287897-500MG
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          Glass bottle 500 mg
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          Description
          OverviewA 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).
          Catalogue Number287897
          Brand Family Calbiochem®
          Synonyms3,3ʹ-Methylenebis(4-hydroxycoumarin), Bishydroxycoumarin, Dicumarol
          References
          ReferencesSeanor, K.L., et al. 2003. Antioxid. Redox. Signal 5, 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.
          Product Information
          CAS number66-76-2
          ATP CompetitiveN
          FormWhite solid
          Hill FormulaC₁₉H₁₂O₆
          Chemical formulaC₁₉H₁₂O₆
          ReversibleN
          Structure formula ImageStructure formula Image
          Applications
          Biological Information
          Primary TargetBlocks 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 permeableY
          Dimensions
          Materials Information
          Toxicological Information
          Safety Information according to GHS
          RTECSGN7875000
          Safety Information
          R PhraseR: 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 PhraseS: 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 InstructionsUnstable in solution; reconstitute just prior to use.
          Packaging Information
          Packaged under inert gas Packaged under inert gas
          Transport Information
          Supplemental Information
          Specifications

          Documentation

          SDS

          Title

          Safety Data Sheet (SDS) 

          Certificates of Analysis

          TitleLot Number
          287897

          References

          Reference overview
          Seanor, K.L., et al. 2003. Antioxid. Redox. Signal 5, 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.

          Revision04-January-2010 RFH
          Synonyms3,3ʹ-Methylenebis(4-hydroxycoumarin), Bishydroxycoumarin, Dicumarol
          DescriptionA 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).
          FormWhite solid
          Intert gas (Yes/No) Packaged under inert gas
          CAS number66-76-2
          RTECSGN7875000
          Chemical formulaC₁₉H₁₂O₆
          Structure formulaStructure formula
          Purity≥98% by titration
          Solubility0.1 N NaOH (15 mg/ml) or Pyridine (50 mg/ml)
          Storage +2°C to +8°C
          Protect from light
          Do Not Freeze Ok to freeze
          Special InstructionsUnstable in solution; reconstitute just prior to use.
          Toxicity Toxic & Carcinogenic / Teratogenic
          Merck USA index14, 3090
          ReferencesSeanor, K.L., et al. 2003. Antioxid. Redox. Signal 5, 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.