Discovery of novel polysubstituted N-alkyl acridone analogues as histone deacetylase isoform-selective inhibitors for cancer therapy

References

• Cheng Y, He C, Wang M, Ma X, Mo F, Yang S, Han J, Wei X. Targeting epigenetic regulators for cancer therapy: mechanisms and advances in clinical trials. Signal Transduct Target Ther. 2019;4:62–100.
   PubMed Web of Science ®Google Scholar
• Bennett RL, Licht JD. Targeting epigenetics in cancer. Annu Rev Pharmacol Toxicol. 2018;58:187–207.
   PubMed Web of Science ®Google Scholar
• Zagni C, Floresta G, Monciino G, Rescifina A. The search for potent, small-molecule HDACIs in cancer treatment: a decade after vorinostat. Med Res Rev. 2017; 37(6):1373–1428.
   PubMed Web of Science ®Google Scholar
• Ramaiah MJ, Tangutur AD, Manyam RR. Epigenetic modulation and understanding of HDAC inhibitors in cancer therapy. Life Sci. 2021;277:119504.
   PubMed Web of Science ®Google Scholar
• Botchkarev VA, Sharov AA. Histone deacetylases in the control of epidermal homeostasis: from chromatin biology toward therapy. J Invest Dermatol. 2022;142(1):12–14.
   PubMed Web of Science ®Google Scholar
• Qiu X, Zhu L, Wang H, Tan Y, Yang Z, Yang L, Wan L. From natural products to HDAC inhibitors: an overview of drug discovery and design strategy. Bioorg Med Chem. 2021;52:116510.
   PubMed Web of Science ®Google Scholar
• Roche J, Bertrand P. Inside HDACs with more selective HDAC inhibitors. Eur J Med Chem. 2016;121:451–483.
   PubMed Web of Science ®Google Scholar
• Milazzo G, Mercatelli D, Di Muzio G, Triboli L, De Rosa P, Perini G, Giorgi FM. Histone deacetylases (HDACs): Histone Deacetylases (HDACs): evolution, specificity, role in transcriptional complexes, and pharmacological actionability. Genes. 2020;11(5):556–604.
   PubMed Web of Science ®Google Scholar
• Yoon S, Eom GH. HDAC and HDAC inhibitor: from cancer to cardiovascular diseases. Chonnam Med J. 2016;52(1):1–11.
   PubMedGoogle Scholar
• Goutas D, Theocharis S, Tsourouflis G. Unraveling the epigenetic role and clinical impact of histone deacetylases in neoplasia. Diagnostics. 2021;11(8):1346–1362.
   Web of Science ®Google Scholar
• Zhang N, Sun P, Jin HZ, Yang YQ, Zhao QY, Zhou L, Guo LL, Yang XH, Lu LM. Chidamide combined with paclitaxel effectively reverses the expression of histone deacetylase in lung cancer. Anticancer Drugs. 2020;31(7):702–708.
   PubMed Web of Science ®Google Scholar
• Kollar J, Frecer V. Selective inhibitors of zinc-dependent histone deacetylases. Therapeutic targets relevant to cancer. Curr Pharm Des. 2015; 21(11):1472–1502.
   PubMed Web of Science ®Google Scholar
• Gong P, Wang Y, Jing Y. Apoptosis induction by histone deacetylase inhibitors in cancer cells: role of Ku70. Int J Mol Sci. 2019;20(7):1601–1615.
   PubMed Web of Science ®Google Scholar
• Schobert R, Biersack B. Multimodal HDAC inhibitors with improved anticancer activity. Curr Cancer Drug Targets. 2018;18(1):39–56.
   PubMed Web of Science ®Google Scholar
• Yang F, Zhao N, Hu Y, Jiang C-S, Zhang H. The development process: from SAHA to hydroxamate HDAC inhibitors with branched CAP region and linear linker. Chem Biodivers. 2020;17(1):e1900427.
   PubMed Web of Science ®Google Scholar
• Qin HT, Li HQ, Liu F. Selective histone deacetylase small molecule inhibitors: recent progress and perspectives. Expert Opin Ther Pat. 2017;27(5):621–636.
   PubMed Web of Science ®Google Scholar
• Peng X, Sun Z, Kuang P, Chen J. Recent progress on HDAC inhibitors with dual targeting capabilities for cancer treatment. Eur J Med Chem. 2020;208:112831.
   PubMed Web of Science ®Google Scholar
• Schaker HL, Haschemi R, Buch T, Kraft FB, Brumme B, Scholer A, Jenke R, Meiler J, Aigner A, Bendas G, et al. Balancing histone deacetylase (HDAC) inhibition and drug-likeness: biological and physicochemical evaluation of class I selective HDAC inhibitors. ChemMedChem. 2022;17(9):e202100755.
   PubMed Web of Science ®Google Scholar
• Ibrahim HS, Abdelsalam M, Zeyn Y, Zessin M, Mustafa AM, Fischer MA, Zeyen P, Sun P, Bulbul EF, Vecchio A, et al. Synthesis, molecular docking and biological characterization of pyrazine linked 2-aminobenzamides as new class I selective histone deacetylase (HDAC) inhibitors with anti-leukemic activity. Int J Mol Sci. 2021;23(1):369–402.
   PubMed Web of Science ®Google Scholar
• Melesina J, Simoben CV, Praetorius L, Bulbul EF, Robaa D, Sippl W. Strategies to design selective histone deacetylase inhibitors. ChemMedChem. 2021;16(9):1336–1359.
   PubMed Web of Science ®Google Scholar
• Yang F, Zhao N, Ge D, Chen Y. Next-generation of selective histone deacetylase inhibitors. RSC Adv. 2019;9(34):19571–19583.
   PubMed Web of Science ®Google Scholar
• Giannini G, Cabri W, Fattorusso C, Rodriquez M. Histone deacetylase inhibitors in the treatment of cancer: overview and perspectives. Future Med Chem. 2012; 4(11):1439–1460.
   PubMed Web of Science ®Google Scholar
• Wang XX, Wan RZ, Liu ZP. Recent advances in the discovery of potent and selective HDAC6 inhibitors. Eur J Med Chem. 2018;143:1406–1418.
   PubMed Web of Science ®Google Scholar
• Linciano P, Benedetti R, Pinzi L, Russo F, Chianese U, Sorbi C, Altucci L, Rastelli G, Brasili L, Franchini S. Investigation of the effect of different linker chemotypes on the inhibition of histone deacetylases (HDACS). Bioorg Chem. 2021;106:104462.
   PubMed Web of Science ®Google Scholar
• Sangwan R, Rajan R, Mandal PK. HDAC as onco target: reviewing the synthetic approaches with SAR study of their inhibitors. Eur J Med Chem. 2018;158:620–706.
   PubMed Web of Science ®Google Scholar
• Zhang L, Zhang J, Jiang Q, Zhang L, Song W. Zinc binding groups for histone deacetylase inhibitors. J Enzyme Inhib Med Chem. 2018;33(1):714–721.
   PubMed Web of Science ®Google Scholar
• Thaler F, Mercurio C. Towards selective inhibition of histone deacetylase isoforms: what has been achieved, where we are and what will be next. ChemMedChem. 2014;9(3):523–526.
   PubMed Web of Science ®Google Scholar
• Wagner FF, Weїwer M, Lewis MC, Holson EB. Small molecule inhibitors of zinc-dependent histone deacetylases. Neurotherapeutics. 2013;10(4):589–604.
   PubMed Web of Science ®Google Scholar
• Yue K, Qin M, Huang C, James CC, Jiang Y, Li X. Comparison of three zinc binding groups for HDAC inhibitors - a potency, selectivity and enzymatic kinetics study. Bioorg Med Chem Lett. 2022;70:128797.
   PubMed Web of Science ®Google Scholar
• Vaidya GN, Rana P, Venkatesh A, Chatterjee DR, Contractor D, Satpute DP, Nagpure M, Jain A, Kumar D. Paradigm shift of “classical” HDAC inhibitors to “hybrid” HDAC inhibitors in therapeutic interventions. Eur J Med Chem. 2021;209:112844.
   PubMed Web of Science ®Google Scholar
• Zhang Q, Wang Z, Chen X, Qiu H, Gu Y, Wang N, Wang T, Wang Z, Ma H, Zhao Y, et al. 8a, a new acridine antiproliferative and pro-apoptotic agent targeting HDAC1/DNMT1. Int J Mol Sci. 2021;22(11):5516–5532.
   PubMed Web of Science ®Google Scholar
• Zhang B, Zhang QT, Liu ZD, Wang N, Jin HX, Liu F, Zhang C, He S. Synthesis and Anticancer Research of N-(2-aminophenyl) benzamide acridine derivatives as dual topoisomerase i and isoform-selective HDAC inhibitors. Chemistryselect. 2020; 5(27):8311–8318.
   Web of Science ®Google Scholar
• Sharma A, Singh K, Almasan A. Histone H2AX phosphorylation: a marker for DNA damage. Methods Mol Biol. 2012;920:613–626.
   PubMedGoogle Scholar
• Carine R, Feyruz VR. Chapter three - HDAC inhibitors: roles of DNA damage and repair. Adv Cancer Res. 2012;116:87–129.
   PubMed Web of Science ®Google Scholar
• Eto S, Saeki K, Yoshitake R, Yoshimoto S, Shinada M, Ikeda N, Kamoto S, Tanaka Y, Kato D, Maeda S, et al. Anti-tumor effects of the histone deacetylase inhibitor vorinostat on canine urothelial carcinoma cells. Plos One. 2019;14(6):e0218382.
   PubMed Web of Science ®Google Scholar
• Hye YP, Young JL, Taehyung K, Jaewon L, Sungpil Y, Wahnsoo C, Chang-Seon M, Hyungsik K. Effects of trichostatin A, a histone deacetylase inhibitor, on the regulation of apoptosis in H-ras-transformed breast epithelial cells. Int J Mol Med. 2008;22:605–611.
   PubMed Web of Science ®Google Scholar