172050 | Anacardic Acid - CAS 16611-84-0 - Calbiochem

172050
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      Overview

      Replacement Information

      Key Spec Table

      Empirical FormulaCAS #
      C₂₂H₃₆O₃16611-84-0

      Pricing & Availability

      Catalogue NumberAvailability Packaging Qty/Pack Price Quantity
      US1172050-10MG
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          Plastic ampoule 10 mg
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          Description
          OverviewA cell-permeable ginkgolic acid (Cat. No. 345887) analog that inhibits protein SUMO (Cat. Nos. 662037, 662039, and 662042) modification (IC50 = 2.2 µM using RanGAP1-C2 as substrate) in an ATP-dependent manner by selectively targeting SUMO-activating enzyme E1 (Cat. Nos. 662073 and 662074) and interfering with E1-SUMO intermediate formation. Both anacardic acid and ginkgolic acid are shown to effectively decrease overall SUMOylation of 293T cellular proteins in a dose-dependent manner, while neither compound is effective in affecting overall cellular protein ubiquitination or histone H4K8 acetylation in 293T cultures, although anacardic acid is shown to inhibit p300 (Cat. No. 506200) and PCAF (Cat. No. 124026) histone acetyltransferase activities in cell-free acetylase assays (by 82% and 86%, respectively, at 10 µM). Also reported to inhibit the activity of prostaglandin synthase, tyrosinase, and lipoxygenase, as well as to enhance Aurora kinase A (Cat. No. 481413), but not Aurora kinase B, autophosphorylation and kinase activity by inducing conformation change and enhancing ATP binding.
          Catalogue Number172050
          Brand Family Calbiochem®
          SynonymsAA, 2-Hydroxy-6-pentadecylbenzoic Acid, 6-Pentadecylsalicylic Acid, Aurora Kinase A Activator, Histone Acetyltransferase Inhibitor III, SUMOylation Inhibitor II, HAT Inhibitor III, p300/CBP Inhibitor III, PCAF Inhibitor I
          References
          ReferencesFukuda, I., et al. 2009. Chem. Biol. 16, 133.
          Kishore, A.H. 2008. J. Med. Chem. 51, 792.
          Balasubramanyam, K., et al. 2003. J. Biol. Chem. 278, 19134.
          Paramashivappa, R., et al. 2002. J. Agric. Food Chem. 50, 7709.
          Product Information
          CAS number16611-84-0
          ATP CompetitiveY
          DeclarationSold under license of U.S. Patent 7,332,629 and related patents.
          FormWhite solid
          Hill FormulaC₂₂H₃₆O₃
          Chemical formulaC₂₂H₃₆O₃
          ReversibleN
          Structure formula ImageStructure formula Image
          Applications
          ApplicationAnacardic Acid, CAS 16611-84-0, is a cell-permeable ginkgolic acid analog that targets SUMO-activating enzyme E1 and inhibits protein SUMO modification (IC50 = 2.2 µM) in an ATP-dependent manner.
          Biological Information
          Primary TargetHAT
          Primary Target IC<sub>50</sub>5 µM against HAT; 8.5 µM against PCAF; 2.2 µM inhibiting protein SUMO modification using RanGAP1-C2 as substrate
          Purity≥95% by HPLC
          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

          Certificates of Analysis

          TitleLot Number
          172050

          References

          Reference overview
          Fukuda, I., et al. 2009. Chem. Biol. 16, 133.
          Kishore, A.H. 2008. J. Med. Chem. 51, 792.
          Balasubramanyam, K., et al. 2003. J. Biol. Chem. 278, 19134.
          Paramashivappa, R., et al. 2002. J. Agric. Food Chem. 50, 7709.
          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.

          Revision10-May-2010 RFH
          SynonymsAA, 2-Hydroxy-6-pentadecylbenzoic Acid, 6-Pentadecylsalicylic Acid, Aurora Kinase A Activator, Histone Acetyltransferase Inhibitor III, SUMOylation Inhibitor II, HAT Inhibitor III, p300/CBP Inhibitor III, PCAF Inhibitor I
          DescriptionA cell-permeable ginkgolic acid (Cat. No. 345887) analog that inhibits protein SUMO (Cat. Nos. 662037, 662039, and 662042) modification (IC50 = 2.2 µM using RanGAP1-C2 as substrate) in an ATP-dependent manner by selectively targeting SUMO-activating enzyme E1 (Cat. Nos. 662073 and 662074) and interfering with E1-SUMO intermediate formation. Both anacardic acid and ginkgolic acid are shown to effectively decrease overall SUMOylation of 293T cellular proteins in a dose-dependent manner, while neither compound is effective in affecting overall cellular protein ubiquitination or histone H4K8 acetylation in 293T cultures, although anacardic acid is shown to inhibit p300 (Cat. No. 506200) and PCAF (Cat. No. 124026) histone acetyltransferase activities in cell-free acetylase assays (by 82% and 86%, respectively, at 10 µM). Also reported to inhibit the activity of prostaglandin synthase, tyrosinase, and lipoxygenase, as well as to enhance Aurora kinase A (Cat. No. 481413), but not Aurora kinase B, autophosphorylation and kinase activity by inducing conformation change and enhancing ATP binding.
          FormWhite solid
          Intert gas (Yes/No) Packaged under inert gas
          CAS number16611-84-0
          Chemical formulaC₂₂H₃₆O₃
          Structure formulaStructure formula
          Purity≥95% by HPLC
          SolubilityDMSO (10 mg/ml), Ethanol (10 mg/ml), or Methanol (10 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
          ReferencesFukuda, I., et al. 2009. Chem. Biol. 16, 133.
          Kishore, A.H. 2008. J. Med. Chem. 51, 792.
          Balasubramanyam, K., et al. 2003. J. Biol. Chem. 278, 19134.
          Paramashivappa, R., et al. 2002. J. Agric. Food Chem. 50, 7709.