Control of a photoswitching chelator by metal ions:<scp>DFT</scp>,<scp>NBO</scp>, and<scp>QTAIM</scp>analysis

Dimić, Dušan; Petković, Milena

doi:10.1002/qua.25018

Cited by 27 publications

(6 citation statements)

References 41 publications

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“…In the theoretical spectrum, the HOMO→LUMO (93%) transition is located at 312 nm, with an oscillator strength of 0.1307. The difference between the experimental and theoretical wavelength is 11 nm, which is acceptable, bearing in mind that the solvent effect through specific solvent–solute interaction can be responsible for the shift [ 38 ]. An explicit solvent model would probably decrease this difference.…”

Section: Resultsmentioning

confidence: 99%

Trimethyltin(IV) Bearing 3-(4-Methyl-2-oxoquinolin-1(2H)-yl)propanoate Causes Lipid Peroxidation-Mediated Autophagic Cell Death in Human Melanoma A375 Cells

Kasalović,

Dimić,

Jelača

et al. 2024

Pharmaceuticals

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A novel trimethyltin(IV) complex (Me3SnL), derived from 3-(4-methyl-2-oxoquinolin-1(2H)-yl)propanoate ligand, has been synthesized and characterized by elemental microanalysis, UV/Vis spectrophotometry, FT-IR and multinuclear (1H, 13C and 119Sn) NMR spectroscopies. Furthermore, the structure of the ligand precursor HL was solved using SC-XRD (single-crystal X-ray diffraction). The prediction of UV/Vis and NMR spectra by quantum-chemical methods was performed and compared to experimental findings. The protein binding affinity of Me3SnL towards BSA was determined by spectrofluorometric titration and subsequent molecular docking simulations. Me3SnL has been evaluated for its in vitro anticancer activity against three human cell lines, MCF-7 (breast adenocarcinoma), A375 (melanoma) and HCT116 (colorectal carcinoma), and three mouse tumor cell lines, 4T1 (breast carcinoma), B16 (melanoma) and CT26 (colon carcinoma), using MTT and CV assays. The strong inhibition of A375 cell proliferation, ROS/RNS upregulation and robust lipid peroxidation lead to autophagic cell death upon treatment with Me3SnL.

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Section: Resultsmentioning

confidence: 99%

Trimethyltin(IV) Bearing 3-(4-Methyl-2-oxoquinolin-1(2H)-yl)propanoate Causes Lipid Peroxidation-Mediated Autophagic Cell Death in Human Melanoma A375 Cells

Kasalović,

Dimić,

Jelača

et al. 2024

Pharmaceuticals

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“…Zn-O2 and Zn-N1, respectively. Generally, all these amounts are coherent with shared (covalent or similar) bonds [33]. Additionally, for all bonds, the total energy density is negative and the ratio is indicating the predominant covalent character [34].…”

Section: Metal-ligand Charge-transfer Interaction (Mlcti) Analysismentioning

confidence: 93%

Synthesis, structure and theoretical simulation of a zinc(II) coordination complex with 2,3-pyridinedicarboxylate

Soudani

Hajji

et al. 2020

Journal of Molecular Structure

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Hydrolytic opening reaction of 2,3-pyridine dicarboxylic anhydride with the zinc dichloride led to form the chelate complex of mono deprotonated 2,3-pyridine dicarboxylic acid, [Zn(2,3-pdcH)2(H2O)2], (2,3-pdcH = 2,3-pyridinedicarboxylic acid). The coordinated compound crystallizes in the monoclinic space group P21/n. The crystal structure of the title compound exhibits a homoleptic complex with distorted octahedral geometry and ligand coordinated via pyridine nitrogen and oxygen atoms from one deprotonated dicarboxylic acid. Intermolecular interactions were analysed by Hirshfeld surfaces. After formation of the metal complex, the crystal packing is stabilized by O-H…O and C-H…O hydrogen bonds. There are moreover hydrophobic interactions, which consist in stacking between the pyridine cycle and the carboxylic/carboxylate groups. NBO and QTAIM analyses have been performed to evaluate the charge delocalization interactions that occur between the Zn(II) central ion and the surrounding ligand donor atoms. The HOMO and LUMO energies and Molecular Electrostatic Potential surface were derived from DFT theoretical calculations. Keywords Zn(II) chelate complex • Hirshfeld surface • Metal-Ligand interaction • 2,3pyridinedicarboxylate ligand • DFT

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“…Open-shell interactions, such as ionic bonds, hydrogen bonds, and van der Waals interactions, have an electron density between 0.001 and 0.04 a.u. and a small but positive Laplacian [ 48 ].…”

Section: Methodsmentioning

confidence: 99%

Theoretical Insights into Different Complexation Modes of Dioxovanadium(V) Compounds with Pyridoxal Semicarbazone/Thiosemicarbazone/S-Methyl-iso-thiosemicarbazone Ligands

Alshammari,

Maisara,

Alshammari

et al. 2024

Molecules

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Vanadium complexes have gained considerable attention as biologically active compounds. In this contribution, three previously reported dioxovanadium(V) complexes with pyridoxal semicarbazone, thiosemicarbazone, and S-methyl-iso-thiosemicarbazone ligands are theoretically examined. The intermolecular stabilization interactions within crystallographic structures were investigated by Hirshfeld surface analysis. These experimental structures were optimized at the B3LYP-D3BJ/6-311++G(d,p)(H,C,N,O,S)/def2-TZVP(V) level of theory, and crystallographic and optimized bond lengths and angles were compared. High correlation coefficients and low mean absolute errors between these two data sets proved that the selected level of theory was appropriate for the description of the system. The changes in structures and stability were examined by adding explicit solvent molecules. The Quantum Theory of Atoms in Molecules (QTAIM) was employed to analyze the intramolecular interactions with special emphasis on the effect of substituents. A good correlation between electron density/Laplacian and interatomic distance was found. Through molecular docking simulations towards Bovine Serum Albumin (BSA), the binding affinity of complexes was further investigated. The spontaneity of binding in the active position of BSA was shown. Further experimental studies on this class of compounds are advised.

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Control of a photoswitching chelator by metal ions:DFT,NBO, andQTAIManalysis

Cited by 27 publications

References 41 publications

Trimethyltin(IV) Bearing 3-(4-Methyl-2-oxoquinolin-1(2H)-yl)propanoate Causes Lipid Peroxidation-Mediated Autophagic Cell Death in Human Melanoma A375 Cells

Trimethyltin(IV) Bearing 3-(4-Methyl-2-oxoquinolin-1(2H)-yl)propanoate Causes Lipid Peroxidation-Mediated Autophagic Cell Death in Human Melanoma A375 Cells

Synthesis, structure and theoretical simulation of a zinc(II) coordination complex with 2,3-pyridinedicarboxylate

Theoretical Insights into Different Complexation Modes of Dioxovanadium(V) Compounds with Pyridoxal Semicarbazone/Thiosemicarbazone/S-Methyl-iso-thiosemicarbazone Ligands

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