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

AZ505 is a cell-permeable, potent, reversible inhibitor of SMYD2 (IC₅₀ = 120 nM, Ki = 300 nM) that binds to the peptide-binding groove of the enzyme.

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Synonyme: N-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

Primary Target: SMYD2
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      Übersicht

      Replacement Information

      Key Spec Table

      CAS #Empirical Formula
      1035227-43-0C₂₉H₃₈Cl₂N₄O₄
      Description
      Overview

      This product has been discontinued.



      A 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
      Quality LevelMQ100
      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
      Global Trade Item Number
      Bestellnummer GTIN
      531661 0

      Documentation

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

      Titel

      Sicherheitsdatenblatt (SDB) 

      Literatur

      Übersicht
      Ferguson, A.D., et al. 2011. Structure 19, 1262.

      Technische Informationen

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      White Paper: Further considerations of antibody validation and usage.
      Datenblatt

      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 Protect from light
      +2°C to +8°C
      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.