EPS002

Sigma-Aldrich

MS-275

A HDAC1 and HDAC3 inhibitor

Synonym(s):
3-pyridinylmethyl [[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]carbamate, MS-275 (Entinostat, SNDX-275), N-(2-Aminophenyl)-4-[N-(pyridine-3ylmethoxycarbonyl)aminomethyl]benzamide
Empirical Formula (Hill Notation):
C21H20N4O3
CAS Number:
Molecular Weight:
376.41
MDL number:
PubChem Substance ID:
NACRES:
NA.41

Quality Level

assay

≥99%

solubility

DMSO: 38 mg/mL

storage temp.

−20°C

SMILES string

Nc1ccccc1NC(=O)c2ccc(CNC(=O)OCc3cccnc3)cc2

InChI

1S/C21H20N4O3/c22-18-5-1-2-6-19(18)25-20(26)17-9-7-15(8-10-17)13-24-21(27)28-14-16-4-3-11-23-12-16/h1-12H,13-14,22H2,(H,24,27)(H,25,26)

InChI key

INVTYAOGFAGBOE-UHFFFAOYSA-N

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General description

Preferentially inhibits HDAC1 (IC50=300 nM) over HDAC3 (IC50=8 μM). Has no inhibitory activity towards HDAC8 (IC50>100 μM).

Application

MS-275 has been used as a histone deacetylase-1 inhibitor.

Biochem/physiol Actions

HDAC inhibitor; antiproliferative.

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

hazcat

Acute Tox. 3 Oral - Repr. 1A

storage_class_code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Certificate of Analysis

Certificate of Origin

Heather MacTavish et al.
PloS one, 5(12), e14462-e14462 (2011-02-02)
Histone deacetylase inhibitors (HDI) dampen cellular innate immune response by decreasing interferon production and have been shown to increase the growth of vesicular stomatitis virus and HSV. As attenuated tumour-selective oncolytic vaccinia viruses (VV) are already undergoing clinical evaluation, the...
Guido Dentesano et al.
Journal of neuroinflammation, 9, 165-165 (2012-07-11)
In physiological conditions, it is postulated that neurons control microglial reactivity through a series of inhibitory mechanisms, involving either cell contact-dependent, soluble-factor-dependent or neurotransmitter-associated pathways. In the current study, we focus on CD200R1, a microglial receptor involved in one of...
HoxC5 and miR-615-3p target newly evolved genomic regions to repress hTERT and inhibit tumorigenesis
TingDong Y et al.
Nature Communications, 100 (2018)
Marta Bombardo et al.
Scientific reports, 8(1), 9391-9391 (2018-06-22)
Adult pancreatic acinar cells have the ability to re-enter the cell cycle and proliferate upon injury or tissue loss. Despite this mitotic ability, the extent of acinar proliferation is often limited and unable to completely regenerate the injured tissue or...
Na Liu et al.
PloS one, 8(1), e54001-e54001 (2013-01-24)
Histone deacetylase (HDAC) inhibitors are promising anti-fibrosis drugs; however, nonselective inhibition of class I and class II HDACs does not allow a detailed elucidation of the individual HDAC functions in renal fibrosis. In this study, we investigated the effect of...

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