Exploiting the biological efficacy of benzimidazole based Schiff base complexes with l-Histidine as a co-ligand: Combined molecular docking, DNA interaction, antimicrobial and cytotoxic studies

Kumaravel, Ganesan; Utthra, Ponnukalai Ponya; Raman, Natarajan

doi:10.1016/j.bioorg.2018.01.024

Cited by 63 publications

(25 citation statements)

References 71 publications

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“…[7] There are numerous reports on the biological activities of Schiff base metal complexes, including their use for anticancer, antibacterial, antifungal, and antioxidant. [8][9][10][11][12] Dinuclear metal complexes have biological activity; they have been found to be better active than the mononuclear Schiff base complexes. [13,14] Therefore, these types of complexes still continue to play very important roles in understanding of various aspects of coordination chemistry of metals.…”

Section: Introductionmentioning

confidence: 99%

Two dinuclear copper (II) and nickel (II) complexes based on 4‐(diethylamino)salicylaldehyde: X‐ray structures, spectroscopic, electrochemical, antibacterial, Hirshfeld surfaces analyses, and time‐dependent density functional theory calculations

Chai

Zhang

et al. 2020

Applied Organom Chemis

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The quinazoline-type ligand 2-(4-diethylamino-2-hydroxyphenyl)-4-methyl-1,-2-dihydroquinazoline 3-oxide (HL 1 ; H is the deprotonatable hydrogen) was prepared. Two 2-D supramolecular complexes [Cu 2 (L 2) 2 (NO 3) 2 ] (1) and [Ni 2 (L 2) 2 (CH 3 COO) 2 ] (2) (L 2 = 1-(2-{[(E)-(4-diethylamino-2-hydroxybenzylidene] amino} phenyl)ethanone oxime) were synthesized using HL 1 and characterized by elemental analysis, spectroscopic methods, and single-crystal X-ray diffraction studies. It revealed that 1 had coordinated two nitrate ions whereas 2 had acetate ions. In the crystal structures, six-coordinated Cu (II) complex 1 formed an infinite 2-D and X-shaped 3-D supramolecular frameworks. Simultaneously, Ni (II) complex 2 assembled into wavy 2-D networks. Furthermore, electrochemical properties and antimicrobial activities of all compounds were as well investigated. Afterwards, the electrophilic and nucleophilic attack sites identified by electrostatic potential (ESP) calculations confirmed that hydrogen bonds were observed in the optimized structure of the crystal, and the closest contact between the active atoms of both complexes was confirmed through Hirshfeld surface analysis and time-dependent density functional theory (TD-DFT) calculations.

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Section: Introductionmentioning

confidence: 99%

Two dinuclear copper (II) and nickel (II) complexes based on 4‐(diethylamino)salicylaldehyde: X‐ray structures, spectroscopic, electrochemical, antibacterial, Hirshfeld surfaces analyses, and time‐dependent density functional theory calculations

Chai

Zhang

et al. 2020

Applied Organom Chemis

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“…Amino acids and its derivatives can have some extent ligand due to their good solubility properties and biological transports. Among amino acids, histidine is very significant bioactive amino acid with plentiful physiological functions and the tendency to take on interaction with proteins [7, 8, 9, 10]. They can probably to form Schiff bases at beyond their isoelectric point with 4-aminoantipyrine derivatives.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical behavior, structural, morphological, Calf Thymus-DNA interaction and in-vitro antimicrobial studies of synthesized Schiff base transition metal complexes

Palanimurugan¹,

Dhanalakshmi²,

Selvapandian³

et al. 2019

Heliyon

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New tetradentate Schiff base transition metal complexes have been derived from salicylidene-4-imino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one and histidine were characterized by CHN analysis, magnetic susceptibility measurements, molar conductance, FAB-MS, IR, 1 H-NMR, UV, CV, EPR, Fluorescence emission, AFM and Powder XRD techniques. AFM images and Powder XRD data endure that the complexes are nano-size grains with polycrystalline structure. The spectral evidences showed that all the metal chelates are square planar geometry except [VOL] complex which exist square-pyramidal geometry. Electrochemical data (CV) for [CuL] and [VOL] complexes in acetonitrile solution indicates that the redox potential of metal ions is affected by the coordinated ligand. Electron Spin Resonance (ESR) spectra of [CuL] and [VOL] complexes were well coinciding with proposed geometries and other reported complexes. CT-DNA interaction studies of [CuL] complex reveals that an intercalation binding mode occurs between complex and DNA base pairs. The in vitro antimicrobial activity of complexes has been tested against the growth of some fungal and bacterial species persist that chelates have better control than ligand.

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“…Electronic spectra of the dinuclear complex, in the presence of increased DNA amounts, exhibit a low hypochromism with no shifts, suggesting interaction with DNA in a nonintercalative mode. In addition, the determined DNA‐binding constant for 1 , 1.43 × 10 5 M −1 , is of the same magnitude order reported for other copper(II)–benzimidazole complexes previously . Although the K b value of 1 is less than the classical intercalating agents, the magnitude of 10 5 suggests that the complex has a strong binding affinity for DNA.…”

Section: Resultsmentioning

confidence: 99%

Dinuclear copper(II) complex with a benzimidazole derivative: Crystal structure, theoretical calculations, and cytotoxic activity

Cassemiro

Santos

Oliveira

et al. 2020

Applied Organom Chemis

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This work describes a facile synthesis of 5,6‐dimethyl‐2‐(pyridin‐2‐yl)‐1‐[(pyridin‐2‐yl)methyl]‐1H‐benzimidazole (dppb) and the preparation of a dinuclear copper(II) complex bearing this ligand in a ring‐like conformation of formula [Cu(dppb)(acn)ClO4]2(ClO4)2·4acn (1), where acn represents acetonitrile. The crystal structure of the complex was determined by single‐crystal X‐ray diffraction experiment, which showed that dppb acts as a bridge in 1 due to its bidentate–monodentate μ‐κ2NN′:κN″coordination mode, and the coordination sphere of each metal center is completed by one acn molecule and one perchlorate ion. The structure of dinuclear copper(II) complex is symmetric and the two square–pyramidal copper(II) centers are separated by 5.381(1) Å. The geometry optimization, electronic structure, and vibrational spectrum of the [Cu(dppb)(acn)ClO4]22+ cation were calculated using the density functional theory method. The geometrical parameters obtained theoretically were remarkably similar to those observed in the crystal structure of 1 and the calculated vibrational frequencies are in satisfactory coherence with experimental data. In solution, the prepared complex can bind to DNA (Kb = 1.43 × 105 M−1) and inhibit the growth of a human chronic myelogenous leukemia cell line (K562) in a concentration‐dependent manner; importantly, it is almost four times more active than the corresponding free benzimidazole.

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Exploiting the biological efficacy of benzimidazole based Schiff base complexes with l-Histidine as a co-ligand: Combined molecular docking, DNA interaction, antimicrobial and cytotoxic studies

Cited by 63 publications

References 71 publications

Two dinuclear copper (II) and nickel (II) complexes based on 4‐(diethylamino)salicylaldehyde: X‐ray structures, spectroscopic, electrochemical, antibacterial, Hirshfeld surfaces analyses, and time‐dependent density functional theory calculations

Two dinuclear copper (II) and nickel (II) complexes based on 4‐(diethylamino)salicylaldehyde: X‐ray structures, spectroscopic, electrochemical, antibacterial, Hirshfeld surfaces analyses, and time‐dependent density functional theory calculations

Electrochemical behavior, structural, morphological, Calf Thymus-DNA interaction and in-vitro antimicrobial studies of synthesized Schiff base transition metal complexes

Dinuclear copper(II) complex with a benzimidazole derivative: Crystal structure, theoretical calculations, and cytotoxic activity

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