1,748
Views
10
CrossRef citations to date
0
Altmetric
Research Paper

Design and synthesis of novel rigid dibenzo[b,f]azepines through ring closure technique as promising anticancer candidates against leukaemia and acting as selective topoisomerase II inhibitors and DNA intercalators

ORCID Icon, , ORCID Icon, ORCID Icon, , , , ORCID Icon & ORCID Icon show all
Article: 2157825 | Received 24 Sep 2022, Accepted 07 Dec 2022, Published online: 11 Jan 2023

References

  • Martínez-Jiménez F, Muiños F, Sentís I, Deu-Pons J, Reyes-Salazar I, Arnedo-Pac C, Mularoni L, Pich O, Bonet J, Kranas H, et al. A compendium of mutational cancer driver genes. Nat Rev Cancer. 2020;20(10):555–572.
  • Hammoud MM, Khattab M, Abdel-Motaal M, Van der Eycken J, Alnajjar R, Abulkhair H, Al‐Karmalawy AA. Synthesis, structural characterization, DFT calculations, molecular docking, and molecular dynamics simulations of a novel ferrocene derivative to unravel its potential antitumor activity. J Biomol Struct Dyn. 2022;1–18.
  • Ezz Eldin RR, Al-Karmalawy AA, Alotaibi MH, Saleh MA. Quinoxaline derivatives as a promising scaffold for breast cancer treatment. New J Chem. 2022;46 (21):9975–9984.
  • Hornberg JJ, Bruggeman FJ, Westerhoff HV, Lankelma J. Cancer: a systems biology disease. Biosystems. 2006;83 (2-3):81–90.
  • Bray F, Ferlay J, Soerjomataram I, Siegel RL, Torre LA, Jemal A. Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J Clin. 2018;68(6):394–424.
  • Rahib L, Smith BD, Aizenberg R, Rosenzweig AB, Fleshman JM, Matrisian LM. Projecting cancer incidence and deaths to 2030: the unexpected burden of thyroid, liver, and pancreas cancers in the United States. Cancer Res. 2014;74(11):2913–2921.
  • Avendaño C, Menendez JC. Medicinal chemistry of anticancer drugs. Amsterdam, Netherlands: Elsevier; 2015.
  • Elshal M, Eid N, El-Sayed I, El-Sayed W, Al-Karmalawy AA. Concanavalin-A shows synergistic cytotoxicity with tamoxifen via inducing apoptosis in estrogen receptor-positive breast cancer: in vitro and molecular docking studies. Pharm Sci. 2021;28(1):76–85.
  • Elmaaty AA, Darwish KM, Chrouda A, Boseila AA, Tantawy MA, Elhady SS, Shaik AB, Mustafa M, Al-Karmalawy AA. In silico and in vitro studies for benzimidazole anthelmintics repurposing as VEGFR-2 antagonists: novel mebendazole-loaded mixed micelles with enhanced dissolution and anticancer activity. ACS Omega. 2022;7(1):875–899.
  • Ma C, Taghour MS, Belal A, Mehany AB, Mostafa N, Nabeeh A, Eissa IH, Al-Karmalawy AA. Design and synthesis of new quinoxaline derivatives as potential histone deacetylase inhibitors targeting hepatocellular carcinoma: in silico, in vitro, and SAR studies. Front Chem. 2021;9:725135.
  • Read AF, Day T, Huijben S. The evolution of drug resistance and the curious orthodoxy of aggressive chemotherapy. Proc Natl Acad Sci USA. 2011;108(supplement_2):10871–10877.
  • Mokhtari RB, Homayouni TS, Baluch N, Morgatskaya E, Kumar S, Das B, Yeger H. Combination therapy in combating cancer. Oncotarget. 2017;8(23):38022–38043.
  • Anighoro A, Bajorath J, Rastelli G. Polypharmacology: challenges and opportunities in drug discovery: miniperspective. J Med Chem. 2014;57(19):7874–7887.
  • Blagosklonny MV. Overcoming limitations of natural anticancer drugs by combining with artificial agents. Trends Pharmacol Sci. 2005;26(2):77–81.
  • Goodsell D, Dickerson RE. Isohelical analysis of DNA groove-binding drugs. J Med Chem. 1986;29(5):727–733.
  • Hammoud MM, Nageeb AS, Morsi MA, Gomaa EA, Elmaaty AA, Al-Karmalawy AA. Design, synthesis, biological evaluation, and SAR studies of novel cyclopentaquinoline derivatives as DNA intercalators, topoisomerase II inhibitors, and apoptotic inducers. New J Chem. 2022;46(23):11422–11436.
  • El-Helby A-GA, Sakr H, Ayyad RR, Mahdy HA, Khalifa MM, Belal A, Rashed M, El-Sharkawy A, Metwaly AM, Elhendawy MA, et al. Design, synthesis, molecular modeling, in vivo studies and anticancer activity evaluation of new phthalazine derivatives as potential DNA intercalators and topoisomerase II inhibitors. Bioorg Chem. 2020;103:104233.
  • Alesawy MS, Al‐Karmalawy AA, Elkaeed EB, Alswah M, Belal A, Taghour MS, Eissa IH. Design and discovery of new 1, 2, 4‐triazolo [4, 3‐c] quinazolines as potential DNA intercalators and topoisomerase II inhibitors. Arch Pharm. 2021;354(3):2000237.
  • Wheate NJ, Brodie CR, Collins JG, Kemp S, Aldrich-Wright JR. DNA intercalators in cancer therapy: organic and inorganic drugs and their spectroscopic tools of analysis. Mini Rev Med Chem. 2007;7(6):627–648.
  • Nitiss JL. DNA topoisomerase II and its growing repertoire of biological functions. Nat Rev Cancer. 2009;9(5):327–337.
  • Wang JC. Cellular roles of DNA topoisomerases: a molecular perspective. Nat Rev Mol Cell Biol. 2002;3(6):430–440.
  • Champoux JJ. DNA topoisomerases: structure, function, and mechanism. Annu Rev Biochem. 2001;70(1):369–413.
  • Kellner U, Sehested M, Jensen PB, Gieseler F, Rudolph P. Culprit and victim–DNA topoisomerase II. Lancet Oncol. 2002;3(4):235–243.
  • Attia EZ, Khalifa BA, Shaban GM, Amin MN, Akil L, Khadra I, Karmalawy AAA, Alnajjar R, Zaki MYW, Aly OM, et al. Potential topoisomerases inhibitors from Asergillus terreus using virtual screening. S Afr J Bot. 2022;149:632–645.
  • Khalifa MM, Al-Karmalawy AA, Elkaeed EB, Nafie MS, Tantawy MA, Eissa IH, Mahdy HA. Topo II inhibition and DNA intercalation by new phthalazine-based derivatives as potent anticancer agents: design, synthesis, anti-proliferative, docking, and in vivo studies. J Enzyme Inhib Med Chem. 2022;37(1):299–314.
  • Ghanem A, Emara HA, Muawia S, Abd El Maksoud AI, Al-Karmalawy AA, Elshal MF. Tanshinone IIA synergistically enhances the antitumor activity of doxorubicin by interfering with the PI3K/AKT/mTOR pathway and inhibition of topoisomerase II: in vitro and molecular docking studies. New J Chem. 2020;44(40):17374–17381.
  • Avendaño C, Menéndez J. Medicinal chemistry of anticancer drugs. Amsterdam, Netherlands: Elsevier; 2015. p. 133–195.
  • Gallego J, Ortiz AR, de Pascual-Teresa B, Gago F. Structure–affinity relationships for the binding of actinomycin D to DNA. J Comput Aided Mol Des. 1997;11(2):114–128.
  • Bailey SA, Graves DE, Rill R. Binding of actinomycin D to the T (G) nT motif of double-stranded DNA: determination of the guanine requirement in nonclassical, non-GpC binding sites. Biochemistry (Mosc). 1994;33(38):11493–11500.
  • David-Cordonnier M-H, Hildebrand M-P, Baldeyrou B, Lansiaux A, Keuser C, Benzschawel K, Lemster T, Pindur U. Design, synthesis and biological evaluation of new oligopyrrole carboxamides linked with tricyclic DNA-intercalators as potential DNA ligands or topoisomerase inhibitors. Eur J Med Chem. 2007;42(6):752–771.
  • Rao AS, Vardhan MV, Reddy NS, Reddy TS, Shaik SP, Bagul C, Kamal A. Synthesis and biological evaluation of imidazopyridinyl-1, 3, 4-oxadiazole conjugates as apoptosis inducers and topoisomerase IIα inhibitors. Bioorg Chem. 2016;69:7–19.
  • Claveria-Gimeno R, Vega S, Abian O, Velazquez-Campoy A. A look at ligand binding thermodynamics in drug discovery. Expert Opin Drug Discov. 2017;12(4):363–377.
  • Schindler W, Blattner H. Über Derivate des Iminodibenzyls Iminostilben-Derivate. HCA. 1961;44(3):753–762.
  • Bhatt PV, Patel PM. Synthesis of 5H-dibenzo(b,f)azepine-5-carboxylic acid [3-chloro-2-(substitutedphenyl)-4-oxoazetidin-1-yl]amide from 5H-dibenzo(b,f) azepine-5-carbonyl chloride. Indian J Chem Sect B. 2005;44B:2082–2086.
  • Shoemaker RH. The NCI60 human tumour cell line anticancer drug screen. Nat Rev Cancer. 2006;6(10):813–823.
  • Patra N, De U, Kang J-A, Kim JM, Ahn MY, Lee J, Jung JH, Chung HY, Moon HR, Kim HS. A novel epoxypropoxy flavonoid derivative and topoisomerase II inhibitor, MHY336, induces apoptosis in prostate cancer cells. Eur J Pharmacol. 2011;658(2-3):98–107.
  • Denizot F, Lang R. Rapid colorimetric assay for cell growth and survival: modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J Immunol Methods. 1986;89(2):271–277.
  • Al-Warhi T, Abo-Ashour MF, Almahli H, Alotaibi OJ, Al-Sanea MM, Al-Ansary GH, Ahmed HY, Elaasser MM, Eldehna WM, Abdel-Aziz HA. Novel [(N-alkyl-3-indolylmethylene)hydrazono]oxindoles arrest cell cycle and induce cell apoptosis by inhibiting CDK2 and Bcl-2: synthesis, biological evaluation and in silico studies. J Enzyme Inhib Med Chem. 2020;35(1):1300–1309.
  • Lo KK-W, Lee TK-M, Lau JS-Y, Poon W-L, Cheng S-H. Luminescent biological probes derived from ruthenium (II) estradiol polypyridine complexes. Inorg Chem. 2008;47(1):200–208.
  • Accelrys Discovery Studio. Accelrys Discovery Studio Visualizer 2.1. San Diego, CA, USA: Accelrys; 2008.
  • Yuan S, Chan HS, Hu Z. Using PyMOL as a platform for computational drug design. Wiley Interdiscip Rev Comput Mol Sci. 2017;7(2):e1298.
  • Khattab M, Al-Karmalawy AA. Computational repurposing of benzimidazole anthelmintic drugs as potential colchicine binding site inhibitors. Future Med Chem. 2021;13(19):1623–1638.
  • Mahmoud DB, Ismail WM, Moatasim Y, Kutkat O, ElMeshad AN, Ezzat SM, El Deeb KS, El-Fishawy AM, Gomaa MR, Kandeil A, et al. Delineating a potent antiviral activity of Cuphea ignea extract loaded nano-formulation against SARS-CoV-2: In silico and in vitro studies. J Drug Deliv Sci Technol. 2021;66:102845.
  • Elebeedy D, Badawy I, Elmaaty AA, Saleh MM, Kandeil A, Ghanem A, Kutkat O, Alnajjar R, Abd El Maksoud AI, Al-Karmalawy AA. In vitro and computational insights revealing the potential inhibitory effect of Tanshinone IIA against influenza A virus. Comput Biol Med. 2022;141:105149.
  • Hammouda MM, Elmaaty AA, Nafie MS, Abdel-Motaal M, Mohamed NS, Tantawy MA, Belal A, Alnajjar R, Eldehna WM, Al‐Karmalawy AA Design and synthesis of novel benzoazoninone derivatives as potential CBSIs and apoptotic inducers: In Vitro, in Vivo, molecular docking, molecular dynamics, and SAR studies. Bioorg Chem. 2022;127:105995.
  • Daina A, Michielin O, Zoete V. SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci Rep. 2017;7(1):42717.
  • Raoa GK, Kaur R, Pai PS. Synthesis and biological evaluation of dibenzo[b,f]azepine-5-carboxylic acid[1-(substituted-phenyl)-ethylidene]-hydrazides. Der Pharma Chemica. 2011;3(3):323–329.
  • Augustine JK, Vairaperumal V, Narasimhan S, Alagarsamy P, Radhakrishnan A. Propylphosphonic anhydride (T3P®): an efficient reagent for the one-pot synthesis of 1,2,4-oxadiazoles, 1,3,4-oxadiazoles, and 1,3,4-thiadiazoles. Tetrahedron. 2009;65(48):9989–9996.
  • ElZahabi HS, Nafie MS, Osman D, Elghazawy NH, Soliman DH, El-Helby AAH, Arafa RK. Design, synthesis and evaluation of new quinazolin-4-one derivatives as apoptotic enhancers and autophagy inhibitors with potent antitumor activity. Eur J Med Chem. 2021;222:113609.
  • Boraei AT, Eltamany EH, Ali IA, Gebriel SM, Nafie MS. Synthesis of new substituted pyridine derivatives as potent anti-liver cancer agents through apoptosis induction: In vitro, in vivo, and in silico integrated approaches. Bioorg Chem. 2021;111:104877.