Synthesis, DFT/TD-DFT theoretical studies, experimental characterization, electrochemical and antioxidant activity of Fe(III) complexes of bis (dimethylglyoximato) guanine

Abane-Merzouk, Lamia; Adkhis, A.; Terrachet-Bouaziz, Souhila; Makhloufi‐Chebli, Malika

doi:10.1016/j.molstruc.2019.02.108

Cited by 8 publications

(2 citation statements)

References 45 publications

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“…This is may be due to high redox activity, of zinc and copper complex, hence both are important for the formation and functioning of several enzymes and proteins, such as cytochrome C oxidase and Cu/Zn superoxide dismutase, which are involved in the processes of respiration, energy metabolism, and DNA synthesis ( Krasnovskaya et al, 2020 ; Kumar et al, 2020 ; Damena et al, 2022a ), because copper is involved in catalysis (electron transfer), while zinc plays a structural role in these proteins. In addition to, this high activity was probably due to the presence of the OH group in addition to oxidation potential of the metal ions and the decrease of the antioxidant activity of the ligands is indicated that the terminal N-substitution in the ligands does not have any appreciable influence much on the antioxidant properties in agreement with previous reported studies ( Ramachandran et al, 2013 ; Fetoh et al, 2018 ; Abane-Merzouk et al, 2019 ; Belkhir-Talbi et al, 2021 ).…”

Section: Resultssupporting

confidence: 90%

Synthesis, characterization, and biological activities of zinc(II), copper(II) and nickel(II) complexes of an aminoquinoline derivative

Damena

Alem

Zeleke³

et al. 2022

Front. Chem.

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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 (KZn(II) = 2.3 × 106, KCu(II) = 2.9 × 106, and KNi(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.

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Section: Resultssupporting

confidence: 90%

Synthesis, characterization, and biological activities of zinc(II), copper(II) and nickel(II) complexes of an aminoquinoline derivative

Damena

Alem

Zeleke³

et al. 2022

Front. Chem.

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“…The potential was scanned in the range -2.0 V to +2.0 V at a scan rate 100 mVs -1 . The cyclic voltammogram of phenylalanine showed one anodic wave and one cathodic wave located at +0.75 V and -0.87 V. In the voltammogram of HL, one anodic wave is observed at +0.95 V which can be attributed to the oxidation of the oxime group [44]. The results of cyclic voltammetric investigations of all the complexes are summarized in Table 1 and the cyclic voltammogram of complex 2, HL and DMF are presented in Figure 8.…”

Section: Cyclic Voltammetrymentioning

confidence: 95%

Synthesis, structural elucidation and electrochemical behavior of some oxime-phenylalanine mixed ligand complexes

Öztoprak¹,

Özkorucuklu²,

Baştemur³

et al. 2021

Bull. Chem. Soc. Eth.

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Four new mixed ligand complexes Me(II)/phenylalanine (phe)/HL [HL =4-(4-bromophenyl- aminoisonitrosoacetyl)biphenyl and Me = Co, Ni, Cu, Zn] were synthesized. These complexes are formulated as: [CoL(phe)(H2O)2], [NiL(phe)(H2O)2], [CuL(phe)(H2O)2] and [ZnL(phe)(H2O)2]. All the compounds were characterized by elemental analyses, FT-IR, magnetic susceptibility measurements, TG/DTA and cyclic voltammetry (CV) experiments. IR spectral data confirmed the coordination of the oxime ligand to the metal ions through the oxime and carbonyl oxygen. The geometrical structures of the complexes have been found to be octahedral. The measured molar conductance values of the complexes in DMF are in agreement with the non-electrolytic nature ofthe complexes. The elemental analyses confirm a 1:1:1 [metal:HL:L(phenylalanine)] molar ratio. Thermal behavior of the compound was investigated by thermal gravimetric analysis (TG) and differential thermal analysis (DTA) techniques. All the complexes were transformed into metal oxides after thermal degradation. The electrochemical properties of both ligand and their complexes were analyzed by cyclic voltammetry (CV) using glassy carbon electrode in DMF solution containing 0.1 M TBAP as supporting electrolyte. KEY WORDS: Oxime, electrochemical characterization, mixed ligand complexes, amino acid, phenylalanine Bull. Chem. Soc. Ethiop. 2020, 34(3), 543-556. DOI: https://dx.doi.org/10.4314/bcse.v34i3.10

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Design and synthesis of three Fe(III) mixed-ligand complexes: Exploration of their biological and phenoxazinone synthase-like activities

Ismael

Abdel‐Mawgoud

Rabia

et al. 2020

Inorganica Chimica Acta

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Synthesis, DFT/TD-DFT theoretical studies, experimental characterization, electrochemical and antioxidant activity of Fe(III) complexes of bis (dimethylglyoximato) guanine

Cited by 8 publications

References 45 publications

Synthesis, characterization, and biological activities of zinc(II), copper(II) and nickel(II) complexes of an aminoquinoline derivative

Synthesis, characterization, and biological activities of zinc(II), copper(II) and nickel(II) complexes of an aminoquinoline derivative

Synthesis, structural elucidation and electrochemical behavior of some oxime-phenylalanine mixed ligand complexes

Design and synthesis of three Fe(III) mixed-ligand complexes: Exploration of their biological and phenoxazinone synthase-like activities

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