Structural and theoretical analysis, molecular docking/dynamics investigation of 3-(1-m-chloridoethylidene)-chromane-2,4‑dione: The role of chlorine atom

Avdović, Edina H.; Dimić, Dušan; Fronc, Marek; Kožı́šek, Jozef; Klein, Erik; Milanović, Žiko; Kesić, Ana; Marković, Zoran

doi:10.1016/j.molstruc.2021.129962

Cited by 26 publications

(7 citation statements)

References 61 publications

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“…The correlation coefficient (R) and mean absolute error (MAE) were used to assess the validity of the linear correlation between the experimental and computed chemical shifts in the NMR spectra. The relatively significant correlation coefficients for 1 HNMR between 0.991 and 0.990, as well as the relatively small values of MAE, suggest that the computed geometries of examined compounds are in good correlation with the experimentally obtained structures [ 30 , 31 , 32 ]. When it comes to the cis isomer, correlation coefficients of 0.973 and 0.969 are a lot lower than for the trans isomer, which indicates that trans isomer is dominant, as predicted by Boltzmann distribution.…”

Section: Resultsmentioning

confidence: 63%

Synthesis and Cytotoxicity Evaluation of Novel Coumarin–Palladium(II) Complexes against Human Cancer Cell Lines

et al. 2022

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Two newly synthesized coumarin–palladium(II) complexes (C1 and C2) were characterized using elemental analysis, spectroscopy (IR and 1H-13C NMR), and DFT methods at the B3LYP-D3BJ/6-311+G(d,p) level of theory. The in vitro and in silico cytotoxicity of coumarin ligands and their corresponding Pd(II) complexes was examined. For in vitro testing, five cell lines were selected, namely human cervical adenocarcinoma (HeLa), the melanoma cell line (FemX), epithelial lung carcinoma (A549), the somatic umbilical vein endothelial cell line (EA.hi926), and pancreatic ductal adenocarcinoma (Panc-1). In order to examine the in silico inhibitory potential and estimate inhibitory constants and binding energies, molecular docking studies were performed. The inhibitory activity of C1 and C2 was investigated towards epidermal growth factor receptor (EGFR), receptor tyrosine kinase (RTK), and B-cell lymphoma 2 (BCL-2). According to the results obtained from the molecular docking simulations, the inhibitory activity of the investigated complexes towards all the investigated proteins is equivalent or superior in comparison with current therapeutical options. Moreover, because of the low binding energies and the high correlation rate with experimentally obtained results, it was shown that, out of the three, the inhibition of RTK is the most probable mechanism of the cytotoxic activity of the investigated compounds.

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Section: Resultsmentioning

confidence: 63%

Synthesis and Cytotoxicity Evaluation of Novel Coumarin–Palladium(II) Complexes against Human Cancer Cell Lines

et al. 2022

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“…The formation of the quasi-six membered ring, O-C-C-C-N-H, with a strong hydrogen bond shifted the band of N-H vibration to lower wavenumbers. This band in similar compounds was joined with the C-H stretching vibration band between 3300 and 3000 cm −1 [25,26]. In addition, there were bands assigned to stretching vibrations of lactone C=O and C-O, of close to 1660 and 1200 cm −1 , respectively.…”

Section: Chemistrymentioning

confidence: 83%

Synthesis, Crystallographic, Quantum Chemical, Antitumor, and Molecular Docking/Dynamic Studies of 4-Hydroxycoumarin-Neurotransmitter Derivatives

Dimić

Kaluđerović

Avdović

et al. 2022

IJMS

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In this contribution, four new compounds synthesized from 4-hydroxycoumarin and tyramine/octopamine/norepinephrine/3-methoxytyramine are characterized spectroscopically (IR and NMR), chromatographically (UHPLC-DAD), and structurally at the B3LYP/6-311++G*(d,p) level of theory. The crystal structure of the 4-hydroxycoumarin-octopamine derivative was solved and used as a starting geometry for structural optimization. Along with the previously obtained 4-hydroxycoumarin-dopamine derivative, the intramolecular interactions governing the stability of these compounds were quantified by NBO and QTAIM analyses. Condensed Fukui functions and the HOMO-LUMO gap were calculated and correlated with the number and position of OH groups in the structures. In vitro cytotoxicity experiments were performed to elucidate the possible antitumor activity of the tested substances. For this purpose, four cell lines were selected, namely human colon cancer (HCT-116), human adenocarcinoma (HeLa), human breast cancer (MDA-MB-231), and healthy human lung fibroblast (MRC-5) lines. A significant selectivity towards colorectal carcinoma cells was observed. Molecular docking and molecular dynamics studies with carbonic anhydrase, a prognostic factor in several cancers, complemented the experimental results. The calculated MD binding energies coincided well with the experimental activity, and indicated 4-hydroxycoumarin-dopamine and 4-hydroxycoumarin-3-methoxytyramine as the most active compounds. The ecotoxicology assessment proved that the obtained compounds have a low impact on the daphnia, fish, and green algae population.

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“…In addition, to further study the reactivity of the collector, we used the multiwfn to calculate the Fukui function and the Electrostatic potential (ESP) 34 . The condensed Fukui function ( f k + and f k − ) and the condensed dual descriptor (CDD) were calculated by functions () 35,36

Nucleophilic attack : {f_{k}}^{+} = q_{k} (N + 1) - q_{k} (N),

Electrophilic attack : {f_{k}}^{-} = q_{k} (N) - q_{k} (N - 1),

CDD = {f_{k}}^{+} - {f_{k}}^{-},

where q k ( N ), q k ( N − 1), and q k ( N + 1) refer to the atomic charges of the systems that are electrically neutral, one less electron (positive ion), and one extra electron (negative ion), respectively.…”

Section: Methodsmentioning

confidence: 99%

“…34 The condensed Fukui function (f k + and f k À ) and the condensed dual descriptor (CDD) were calculated by functions ( 7)-( 9). 35,36 Nucleophilic attack :…”

Section: Dft Calculationsmentioning

confidence: 99%

Amide group enhanced self‐assembly and adsorption of thioether‐containing hydroxamic acid on cassiterite surface

et al. 2023

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Modified surfactants can regulate their adsorption at the target surface and are essential for various separation applications such as froth flotation. Thioether‐containing hydroxamic acid (BTHA) is an excellent oxidized‐ore collector with poor dispersibility. Herein, acylamino, which possesses the ability to improve the surfactants' self‐assembly and dispersion, was introduced to synthesize N‐[6‐(hydroxyamino)‐6‐oxohexyl] benzylthioacetamide (BTAHA); thus, applying it to cassiterite flotation. Surface tension, adsorption capacity, in situ AFM, and surface energy results reveal BTAHA displays strong bubble stability and readily adsorbs onto the mineral's surface, promoting hydrophobic flotation. BTAHA is an effective cassiterite collector and has good separation effects on cassiterite against calcite. It can form Van der Waals forces and five‐membered hydroxamate‐(O,O)‐Sn rings with Sn atoms on cassiterite surfaces via thioether and hydroxamate groups. Meanwhile, the presence of intermolecular hydrogen bond between the amide groups facilitates the self‐assembly of the collectors on the cassiterite surface, and has broad industrial application prospects in various separation processes.

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Structural and theoretical analysis, molecular docking/dynamics investigation of 3-(1-m-chloridoethylidene)-chromane-2,4‑dione: The role of chlorine atom

Cited by 26 publications

References 61 publications

Synthesis and Cytotoxicity Evaluation of Novel Coumarin–Palladium(II) Complexes against Human Cancer Cell Lines

Synthesis and Cytotoxicity Evaluation of Novel Coumarin–Palladium(II) Complexes against Human Cancer Cell Lines

Synthesis, Crystallographic, Quantum Chemical, Antitumor, and Molecular Docking/Dynamic Studies of 4-Hydroxycoumarin-Neurotransmitter Derivatives

Amide group enhanced self‐assembly and adsorption of thioether‐containing hydroxamic acid on cassiterite surface

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