531661 SMYD2 Inhibitor, AZ505 - CAS 1035227-43-0 - Calbiochem

531661
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      Overview

      Replacement Information

      Key Specifications Table

      Empirical FormulaCAS #
      C₂₉H₃₈Cl₂N₄O₄ 1035227-43-0

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      5316610001
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          Glass bottle 5 mg
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          Description
          OverviewA cell-permeable benzooxazinyl-ethylaminoethyl-propanamide compound that acts as a potent and reversible inhibitor of SMYD2 (IC50 = 120 nM, Ki = 300 nM, Kd = 500 nM). Shown to bind to the peptide-binding groove of the enzyme. This binding is dependent on the presence of S-adenosylmethionine (SAM). The inhibition appears to be competitive with respect to substrate and uncompetitive with respect to SAM. Displays ~700-fold greater selectivity over SMYD3, DOT1L, EZH2, GLP, G9a and SET7/9 protein lysine methyl transferases (IC50 > 83.3 µM). Inhibits SMYD2-mediated p53-K370 methylation in U2OS cells (at ~10 µM), but does not affect methylation in cells transfected with a Y240F mutant.

          Please note that the molecular weight for this compound is batch-specific due to variable water content.
          Catalogue Number531661
          Brand Family Calbiochem®
          SynonymsN-Cyclohexyl-3-(3,4-dichlorophenethylamino)-N-(2-(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethylamino)ethyl)propanamide, HMTase Inhibitor XV
          References
          ReferencesFerguson, A.D., et al. 2011. Structure 19, 1262.
          Product Information
          CAS number1035227-43-0
          FormOff-white solid
          FormulationSupplied as a di-trifluoroacetate salt.
          Hill FormulaC₂₉H₃₈Cl₂N₄O₄
          Chemical formulaC₂₉H₃₈Cl₂N₄O₄
          ReversibleY
          Applications
          Biological Information
          Primary TargetSMYD2
          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

          SMYD2 Inhibitor, AZ505 - CAS 1035227-43-0 - Calbiochem SDS

          Title

          Safety Data Sheet (SDS) 

          References

          Reference overview
          Ferguson, A.D., et al. 2011. Structure 19, 1262.
          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.

          Revision17-April-2015 JSW
          SynonymsN-Cyclohexyl-3-(3,4-dichlorophenethylamino)-N-(2-(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethylamino)ethyl)propanamide, HMTase Inhibitor XV
          DescriptionA cell-permeable benzooxazinyl-ethylaminoethyl-propanamide compound that inhibits SMYD2-mediated p53 peptide (aa 361-380) K370me monomethylation (IC50 = 120 nM; [SAM] = [p53 peptide] = 1 µM; pH 7.4 for 90 min) in a substrate-competitive, but cofactor S-adenosylmethionine-(AdoMet/SAM) uncompetitive manner (Ki = 0.3 µM) by targeting SAM-bound SMYD2 at the substrate-binding site (Kd = 0.5 µM) via simultaneous interactions with SAM donor methyl group as well as residues from the core SET, I-SET, and post-SET domains, while exhibiting little potency toward DOT1L, EZH2, G9A, GLP, SET7/9, or SMYD3 (IC50 > 83.3 µM). Shown to effectively abolish cellular p53 K370me in U2OS wt SMYD2 transfectants to the same level seen in U2OS transfected with inactive SMYD2 Y240F mutant (10 µM for 24 h).
          FormOff-white solid
          FormulationSupplied as a di-trifluoroacetate salt.
          Intert gas (Yes/No) Packaged under inert gas
          CAS number1035227-43-0
          Chemical formulaC₂₉H₃₈Cl₂N₄O₄
          Purity≥95% by HPLC
          SolubilityDMSO (50 mg/ml). Use only fresh DMSO for reconstitution.
          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
          ReferencesFerguson, A.D., et al. 2011. Structure 19, 1262.