Synthesis of Cinnamoylhydroxamic Acid Derivatives Bearing Sulfonamide, Amide Bonds as Connecting Unit Targeting Histone Deacetylases
Main Article Content
Abstract
Based on the strong activity of belinostat, the study synthesized of some cinnamoylhydroxamic acid derivatives with the aim of creating new compounds that have the potential to selectively inhibit HDAC to contribute to cancer treatment. N-hydroxycinnamamide serves as both ZBG and the linker group. The derivatives orient to the HDAC2 and HDAC8 enzymes by molecular docking. Compound 9a (bearing sulfonamide) exhibited as the most potential candidate to inhibit the function of HDAC2 enzyme.
Keywords:
Cancer, histone deacetylase, hydroxamic acid, sulfonamide.*
References
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[4] T. Kouzarides, Histone Acetylases and Deacetylases in Cell Proliferation, Current Opinion in Genetics and Development, Vol. 9, 1999, pp. 40-48.
[5] P. A. Marks, R. Breslow, Dimethyl Sulfoxide to Vorinostat: Development of This Histone Deacetylase Inhibitor as An Anticancer Drug, Nature Biotechnology, Vol. 25, pp. 84-90.
[6] H. M. Prince, M. Dickinson, A. Khot, Romidepsin for Cutaneous T-Cell Lymphoma, Future Oncology, Vol. 9, 2013, pp. 1819-1827.
[7] H. Z. Lee, V. E. Kwitkowski, P. L. Del Valle et al., FDA Approval: Belinostat for The Treatment of Patients With Relapsed or Refractory Peripheral T-cell Lymphoma, Clinical Cancer Research, Vol. 21, 2015, pp. 2666-2670.
[8] K. P. G. Jones, Panobinostat: First Global Approval, Drugs, Vol. 75, 2015, pp. 695-704.
[9] F. Angeletti, G. Fossati, A. Pattarozzi et al., Inhibition of the Autophagy Pathway Synergistically Potentiates the Cytotoxic Activity of Givinostat (ITF2357) on Human Glioblastoma Cancer Stem Cells, Frontiers in Molecular Neuroscience, Vol. 9, 2016, pp. 107.
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[11] H. Rajak, A. Singh, K. Raghuwanshi et al., A Structural Insight Into Hydroxamic Acid Based Histone Deacetylase Inhibitors for The Presence of Anticancer Activity, Current Medicinal Chemistry, No. 21, 2014, pp. 2642-2664.
[12] Y. Zhang, P. Yang, C. J. Chou et al., Development of N-Hydroxycinnamamide-Based Histone Deacetylase Inhibitors With an Indole-Containing Cap Group, ACS Medicinal Chemistry Letters, Vol. 4, 2013, pp. 235-238.
[13] X. Li, E. S. Inks et al., Discovery of the First N-Hydroxycinnamamide-Based Histone Deacetylase 1/3 Dual Inhibitors With Potent Oral Antitumor Activity, Journal of Medicinal Chemistry, Vol. 57, 2014, pp. 3324-3341.
[14] S. Tu, H. Yuan, J. Hu, Design, Synthesis and Biological Evaluation of Nitro Oxide Donating
N-Hydroxycinnamamide Derivatives as Histone Deacetylase Inhibitors, Chemical and Pharmaceutical Bulletin, Vol. 62, 2014, pp. 1185-1191.
[15] N. Q. Cuong, T. Q. De et al., Design, Synthesis and Evaluation of Belinostat Analogues Targeting Histone Deacetylase (HDAC) Enzymes In Silico, Can Tho University Journal of Science, Vol. 56, 2020, pp. 1-9.
[16] N. Q. Cuong., D. H. Phuc, B. T. B. Hue, N. T. Tuan, T. T. Men, T. Q. De, Synthesis and Evaluation of Biological Activities of Two Belinostat Analogs Bearing Fluorine at The CAP, VNUHCM Journal of Natural Sciences, Vol. 7, 2023, pp. 2522-2531.
[17] H. P. Nguyen, T. Q. De, N. Q. Cuong, T. P. Hoa, T. D. Binh, H. N. Thao, S. G. Yang, Anti-Multiple Myeloma Potential of Resynthesized Belinostat Derivatives: An Experimental Study on Cytotoxic Activity, Drug Combination, and Docking Studies, RSC Advances, Vol. 12, 2022, pp. 22108-22118.
[18] P. H. Nguyen, B. T. B. Hue, M. Q. Pham, T. P. Hoa, T. Q. De, H. Jung, S. G. Yang, Novel Histone Deacetylase 6 Inhibitors Using Benzimidazole as Caps for Cancer Treatment, New Journal of Chemistry, Vol. 47, 2023,
pp. 7622-7631.
[19] N. H. Ngoc, N. Q. Cuong, K. A. T. Vo, T. T. T. Nguyen, D. T. Nghiem, N. T. Ha, Q. L. Dang, Insight Into the Role of Phytoalexin Naringenin and Phytohormone Abscisic Acid in Defense Against Phytopathogens Phytophthora Infestans and Magnaporthe Oryzae: In Vitro and in Silico Approaches, Physiological and Molecular Plant Pathology, Vol. 127, 2023, pp. 102123.