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Template synthesis, DNA binding, antimicrobial activity, Hirshfeld surface analysis, and 1D helical supramolecular structure of a novel binuclear copper(ii) Schiff base complex.

ABSTRACT: A new binuclear copper(ii) Schiff base complex [Cu₂ L₂ ^- (NO₃)₂]·2CH₃OH (1) [L = 2,6-bis((E)-(p-tolylimino)methyl)-4-methoxyphenol] was synthesized using a template method in which the tridentate N₂O Schiff base ligand was derived from [1 + 2] condensation of 2,6-diformyl-4-methoxyphenol and p-methyl aniline in the presence of copper(ii) ions as the template agent. The X-ray diffraction analyses revealed that this complex crystallizes in the monoclinic system with space group P2₁/n. The most remarkable structural feature of 1 is that it contains two types of 1D right-handed helical chains. The molecules are linked by intermolecular hydrogen bonds and π⋯π interactions, then a 3D supramolecular network was constructed. Moreover, the intermolecular interactions on the crystal packing of 1 have been further studied using Hirshfeld surface analysis and corresponding 2D fingerprint plots. Binding interaction of this complex with calf thymus DNA (CT-DNA) has been investigated using absorption and emission studies, viscosity experiments and circular dichroism studies. Complex 1 shows significant binding to the DNA. The results of fluorescence spectroscopy and UV absorption spectroscopy, CD spectroscopy and viscosity indicated that this complex interacted with CT-DNA in a groove binding mode where the binding constant was 1.3 ± 0.2 × 10⁴ L mol^-1. Our fluorimeteric study showed that the reaction between 1 and CT-DNA was exothermic (ΔH = 59.6 kJ mol^-1; ΔS = 268.79 J mol^-1 K^-1). Antibacterial activities of the complex were screened by the disc diffusion method against three Gram-positive bacteria (Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 23212 and S. epidermidis ATCC 34384), and three Gram-negative bacteria (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853 and Klebsiella pneumonia ATCC 70063). The results indicated that this complex demonstrated acceptable antibacterial activities.

SUBMITTER: Goudarziafshar H

PROVIDER: S-EPMC9069724 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature

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Template synthesis, DNA binding, antimicrobial activity, Hirshfeld surface analysis, and 1D helical supramolecular structure of a novel binuclear copper(ii) Schiff base complex.

Goudarziafshar Hamid H Yousefi Somaieh S Abbasi Tyula Yunes Y Dušek Michal M Eigner Václav V

RSC advances 20220505 22

A new binuclear copper(ii) Schiff base complex [Cu2 L2 - (NO3)2]·2CH3OH (1) [L = 2,6-bis((E)-(p-tolylimino)methyl)-4-methoxyphenol] was synthesized using a template method in which the tridentate N2O Schiff base ligand was derived from [1 + 2] condensation of 2,6-diformyl-4-methoxyphenol and p-methyl aniline in the presence of copper(ii) ions as the template agent. The X-ray diffraction analy ...[more]

PMID: 35530396

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Project description:A series of Schiff bases (3.a-f) bearing benzimidazole moiety was successfully synthesized in ethanol by refluxing Oct-2-ynoic acid (1,3-dihydrobenzimidazole-2-ylidene)amide with substituted amines. Fourier transform infrared (FTIR), ultra violet light (UV-VIS), elemental analysis, proton (1H) and carbon (13C) nuclear magnetic resonance spectroscopy were used to characterize the newly synthesized Schiff bases. Micro dilution method was used to determine the minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) of the Schiff bases, against 14 human pathogenic bacteria (8 Gram negative and 6 Gram positive) and against 7 fungal strains (5 Aspergillus and 2 Fusarium) representatives. Antimalarial activity against Plasmodium falciparum and antitrypanosomal property against Trypanosoma brucei was studied in vitro at a single dose concentration of the Schiff bases. Cytotoxicity of the Schiff bases was assessed against human cervix adenocarcinoma (HeLa) cells. Results obtained show that the newly synthesized Schiff bases are very potent antimicrobial agents. Gram negative bacteria Klebsiella pneumonia and Escherichia coli were more affected on exposure to Compounds 3.c-f (MIC 7.8 µg/mL) which in turn exhibited more antibacterial potency than nalidixic acid reference drug that displayed MICs between 64 and 512 µg/mL against K. pneumonia and E. coli respectively. The test compounds also demonstrated high cytotoxic effect against Aspergillus flavus and Aspergillus carbonarius as they displayed MFC 7.8 and 15.6 µg/mL. Compound 3.c exhibited the highest fungicidal property from this series with MFC alternating between 7.8 and 15.6 µg/mL against the investigated strains. The malarial activity revealed Compounds 3.c and 3.d as the more potent antiplasmodial compounds in this group exhibiting 95% and 85% growth inhibition respectively. The IC50 of Compounds 3.c and 3.d were determined and found to be IC50 26.96 and 28.31 µg/mL respectively. Compound 3.a was the most cytotoxic agent against HeLa cells in this group with 48% cell growth inhibition. Compounds 3.c, 3.d and 3.f were biocompatible with HeLa cells and displayed low toxicity. With a very low cytotoxic effect against HeLa, compound 3.c stands out to be a very good antiparasitic agent and consideration to further evaluate the candidate drug against others cell lines is necessary.

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Dataset Information

Template synthesis, DNA binding, antimicrobial activity, Hirshfeld surface analysis, and 1D helical supramolecular structure of a novel binuclear copper(ii) Schiff base complex.

Publications

Template synthesis, DNA binding, antimicrobial activity, Hirshfeld surface analysis, and 1D helical supramolecular structure of a novel binuclear copper(ii) Schiff base complex.

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