Synthesis, characterization, crystal structures, DFT, TD-DFT, molecular docking and DNA binding studies of novel copper(II) and zinc(II) complexes bearing halogenated bidentate N,O-donor Schiff base ligands

Kargar, Hadi; Behjatmanesh–Ardakani, Reza; Torabi, Vajiheh; Kashani, M.; Chavoshpour-Natanzi, Zahra; Kazemi, Zahra; Mirkhani, Valiollah; Sahraei, Atefeh; Tahir, Muhammad Nawaz; Ashfaq, Muhammad; Munawar, Khurram Shahzad

doi:10.1016/j.poly.2020.114988

Cited by 91 publications

(32 citation statements)

References 51 publications

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“…Moreover, a very weak vibrational band was observed at 598 cm –1 for ν(Zn–O) and a medium band at 529 cm –1 for ν(Zn–N) bonds of the zinc complex and medium bands at 607 and 544 cm –1 for ν(Cu–O and Cu–N) bonds of the copper complex, in line with literature data. 2 , 15 , 24 , 70 , 71 This indicates that both Zn(II) and Cu(II) metals were bonded to the donor atoms of the ligand during the complexation process.…”

Section: Resultsmentioning

confidence: 99%

Novel Zinc(II) and Copper(II) Complexes of 2-((2-Hydroxyethyl)amino)quinoline-3-carbaldehyde for Antibacterial and Antioxidant Activities: A Combined Experimental, DFT, and Docking Studies

Damena

Alem

Zeleke³

et al. 2022

ACS Omega

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In the present work, two novel complexes of zinc(II) and copper(II) were synthesized from the ligand 2-((2-hydroxyethyl)amino)quinoline-3-carbaldehyde ( H 2 L ) in a 1:2 metal-to-ligand ratio in methanol. The complexes were characterized by UV–visible spectroscopy, fluorescence spectroscopy, Fourier transform infrared (FT-IR) spectroscopy, powder X-ray diffraction (XRD), scanning electron microscopy-energy-dispersive X-ray spectroscopy (SEM-EDX), mass spectrometry (MS), nuclear magnetic resonance (NMR) spectroscopy, and thermogravimetric analysis (TGA) experimental techniques and density functional theory (DFT) calculations. The spectral data revealed that the mono-deprotonated ( HL ) ligand acted as a bidentate ligand, which bound to both Zn(II) and Cu(II) ions via the nitrogen atom of the amine (N–H) and the hydroxyl (O–H) groups through the deprotonated oxygen atom. Formation constants and thermal analysis indicated that both metal complexes are stable up to 100 °C with thermodynamically favored chemical reactions. The Cu(II) complex showed antibacterial activities with the zones of inhibition of 20.90 ± 2.00 mm against Pseudomonas aeruginosa , 19.69 ± 0.71 mm against Staphylococcus aureus , and 18.58 ± 1.04 mm against Streptococcus pyogenes . These results are relatively higher compared with the Zn(II) complex at the same concentration. The minimum inhibitory concentration (MIC) results for the complexes also showed similar trends against the three bacteria. On the other hand, radical scavenging activities of both Cu(II) and Zn(II) complexes showed half-maximal inhibitory concentrations (IC 50 ) of 4.72 and 8.2 μg/mL, respectively, while ascorbic acid (a positive control) has a value of 4.28 μg/mL. The Cu(II) complex exhibited better communication with the positive control, indicating its potential use for biological activities. The calculated and in silico molecular docking results also strongly support the experimental results.

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Section: Resultsmentioning

confidence: 99%

Novel Zinc(II) and Copper(II) Complexes of 2-((2-Hydroxyethyl)amino)quinoline-3-carbaldehyde for Antibacterial and Antioxidant Activities: A Combined Experimental, DFT, and Docking Studies

Damena

Alem

Zeleke³

et al. 2022

ACS Omega

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“…Currently, structural modification based on chromophore-based drug design gains a paramount attention among the scientific community [44] , [45] , [46] . Culletta and researchers [47] made an in silico inhibition activities of the designed pharmacophores against the different proteins of SARS-CoV-2.…”

Section: Resultsmentioning

confidence: 99%

In silico anti-SARS-CoV-2 activities of five-membered heterocycle-substituted benzimidazoles

Mudi

Mahato

Verma

et al. 2022

Journal of Molecular Structure

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“…Molecular docking is a valuable technique to predict the stable structure of receptor–ligand complex for better recognition of the interaction details in drug discovery process. This method is frequently employed as virtual searching tools in primary steps of drug design and development [ 44 , 45 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, spectroscopic characterization, and thermal studies of novel Schiff base complexes: theoretical simulation studies on coronavirus (COVID-19) using molecular docking

2021

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Novel Schiff base ligand was prepared by the condensation of 2,2-(ethylenedioxy)bis(ethylamine) and imidazole-2-carboxaldehyde in a 1:2 ratio, and its complexes with Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), and Cd(II) metal ions were synthesized in a 1:1 ratio. Various methods were used to identify the Schiff base ligand and complexes. Characterization techniques such as infrared, UV, and 1 H NMR spectral tests, elemental analysis, molar conductivity, magnetic properties, thermal analysis, BET surface area, and theoretically by DFT were used to help further understanding of the complex structures. For all complexes, the ligand behaved as a neutral tetradentate ligand with NOON donor atoms and spectroscopic studies indicated an octahedral structure. The electrolytic behavior of the complexes was revealed by the molar conductivity measurements. In addition, thermogravimetric analysis was used to investigate the decomposition of the complexes and Schiff base ligand. According to the results obtained, the antibacterial activity of the metal complexes is higher than that of the Schiff base ligand against one or more bacterial species. The results showed that Cd(II) complex exhibits enhanced activity against Aspergillus flavus and Ni(II) complex against Candida albicans than the standard drug ketoconazole. The Mn(II) complex had stronger activity against human breast cancer cell line (MCF-7) than the other complexes. Antiviral drug development is critical in the latest outbreak of a novel coronavirus (SARS-CoV-2). The new coronavirus was screened using molecular docking. Supplementary Information The online version contains supplementary material available at 10.1007/s13738-021-02359-w.

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Synthesis, characterization, crystal structures, DFT, TD-DFT, molecular docking and DNA binding studies of novel copper(II) and zinc(II) complexes bearing halogenated bidentate N,O-donor Schiff base ligands

Cited by 91 publications

References 51 publications

Novel Zinc(II) and Copper(II) Complexes of 2-((2-Hydroxyethyl)amino)quinoline-3-carbaldehyde for Antibacterial and Antioxidant Activities: A Combined Experimental, DFT, and Docking Studies

Novel Zinc(II) and Copper(II) Complexes of 2-((2-Hydroxyethyl)amino)quinoline-3-carbaldehyde for Antibacterial and Antioxidant Activities: A Combined Experimental, DFT, and Docking Studies

In silico anti-SARS-CoV-2 activities of five-membered heterocycle-substituted benzimidazoles

Synthesis, spectroscopic characterization, and thermal studies of novel Schiff base complexes: theoretical simulation studies on coronavirus (COVID-19) using molecular docking

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