Overview

  • Product name

    Entinostat (MS-275)
  • Description

    HDAC1 and HDAC3 inhibitor
  • Alternative names

    • Entinosta (MS-275)
    • Entinostat
    • MS-275
    • SNDX-275
  • Biological description

    Benzamide derivative that inhibits histone deacetylase 1 (HDAC1) and HDAC2. Not active against HDAC4, 6, 8 and 10 (IC50 >100μM). Exhibits anticancer chemotherapeutic, anti-metastatic, and neuroprotective properties. In vitro, it increases transcription of E-cadherin and decreases transcription of N-cadherin, decreasing tubulin-based microtentacles, reversing epithelial-to-mesenchymal transition (EMT) and inhibiting cell migration. Upregulates natural killer cell activating receptor NKG2D. Increases ability of natural killer cells to destroy cancer cells. Down regulates cellular FLICE-inhibiting protein (c-FLIP), increasing caspase activation and inducing apoptosis in animal models. Inhibition of HDAC1 in the nucleus accumbens (NAcc) inhibits cocaine-induced plasticity and behavioral changes in rodent models. Decreases amyloid-beta (Abeta) deposition in the hippocampus and cortex of animal models.

  • Purity

    > 99%
  • CAS Number

    209783-80-2
  • Chemical structure

    Chemical Structure

Properties

  • Chemical name

    Pyridin-3-ylmethyl N-[[4-[(2-aminophenyl)carbamoyl]phenyl]methyl]carbamate
  • Molecular weight

    376.41
  • Molecular formula

    C21H20N4O3
  • PubChem identifier

    4261
  • Storage instructions

    Shipped at Room Temperature. Store at Room Temperature.
  • Solubility overview

    Soluble in DMSO to 100 mM
  • Handling

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Toxic, refer to SDS for further information.

    Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

  • SMILES

    C1=CC=C(C(=C1)N)NC(=O)C2=CC=C(C=C2)CNC(=O)OCC3=CN=CC=C3
  • Source

    Synthetic

References

This product has been referenced in:

  • Zhu S  et al. The narrow-spectrum HDAC inhibitor entinostat enhances NKG2D expression without NK cell toxicity, leading to enhanced recognition of cancer cells. Pharm Res 32:779-92 (2015). Read more (PubMed: 24203492) »
  • Shah P  et al. Histone deacetylase inhibitor entinostat reverses epithelial to mesenchymal transition of breast cancer cells by reversing the repression of E-cadherin. Breast Cancer Res Treat 143:99-111 (2014). Read more (PubMed: 24305977) »
  • Kennedy PJ  et al. Class I HDAC inhibition blocks cocaine-induced plasticity by targeted changes in histone methylation. Nat Neurosci 16:434-40 (2013). Read more (PubMed: 23475113) »

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