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Research Article

Key structural requirements of benzamide derivatives for histone deacetylase inhibition: design, synthesis and biological evaluation

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Pages 859-872 | Received 30 Apr 2023, Accepted 18 Mar 2024, Published online: 16 Apr 2024

References

  • Motofei Ion G. Biology of cancer; from cellular cancerogenesis to supracellular evolution of malignant phenotype. Cancer Invest. 36(5), 309–317 (2018).
  • Takeshima H, Ushijima T. Accumulation of genetic and epigenetic alterations in normal cells and cancer risk. NPJ Precis. Oncol. 3(1), 1–8 (2019).
  • Akram MD, Iqbal M, Daniyal M et al. Awareness and current knowledge of breast cancer. Biol. Res. 50(1), 1–23 (2017).
  • Audia J, Campbell R. Histone modifications and cancer. Csh. Perspect. Biol. 8(4), a019521 (2016).
  • Verza F, Das U, Fachin A et al. Roles of histone deacetylases and inhibitors in anticancer therapy. Cancers 12(6), 1664 (2020).
  • Kozikowski A, Butler K. Chemical origins of isoform selectivity in histone deacetylase inhibitors. Curr. Pharm. Design 14(6), 505–528 (2008).
  • Mottamal M, Zheng SH, Huang Tien L et al. Histone deacetylase inhibitors in clinical studies as templates for new anticancer agents. Molecules 20(3), 3898–3941 (2015).
  • Dai W, Zhou J, Jin B et al. Class III-specific HDAC inhibitor Tenovin-6 induces apoptosis, suppresses migration and eliminates cancer stem cells in uveal melanoma. Sci. Rep. 6(1), 1–14 (2016).
  • Yoon S, Eom G. HDAC and HDAC inhibitor: from cancer to cardiovascular diseases. Chonnam. Med. J. 52(1), 1–11 (2016).
  • Mrakovcic M, Kleinheinz J, Fröhlich L. p53 at the crossroads between different types of HDAC inhibitor-mediated cancer cell death. Inte. J. Mol. Sci. 20(10), 2415 (2019).
  • Hamze A. How do we improve histone deacetylase inhibitor drug discovery? Exp. Opin. Drug. Dis. 15(5), 527–529 (2020).
  • Cheshmazar N, Hamzeh-Mivehroud M, Charoudeh Hojjatollah N et al. Current trends in development of HDAC-based chemotherapeutics. Life Sci. 308, 120946 (2022).
  • Melesina J, Simoben C, Praetorius L et al. Strategies to design selective histone deacetylase inhibitors. Chem. Med. Chem. 16(9), 1336–1359 (2021).
  • Patel V, Shirbhate E, Tiwari P et al. Multi-targeted HDAC inhibitors as anticancer agents: current status and future prospective. Curr. Med. Chem. 30(24), 2762–2795 (2023).
  • He J, Wang S, Liu X et al. Synthesis and biological evaluation of HDAC inhibitors with a novel zinc binding group. Front Chem. 8, 256 (2020).
  • Yao D, Li CH, Jiang J et al. Design, synthesis and biological evaluation of novel HDAC inhibitors with improved pharmacokinetic profile in breast cancer. Eur. J. Med. Chem. 205, 112648 (2020).
  • Nepali K, Liou J. Recent developments in epigenetic cancer therapeutics: clinical advancement and emerging trends. J. Biomed. Sci. 28(1), 1–58 (2021).
  • Stojkovska J, Zvicer J, Milivojević M et al. Validation of a novel perfusion bioreactor system in cancer research. Hem. Ind. 74(3), 187–196 (2020).
  • Cheshmazar N, Hemmati S, Hamzeh-Mivehroud M et al. Development of new inhibitors of HDAC1-3 Enzymes aided by in silico design strategies. J. Chem. Inf. Model. 62(10), 2387–2397 (2022).
  • Marek M, Shaik T, Heimburg T et al. Characterization of histone deacetylase 8 (HDAC8) selective inhibition reveals specific active site structural and functional determinants. J. Med. Chem. 61(22), 10000–10016 (2018).
  • Zessin M, Kutil Z, Meleshin M et al. One-atom substitution enables direct and continuous monitoring of histone deacylase activity. Biochemistry 58(48), 4777–4789 (2019).
  • Heimburg T, Kolbinger F, Zeyen P et al. Structure-based design and biological characterization of selective histone deacetylase 8 (HDAC8) inhibitors with anti-neuroblastoma activity. J. Med. Chem. 60(24), 10188–10204 (2017).
  • Mosdam T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxic assay. J. Immunol. Methods 65, 55–63 (1983).
  • Liu T, Wan Y, Xiao Y et al. Dual-target inhibitors based on HDACs: novel antitumor agents for cancer therapy. J. Med. Chem. 63(17), 8977–9002 (2020).
  • Finnin M, Donigian J, Cohen A et al. Structures of a histone deacetylase homologue bound to the TSA and SAHA inhibitors. Nature 401(6749), 188–193 (1999).
  • Gfeller D, Grosdidier A, Wirth M et al. SwissTargetPrediction: a web server for target prediction of bioactive small molecules. Nucleic. Acids Res. 42(W1), W32–W38 (2014).
  • Hu J, Wang Y, Li Y et al. Structure-based optimization of a series of selective BET inhibitors containing aniline or indoline groups. Eur. J. Med. Chem. 150, 156–175 (2018).
  • Bressi J, Jennings A, Skene R et al. Exploration of the HDAC2 foot pocket: synthesis and SAR of substituted N-(2-aminophenyl) benzamides. Bioorg. Med. Chem. Lett. 20(10), 3142–3145 (2010).
  • Vannini A, Volpari C, Filocamo G et al. Crystal structure of a eukaryotic zinc-dependent histone deacetylase, human HDAC8, complexed with a hydroxamic acid inhibitor. Proc. Natl Acad. Sci. USA 101(42), 15064–15069 (2004).
  • Molsoft L. Drug-Likeness and molecular property prediction (2018). www.molsoft.com/mprop/
  • Ghose A, Viswanadhan V, Wendoloski J. A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases. J. Comb. Chem. 1(1), 55–68 (1999).
  • Veber D, Johnson S, Cheng H et al. Molecular properties that influence the oral bioavailability of drug candidates. J. Med. Chem. 45(12), 2615–2623 (2002).
  • Egan W, Merz K, Baldwin JJ. Prediction of drug absorption using multivariate statistics. J. Med. Chem. 43(21), 3867–3877 (2000).
  • Muegge I, Heald S, Brittelli D. Simple selection criteria for drug-like chemical matter. J. Med. Chem. 44(12), 1841–1846 (2001).

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