FK228

• CAT Number: A000730
• CAS Number: 128517-07-7
• Molecular Formula: C₂₄H₃₆N₄O₆S₂
• Molecular Weight: 540.70
• Purity: ≥95%
• Synonyms: FR 901228, NSC 630176
• Target: Epigenetics
• Solubility: >27mg/mL in DMSO
• Storage: 3 years -20C powder
• IUPAC Name: (1S,4S,7Z,10S,16E,21R)-7-ethylidene-4,21-di(propan-2-yl)-2-oxa-12,13-dithia-5,8,20,23-tetrazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone
• InChI: InChI=1S/C24H36N4O6S2/c1-6-16-21(30)28-20(14(4)5)24(33)34-15-9-7-8-10-35-36-12-17(22(31)25-16)26-23(32)19(13(2)3)27-18(29)11-15/h6-7,9,13-15,17,19-20H,8,10-12H2,1-5H3,(H,25,31)(H,26,32)(H,27,29)(H,28,30)/b9-7+,16-6-/t15-,17-,19-,20+/m1/s1
• InChIKey: OHRURASPPZQGQM-GCCNXGTGSA-N
• SMILES: C/C=C\1/C(=O)N[C@H](C(=O)O[C@H]\2CC(=O)N[C@@H](C(=O)N[C@H](CSSCC/C=C2)C(=O)N1)C(C)C)C(C)C

FK228 (Romidepsin)（Cat No.:A000730）is a potent histone deacetylase (HDAC) inhibitor with strong antitumor activity. By inhibiting HDACs, FK228 promotes the accumulation of acetylated histones, leading to the reactivation of tumor suppressor genes and the induction of apoptosis in cancer cells. It is primarily used in cancer research, especially in studying T-cell lymphomas and other malignancies. FK228 has shown significant efficacy in clinical settings for cutaneous and peripheral T-cell lymphoma, making it a key molecule for understanding epigenetic regulation and developing novel cancer therapies.

Reference

1: Saijo K, Imamura J, Narita K, Oda A, Shimodaira H, Katoh T, Ishioka C. Biochemical, biological, and structural properties of romidepsin (FK228) and its analogs as novel HDAC/PI3K dual inhibitors. Cancer Sci. 2014 Dec 10. doi: 10.1111/cas.12585. [Epub ahead of print] PubMed PMID: 25492515.2: Foss F, Coiffier B, Horwitz S, Pro B, Prince HM, Sokol L, Greenwood M, Lerner A, Caballero D, Baran E, Kim E, Nichols J, Balser B, Wolfson J, Whittaker S. Tolerability to romidepsin in patients with relapsed/refractory T-cell lymphoma. Biomark Res. 2014 Sep 8;2:16. doi: 10.1186/2050-7771-2-16. eCollection 2014. PubMed PMID: 25279222; PubMed Central PMCID: PMC4181623.3: Oda A, Saijo K, Ishioka C, Narita K, Katoh T, Watanabe Y, Fukuyoshi S, Takahashi O. Predicting the structures of complexes between phosphoinositide 3-kinase (PI3K) and romidepsin-related compounds for the drug design of PI3K/histone deacetylase dual inhibitors using computational docking and the ligand-based drug design approach. J Mol Graph Model. 2014 Nov;54:46-53. doi: 10.1016/j.jmgm.2014.08.007. Epub 2014 Sep 8. PubMed PMID: 25254927.4: Yu P, Petrus MN, Ju W, Zhang M, Conlon KC, Nakagawa M, Maeda M, Bamford RN, Waldmann TA. Augmented efficacy with the combination of blockade of the Notch-1 pathway, bortezomib and romidepsin in a murine MT-1 adult T-cell leukemia model. Leukemia. 2014 Aug 14. doi: 10.1038/leu.2014.241. [Epub ahead of print] PubMed PMID: 25118879.5: Finn N, Larouche JF. Romidepsin used as monotherapy in sequence with allogeneic stem cell transplant in a patient with peripheral T-cell lymphoma. Case Rep Hematol. 2014;2014:404078. doi: 10.1155/2014/404078. Epub 2014 Jul 7. PubMed PMID: 25105035; PubMed Central PMCID: PMC4109362.6: Satwani P, Bavishi S, Saha A, Zhao F, Ayello J, van de Ven C, Chu Y, Cairo MS. Upregulation of NKG2D ligands in acute lymphoblastic leukemia and non-Hodgkin lymphoma cells by romidepsin and enhanced in vitro and in vivo natural killer cell cytotoxicity. Cytotherapy. 2014 May 20. pii: S1465-3249(14)00548-9. doi: 10.1016/j.jcyt.2014.03.008. [Epub ahead of print] PubMed PMID: 24856896.7: Romidepsin is effective and well-tolerated in patients ≥60 years old with relapsed or refractory peripheral T-cell lymphoma (PTCL): analysis from phase 2 trials. Clin Adv Hematol Oncol. 2014 Feb;12(2 Suppl 5):17-8. PubMed PMID: 24852793.8: Wei DG, Chiang V, Fyne E, Balakrishnan M, Barnes T, Graupe M, Hesselgesser J, Irrinki A, Murry JP, Stepan G, Stray KM, Tsai A, Yu H, Spindler J, Kearney M, Spina CA, McMahon D, Lalezari J, Sloan D, Mellors J, Geleziunas R, Cihlar T. Histone deacetylase inhibitor romidepsin induces HIV expression in CD4 T cells from patients on suppressive antiretroviral therapy at concentrations achieved by clinical dosing. PLoS Pathog. 2014 Apr 10;10(4):e1004071. doi: 10.1371/journal.ppat.1004071. eCollection 2014 Apr. PubMed PMID: 24722454; PubMed Central PMCID: PMC3983056.9: Karthik S, Sankar R, Varunkumar K, Ravikumar V. Romidepsin induces cell cycle arrest, apoptosis, histone hyperacetylation and reduces matrix metalloproteinases 2 and 9 expression in bortezomib sensitized non-small cell lung cancer cells. Biomed Pharmacother. 2014 Apr;68(3):327-34. doi: 10.1016/j.biopha.2014.01.002. Epub 2014 Jan 15. PubMed PMID: 24485799.10: Coiffier B, Pro B, Prince HM, Foss F, Sokol L, Greenwood M, Caballero D, Morschhauser F, Wilhelm M, Pinter-Brown L, Padmanabhan Iyer S, Shustov A, Nielsen T, Nichols J, Wolfson J, Balser B, Horwitz S. Romidepsin for the treatment of relapsed/refractory peripheral T-cell lymphoma: pivotal study update demonstrates durable responses. J Hematol Oncol. 2014 Jan 23;7(1):11. doi: 10.1186/1756-8722-7-11. PubMed PMID: 24456586; PubMed Central PMCID: PMC4016573.