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Entinostat (MS275; SNDX275)

Alias: MS-275; MS 2275; MS-2275; SNDX275; MS2275; SNDX275;MS275; MS 275; SNDX-275; SNDX 275; Entinostat
Cat No.:V0256 Purity: ≥98%
COA Product Data Instructions for use SDS
Entinostat (formerly known as MS-275; SNDX-275) is a potent, benzamide-based and class-selective but generally pan-HDAC (histone deacetylase) inhibitor with potential anticancer activity.
Entinostat (MS275; SNDX275) Chemical Structure CAS No.: 209783-80-2
Product category: HDAC
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Purity: ≥98%

COA
MSDS
NMR
COA
MSDS
NMR
Instructions
Product Description

Entinostat (formerly known as MS-275; SNDX-275) is a potent, benzamide-based and class-selective but generally pan-HDAC (histone deacetylase) inhibitor with potential anticancer activity. It is more selective for HDAC1/2/3 over HDACs 4, 6, 8, and 10, and it strongly inhibits HDAC1, HDAC2, and HDAC3 with IC50 values of 0.24, 0.45, and 0.25 μM in cell-free experiments, respectively. By attaching to and inhibiting histone deacetylase, an enzyme that controls chromatin structure and gene transcription, entinostat may have anticancer properties. In human leukemia cells, this agent appears to have dose-dependent effects, including, at low drug concentrations, cyclin-dependent kinase inhibitor 1A (p21/CIP1/WAF1)-dependent growth arrest and differentiation.

Biological Activity I Assay Protocols (From Reference)
Targets
HDAC1 ( IC50 = 243 nM ); HDAC3 ( IC50 = 248 nM ); HDAC2 ( IC50 = 453 nM )
ln Vitro

Entinostat (MS-275) has a binding affinity of 282 nM for HDAC1 and 156 nM for HDAC2[1]. The effects of Entinostat (MS-275), an HDAC inhibitor, on differentiation and apoptosis have been studied in primary acute myelogenous leukemia blasts and human leukemia and lymphoma cells (U937, HL-60, K562, and Jurkat). In every cell line, MS-275 exhibits effects that are dependent on dosage. MS-275 has strong antiproliferative activity when given at low concentrations (e.g., 1 μM), causing p21CIP1/WAF1-mediated growth arrest and differentiation markers (CD11b) to be expressed in U937 cells. Potently inducing cell death, Entinostat (MS-275) causes apoptosis in approximately 70% of cells after 48 hours[2].
ln Vivo
Entinostat (MS-27-275) at 49 mg/kg shows marked antitumor effects against the tumor lines KB-3-1, 4-1St, and St-4, and a moderate effect against the Capan-1 tumor. There are notable results when using entinostat at doses of 24.5 mg/kg and 12.3 mg/kg in treating these tumors. Furthermore, 4–24 hours after oral Entinostat administration, HT-29 tumor xenografts appear to have higher levels of histone acetylation[3]. When MS-275 (3.5 mg/kg i.p.) is given once daily to rats with experimental autoimmune neuritis (EAN) starting at the earliest neurological symptoms, it significantly lessens the severity and duration of EAN, as well as the local buildup of macrophages, T cells, and B cells, as well as the demyelination of sciatic nerves. Furthermore, in the sciatic nerves of EAN rats, MS-275 treatment raises the percentage of infiltrated Foxp3+ cells and anti-inflammatory M2 macrophages[4].
Enzyme Assay
HDAC activity biochemical assays are performed by Nanosyn in 384-well microplates with a reaction volume of 10 μL. Five microliters of a 2× HDAC inhibitor (such as Entinostat), four microliters of 2.5× enzyme, and one microliter of 10× substrate are combined with assay buffer (100 mM HEPES, pH 7.5, 25 mM KCl, 0.1% BSA, 0.01% Triton X-100, 1% DMSO) in a typical enzymatic reaction. In the enzymatic assays, the final concentration of each HDAC ranges from 0.5 to 5 nM. In every experiment, a final substrate concentration of 1 μM FAM-RHKK(Ac)-NH2 or FAM-RHKK(trifluoroacetyl)-NH2 is employed, and it is discovered to be lower than the calculated Km,app for every enzyme[1].
Cell Assay
SH-SY5Y cells are split twice a week and kept in a humidified incubator with 5% CO2 at 37°C under standard culture conditions. After plating cells at a density of 2500 cells per well in a 20-μL volume of DMEM/F-12 culture media supplemented with 10% FBS, the cells are left to adhere for the entire night in black 384-well plates. After being serially diluted in 100% DMSO the next day, HDAC inhibitors (such as Entinostat) are then cross-diluted into culture media. To achieve the desired inhibitor final concentration (e.g., 0.1% DMSO), 5 μL of the compound (e.g., Entinostat) diluted in media is added to the appropriate well of the cell plate. Cellular ATP levels are quantified using CellTiter-Glo reagents after treated cells are incubated for 6, 24, 48, 72, or 96 hours under standard tissue culture conditions. Similarly, media from different cell plates are aspirated after 6 hours of incubation with HDAC inhibitors (such as Entinostat), and cells are once again washed with media free of inhibitors. After 24, 48, 72, or 96 hours of incubation, the cells are given 25 μL of media supplemented with 10% FBS and 0.1% DMSO (no inhibitors), and the levels of cellular ATP are measured using CellTiter-Glo. An Envision Instrument with a 0.1 s count time is used to measure luminosity at each time point[1].
Animal Protocol
Mice: Subcutaneous injection of A2780 cells (9×106) in PBS suspension is administered subcutaneously into the flank of a naked mouse. For the remaining tumor lines, KB-3-1, HCT-15, 4-1St, Calu-3, St-4, Capan-1, and HT-29, the tumors are passaged multiple times prior to initiating in vivo antitumor testing. A trocar needle is used to implant a tumor lump, measuring 2-3 mm in diameter, subcutaneously into the flank of a nude mouse. Once the tumors are confirmed to have grown in the body (tumor size, 20-100 mm3), treatment with the drugs is initiated in four or five mice per experimental group. For four weeks, one oral dose of entinostat is given five days a week. Tumor width and length are measured twice a week, and the volume of the tumor is computed.
Rats: Male Lewis rats (weight: 170-200 g, 8-10 weeks) are kept in a 12-hour light/dark cycle with unrestricted access to food and drink. Six rats per group receive an intraperitoneal injection of MS-275 (3.5 mg/kg) every day from day 10 to day 14 as part of a therapeutic treatment. MS-275 is dissolved in phosphate buffered saline (PBS) for injection, and control rats are administered the same volume (1 mL) of PBS.
References

[1]. Histone deacetylase (HDAC) inhibitor kinetic rate constants correlate with cellular histone acetylation but not transcription and cell viability. J Biol Chem. 2013 Sep 13;288(37):26926-43.

[2]. The histone deacetylase inhibitor MS-275 promotes differentiation or apoptosis in human leukemia cells through a process regulated by generation of reactive oxygen species and induction of p21CIP1/WAF1 1. Cancer Res. 2003 Jul 1;63(13):3637-45.

[3].A synthetic inhibitor of histone deacetylase, MS-27-275, with marked in vivo antitumor activity against human tumors. Proc Natl Acad Sci U S A, 1999, 96(8), 4592-4597.

[4]. MS-275, an histone deacetylase inhibitor, reduces the inflammatory reaction in rat experimental autoimmune neuritis. Neurosci, 2010, 169, 370-377.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H20N4O3
Molecular Weight
376.41
Exact Mass
376.15
Elemental Analysis
C, 67.01; H, 5.36; N, 14.88; O, 12.75
CAS #
209783-80-2
Related CAS #
209783-80-2
Appearance
White off white solid powder
SMILES
C1=CC=C(C(=C1)N)NC(=O)C2=CC=C(C=C2)CNC(=O)OCC3=CN=CC=C3
InChi Key
INVTYAOGFAGBOE-UHFFFAOYSA-N
InChi Code
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)
Chemical Name
pyridin-3-ylmethyl N-[[4-[(2-aminophenyl)carbamoyl]phenyl]methyl]carbamate
Synonyms
MS-275; MS 2275; MS-2275; SNDX275; MS2275; SNDX275;MS275; MS 275; SNDX-275; SNDX 275; Entinostat
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 50~75 mg/mL (132.8~199.3 mM)
Water: <1 mg/mL
Ethanol: <1 mg/mL
Solubility (In Vivo)
2% DMSO+30% PEG 300: 10mg/mL
 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.6567 mL 13.2834 mL 26.5668 mL
5 mM 0.5313 mL 2.6567 mL 5.3134 mL
10 mM 0.2657 mL 1.3283 mL 2.6567 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT02569320 Active
Recruiting		 Drug: Entinostat
Drug: Nivolumab		 Renal Cell Carcinoma Roberto Pili August 31, 2018 Phase 2
NCT02936752 Active
Recruiting		 Drug: Entinostat
Biological: Pembrolizumab		 Myelodysplastic Syndrome National Cancer Institute
(NCI)		 April 3, 2017 Phase 1
NCT03501381 Active
Recruiting		 Drug: Entinostat
Drug: Interleukin-2		 Renal Cell Carcinoma Roberto Pili May 24, 2018 Phase 2
NCT03978624 Active
Recruiting		 Drug: Pembrolizumab
Drug: Entinost		 Bladder Cancer UNC Lineberger Comprehensive
Cancer Center		 September 23, 2020 Phase 2
NCT03280563 Active
Recruiting		 Drug: Entinostat
Drug: Exemestane		 Breast Neoplasms Hoffmann-La Roche December 26, 2017 Phase 1
Phase 2
Biological Data
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