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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.

SMYD2 Inhibitor, AZ505 - CAS 1035227-43-0 - Calbiochem MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.

Synonyms: 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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Overview

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
Catalogue Number GTIN
531661 0

Documentation

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

Title

Safety Data Sheet (SDS) 

References

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

Technical Info

Title
Characterization of Estrogen Receptor α Phosphorylation Sites in Breast Cancer Tissue Using the SNAP i.d® 2.0 System
White Paper: Further considerations of antibody validation and usage.
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 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.