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Research Papers

Design, synthesis and biological evaluation of 2,4-pyrimidinediamine derivatives as ALK and HDACs dual inhibitors for the treatment of ALK addicted cancer

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Pages 2512-2529 | Received 04 Aug 2022, Accepted 01 Sep 2022, Published online: 13 Sep 2022

References

  • Chiarle R, Voena C, Ambrogio C, et al. Inghirami, The anaplastic lymphoma kinase in the pathogenesis of cancer. Nat Rev Cancer 2008;8:11–23.
  • Morris SW, Kirstein MN, Valentine MB, et al. Fusion of a kinase gene, ALK, to a nucleolar protein gene, NPM, in non-Hodgkin’s lymphoma. Science 1995;267:316–7.
  • Rikova K, Guo A, Zeng Q, et al. Global survey of phosphotyrosine signaling identifies oncogenic kinases in lung cancer. Cell 2007;131:1190–203.
  • Zhu M, Li W, Zhao T, et al. Fragment-based modification of 2,4-diarylaminopyrimidine derivatives as ALK and ROS1 dual inhibitors to overcome secondary mutants. Bioorg Med Chem 2020;28:115719.
  • Soda M, Choi YL, Enomoto M, et al. Identification of the transforming EML4-ALK fusion gene in non-small-cell lung cancer. Nature 2007;448:561–6.
  • Kwak EL, Bang YJ, Camidge DR, et al. Anaplastic lymphoma kinase inhibition in non-small-cell lung cancer. N Engl J Med 2010;363:1693–703.
  • Gristina V, La Mantia M, Iacono F, et al. The emerging therapeutic landscape of ALK inhibitors in non-small cell lung cancer. Pharmaceuticals (Basel) 2020;13:474.
  • Doebele RC, Pilling AB, Aisner DL, et al. Mechanisms of resistance to crizotinib in patients with ALK gene rearranged non-small cell lung cancer. Clin Cancer Res 2012;18:1472–82.
  • Bolden JE, Peart MJ, Johnstone RW. Anticancer activities of histone deacetylase inhibitors. Nat Rev Drug Discov 2006;5:769–84.
  • Ververis K, Hiong A, Karagiannis TC, et al. Histone deacetylase inhibitors (HDACIs): multitargeted anticancer agents. Biologics 2013;7:47–60.
  • Ropero S, Esteller M. The role of histone deacetylases (HDACs) in human cancer. Mol Oncol 2007;1:19–25.
  • Li Y, Seto E. HDACs and HDAC inhibitors in cancer development and therapy. Cold Spring Harb Perspect Med 2016;6:a026831.
  • Makena MR, Nguyen TH, Koneru B, et al. Vorinostat and fenretinide synergize in preclinical models of T-cell lymphoid malignancies. Cancer Res 2021;32:34–43.
  • Marampon F, Di Nisio V, Pietrantoni I, et al. Pro-differentiating and radiosensitizing effects of inhibiting HDACs by PXD-101 (Belinostat) in in vitro and in vivo models of human rhabdomyosarcoma cell lines. Cancer Lett 2019;461:90–101.
  • Paillas S, Then CK, Kilgas S, et al. The histone deacetylase inhibitor romidepsin spares normal tissues while acting as an effective radiosensitizer in bladder tumors in vivo. Int J Radiat Oncol Biol Phys 2020;107:212–21.
  • Prince HM, Bishton MJ, Johnstone RW. Panobinostat (LBH589): a potent pan-deacetylase inhibitor with promising activity against hematologic and solid tumors. Future Oncol 2009;5:601–12.
  • Liu T, Guan F, Wang Y, et al. MS-275 combined with cisplatin exerts synergistic antitumor effects in human esophageal squamous cell carcinoma cells. Toxicol Appl Pharmacol 2020;395:114971.
  • Yun MR, Lim SM, Kim SK, et al. Enhancer remodeling and microRNA alterations are associated with acquired resistance to ALK inhibitors. Cancer Res 2018;78:3350–62.
  • Stockhammer P, Ho CSL, Hegedus L, et al. HDAC inhibition synergizes with ALK inhibitors to overcome resistance in a novel ALK mutated lung adenocarcinoma model. Lung Cancer 2020;144:20–9.
  • Fukuda K, Takeuchi S, Arai S, et al. Epithelial-to-mesenchymal transition is a mechanism of ALK inhibitor resistance in lung cancer independent of ALK mutation status. Cancer Res 2019;79:1658–70.
  • Fukuda K, Takeuchi S, Katayama R, et al. HDAC inhibition overcomes crizotinib-resistance by mesenchymal-epithelial transition (MET) in EML4-ALK lung cancer cells. J Thorac Oncol 2017;12:S382–S383.
  • Hagiwara K, Tokunaga T, Iida H, et al. Combined inhibition of ALK and HDAC induces synergistic cytotoxicity in neuroblastoma cell lines. Anticancer Res 2019;39:3579–84.
  • Pan T, Dan Y, Guo D, et al. Discovery of 2,4-pyrimidinediamine derivatives as potent dual inhibitors of ALK and HDAC. Eur J Med Chem 2021;224:113672.
  • Masanas M, Masiá N, Suárez‐Cabrera L, et al. The oral KIF11 inhibitor 4SC‐205 exhibits antitumor activity and potentiates standard and targeted therapies in primary and metastatic neuroblastoma models. Clin Trans Med 2021;11:e523.
  • Wu G, Robertson DH, Brooks CL, 3rd, et al. Detailed analysis of grid-based molecular docking: A case study of CDOCKER-A CHARMm-based MD docking algorithm. J Comput Chem 2003;24:1549–62.