Dataset Information

Zn(II) Complex of Plant Phenolic Chlorogenic Acid: Antioxidant, Antimicrobial and Structural Studies.

ABSTRACT: The structure of the Zn(II) complex of 5-caffeoylquinic acid (chlorogenic acid, 5-CQA) and the type of interaction between the Zn(II) cation and the ligand were studied by means of various experimental and theoretical methods, i.e., electronic absorption spectroscopy UV/Vis, infrared spectroscopy FT-IR, elemental, thermogravimetric and density functional theory (DFT) calculations at B3LYP/6-31G(d) level. DPPH (2,2-diphenyl-1-picrylhydrazyl), ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), FRAP (ferric reducing antioxidant power), CUPRAC (cupric reducing antioxidant power) and trolox oxidation assays were applied in study of the anti-/pro-oxidant properties of Zn(II) 5-CQA and 5-CQA. The antimicrobial activity of these compounds against Escherichiacoli, Pseudomonasaeruginosa, Bacillussubtilis, Staphylococcusaureus, Salmonellaenteritidis and Candidaalbicans was tested. An effect of Zn(II) chelation by chlorogenic acid on the anti-/pro-oxidant and antimicrobial activities of the ligand was discussed. Moreover, the mechanism of the antioxidant properties of Zn(II) 5-CQA and 5-CQA were studied on the basis of the theoretical energy descriptors and thermochemical parameters. Zn(II) chlorogenate showed better antioxidant activity than chlorogenic acid and commonly applied natural (L-ascorbic acid) and synthetic antioxidants (butylated hydroxyanisol (BHA) and butylated hydroxytoluene (BHT)). The pro-oxidant activity of Zn(II) 5-CQA was higher than the ligand and increased with the rise of the compound concentration The type of Zn(II) coordination by the chlorogenate ligand strongly affected the antioxidant activity of the complex.

SUBMITTER: Kalinowska M

PROVIDER: S-EPMC7504324 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

Zn(II) Complex of Plant Phenolic Chlorogenic Acid: Antioxidant, Antimicrobial and Structural Studies.

Kalinowska Monika M Sienkiewicz-Gromiuk Justyna J Świderski Grzegorz G Pietryczuk Anna A Cudowski Adam A Lewandowski Włodzimierz W

Materials (Basel, Switzerland) 20200824 17

The structure of the Zn(II) complex of 5-caffeoylquinic acid (chlorogenic acid, 5-CQA) and the type of interaction between the Zn(II) cation and the ligand were studied by means of various experimental and theoretical methods, i.e., electronic absorption spectroscopy UV/Vis, infrared spectroscopy FT-IR, elemental, thermogravimetric and density functional theory (DFT) calculations at B3LYP/6-31G(d) level. DPPH (2,2-diphenyl-1-picrylhydrazyl), ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic ...[more]

PMID: 32847095

Shared Molecules

Only show the datasets with similarity scores above: 0.5

Threshold

0.5

Similar Datasets

Project description:Research into heterocyclic ligands has increased in popularity due to their versatile applications in the biomedical field. Quinoline derivatives with their transition metal complexes are popular scaffolding molecules in the ongoing pursuit of newer and more effective bioactive molecules. Subsequently, this work reports on the synthesis and possible biological application of new Zn(II) and Co(II) complexes with a bidentate quinoline derivative ligand (H2 L), [(H2 L):(E)-2-(((6-fluoro-2-((2-hydroxyethyl)amino)quinolin-3-yl)methylene)amino)ethanol]. The ligand and its metal complexes were structurally characterized by spectroscopic methods (1H NMR, 13C NMR, Fourier transform infrared (FTIR), UV-vis, fluorescence, and mass spectroscopy), as well as by thermogravimetric and elemental analysis methods. The spectroscopic findings were further supported by density functional theory (DFT) and time-dependent (TD)-DFT calculations. The biological application was examined by investigating the inhibitory action of the complexes against bacterial strains using diffusion and agar dilution methods, and their profiles against two Gram-positive and Gram-negative bacterial strains were supported by molecular docking analysis. To rationalize the in vitro activity and establish the possible mechanism of action, the interactions and binding affinity of the ligand and complexes were investigated against three different bacterial enzymes (Escherichia coli DNA gyrase (PDB ID 6f86), E. coli dihydrofolate reductase B (PDB ID: 7r6g), and Staphylococcus aureus tyrosyl-tRNA synthetase (PDB ID: 1JIJ)) using AutoDock with the standard protocol. The MIC value of 0.20 μg/mL for zinc complex against E. coli and associated binding affinities -7.2 and -9.9 kcal/mol with DNA gyrase (PDB ID 6f86) and dihydrofolate reductase B (PDB ID: 7r6g), as well as the MIC value of 2.4 μg/mL for cobalt(II) complex against Staphylococcus aureus and the associated binding affinity of -10.5 kcal/mol with tyrosyl-tRNA synthetase (PDB ID: 1JIJ), revealed that the complexes' inhibitory actions were strong and comparable with those of the standard drug in the experiments. In addition, the ability of the new quinoline-based complexes to scavenge 1,1-diphenyl-picrylhydrazyl radicals was investigated; the findings suggested that the complexes exhibit potent antioxidant activities, which may be of therapeutic significance.

Project description:A new chlorobenzylidene imine ligand, (E)-1-((5-chloro-2-hydroxybenzylidene)amino) naphthalen-2-ol (HL), and its [Zn(L)(NO3)(H2O)3], [La(L)(NO3)2(H2O)2], [VO(L)(OC2H5)(H2O)2], [Cu(L)(NO3)(H2O)3], and [Cr(L)(NO3)2(H2O)2], complexes were synthesized and characterized. The characterization involved elemental analysis, FT-IR, UV/Vis, NMR, mass spectra, molar conductance, and magnetic susceptibility measurements. The obtained data confirmed the octahedral geometrical structures of all metal complexes, while the [VO(L)(OC2H5)(H2O)2] complex exhibited a distorted square pyramidal structure. The complexes were found to be thermally stable based on their kinetic parameters determined using the Coats-Redfern method. The DFT/B3LYP technique was employed to calculate the optimized structures, energy gaps, and other important theoretical descriptors of the complexes. In vitro antibacterial assays were conducted to evaluate the complexes' potential against pathogenic bacteria and fungi, comparing them to the free ligand. The compounds exhibited excellent fungicidal activity against Candida albicans ATCC: 10231 (C. albicans) and Aspergillus negar ATCC: 16404 (A. negar), with inhibition zones of HL, [Zn(L)(NO3)(H2O)3], and [La(L)(NO3)2(H2O)2] three times higher than that of the Nystatin antibiotic. The DNA binding affinity of the metal complexes and their ligand was investigated using UV-visible, viscosity, and gel electrophoresis methods, suggesting an intercalative binding mode. The absorption studies yielded Kb values ranging from 4.40 × 105 to 7.30 × 105 M-1, indicating high binding strength to DNA comparable to ethidium bromide (value 107 M-1). Additionally, the antioxidant activity of all complexes was measured and compared to vitamin C. The anti-inflammatory efficacy of the ligand and its metal complexes was evaluated, revealing that [Cu(L)(NO3)(H2O)3] exhibited the most effective activity compared to ibuprofen. Molecular docking studies were conducted to explore the binding nature and affinity of the synthesized compounds with the receptor of Candida albicans oxidoreductase/oxidoreductase INHIBITOR (PDB ID: 5V5Z). Overall, the combined findings of this work demonstrate the potential of these new compounds as efficient fungicidal and anti-inflammatory agents. Furthermore, the photocatalytic effect of the Cu(II) Schiff base complex/GO was examined.

Dataset Information

Zn(II) Complex of Plant Phenolic Chlorogenic Acid: Antioxidant, Antimicrobial and Structural Studies.

Publications

Zn(II) Complex of Plant Phenolic Chlorogenic Acid: Antioxidant, Antimicrobial and Structural Studies.

Shared Molecules

Only show the datasets with similarity scores above: 0.5

Threshold

0.5

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets