1,187
Views
2
CrossRef citations to date
0
Altmetric
Research Papers

Triazoloquinoxalines-based DNA intercalators-Topo II inhibitors: design, synthesis, docking, ADMET and anti-proliferative evaluations

ORCID Icon, , , , ORCID Icon, ORCID Icon, ORCID Icon & ORCID Icon show all
Pages 1556-1567 | Received 14 Mar 2022, Accepted 16 May 2022, Published online: 29 May 2022

References

  • Soni A, Khurana P, Singh T, Jayaram B. A DNA intercalation methodology for an efficient prediction of ligand binding pose and energetics. Bioinformatics 2017;33:1556–96.
  • Braña MF, Cacho M, Gradillas A, et al. Intercalators as anticancer drugs. Curr Pharm Des 2001;7:1745–80.
  • Graves DE, Velea LM. Intercalative binding of small molecules to nucleic acids. Curr Org Chem 2000;4:915–29.
  • Goftar MK, Kor NM, Kor ZM. DNA intercalators and using them as anticancer drugs. Int J Adv Biol Biom Res 2014;2:811–22.
  • Strekowski L, Wilson B. Noncovalent interactions with DNA: an overview. Mutat Res 2007;623:3–13.
  • Paul A, Bhattacharya S. Chemistry and biology of DNA-binding small molecules. Curr Sci 2012;102:212–31.
  • El‐Helby AGA, Ayyad RRA, Sakr H, et al. design, synthesis, molecular docking, and anticancer activity of phthalazine derivatives as VEGFR‐2 inhibitors. Archiv Der Pharmazie 2017;350:1700240.
  • Gago F. Stacking interactions and intercalative DNA binding. Methods 1998;14:277–92.
  • C, Avendano J, Menéndez DNA intercalators and topoisomerase inhibitors, medicinal  chemistry of anticancer drugs. 2nd edition, Amsterdam, The Netherlands, Oxford, UK: Elsevier; 2008. 199–228 p.
  • Minotti G, Menna P, Salvatorelli E, et al. Anthracyclines: molecular advances and pharmacologic developments in antitumor activity and cardiotoxicity. Pharmacol Rev 2004;56:185–229.
  • 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;11:114–28.
  • Kumar S, Pandya P, Pandav K, et al. Structural studies on ligand-DNA systems: a robust approach in drug design. J Biosci 2012;37:553–61.
  • Palchaudhuri R, Hergenrother P. DNA as a target for anticancer compounds: methods to determine the mode of binding and the mechanism of action. Curr Opin Biotechnol 2007;18:497–503.
  • Takenaka S, Takagi M. Threading intercalators as a new DNA structural probe. Bull Chem Soc Jpn 1999;72:327–37.
  • Guerra CF, Bickelhaupt FM. WatsonCrick hydrogen bonds: nature and role in DNA replication. Modern Methods Theor Phys Chem Biopolymers 2006;19:79–97.
  • Liu LF. DNA topoisomerase poisons as antitumor drugs. Annu Rev Biochem 1989;58:351–75.
  • Chilin A, Marzaro G, Marzano C, et al. Synthesis and antitumor activity of novel amsacrine analogs: the critical role of the acridine moiety in determining their biological activity. Bioorg Med Chem 2009;17:523–9.
  • Villamon E, Gonzalez-Fernandez J, Such E, et al. Imiquimod inhibits growth and induces differentiation of myeloid leukemia cell lines. Cancer Cell Int 2018;18:15.
  • Moarbess G, Deleuze-Masquefa C, Bonnard V, et al. In vitro and in vivo anti-tumoral activities of imidazo[1,2-a]quinoxaline, imidazo[1,5-a]quinoxaline, and pyrazolo[1,5-a]quinoxaline derivatives. Bioorg Med Chem 2008;16:6601–10.
  • Kaneko D, Ninomiya M, Yoshikawa R, et al. Synthesis of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole derivatives as potent antiproliferative agents via a hybrid pharmacophore approach. Bioorg Chem 2020;104:104293.
  • El-Adl K, El-Helby AA, Sakr H, Elwan A. Design, synthesis, molecular docking and anti-proliferative evaluations of [1,2,4]triazolo[4,3-a]quinoxaline derivatives as DNA intercalators and Topoisomerase II inhibitors. Bioorg Chem 2020;105:104399.
  • El-Adl K, El-Helby AA, Sakr H, Elwan A. [1,2,4]Triazolo[4,3-a]quinoxaline and [1,2,4]triazolo[4,3-a]quinoxaline-1-thiol derived DNA intercalators: design, synthesis, molecular docking, in silico ADMET profile and anti-proliferative evaluations. New J. Chem 2021;45:881–97.
  • Eissa IH, Metwaly AM, Belal A, Mehany ABM, et al. Discovery and antiproliferative evaluation of new quinoxalines as potential DNA intercalators and topoisomerase II inhibitors. Arch Pharm 2019;352:e1900123.
  • Ibrahim MK, Taghour MS, Metwaly AM, et al. Design, synthesis, molecular modeling and anti-proliferative evaluation of novel quinoxaline derivatives as potential DNA intercalators and topoisomerase II inhibitors. Eur J Med Chem 2018;155:117–34.
  • Eissa IH, El-Naggar AM, El-Sattar NEAA, Youssef ASA. Design and discovery of novel quinoxaline derivatives as dual DNA intercalators and topoisomerase II inhibitors. Anticancer Agents Med Chem 2018;18:195–209.
  • Mahata T, Kanungo A, Ganguly S, et al. The benzyl moiety in a quinoxaline-based scaffold acts as a DNA intercalation switch. Angew Chem Int Ed Engl 2016;55:7733–6.
  • Oyallon B, Brachet-Botineau M, Logé C, et al. Structure-based design of novel quinoxaline-2-carboxylic acids and analogues as Pim-1 inhibitors. Eur J Med Chem 2018;154:101–9.
  • Park Y-S, Shin W-S, Kim C-S, et al. Molecular and cellular toxicological profiling of DNA bis-intercalator, quinoxaline compounds: echinomycin as the versatile lead. J. Biochem. Mol. Toxicol 2018;14:9–18.
  • Varrica MG, Zagni C, Mineo PG, et al. DNA intercalators based on (1,10-phenanthrolin-2-yl)isoxazolidin-5-yl core with better growth inhibition and selectivity than cisplatin upon head and neck squamous cells carcinoma. Eur J Med Chem 2018;143:583–90.
  • El‐Adl K, Sakr H, Nasser M, et al. 5‐(4‐Methoxybenzylidene)thiazolidine‐2,4‐dione‐derived VEGFR‐2 inhibitors: design, synthesis, molecular docking, and anticancer evaluations. Arch Pharm 2020;353:e2000079.
  • El-Adl K, El-Helby A-GA, Sakr H, El-Hddad SSA. Design, synthesis, molecular docking, and anticancer evaluations of 1-benzylquinazoline-2,4(1H,3H)-dione bearing different moieties as VEGFR-2 inhibitors. Arch Pharm 2020;353:e2000068.
  • El-Adl K, El-Helby A-GA, Sakr H, et al. Design, synthesis, molecular docking and anticancer evaluations of 5-benzylidenethiazolidine-2,4-dione derivatives targeting VEGFR-2 enzyme. Bioorg Chem 2020;102:104059.
  • El‐Helby A‐GA, Sakr H, Eissa IH, et al. Benzoxazole/benzothiazole‐derived VEGFR‐2 inhibitors: design, synthesis, molecular docking, and anticancer evaluations. Archiv Der Pharmazie 2019;352:1900178.
  • El‐Helby A‐GA, Sakr H, Eissa IH, et al. Design, synthesis, molecular docking, and anticancer activity of benzoxazole derivatives as VEGFR‐2 inhibitors. Archiv Der Pharmazie 2019;352:1900113.
  • El-Helby A-GA, Sakr H, Ayyad RRA, et al. Design, synthesis, in vitro anti-cancer activity, ADMET profile and molecular docking of novel triazolo[3,4-a]phthalazine derivatives targeting VEGFR-2 enzyme. Anti-Cancer Agents Med Chem 2018;18:1184–96.
  • 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 1994;33:11493–500.
  • Alesawy MS, Ibrahim MK, Eissa IH, El‐Adl K. Design, synthesis, in silico ADMET, docking, and antiproliferative evaluations of [1,2,4]triazolo[4,3‐ c] quinazolines as classical DNA intercalators. Arch Pharm 2022;355:e2100412.
  • Eissa IH, Ibrahim MK, Alesawy MS, El‐Adl K. Antiproliferative evaluations of triazoloquinazolines as classical DNA intercalators: design, synthesis, ADMET profile, and molecular docking. Arch Pharm 2022;355:e2100487.
  • El-Adl K, Ibrahim M-K, Alesawy MS, et al. Triazoloquinazoline derived classical DNA intercalators: design, synthesis, in silico ADME profile, docking, and antiproliferative evaluations. Arch Pharm 2022;e2100506.
  • El-Adl K, Ibrahim MK, Alesawy MSI, Eissa IH. [1,2,4]Triazolo[4,3-c]quinazoline and bis([1,2,4]triazolo)[4,3-a:4',3'-c]quinazoline derived DNA intercalators: design, synthesis, in silico ADMET profile, molecular docking and anti-proliferative evaluation studies. Bioorg Med Chem 2021;30:115958.
  • Tan AC, Konczak I, Ramzan I, Sze DM. Native Australian fruit polyphenols inhibit cell viability and induce apoptosis in human cancer cell lines. Nutr Cancer 2011;63:444–55.
  • Sudan S, Rupasinghe HP. Flavonoid-enriched apple fraction AF4 induces cell cycle arrest, DNA topoisomerase II inhibition, and apoptosis in human liver cancer HepG2 cells. Nutr Cancer 2014;66:1237–46.
  • Depowski PL, Rosenthal SI, Brien TP, et al. Topoisomerase IIalpha expression in breast cancer: correlation with outcome variables. Mod Pathol 2000;13:542–7.
  • Kang K, Oh SH, Yun JH, et al. A novel topoisomerase inhibitor, daurinol, suppresses growth of HCT116 cells with low hematological toxicity compared to etoposide. Neoplasia 2011;13:1043–57.
  • Wu CC, Li YC, Wang YR, et al. On the structural basis and design guidelines for type II topoisomerase-targeting anticancer drugs. Nucleic Acids Res 2013;41:10630–40.
  • Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55–63.
  • Scudiero DA, Shoemaker RH, Paull KD, et al. Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines. Cancer Res 1988;48:4827–33.
  • Freimoser FM, Jakob CA, Aebi M, Tuor U. The MTT [3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] assay is a fast and reliable method for colorimetric determination of fungal cell densities. Appl Environ Microbiol 1999;65:3727–9.
  • Soliman AM, Amer AA. Synthesis and antimicrobial activity of some novel quinoxalines. Synthetic Commun Int J Rapid Commun Synthetic Organic Chem 2012;42:1401–10.
  • Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev 1997;23:3–25.
  • Pires DEV, Blundell TL, Ascher DB. pkCSM: predicting small-molecule pharmacokinetic and toxicity properties using graph-based signatures. J Med Chem 2015;58:4066–72.
  • Beig A, Agbaria R, Dahan A. Oral delivery of lipophilic drugs: the tradeoff between solubility increase and permeability decrease when using cyclodextrin-based formulations. PLOS One 2013;8:e68237.