178493 | Apoptosis Activator III, Embelin - CAS 550-24-3 - Calbiochem

178493
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      Overview

      Replacement Information

      Key Specifications Table

      Empirical FormulaCAS #
      C₁₇H₂₆O₄ 550-24-3

      Pricing & Availability

      Catalog NumberAvailability Packaging Qty/Pack Price Quantity
      178493-10MG
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          Plastic ampoule 10 mg
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          Description
          OverviewA cell-permeable benzoquinone compound that exhibits antitumor properties. Specifically antagonizes XIAP (X-linked inhibitor of apoptosis)-mediated inhibition of caspase-9 activation by directly targeting the Smac and caspase-9 binding domain BIR3 (IC50 = 4.1 µM in a competitive binding assay with Smac peptide). Selectively induces caspase-9-mediated apoptosis in prostate cancer cells with high levels of XIAP (IC50 = 3.7 and 5.7 µM for PC-3 and LnCap, respectively), while exhibiting much less effect towards cells with low level XIAP (IC50 = 19.3 and 20.1 µM for WI-38 and PrEC, respectively). Also shown to sensitize XIAP overexpressing Jurkat cells to Etoposide -induced apoptosis. A non-competitive PCAF (p300/CBP associated factor)-specific lysine acetyltransferase (KAT) inhibitor (IC50 = 7.2 µM).
          Catalogue Number178493
          Brand Family Calbiochem®
          SynonymsEmbelin, Embelia ribes, XIAP inhibitor, Embelin, 2,5-Dihydroxy-3-undecyl-1,4-benzoquinone
          References
          ReferencesModak, R., et al. 2013. ACS Chem. Biol. 8, In press.
          Nikolovska-Coleska, Z., et al. 2004. J. Med. Chem. 47, 2430.
          Product Information
          CAS number550-24-3
          ATP CompetitiveN
          FormOrange solid
          Hill FormulaC₁₇H₂₆O₄
          Chemical formulaC₁₇H₂₆O₄
          ReversibleN
          Structure formula ImageStructure formula Image
          Applications
          Biological Information
          Primary TargetBIR3
          Primary Target IC<sub>50</sub>4.1 µM in antagonizing XIAP (X-linked inhibitor of apoptosis)-mediated inhibition of caspase-9 activation by directly targeting the Smac and caspase-9 binding domain BIR3 in a competitive binding assay with Smac peptide
          PuritySingle spot by TLC
          Physicochemical Information
          Cell permeableY
          Dimensions
          Materials Information
          Toxicological Information
          Safety Information according to GHS
          Safety Information
          Product Usage Statements
          Storage and Shipping Information
          Ship Code Ambient Temperature Only
          Toxicity Standard Handling
          Storage +2°C to +8°C
          Protect from Light Protect from light
          Do not freeze Ok to freeze
          Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
          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
          178493

          References

          Reference overview
          Modak, R., et al. 2013. ACS Chem. Biol. 8, In press.
          Nikolovska-Coleska, Z., et al. 2004. J. Med. Chem. 47, 2430.
          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.

          Revision11-April-2013 JSW
          SynonymsEmbelin, Embelia ribes, XIAP inhibitor, Embelin, 2,5-Dihydroxy-3-undecyl-1,4-benzoquinone
          DescriptionA cell-permeable, benzoquinone compound that exhibits anti-tumor properties. Shown to specifically antagonize X-linked inhibitor of apoptosis- (XIAP) mediated inhibition of caspase-9 activation by directly targeting the Smac and caspase-9 binding domain BIR3 (IC50 = 4.1 µM in a competitive binding assay using Smac peptide). Also selectively induces caspase-9-mediated apoptosis in prostate cancer cells expressing high levels of XIAP (IC50 = 3.7 µM for PC-3 cells and 5.7 µM for LnCap cells), while exhibiting lesser effects toward cells with low levels of XIAP (IC50 = 19.3 µM for WI-38 cells and 20.1 µM for PrEC cells). Reported to sensitize XIAP-overexpressing Jurkat cells to Etoposide- (Cat. No. 341245) induced apoptosis. A non-competitive PCAF (p300/CBP associated factor)-specific lysine acetyltransferase (KAT) inhibitor (IC50 = 7.2 µM).
          FormOrange solid
          Intert gas (Yes/No) Packaged under inert gas
          CAS number550-24-3
          Chemical formulaC₁₇H₂₆O₄
          Structure formulaStructure formula
          PuritySingle spot by TLC
          SolubilityDMSO (10 mg/ml) or Methanol (5 mg/ml)
          Storage +2°C to +8°C
          Protect from light
          Do Not Freeze Ok to freeze
          Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
          Toxicity Standard Handling
          ReferencesModak, R., et al. 2013. ACS Chem. Biol. 8, In press.
          Nikolovska-Coleska, Z., et al. 2004. J. Med. Chem. 47, 2430.