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Metal(II) Complexes of the Fluoroquinolone Fleroxacin: Synthesis, Characterization and Biological Profile.

ABSTRACT: A series of complexes of divalent transition metals (Cu(II), Mn(II), Zn(II), Co(II) and Ni(II)) with the quinolone antibacterial agent fleroxacin, in the absence or presence of an α-diimine such as 2,2'-bipyridine, 1,10-phenanthroline or 2,2'-bipyridylamine, were prepared and characterized. The complexes were characterized by various physicochemical and spectroscopic techniques and by single-crystal X-ray crystallography. The in vitro antibacterial activity of the complexes was studied against the bacterial strains Staphylococcus aureus, Bacillus subtilis and Xanthomonas campestris and was higher than that of free quinolone. The affinity of the complexes for bovine and human serum albumin was studied by fluorescence emission spectroscopy and the determined binding constants showed tight and reversible binding to the albumins. The interaction of the complexes with calf-thymus DNA was studied by various techniques, which showed that intercalation was the most plausible mode of interaction.

SUBMITTER: Kostelidou A

PROVIDER: S-EPMC9144902 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature

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Metal(II) Complexes of the Fluoroquinolone Fleroxacin: Synthesis, Characterization and Biological Profile.

Kostelidou Alexandra A Perdih Franc F Kljun Jakob J Dimou Foteini F Kalogiannis Stavros S Turel Iztok I Psomas George G

Pharmaceutics 20220420 5

A series of complexes of divalent transition metals (Cu(II), Mn(II), Zn(II), Co(II) and Ni(II)) with the quinolone antibacterial agent fleroxacin, in the absence or presence of an <i>α</i>-diimine such as 2,2'-bipyridine, 1,10-phenanthroline or 2,2'-bipyridylamine, were prepared and characterized. The complexes were characterized by various physicochemical and spectroscopic techniques and by single-crystal X-ray crystallography. The in vitro antibacterial activity of the complexes was studied ag ...[more]

PMID: 35631484

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Project description:Herein, we report novel Co(II) and V(IV) complexes synthesized from an (E)-2-(((2-((2-hydroxyethyl)amino)quinolin-3-yl)methylene)amino)ethan-1-ol ligand (L), cobalt(II) chloride hexahydrate, and vanadyl(IV) sulfate in methanolic solutions. The ligand and the complexes were characterized by 1H NMR spectroscopy,13C NMR spectroscopy, UV-visible spectroscopy, fluorescence spectroscopy, FT-IR spectroscopy, powder X-ray diffraction (PXRD), scanning electron microscopy-energy dispersive X-ray spectroscopy (SEM-EDX), mass spectroscopy (MS), thermal analysis, and molar conductance. The FT-IR spectral data showed that the ligand adopted a tridentate fashion when binding with the metal ions via the nitrogen atoms of the imine (C=N) and amine (N-H), and the oxygen atom of the hydroxyl group (O-H). The PXRD and SEM results indicated that the complexes are amorphous in nature. The density functional theory (DFT) calculated absorption and IR spectra agree very well with the corresponding experimental results. The antibacterial activities of the free ligand and its complexes were evaluated using a paper disk diffusion method. The complexes have better percent activitiy index than the free ligand. The cobalt complex exhibited a more recognizable antibacterial activity than the vanadium complex, specifically against Pseudomonas aeruginosa with a mean inhibition zone of 18.62 ± 0.19 mm, when compared with the positive control, ciprofloxacin, with a mean inhibition zone of 22.98 ± 0.08 mm at the same concentration. Furthermore, the antioxidant activities of the free ligand and its metal complexes were also determined in vitro using 2,2-diphenyl-1-picrylhydrazyl. The ligand exhibited less in vitro antioxidant activity than its transition metal complexes, in which the cobalt complex has a better antioxidant activity with half-inhibitory concentrations (IC50 of 16.01 μg/mL) than the ligand and the vanadium complex. Quantum molecular descriptors from the DFT calculations further support the experimental results. Molecular docking analysis also shed more light on the biological activities of the novel cobalt and vanadium complexes.

Project description:Interest is increasingly focused on the use of transition metal complexes as biochemical, medical, analytical, pharmaceutical, agronomic, anticancer, and antibacterial agents. In this study, three complexes of [Zn(H2L)Cl] (1), [Cu(H2L)(H2O)(NO3)] (2) and [Ni(H2L)(NO3)].2H2O (3) were synthesized from a 2-chloroquinoline-3-carbaldehyde derived ligand [H3L = ((E)-2-(((2-((2-hydroxyethyl)amino)quinolin-3-yl)methylene)amino)ethanol. The compounds were characterized using physicochemical and spectroscopic methods. The results demonstrate that the free ligand behaves as a tridentate ligand with one oxygen and two nitrogen (ONN) donor atoms in 1:1 metal:ligand ratio. The formation constants of the complexes were found to be (K Zn(II) = 2.3 × 106, K Cu(II) = 2.9 × 106, and K Ni(II) = 3.8 × 105). The thermodynamic parameters indicated that the reactions were spontaneous with exothermic nature of metal-ligand interaction energies. Based on the analyses of the experimental (EDX, FTIR, PXRD, MS and TGA) and DFT results, a distorted tetrahedral, a distorted square pyramidal and square planar geometry for Zn(II), Cu(II) and Ni(II) complexes, respectively, were proposed. The B3LYP calculated IR frequencies and TD-B3LYP calculated absorption spectra were found to be in good agreement with the corresponding experimental results. The powder XRD data confirmed that the Zn(II), Cu(II) and Ni(II) complexes have polycrystalline nature with average crystallite sizes of 27.86, 33.54, 37.40 Å, respectively. In vitro antibacterial activity analyses of the complexes were studied with disk diffusion method, in which the complexes showed better activity than the precursor ligand. Particularly the Cu(II) complex showed higher percent activity index (62, 90%), than both Zn(II) (54, 82%) and Ni(II) (41, 68%) complexes against both E. coli and P. aeruginosa, respectively. Using the DPPH assay, the complexes were further assessed for their antioxidant capacities. All metal complexes showed improved antioxidant activity than the free ligand. Zn(II) and Cu(II) complexes, which had IC50 values of 10.46 and 8.62 μg/ml, respectively, showed the best antioxidant activity. The calculated results of Lipinski's rule of five also showed that the target complexes have drug-like molecular nature and similarly, the results of binding mode of action of these compounds against E. coli DNA gyrase B and P. aeruginosa LasR.DNA were found to be in good agreement with the in vitro biological activities.

Dataset Information

Metal(II) Complexes of the Fluoroquinolone Fleroxacin: Synthesis, Characterization and Biological Profile.

Publications

Metal(II) Complexes of the Fluoroquinolone Fleroxacin: Synthesis, Characterization and Biological Profile.

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