μ-phenoxide bridged mixed ligand Cu(II) complex: Synthesis, 3D supramolecular architecture, DFT, energy frameworks and antimicrobial studies

Patil, Mallikarjunagouda B.; Krishnegowda, Hema M.; Karthik, C.S.; Kudigana, Pampa J.; Mallu, P.; Neratur, Lokanath K.

doi:10.1016/j.poly.2020.114571

Cited by 34 publications

(6 citation statements)

References 54 publications

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“…The most positive area was obviously distributed on the nitrogen atoms from the pyridine rings, indicating possible nucleophilic attack sites. [ 64 ] The reaction sites verified by ESP calculation were in good agreement with the data obtained from the experiment.…”

Section: Resultssupporting

confidence: 78%

Antimicrobial activities of two 1‐D, 2‐D, and 3‐D mononuclear Mn (II) and dinuclear Bi (III) complexes: X‐ray structures, spectroscopic, electrostatic potential, Hirshfeld surface analysis, and time‐dependent/density functional theory studies

Chai

Zhang

et al. 2022

Applied Organom Chemis

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Two mononuclear and dinuclear octahedral complexes, [Mn(L1)2Cl2] (1) and [Bi2(L2)2Cl8] (2) (L1 = 2‐(2‐pyridyl)‐4‐methyl‐1,2‐dihydroquinazoline‐N3‐oxide, L2 = 2‐(3‐pyridyl)‐4‐methyl‐1,2‐dihydroquinazoline‐N3‐oxide) were prepared by natural volatilization method. The ligands and both complexes were compared with spectroscopic methods, as well as characterized by elemental analysis. The photoluminescence behaviors of both complexes in different solvents were also investigated. The coordination possibility of ligands toward Mn (II)/Bi (III) was verified using X‐ray crystallography, and it revealed that the ratio of ligand to metal was 2:1 in 1, whereas 1:1 in 2. The adjacent molecules of six‐coordinated complex 1 constituted an infinite 1‐D chain, 2‐D network, and ladder‐like 3‐D supramolecular frameworks. Most strikingly, hexa‐coordinated complex 2 with dinuclear structure formed an infinite 1‐D chain, 2‐D layered and meter‐shaped 3‐D supramolecular skeleton. Density functional theory (DFT) calculation was used to optimize the geometry of complexes, compute the electrostatic potential diagrams, and evaluate the HOMO‐LUMO energy gap. The electronic transition simulated through time‐dependent (TD)‐DFT level of calculation rationalized the experimental data. The antibacterial properties of all compounds were evaluated against Gram‐positive and Gram‐negative bacterial strains. In addition, the Hirshfeld surface was utilized to quantify some hydrogen bonding interactions and their contributions.

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Section: Resultssupporting

confidence: 78%

Antimicrobial activities of two 1‐D, 2‐D, and 3‐D mononuclear Mn (II) and dinuclear Bi (III) complexes: X‐ray structures, spectroscopic, electrostatic potential, Hirshfeld surface analysis, and time‐dependent/density functional theory studies

Chai

Zhang

et al. 2022

Applied Organom Chemis

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“…Whereas the inactive compounds did not show an affinity for the enzymes, our docking protocol identified two possible major targets for some molecules of this class of compounds, namely lipoteichoic acid flippase (LtaA) and lipoprotein signal peptidase II (LspA). To our knowledge, our study is the first reported attempt to computationally identify MRSA biological targets of antibiotic rhenium complexes [93][94][95][96][97]. Experimental data are required in the future to confirm the in silico results, but our data are in line with the limited mechanistic studies that have previously been published on microbicidal rhenium species.…”

Section: Discussionsupporting

confidence: 80%

Antimicrobial Activity of Rhenium Di- and Tricarbonyl Diimine Complexes: Insights on Membrane-Bound S. aureus Protein Binding

et al. 2022

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Antimicrobial resistance is one of the major human health threats, with significant impacts on the global economy. Antibiotics are becoming increasingly ineffective as drug-resistance spreads, imposing an urgent need for new and innovative antimicrobial agents. Metal complexes are an untapped source of antimicrobial potential. Rhenium complexes, amongst others, are particularly attractive due to their low in vivo toxicity and high antimicrobial activity, but little is known about their targets and mechanism of action. In this study, a series of rhenium di- and tricarbonyl diimine complexes were prepared and evaluated for their antimicrobial potential against eight different microorganisms comprising Gram-negative and -positive bacteria. Our data showed that none of the Re dicarbonyl or neutral tricarbonyl species have either bactericidal or bacteriostatic potential. In order to identify possible targets of the molecules, and thus possibly understand the observed differences in the antimicrobial efficacy of the molecules, we computationally evaluated the binding affinity of active and inactive complexes against structurally characterized membrane-bound S. aureus proteins. The computational analysis indicates two possible major targets for this class of compounds, namely lipoteichoic acids flippase (LtaA) and lipoprotein signal peptidase II (LspA). Our results, consistent with the published in vitro studies, will be useful for the future design of rhenium tricarbonyl diimine-based antibiotics.

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“…Therefore, the lower E HOMO of 1 indicated that it can easily release electrons to the unoccupied orbital of the copper ion. [ 59,60 ] The HOMO–LUMO energy gap values of α / β orbitals of 1 were 3.554 and 2.418 eV whereas the energy gap of 2 was 1.321 eV. The energy difference (ΔE = E LUMO – E HOMO ) between the HOMO and LUMO frontier orbitals was closely related to many properties of the molecule, which can forecast the stability of metal complexes.…”

Section: Resultsmentioning

confidence: 99%

Two mono‐ and dinuclear Cu (II) complexes derived from 3‐ethoxy salicylaldehyde: X‐ray structures, spectroscopic, electrochemical, antibacterial activities, Hirshfeld surfaces analyses, and time‐dependent density functional theory studies

Chai

et al. 2021

Applied Organom Chemis

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The quinazoline-type ligand 2-(3-ethoxy-2-hydroxyphenyl)-4-methyl-1,-2-dihydroquinazolin 3-oxide (HL 1 , H is the deprotonatable hydrogen) was synthesized. Two mono-and dinuclear Cu (II) complexes, [Cu(L 2 ) 2 ]Á2CH 3 OH (1),amino}phenyl)ethanone oxime), were obtained via complexation of HL 1 with Cu (II) acetate monohydrate or Cu (II) nitrate trihydrate in methanol. HL 1 and both complexes were characterized by elemental analyses and spectroscopic methods. The structures of complexes were confirmed by single-crystal X-ray crystallography and the ratio of ligand to metal in 1 was 2:1 whereas 2 was 1:1. In the crystal structures, hexa-coordinated Cu (II) complex 1 was assembled into an infinite 1-D, 2-D network and 3-D supramolecular framework. Complex 2 included four deprotonated (L 2 ) À units, four coordinated Cu (II) and two coordinated nitrate anions, forming an infinite 2-D layer and interesting butterfly-shaped 3-D supramolecular skeleton. Specifically, the Cu1 and Cu4 centers were four-coordinated, while the Cu2 and Cu3 centers were penta-coordinated in 2. Furthermore, electrochemical properties and antibacterial activities of both complexes were also investigated. In addition, the electron paramagnetic resonance (EPR) spectra of 1 and 2 were also studied. The optimal geometries, HOMO-LUMO energies and molecular electrostatic potential diagrams of two complexes were calculated using density functional theory (DFT)/B3LYP, and specific electronic transitions in the UVvis spectra of 1 and 2 were recorded by time-dependent DFT (TD-DFT) calculations. Additionally, the noncovalent interactions between both complexes were also confirmed by Hirshfeld surfaces.

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μ-phenoxide bridged mixed ligand Cu(II) complex: Synthesis, 3D supramolecular architecture, DFT, energy frameworks and antimicrobial studies

Cited by 34 publications

References 54 publications

Antimicrobial activities of two 1‐D, 2‐D, and 3‐D mononuclear Mn (II) and dinuclear Bi (III) complexes: X‐ray structures, spectroscopic, electrostatic potential, Hirshfeld surface analysis, and time‐dependent/density functional theory studies

Antimicrobial activities of two 1‐D, 2‐D, and 3‐D mononuclear Mn (II) and dinuclear Bi (III) complexes: X‐ray structures, spectroscopic, electrostatic potential, Hirshfeld surface analysis, and time‐dependent/density functional theory studies

Antimicrobial Activity of Rhenium Di- and Tricarbonyl Diimine Complexes: Insights on Membrane-Bound S. aureus Protein Binding

Two mono‐ and dinuclear Cu (II) complexes derived from 3‐ethoxy salicylaldehyde: X‐ray structures, spectroscopic, electrochemical, antibacterial activities, Hirshfeld surfaces analyses, and time‐dependent density functional theory studies

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