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Entinostat

Catalog No. T6233   CAS 209783-80-2
Synonyms: SNDX-275, MS-275

Entinostat (MS-275) (MS-275) is an inhibitor of HDACs that inhibits HDAC1 and HDAC3 (IC50s: 0.18/0.74 μM).

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Entinostat Chemical Structure
Entinostat, CAS 209783-80-2
Pack Size Availability Price/USD Quantity
10 mg In stock $ 50.00
25 mg In stock $ 72.00
50 mg In stock $ 90.00
100 mg In stock $ 126.00
200 mg In stock $ 193.00
1 mL * 10 mM (in DMSO) In stock $ 50.00
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Purity: 99.52%
Purity: 99.11%
Purity: 98%
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Biological Description
Chemical Properties
Storage & Solubility Information
Description Entinostat (MS-275) (MS-275) is an inhibitor of HDACs that inhibits HDAC1 and HDAC3 (IC50s: 0.18/0.74 μM).
Targets&IC50 HDAC1:0.18 μM(cell free), HDAC3:0.74 μM(cell free)
In vitro MS275 is partial inhibitors of HeLa nuclear extract HDAC activity, however, showing full and potent inhibition of HDAC1 and 3 isoenzymes. MS275 display a substrate competitive inhibition of HDAC1 (Ki: 1.3 μM) [1]. MS-275 inhibited partially purified human HDA and caused hyperacetylation of nuclear histones in various tumor cell lines. MS-27-275 induced p21(WAF1/CIP1) and gelsolin and changed the cell cycle distribution, decrease of S-phase cells, and increase of G1-phase cells. The in vitro sensitivity spectrum of MS-27-275 against various human tumor cell lines showed a pattern different than that of a commonly used antitumor agent, 5-fluorouracil [2]. MS-275 displayed dose-dependent effects in human leukemia and lymphoma cells and primary acute myelogenous leukemia blasts in relation to differentiation and apoptosis. When administered at a low concentration (e.g., 1 micro M), MS-275 exhibited potent antiproliferative activity, inducing p21(CIP1/WAF1)-mediated growth arrest and expression of differentiation markers (CD11b) in U937 cells [3].
In vivo MS-27-275 administered orally strongly inhibited the growth in seven of eight tumor lines implanted into nude mice, although most of these did not respond to 5-fluorouracil [2]. MS-275 administration (3.5 mg/kg i.p.) to Experimental autoimmune neuritis (EAN) rats once daily from the appearance of first neurological signs greatly reduced the severity and duration of EAN and attenuated local accumulation of macrophages, T cells and B cells, and demyelination of sciatic nerves [4].
Kinase Assay The HDAC enzyme activity assay was done as described. Briefly, 40 μl HeLa cell nuclear extract, 29 μl enzyme buffer [15 mM Tris HCl pH 8.1, 0.25 mM EDTA, 250 mM NaCl, 10% (v/v) glycerol]; for recombinant HDAC isoenzymes, 0.1 mg/ml bovine serum albumin (BSA was added) and 1 μl compound were added per well of a microtiter plate. The reaction was started by addition of 30 μl substrate (Ac-NH-GGK(Ac)-AMC final 25 μM). After incubation for 90 min at 30°C, reaction was terminated by adding 25 μl stop solution (50 mM Tris HCl pH 8, 100 mM NaCl, 0.5 mg/ml trypsin, 2 μM TSA). After 40 min incubation at room temperature, fluorescence was measured using a Wallac Victor 1420 multilabel counter (Excitation 355 nm, Emission 460 nm). The HDAC1, 3, 6 and 8 assays were done with slight modifications. About 14 ng/well HDAC1, 2 ng/well HDAC3 or 10 ng/well HDAC6 were incubated with 6, 25 or 10 lM Ac-NH-GGK(Ac)-AMC, respectively, for 2 or 3 hr at 30°C. In contrast, 100 ng/well HDAC8 were incubated with 50 μM Ac-NH-RHK(Ac)K(Ac)-AMC for 3 hr at 30°C. Termination of the reaction and all further steps were done as described earlier for HeLa cell nuclear extracts. For the enzyme kinetic studies with HDAC1, selected HDAC inhibitor (around IC50 value), as well as Ac-NH-GGK(Ac)-AMC substrate (up to 100 μM) concentrations, were evaluated under standard conditions as described earlier [1].
Cell Research Cancer cells (5 × 10^3) were seeded into each well of 96-well plates and were cultured with graded concentrations of the drugs for 3 days. The cells were stained with 0.1 mg/ml neutral red for 1 h in a CO2-incubator, and, after aspiration of the medium, OD540 of the neutral red solubilized with 50 μl of ethanol and 150 μl of 0.1 M Na2HPO4 was measured. The IC50 value was determined by plotting growth inhibition of the cells against the logarithm of the drug concentration [2].
Animal Research A2780 cells (9 × 10^6) grown in vitro were suspended in PBS and were injected subcutaneously into the flank of nude mouse. For the other tumor lines, KB-3-1, HCT-15, 4-1St, Calu-3, St-4, Capan-1, and HT-29, tumors were passaged several times before starting in vivo antitumor testing, and a tumor lump (2–3 mm in diameter) was transplanted subcutaneously into the flank of a nude mouse by using a trocar needle. Treatment (four or five mice in each experimental group) with the drugs was started after the tumors were confirmed to have grown in the body (tumor size, 20–100 mm3). MS-27-275 and compound 2, both dissolved with 0.05 N HCl, 0.1% Tween 80, and 5-fluorouracil (5-FU) and diluted with physiological saline, were administered orally once daily 5 days per week for 4 weeks. Tumor length and width were monitored twice weekly, and tumor volume was calculated as described [2].
Synonyms SNDX-275, MS-275
Molecular Weight 376.41
Formula C21H20N4O3
CAS No. 209783-80-2

Storage

Powder: -20°C for 3 years | In solvent: -80°C for 1 year

Solubility Information

DMSO: 37.6 mg/mL (100 mM)

TargetMolReferences and Literature

1. Beckers T, et al. Distinct pharmacological properties of second generation HDAC inhibitors with the benzamide or hydroxamate head group. Int J Cancer. 2007 Sep 1;121(5):1138-48. 2. Saito A, et al. 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. 3. Rosato RR, et al. 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. 4. Zhang ZY, et al. MS-275, an histone deacetylase inhibitor, reduces the inflammatory reaction in rat experimental autoimmune neuritis. Neuroscience. 2010 Aug 11;169(1):370-7. 5. Moreno-Yruela C, Zhang D, Wei W, et al. Class I Histone Deacetylases (HDAC1‒3) are Histone Lysine Delactylases[J]. bioRxiv. 2021 6. Wellinger L C, Hogg S J, Newman D M, et al. BET Inhibition Enhances TNF Mediated Anti-Tumor Immunity[J]. bioRxiv. 2021 7. Lagosz K B, Bysiek A, Macina J M, et al. HDAC3 Regulates Gingival Fibroblast Inflammatory Responses in Periodontitis[J]. Journal of dental research. 2019: 0022034519885088.

TargetMolCitations

1. Moreno-Yruela C, Zhang D, Wei W, et al. Class I Histone Deacetylases (HDAC1‒3) are Histone Lysine Delactylases. Science advances. 2022, 8(3): eabi6696. 2. Wellinger L C, Hogg S J, Newman D M, et al. BET Inhibition Enhances TNF Mediated Anti-Tumor Immunity. Cancer Immunology Research. 2022, 10(1): 87-107. 3. Wellinger L C, Hogg S J, Newman D M, et al. Bet inhibition enhances TNF-mediated antitumor immunity. Cancer Immunology Research. 2022, 10(1): 87-107 4. Zierfuss B, Weinhofer I, Buda A, et al. Targeting foam cell formation in inflammatory brain diseases by the histone modifier MS‐275. Annals of Clinical and Translational Neurology. 2020, 7(11): 2161-2177 5. Zhang L, Shi J, Du D, et al. Ketogenesis acts as an endogenous protective programme to restrain inflammatory macrophage activation during acute pancreatitis. eBioMedicine. 2022, 78: 103959. 6. Jiang X C, Tu F H, Wei L Y, et al. Discovery of a Novel G-Quadruplex and Histone Deacetylase (HDAC) Dual-Targeting Agent for the Treatment of Triple-Negative Breast Cancer. Journal of Medicinal Chemistry. 2022 7. Lagosz K B, Bysiek A, Macina J M, et al. HDAC3 Regulates Gingival Fibroblast Inflammatory Responses in Periodontitis. Journal of Dental Research. 2019: 0022034519885088 8. Wang C, Huang M, Lin Y, et al.ENO2-derived phosphoenolpyruvate functions as an endogenous inhibitor of HDAC1 and confers resistance to antiangiogenic therapy.Nature Metabolism.2023: 1-22. 9. Villoria-González A, Zierfuss B, Parzer P, et al.Efficacy of HDAC Inhibitors in Driving Peroxisomal β-Oxidation and Immune Responses in Human Macrophages: Implications for Neuroinflammatory Disorders.Biomolecules.2023, 13(12): 1696.

Related compound libraries

This product is contained In the following compound libraries:
Anti-Cancer Clinical Compound Library Anti-Cancer Drug Library Anti-Cancer Approved Drug Library Anti-Cancer Active Compound Library Epigenetics Compound Library Anti-Cancer Compound Library NO PAINS Compound Library FDA-Approved & Pharmacopeia Drug Library Bioactive Lipid Compound Library Bioactive Compound Library

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Keywords

Entinostat 209783-80-2 Apoptosis Autophagy Chromatin/Epigenetic DNA Damage/DNA Repair HDAC MS275 SNDX 275 Inhibitor inhibit SNDX275 SNDX-275 MS-275 MS 275 Histone deacetylases inhibitor

 

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