Journals / Ankara Üniversitesi Eczacılık Fakültesi Dergisi / 2020 / Cilt: 44 Sayı: 3

MOLECULAR DOCKING STUDIES ON SOME BENZAMIDE DERIVATIVES AS TOPOISOMERASE INHIBITORS

TOPOİZOMERAZ İNHİBİTÖRLERİ OLARAK BAZI BENZAMİD TÜREVLERİ ÜZERİNDE MOLEKÜLER DOKİNG ÇALIŞMALARI

Serap Yilmaz(TRAKYA ÜNİVERSİTESİ)0000-0002-6458-2658
Sanaz Ataei(ANKARA ÜNİVERSİTESİ)0000-0002-4752-1968
İlkay Yıldız(ANKARA ÜNİVERSİTESİ)0000-0001-9526-0232
Pages
470–480
Publication Date
2020-09-30
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Objective: In order to examine the interactions of some benzamide derivatives, which are thought to exhibit anti-cancer activity, with human Topo I and IIα enzymes at the molecular level, docking studies were carried out on these enzymes.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:Objective: In order to examine the interactions of some benzamide derivatives, which are thought to exhibit anti-cancer activity, with human Topo I and IIα enzymes at the molecular level, docking studies were carried out on these enzymes.
📊
Key Findings & Data:Objective: In order to examine the interactions of some benzamide derivatives, which are thought to exhibit anti-cancer activity, with human Topo I and IIα enzymes at the molecular level, docking studies were carried out on these enzymes.
💡
Conclusion & Impact:Objective: In order to examine the interactions of some benzamide derivatives, which are thought to exhibit anti-cancer activity, with human Topo I and IIα enzymes at the molecular level, docking studies were carried out on these enzymes.
🔬Design:Araştırma Makalesi
📍Scope:Comprehensive Sample
⚙️Variables:Antikanser · Benzamid · Doking

Abstract

Objective: In order to examine the interactions of some benzamide derivatives, which are thought to exhibit anti-cancer activity, with human Topo I and IIα enzymes at the molecular level, docking studies were carried out on these enzymes.

Özet

Amaç: Antikanser aktivite göstereceği düşünülen Bazı benzamid türevlerinin insan Topo I ve IIα enzimleri ile moleküler düzeydeki etkileşimlerinin incelenmesi amacıyla bu enzimler üzerinden doking çalışmaları gerçekleştirilmiştir.

🔖

Cite This Article

Yilmaz, S., Ataei, S., Yıldız, İ. (2020). MOLECULAR DOCKING STUDIES ON SOME BENZAMIDE DERIVATIVES AS TOPOISOMERASE INHIBITORS. Ankara Üniversitesi Eczacılık Fakültesi Dergisi, Cilt: 44 Sayı: 3, 470–480. https://doi.org/10.33483/jfpau.789537

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References (42)

  1. Holden, J.A. (2001). DNA Topoisomerases as anticancer drug targets from the laboratory to the clinic. Current Medicinal Chemistry-Anti-Cancer Agents. 1(1), 1-25.
  2. Topcu, Z. (2001). DNA topoisomerases as targets for anticancer drugs. Journal of clinical pharmacy and therapeutics. 26(6), 405-416.
  3. Wang, J.C. (1996). DNA topoisomerases. Annual review of biochemistry. 65(1), 635-692.
  4. Berger, J.M. (1998). Structure of DNA topoisomerases. Biochimica et Biophysica Acta (BBA)-Gene Structure and Expression. 1400 (1-3), 3-18.
  5. Kaufmann, S.H. (1998). Cell death induced by topoisomerase-targeted drugs: more questions than answers. Biochimica et Biophysica Acta (BBA)-Gene Structure and Expression. 1400 (1-3), 195-211.
  6. Pommier, Y. (1998). Diversity of DNA topoisomerases I and inhibitors. Biochimie. 80(3), 255-270.
  7. Redinbo, M.R., Stewart, L., Kuhn, P., Champoux, J.J., Hol, W.G. (1998). Crystal structures of human topoisomerase I in covalent and noncovalent complexes with DNA. Science. 279 (5356), 1504-1513.
  8. Cowell, I.G., Sondka, Z., Smith, K., Lee, K.C., Manville, C.M., Sidorczuk-Lesthuruge, M., Rance, H.A., Padget, K., Jackson, G.H., Adachi, N. (2012). Model for MLL translocations in therapy-related leukemia involving topoisomerase IIβ-mediated DNA strand breaks and gene proximity. Proceedings of the National Academy of Sciences. 109(23), 8989-8994.
  9. Wang, J.C. (2002). Cellular roles of DNA topoisomerases: a molecular perspective. Nature reviews Molecular cell biology. 3(6), 430-440.
  10. Pommier, Y., Leo, E., Zhang, H., Marchand, C. (2010). DNA topoisomerases and their poisoning by anticancer and antibacterial drugs. Chemistry & biology. 17(5), 421-433.
  11. Giovanella, B.C., Stehlin, J.S., Wall, M.E., Wani, M.C., Nicholas, A.W., Liu, L.F., Silber, R., Potmesil, M. (1989). DNA topoisomerase I--targeted chemotherapy of human colon cancer in xenografts. Science. 246(4933),1046-1048
  12. Husain, I., Mohler, J.L., Seigler, H.F., Besterman, J.M. (1994). Elevation of topoisomerase I messenger RNA, protein, and catalytic activity in human tumors: demonstration of tumor-type specificity and implications for cancer chemotherapy. Cancer research. 54(2), 539-546.
  13. Lima, C.D., Wang, J.C., Mondragón, A. (1994). Three-dimensional structure of the 67K N-terminal fragment of E. coli DNA topoisomerase I. Nature. 367(6459), 138-146.
  14. Garcia-Carbonero, R., Supko, J.G. (2002). Current perspectives on the clinical experience, pharmacology, and continued development of the camptothecins. Clinical Cancer Research. 8(3), 641-661.
  15. Wall, M.E., Wani, M.C., Cook, C., Palmer, K.H., McPhail, A.A., Sim, G. (1966). Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from camptotheca acuminata1, 2. Journal of the American Chemical Society. 88(16), 3888-3890.
  16. Thomas, C.J., Rahier, N.J., Hecht, S.M. (2004). Camptothecin: current perspectives. Bioorganic & medicinal chemistry. 12(7), 1585-1604.
  17. Teicher, B.A. (2008). Next generation topoisomerase I inhibitors: Rationale and biomarker strategies. Biochemical pharmacology. 75(6), 1262-1271.
  18. Nitiss, J.L. (2009). DNA topoisomerase II and its growing repertoire of biological functions. Nature Reviews Cancer. 9(5), 327-337.
  19. Pogorelcnik, B., Perdih, A., Solmajer, T. (2013). Recent advances in the development of catalytic inhibitors of human DNA topoisomerase IIα as novel anticancer agents. Current medicinal chemistry. 20, 694-709.
  20. Schmidt, B.H., Osheroff, N., Berger, J.M. (2012). Structure of a topoisomerase II–DNA–nucleotide complex reveals a new control mechanism for ATPase activity. Nature structural & molecular biology. 19, 1147.
  21. Larsen, A.K., Escargueil, A.E., Skladanowski, A. (2003). Catalytic topoisomerase II inhibitors in cancer therapy. Pharmacology & therapeutics. 99, 167-181.
  22. Farr, C.J., Antoniou-Kourounioti, M., Mimmack, M.L., Volkov, A., Porter, A.C. (2014). The α isoform of topoisomerase II is required for hypercompaction of mitotic chromosomes in human cells. Nucleic acids research. 42, 4414-4426.
  23. Arcy, D. N., Gabrielli, B. (2017). Topoisomerase II inhibitors and poisons, and the influence of cell cycle checkpoints. Current Medicinal Chemistry. 24, 1504-1519.
  24. McClendon, A.K., Rodriguez, A.C., Osheroff, N. (2005). Human topoisomerase IIα rapidly relaxes positively supercoiled DNA implications for enzyme action ahead of replication forks. Journal of Biological Chemistry. 280, 39337-39345.
  25. Hande, K. (1998). Etoposide: four decades of development of a topoisomerase II inhibitor. European journal of cancer. 34, 1514-1521.
  26. Zhang, J., Yang, P.L., Gray, N.S. (2009). Targeting cancer with small molecule kinase inhibitors. Nature Reviews Cancer. 9, 28-39.
  27. Lu, A., Luo, H., Shi, M., Wu, G., Yuan, Y., Liu, J., Tang, F. (2011). Design, synthesis and docking studies on benzamide derivatives as histone deacetylase inhibitors. Bioorganic & medicinal chemistry letters. 21, 4924-4927.
  28. Aboraia, A.S., Yee, S.W., Gomaa, M.S., Shah, N., Robotham, A.C., Makowski, B., Prosser, D., Brancale, A., Jones, G., Simons, C. (2010). Synthesis and CYP24A1 inhibitory activity of N-(2-(1H-imidazol-1-yl)-2-phenylethyl) arylamides. Bioorganic & medicinal chemistry. 18, 4939-4946.
  29. Li, Y., Zhou, Y., Qian, P., Wang, Y., Jiang, F., Yao, Z., Hu, W., Zhao, Y., Li, S. (2013). Design, synthesis and bioevalution of novel benzamides derivatives as HDAC inhibitors. Bioorganic & medicinal chemistry letters. 23, 179-182.
  30. Mao, W., et al., (2012). Design, synthesis, and pharmacological evaluation of benzamide derivatives as glucokinase activators. Bioorganic & medicinal chemistry. 20(9): p. 2982-2991.
  31. Fiorino, F., Eiden, M., Giese, A., Severino, B., Esposito, A., Groschup, M.H., Perissutti, E., Magli, E., Incisivo, G.M., Ciano, A. (2012). Synthesis of benzamide derivatives and their evaluation as antiprion agents. Bioorganic & medicinal chemistry. 20, 5001-5011.
  32. Kamal, A., Suresh, P., Ramaiah, M.J., Srinivasa Reddy, T., Kapavarapu, R.K., Rao, B.N., Imthiajali, S., Lakshminarayan Reddy, T., Pushpavalli, S.N.C.V.L., Shankaraiah, N., Pal-Bhadra, M. (2013). 4β-[4′-(1-(Aryl)ureido)benzamide] podophyllotoxins as DNA topoisomerase I and IIα inhibitors and apoptosis inducing agents. Bioorganic & Medicinal Chemistry. 21, 5198-5208.
  33. Kamal, A., Suresh, P., Ramaiah, M.J., Mallareddy, A., Imthiajali, S., Pushpavalli, S.N.C.V.L., Lavanya, A., Pal-Bhadra, M. (2012). Synthesis and biological evaluation of 4β-sulphonamido and 4β-[(4′-sulphonamido)benzamide]podophyllotoxins as DNA topoisomerase-IIα and apoptosis inducing agents. Bioorganic & Medicinal Chemistry. 20, 2054-2066.
  34. Acar, C., Yalcin, G., Ertan-Bolelli, T., Onurdag, F.K., Okten, S., Sener, F., Yildiz, I. (2020). Synthesis and molecular docking studies of some novel antimicrobial benzamides. Bioorganic Chemistry. 94, 103368.
  35. Wendorff, T.J., Schmidt, B.H., Heslop, P., Austin, C.A., Berger, J.M. (2012). The structure of DNA-bound human topoisomerase II alpha: conformational mechanisms for coordinating inter-subunit interactions with DNA cleavage. Journal of molecular biology. 424, 109-124.
  36. Wang, Y.-R., Chen, S.-F., Wu, C.-C., Liao, Y.-W., Lin, T.-S., Liu, K.-T., Chen, Y.-S., Li, T.-K., Chien, T.-C., Chan, N.-L. (2017). Producing irreversible topoisomerase II-mediated DNA breaks by site-specific Pt (II)-methionine coordination chemistry. Nucleic acids research. 45, 10861-10871.
  37. Accelrys, Discovery Studio 3.5 2012.
  38. Momany, F.A., Rone, R. (1992). Validation of the general purpose QUANTA® 3.2/CHARMm® force field. Journal of Computational Chemistry. 13, 888-900.
  39. Crisfield, M. (1979). A faster modified Newton-Raphson iteration. Computer Methods in Applied Mechanics and Engineering. 20, 267-278.
  40. Wu, G., Robertson, D.H., Brooks III, C.L., Vieth, M. (2003). Detailed analysis of grid‐based molecular docking: A case study of CDOCKER—A CHARMm‐based MD docking algorithm. Journal of computational chemistry. 24, 1549-1562.
  41. Cowell, I.G., Sondka, Z., Smith, K., Lee, K.C., Manville, C.M., Sidorczuk-Lesthuruge, M., Rance, H.A., Padget, K., Jackson, G.H., Adachi, N. (2012). Model for MLL translocations in therapy-related leukemia involving topoisomerase IIβ-mediated DNA strand breaks and gene proximity. Proceedings of the National Academy of Sciences. 109(23), 8989-8994.
  42. Wang, J.C. (2002). Cellular roles of DNA topoisomerases: a molecular perspective. Nature reviews Molecular cell biology. 3(6), 430-440.