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EPS002

Sigma-Aldrich

MS-275

A HDAC1 and HDAC3 inhibitor

Synonym(s):

MS-275 (Entinostat, SNDX-275), 3-pyridinylmethyl [[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]carbamate, N-(2-Aminophenyl)-4-[N-(pyridine-3ylmethoxycarbonyl)aminomethyl]benzamide

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About This Item

Empirical Formula (Hill Notation):
C21H20N4O3
CAS Number:
209783-80-2
Molecular Weight:
376.41
MDL number:
MFCD03453552
UNSPSC Code:
12352200
PubChem Substance ID:
329799578
NACRES:
NA.41

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

Gene Information

human ... HDAC1(3065) , HDAC10(83933) , HDAC11(79885) , HDAC2(3066) , HDAC3(8841) , HDAC4(9759) , HDAC5(10014) , HDAC6(10013) , HDAC7(51564) , HDAC8(55869) , HDAC9(9734)

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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
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H360

Hazard Classifications

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

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
HoxC5 and miR-615-3p target newly evolved genomic regions to repress hTERT and inhibit tumorigenesis
TingDong Y et al.
Nature Communications, 100 (2018)
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
Xuelian Xu et al.
PloS one, 6(2), e17138-e17138 (2011-03-02)
Pediatric acute myeloid leukemia (AML) remains a challenging disease to treat even with intensified cytarabine-based chemotherapy. Histone deacetylases (HDACs) have been reported to be promising therapeutic targets for treating AML. However, HDAC family members that are involved in chemotherapy sensitivities
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