Synthesis, characterization and catecholase-like activity of new Schiff base metal complexes derived from visnagin: Theoretical and experimental study

Beyazit, Neslihan; Çatıkkaş, Berna; Bayraktar, Sahin; Demetgül, Cahıt

doi:10.1016/j.molstruc.2016.04.047

Cited by 43 publications

(29 citation statements)

References 43 publications

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“…The 13 C NMR spectrum of the ligand in DMSO‐ d 6 (Figure ) showed signals at 175.61 and 164.91 ppm which may be attributed to carbon atoms of carbonyl groups of benzopyrone ( 6 C=O) and antipyrine ( 17 C═O) moieties, respectively . The signal of azomethine carbon ( 12 C═N) was observed at 153.29 ppm, while other carbons of benzopyrone moiety are slightly shifted .…”

Section: Resultsmentioning

confidence: 98%

“…The IR spectrum of the ligand displayed strong to medium peaks at 3500, 1662, 1640, 1599 and 1307 cm −1 , ascribed to the phenolic ν(OH) stretching vibration, carbonyl groups of benzopyrone and antipyrine moieties, azomethine group and phenolic C─O stretching, respectively . The bonding behaviour of the ligand was established from comparing the IR spectra of both parent ligand and its complexes.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and characterization of novel chromone Schiff base complexes as p53 activators

Shakdofa

Mousa²,

Labib³

et al. 2018

Applied Organom Chemis

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A series of chromone Schiff base complexes were prepared and analytically as well as spectroscopically characterized. The ligand was found to act as a monobasic tridentate ligand bonded covalently or coordinatively to the metal ion via deprotonated hydroxyl group, azomethine nitrogen atom and carbonyl oxygen atom of antipyrine moiety. Both electronic spectra and magnetic measurements indicated an octahedral or a distorted octahedral geometry around the metal ions for all metal complexes except the nickel complex, which had a tetrahedral geometry. In addition, the ability of the newly prepared compounds to activate the tumour suppressor p53 in cancer cells was studied, with zinc and copper complexes showing promising activities for p53 ubiquitination compared with diphenylimidazole (reference drug).

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of novel chromone Schiff base complexes as p53 activators

Shakdofa

Mousa²,

Labib³

et al. 2018

Applied Organom Chemis

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“…It can be seen from Figure that the negative potential regions of HL are mainly localized around the phenolic oxygen and azomethine nitrogen atom, making these sites favored coordination sites for attack by the metal ions. Analysis of the MEP provides necessary information about the reactive sites of electrophilic and nucleophilic attack for the title molecules …”

Section: Resultsmentioning

confidence: 99%

Physicochemical characterization of nanobidentate ferrocene‐based Schiff base ligand and its coordination complexes: Antimicrobial, anticancer, density functional theory, and molecular operating environment studies

Mahmoud

2019

J Chinese Chemical Soc

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A novel bidentate Schiff base ligand (HL, Nanobidentate Ferrocene based Schiff base ligand L (has one replaceable proton H)) was prepared via the condensation of 2‐amino phenol with 2‐acetyl ferrocene. The ligand was characterized using elemental analysis, mass spectrometry, infrared (IR) spectroscopy, 1proton nuclear magnetic resonance (H‐NMR) spectroscopy, scanning electron microscopy (SEM), and thermal analysis. The corresponding 1:1 metal complexes with some transition‐metal ions were additionally characterized by their elemental analysis, molar conductance, SEM, and thermogravimetric ana1ysis (TGA). The complexes had the general formula [M(L)(Cl)(H2O)3]xCl·nH2O (M = Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II)), (x = 0 for Mn(II), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II), x = 1 for Cr(III) and Fe(III)), (n = 1 for Cr(III), n = 3 for Mn(II) and Co(II), n = 4 for Fe(III), Ni(II), Cu(II), Zn(II), and Cd(II)). Density functional theory calculations on the HL ligand were also carried out in order to clarify molecular structures by the B31YP exchange‐correlation function. The results were subjected to molecular orbital diagram, highest occupied mo1ecu1ar orbital–lowest occupied molecular orbital, and molecular electrostatic potential calculations. The parent Schiff base and its eight metal complexes were assayed against four bacterial species (two Gram‐negative and two‐Gram positive) and four different antifungal species. The HL ligand was docked using molecular operating environment 2008 with crystal structures of oxidoreductase (1CX2), protein phosphatase of the fungus Candida albicans (5JPE), Gram(−) bacteria Escherichia coli (3T88), Gram(+) bacteria Staphylococcus aureus (3Q8U), and an androgen‐independent receptor of prostate cancer (1GS4). In order to assess cytotoxic nature of the prepared HL ligand and its complexes, the compounds were screened against the Michigan cancer foundation (MCF)‐7 breast cancer cell line, and the IC50 values of compounds were calculated.

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“…It can be seen from Figure that negative potential regions of GFV are mainly localized around the two oxygen atoms of methoxy group and oxygen atom of furan ring making these sites favoured coordination sites for attack by metal ions. Analysis of MEP provides necessary information about the reactive sites of electrophilic and nucleophilic attack for the title molecules …”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization, density functional theory, X‐ray study, thermal stability, and biological and MOE relevance of metal complexes of griseofulvin

Mahmoud

2018

Applied Organom Chemis

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Metal(II) and metal(III) coordination compounds of griseofulvin (GFV) drug were synthesized. The structure of the ligand was determined on the basis of elemental analyses, infrared and 1 H NMR spectroscopies and thermal studies.GFV behaved as a neutral tridentate chelating agent and coordinated to metal ions through three oxygen atoms: two methoxy groups and oxygen atom of furan ring. Metal complexes were characterized by means of elemental analyses and molar conductance, spectral (infrared, electron spin resonance) and thermal studies. All the complexes showed molar conductance behaviour corresponding to an electrolytic nature. All the complexes showed octahedral geometry, except [Zn(GFV)Cl]Cl that showed tetrahedral geometry. Density functional theory (DFT) calculations were employed to understand and estimate the contribution of each interaction in the formation of the assembly using several theoretical models. The computed parameters from DFT calculations for structure optimizations and vibrational frequencies were in good agreement with the experimental data. Newly synthesized metal complexes in addition to GFV were examined against opportunistic pathogens. The biological applications of complexes were studied with two Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and two Gram-negative bacteria (Escherichia coli and Neisseria gonorrhoeae) as well as their antifungal activity against Candida albicans. Results suggested that metal complexes were more biologically sensitive than free ligand. The complexes showed a moderate inhibition of MCF7 breast cancer cell line growth. Molecular docking studies further helped in understanding the mode of action of the compounds through their various interactions with the crystal structures of: human serum albumin (PDB: 5FUO), Staphylococcus aureus nucleoside (PDB: 3Q8U), human acetylcholinesterase (PDB: 1B41) and the human DNA-Topo I complex (PDB: 1SC7).

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Synthesis, characterization and catecholase-like activity of new Schiff base metal complexes derived from visnagin: Theoretical and experimental study

Cited by 43 publications

References 43 publications

Synthesis and characterization of novel chromone Schiff base complexes as p53 activators

Synthesis and characterization of novel chromone Schiff base complexes as p53 activators

Physicochemical characterization of nanobidentate ferrocene‐based Schiff base ligand and its coordination complexes: Antimicrobial, anticancer, density functional theory, and molecular operating environment studies

Synthesis, characterization, density functional theory, X‐ray study, thermal stability, and biological and MOE relevance of metal complexes of griseofulvin

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