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Experimental biological studies of novel tetradentate hydrazone Cu(II) complexes for potential applications in medicinal chemistry

Authors

  • Cansu Topkaya Muğla Sıtkı Koçman University

DOI:

https://doi.org/10.20450/mjcce.2024.2751

Keywords:

heterocyclic compounds, copper (II) complexes, DNA binding, DNA cleavage

Abstract

A series of mononuclear Cu(II) complexes were synthesized using a potential tetradentate hydrazone ligand obtained from the reaction between phenylhydrazine groups and 2,5-thiophenedicarboxaldehyde. The structures of ligands and complexes were elucidated through various spectroscopic techniques, confirming their composition. All complexes were found to adopt four-coordinated geometries, indicating the formation of stable structures. Spectroscopic analysis revealed that the hydrazone ligand coordinated with the Cu(II) metal ions as a dibasic tetradentate ligand by utilizing the phenolic oxygen and azomethine nitrogen atoms. The binding affinity of the complexes with calf thymus DNA (CT-DNA) was investigated using absorption and viscosity measurements, demonstrating their interaction through the intercalation mode. The binding studies showed that the Cu(II) complexes exhibited varying degrees of binding affinity, with Cu(L4) demonstrating the highest affinity, followed by Cu(L1), Cu(L2), and Cu(L3). Moreover, the DNA fragmentation properties of the Cu(II) complexes were evaluated, suggesting their potential utilization in pharmaceutical applications. The obtained results highlight the significance of these novel complexes in the field of medicinal chemistry.

References

(1) Martorana, A.; Gentile, C.; Perricone, U.; Piccionello, A. P.; Bartolotta, R.; Terenzi, A.; Lauria, A., Synthesis, antiproliferative activity, and in silico insights of new 3-benzoylamino-benzo[b]thiophene derivatives. Eur. J. Med. Chem. 2015, 90, 537–542.

(2) Dua, R.; Shrivastava, S.; Sonwane, S. K.; Srivastava, S. K., Pharmacological significance of synthetic heter-ocycles scaffold: a review. Adv. Biol. Researc. 2011, 5(3), 120–137.

(3) Pathania, S.; Chawla, P. A., Thiophene-based deriva-tives as anticancer agents: An overview on decade's work. Bioorg. Chem. 2020, 101, 104026.

(4) Zemede, Y. B.; Kumar, A., Synthesis, characterization, corrosion inhibition and biological evaluation of schiff bases. Int. J. Chem. Tech. Res. 2015, 7(1), 279–289.

(5) Dhorajiya, B. D.; Ibrahim, A. S.; Badria, F. A.; Dholakiya, B. Z., Design and synthesis of novel nu-cleobase-based barbiturate derivatives as potential an-ticancer agents. Med. Chem. Res. 2014, 23, 839–849.

(6) Kırkan, B.; Güp, R., Synthesis of new azo dyes and copper(II) complexes derived from barbituric acid and 4-aminobenzoylhydrazone. Turk. J. Chem. 2008, 32(1), 9–19.

(7) Güp, R.; Kırkan, B., Synthesis and spectroscopic stud-ies of copper(II) and nickel(II) complexes containing hydrazonic ligands and heterocyclic coligand. Spec-trochim. Acta A. 2005, 62(4–5), 1188–1197.

(8) Dilek, N.; Güneş, B.; Büyükgüngör, O.; Güp, R., Crys-tal structure of bis(isothiocyanato)[2,6-diacetylpyridine bis(4-hydroxybenzoylhydrazone)] Fe(III) chloride bis(dimethylformamide) solvate. Crys-tallogr. Rep. 2013, 58, 98–104.

(9) Göktürk, T.; Topkaya, C.; Sakallı Çetin, E.; Güp, R., New trinuclear nickel(II) complexes as potential topoi-somerase I/IIα inhibitors: in vitro DNA binding, cleav-age and cytotoxicity against human cancer cell lines. Chem. Pap. 2022, 76, 1–12.

(10) Topkaya, C. G.; Göktürk, T.; Hökelek, T.; Çetin, E. S.; Kıncal, S.; Güp, R., In vitro DNA interaction, topoi-somerase I/II inhibition and cytotoxic properties of polymeric copper(II) complex bridged with perchlo-rate ion containing N4-type schiff base ligand. J. Mol. Struct. 2022, 1266, 133453.

(11) Güp, R.; Erer, O.; Dilek, N., One-pot synthesis of a new 2-substituted 1,2,3-triazole 1-oxide derivative from dipyridyl ketone and isonitrosoacetophenone hydrazone: nickel(II) complex, DNA binding and cleavage properties. Bioorg. Chem. 2017, 71, 325–333.

(12) Saleem, M.; Sharma, M.; Mahajan, S.; Sheikh, H. N.; Kalsotra, B. L., Synthesis and characterization of group-6 metal carbonyl complexes of aroyl hydrazone derivatives. E-J. Chem. 2012, 9(2), 807–815.

(13) Abdel Aziz, A. A.; Seda, S. H., Synthesis, spectral characterization, SEM, antimicrobial, antioxidative ac-tivity evaluation, DNA binding and DNA cleavage in-vestigation of transition metal(II) complexes derived from a tetradentate Schiff base bearing thiophene moiety. J. Fluoresc. 2017, 27(3), 1051–1062.

(14) Gök, Y.; Bekaroglu, Ö., The synthesis and complex formatirn of stererisomers of some new α-dioximes. Synth. React. Inorg. Met. 1981, 11(7), 621–634.

(15) Güp, R.; Kırkan, B. Synthesis and spectroscopic stud-ies of mixed-ligand and polymeric dinuclear transition metal complexes with bis-acylhydrazone tetradentate ligands and 1,10-phenanthroline. Spectrochim. Acta A. 2006, 64(3), 809–818.

(16) Rathi, P.; Singh, D. P., Synthesis, antimicrobial, anti-oxidant and molecular docking studies of thiophene based macrocyclic Schiff base complexes. J. Mol. Struct. 2015, 1100, 208–219.

(17) Satyanarayan, S.; Dabrowiak, J. C.; Chaires, B., Tris(phenanthroline) ruthenium(II) enantiomer interac-tions with DNA: mode and specificity of binding. Bio-chem. 1993, 32, 2573–2584.

(18) Satyanarayan, S.; Dabrowiak, J. C.; Chaires, B., Nei-ther Δ-nor-λ-tris(phenanthroline) ruthenium(II) binds to DNA by classical intercalation. Biochem. 1992, 31(39), 9319–9324.

(19) Güp, R.; Gökçe, C.; Aktürk, S., Copper(II) complexes with 4-hydroxyacetophenone-derived acylhydrazones: synthesis, characterization, DNA binding and cleavage properties. Spectrochim. Acta A. 2015, 134, 484–491.

(20) Ozawa, T.; Hanaki, A.; Onodera, K., Spectroscopic studies on the production of hydroxyl radicals from the reactions of copper(II) polyamine-n-polycarboxylate complexes with hydrogen peroxide. Polyhedron, 1992, 11(7), 735–739.

(21) Raman, N.; Pothiraj, K.; Baskaran, T., DNA interac-tion, antimicrobial, electrochemical and spectroscopic studies of metal(II) complexes with tridentate hetero-cyclic Schiff base derived from 2′-methylacetoacetanilide. J. Mol. Struct. 2011, 1000 (1–3), 135–144.

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Published

2024-04-22 — Updated on 2024-04-23

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How to Cite

Topkaya, C. (2024). Experimental biological studies of novel tetradentate hydrazone Cu(II) complexes for potential applications in medicinal chemistry. Macedonian Journal of Chemistry and Chemical Engineering, 43(1). https://doi.org/10.20450/mjcce.2024.2751 (Original work published April 22, 2024)

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Section

Inorganic Chemistry