MS-275 (Entinostat, SNDX-275)

• CAT Number: I002611
• CAS Number: 209783-80-2
• Molecular Formula: C₂₁H₂₀N₄O₃
• Molecular Weight: 376.41
• Purity: ≥95%
• Target: HDAC
• Solubility: DMSO ≥72mg/mL Water <1.2mg/mL Ethanol <1.2mg/mL
• Storage: 3 years -20C powder
• IC50: 0.51 μM(HDAC1); 1.7 μM(HDAC3)
• InChI: 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)
• InChIKey: INVTYAOGFAGBOE-UHFFFAOYSA-N
• SMILES: C1=CC=C(C(=C1)N)NC(=O)C2=CC=C(C=C2)CNC(=O)OCC3=CN=CC=C3

Entinostat(CAT: I002611), also known as MS-275 or SNDX-275, is a potent inhibitor of histone deacetylase 1 (HDAC1) and histone deacetylase 3 (HDAC3). As an HDAC inhibitor, entinostat affects the acetylation status of histone proteins, leading to changes in gene expression and chromatin remodeling. By inhibiting HDAC1 and HDAC3, entinostat has the potential to modulate epigenetic processes and regulate gene transcription. This compound has been investigated for its therapeutic potential in various diseases, including cancer.

Reference

1:Treatment with Entinostat heals experimental cholera by affecting physical and chemical barrier functions of intestinal epithelia. Sarker P, Banik A, Stromberg R, Gudmundsson GH, Raqib R, Agerberth B.Antimicrob Agents Chemother. 2017 Apr 24. pii: AAC.02570-16. doi: 10.1128/AAC.02570-16. [Epub ahead of print] PMID: 28438947 2:Entinostat: a promising treatment option for patients with advanced breast cancer. Connolly RM, Rudek MA, Piekarz R.Future Oncol. 2017 Mar 9. doi: 10.2217/fon-2016-0526. [Epub ahead of print] PMID: 28326839 3:Combination epigenetic therapy in metastatic colorectal cancer (mCRC) with subcutaneous 5-azacitidine and entinostat; a phase 2 consortium/stand Up 2 cancer study. Azad NS, El-Khoueiry A, Yin J, Oberg AL, Flynn P, Adkins D, Sharma A, Weisenberger DJ, Brown T, Medvari P, Jones PA, Easwaran H, Kamel I, Bahary N, Kim G, Picus J, Pitot HC, Erlichman C, Donehower R, Shen H, Laird PW, Piekarz R, Baylin S, Ahuja N.Oncotarget. 2017 Feb 5. doi: 10.18632/oncotarget.15108. [Epub ahead of print] PMID: 28186961 Free Article4:An HDAC Inhibitor, Entinostat/MS-275, Partially Prevents Delayed Cranial Suture Closure in Heterozygous Runx2 Null Mice. Bae HS, Yoon WJ, Cho YD, Islam R, Shin HR, Kim BS, Lim JM, Seo MS, Cho SA, Choi KY, Baek SH, Kim HG, Woo KM, Baek JH, Lee YS, Ryoo HM.J Bone Miner Res. 2017 May;32(5):951-961. doi: 10.1002/jbmr.3076. Epub 2017 Feb 28. PMID: 28052439 5:The interplay of epigenetic therapy and immunity in locally recurrent or metastatic estrogen receptor-positive breast cancer: Correlative analysis of ENCORE 301, a randomized, placebo-controlled phase II trial of exemestane with or without entinostat. Tomita Y, Lee MJ, Lee S, Tomita S, Chumsri S, Cruickshank S, Ordentlich P, Trepel JB.Oncoimmunology. 2016 Aug 31;5(11):e1219008. doi: 10.1080/2162402X.2016.1219008. eCollection 2016. PMID: 27999738 Free PMC Article6:Combination Epigenetic Therapy in Advanced Breast Cancer with 5-Azacitidine and Entinostat: A Phase II National Cancer Institute/Stand Up to Cancer Study. Connolly RM, Li H, Jankowitz RC, Zhang Z, Rudek MA, Jeter SC, Slater SA, Powers P, Wolff AC, Fetting JH, Brufsky A, Piekarz R, Ahuja N, Laird PW, Shen H, Weisenberger DJ, Cope L, Herman JG, Somlo G, Garcia AA, Jones PA, Baylin SB, Davidson NE, Zahnow CA, Stearns V.Clin Cancer Res. 2016 Dec 15. doi: 10.1158/1078-0432.CCR-16-1729. [Epub ahead of print] PMID: 27979916 7:Erratum: The histone deacetylase inhibiting drug Entinostat induces lipid accumulation in differentiated HepaRG cells. Nunn AD, Scopigno T, Pediconi N, Levrero M, Hagman H, Kiskis J, Enejder A.Sci Rep. 2016 Nov 28;6:37204. doi: 10.1038/srep37204. No abstract available. PMID: 27892955 Free PMC Article8:Targeting SALL4 by entinostat in lung cancer. Yong KJ, Li A, Ou WB, Hong CK, Zhao W, Wang F, Tatetsu H, Yan B, Qi L, Fletcher JA, Yang H, Soo R, Tenen DG, Chai L.Oncotarget. 2016 Nov 15;7(46):75425-75440. doi: 10.18632/oncotarget.12251. PMID: 27705911 Free PMC Article9:Entinostat up-regulates the CAMP gene encoding LL-37 via activation of STAT3 and HIF-1α transcription factors. Miraglia E, Nylén F, Johansson K, Arnér E, Cebula M, Farmand S, Ottosson H, Strömberg R, Gudmundsson GH, Agerberth B, Bergman P.Sci Rep. 2016 Sep 16;6:33274. doi: 10.1038/srep33274. PMID: 27633343 Free PMC Article10:The histone deacetylase inhibiting drug Entinostat induces lipid accumulation in differentiated HepaRG cells. Nunn AD, Scopigno T, Pediconi N, Levrero M, Hagman H, Kiskis J, Enejder A.Sci Rep. 2016 Jun 20;6:28025. doi: 10.1038/srep28025. PMID: 27320682 Free PMC Article