Low-dimensional compounds containing bioactive ligands. Part VI: Synthesis, structures, in vitro DNA binding, antimicrobial and anticancer properties of first row transition metal complexes with 5-chloro-quinolin-8-ol

Potočňák, Ivan; Vranec, Peter; Farkasová, Veronika; Sabolová, Danica; Vataščinová, Michaela; Kudláčová, Júlia; Radojević, Ivana D.; Čomić, Ljiljana R.; Marković, Bojana Simović; Volarević, Vladislav; Arsenijević, Nebojša; Trifunović, Srećko R.

doi:10.1016/j.jinorgbio.2015.10.015

Cited by 51 publications

(11 citation statements)

References 42 publications

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“…The ν (C=N) band of the quinoline moiety, initially located at 1476 cm −1 before binding, is shifted to lower wavelength number (1468 cm −1 ) after chelation to NiO (Figure S5). This change is typical of a quinoline group coordinated to Lewis acidic metals . The observation of the ν (OH) band of the phenol is more difficult, as it appears as a broad band of medium intensity around 3400 cm −1 and it overlaps with those of the hydroxy groups of NiO.…”

Section: Resultsmentioning

confidence: 99%

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A Comparative Investigation of the Role of the Anchoring Group on Perylene Monoimide Dyes in NiO‐Based Dye‐Sensitized Solar Cells

et al. 2020

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The anchoring group of a sensitizer may strongly affect the overall properties and stability of the resulting dye‐sensitized solar cells (DSSCs) and dye‐sensitized photoelectrosynthetic solar cells (DSPECs). The properties of seven perylene monoimide (PMI) dyes have been comprehensively studied for their immobilization on nanocrystalline NiO film. The PMI dyes differ only by the nature of the anchoring group, which are: carboxylic acid (PMI‐CO2H), phosphonic acid (PMI‐PO3H2), acetyl acetone (PMI‐acac), pyridine (PMI‐Py), aniline (PMI‐NH2), hydroxyquinoline (PMI‐HQ), and dipicolinic acid (PMI‐DPA). The dyes are investigated by cyclic voltammetry and spectroelectrochemistry and modeled by TD‐DFT quantum chemical calculations. The mode of binding of these anchoring groups is investigated by infrared spectroscopy and the stability of the binding to NiO surface is studied by desorption experiments in acidic and basic media. The phosphonic acid group is found to offer the strongest binding to the NiO surface in terms of stability and dye loading. Finally, a photophysical study by ultrafast transient absorption spectroscopy shows that all dyes inject a hole in NiO with rate constants on a subpicosecond timescale and display similar charge recombination kinetics. The photovoltaic properties of the dyes show that PMI‐HQ and PMI‐acac give the highest photovoltaic performances, owing to a lower degree of aggregation on the surface.

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Section: Resultsmentioning

confidence: 99%

“…The interpretation of the IR spectrum of PMI‐HQ can be made according to that of the Ni II quinolinol complex . The ν (C=N) band of the quinoline moiety, initially located at 1476 cm −1 before binding, is shifted to lower wavelength number (1468 cm −1 ) after chelation to NiO (Figure S5).…”

Section: Resultsmentioning

confidence: 99%

A Comparative Investigation of the Role of the Anchoring Group on Perylene Monoimide Dyes in NiO‐Based Dye‐Sensitized Solar Cells

et al. 2020

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“…Two complexes were dissolved with trace amounts of DMF respectively, and then added plenty of water to dilute it (DMF content is very small, therefore it can be ignored) . The powder recovered after evaporating the above solution was tested by XRD (Figure ), which showed that these complexes are also stable in solution.…”

Section: Methodsmentioning

confidence: 99%

Two Mn^II, Cu^II complexes derived from 3,5‐bis(1‐imidazoly) pyridine: Synthesis, DNA binding, Molecular docking and cytotoxicity studies

Zhu

Liu

et al. 2018

Applied Organom Chemis

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Two complexes [MnL 2 (H 2 O) 2 ]·2ClO 4 (complex 1) and [CuL(H 2 O) 3 ]·2NO 3 (complex 2) (where L = 3,5-bis(1-imidazoly) pyridine) were designed and synthesized. The structures of the complexes were characterized by X-ray crystallography, elemental analyses, and infrared spectrum. The interaction capacity of the complexes with calf thymus DNA has been investigated by UV and fluorescence spectroscopy. Gel electrophoresis assay demonstrated the ability of the complexes to cleave the pBR322 plasmid DNA. Efficient binding properties of DNA were established by UV-vis, fluorescence, and gel electrophoresis. The intrinsic binding constants (K b ) were calculated to be 0.1524, 0.1041 for complexes 1-2, respectively. The cytotoxic activity of the two complexes exhibited a higher cytotoxicity against HeLa cell lines and lower cytotoxicity toward the normal cell lines. Flow cytometry demonstrated the cancer cell inhibitory rate of two complexes. Furthermore, computer-aided molecular docking studies were performed to visualize the binding mode of the drug candidate at the molecular level. Interestingly, complex 1 exhibited a significant cancer cell inhibitory rate than cisplatin and other complexes.

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“…These spectral attributes specified an intercalative binding mode among the nano-sized complexes and DNA. 57,58 As a result of these spectral attributes, the DNA duplex is subsequently stabilized. The recognized hypochromism is owed to the π-stacking interactions among the DNA base pairs and the complexes aromatic chromophore, similar to the well-known intercalator ethidium bromide.…”

Section: Uv-visible Spectroscopymentioning

confidence: 99%

DNA interaction, biological, and structural identification studies of bivalent nano‐sized Nickel, Palladium, and Platinum chelates of 2‐(((Z)‐6‐chloro‐3‐((E)‐([2‐hydroxyphenyl]imino)methyl)‐4H‐chromen‐4‐ylidene)amino)phenol Schiff base ligand

Alaghaz,

Alamier,

Almashnowi

2024

Applied Organom Chemis

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New nano‐sized Ni(II), Pd(II), and Pt(II) Schiff base chelates of 2‐(((Z)‐6‐chloro‐3‐((E)‐([2‐hydroxyphenyl]imino)methyl)‐4H‐chromen‐4‐ylidene)amino)phenol were designed and manufactured. The structural characterization of these isolated compounds was accomplished through spectral measurements, thermal and elemental analyses, and magnetic moment and conductivity determinations. The nano‐sized metal(II) complexes molar conductance indicated that they exhibited non‐electrolytic behavior. The UV–Vis spectral data and magnetic moment provided evidence for producing octahedral geometries in the nano‐sized complexes of Ni(II), Pd(II), and Pt(II). Metal chelates' thermal characteristics and decomposition kinetics were examined through Coats‐Redfern technique. The kinetic aspects, including pre‐exponential factor (A), the entropy of activation (ΔS), and activation energy (E) were enumerated. The X‐ray diffraction (XRD) calculations results of the trivalent metal complexes showed that sharp and intense diffraction peaks signify their crystalline properties with nanoscale particle size, and another proof was obtained from the images of SEM, TEM, EDX, and AFM also homogeneous distribution over the complex surface was confirmed. Molecular modeling techniques were adopted to optimize the metal complexes geometry. The viscosity and UV–Vis absorption determinations were utilized to assess the calf thymus DNA (CT‐DNA) interaction with the nano‐sized metal(II) chelates. The acquired data revealed that the complexes exhibit a non‐intercalative or incomplete binding pattern when interacting with DNA. The calculated DNA‐complexes binding constants are 3.93 ± 0.02 × 10,4 1.67 ± 0.3 × 105 and 2.88 ± 0.03 × 105 M−1, for nano‐sized Ni(II), Pd(II) and Pt(II) Schiff base chelates, successively. Both Gram‐negative (Escherichia coli and Pseudomonas aeruginosa) and Gram‐positive (Bacillus subtilis and Streptococcus pneumoniae) micro‐organisms were tested against H2L Schiff base ligand and its nano‐sized metal(II) complexes. Candida albicans and Aspergillus fumigatus were tested for antifungal activity, revealing that most complexes had activity lower than H2L ligand, while the complex of Ni(II) exhibited no discernible antifungal activities. Furthermore, the manufactured complexes underwent testing for their in‐vitro anticancer and antibacterial effectiveness. Furthermore, the complexes antioxidant activity was appraised through DPPH and ABTS inhibition tests, revealing distinct scavenging abilities on DPPH radicals. The complexes were ordered according to their scavenging capacity as follows: Ni(II) complex > Pd(II) complex > Pt(II) complex. Finally, the study of cell cycle arrest by the Ni(II), Pd(II), and Pt(II) complexes on HEPG2 has also been performed through flow cell cytometry.

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Low-dimensional compounds containing bioactive ligands. Part VI: Synthesis, structures, in vitro DNA binding, antimicrobial and anticancer properties of first row transition metal complexes with 5-chloro-quinolin-8-ol

Cited by 51 publications

References 42 publications

A Comparative Investigation of the Role of the Anchoring Group on Perylene Monoimide Dyes in NiO‐Based Dye‐Sensitized Solar Cells

A Comparative Investigation of the Role of the Anchoring Group on Perylene Monoimide Dyes in NiO‐Based Dye‐Sensitized Solar Cells

Two Mn^II, Cu^II complexes derived from 3,5‐bis(1‐imidazoly) pyridine: Synthesis, DNA binding, Molecular docking and cytotoxicity studies

DNA interaction, biological, and structural identification studies of bivalent nano‐sized Nickel, Palladium, and Platinum chelates of 2‐(((Z)‐6‐chloro‐3‐((E)‐([2‐hydroxyphenyl]imino)methyl)‐4H‐chromen‐4‐ylidene)amino)phenol Schiff base ligand

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Low-dimensional compounds containing bioactive ligands. Part VI: Synthesis, structures, in vitro DNA binding, antimicrobial and anticancer properties of first row transition metal complexes with 5-chloro-quinolin-8-ol

Cited by 51 publications

References 42 publications

A Comparative Investigation of the Role of the Anchoring Group on Perylene Monoimide Dyes in NiO‐Based Dye‐Sensitized Solar Cells

A Comparative Investigation of the Role of the Anchoring Group on Perylene Monoimide Dyes in NiO‐Based Dye‐Sensitized Solar Cells

Two MnII, CuII complexes derived from 3,5‐bis(1‐imidazoly) pyridine: Synthesis, DNA binding, Molecular docking and cytotoxicity studies

DNA interaction, biological, and structural identification studies of bivalent nano‐sized Nickel, Palladium, and Platinum chelates of 2‐(((Z)‐6‐chloro‐3‐((E)‐([2‐hydroxyphenyl]imino)methyl)‐4H‐chromen‐4‐ylidene)amino)phenol Schiff base ligand

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Two Mn^II, Cu^II complexes derived from 3,5‐bis(1‐imidazoly) pyridine: Synthesis, DNA binding, Molecular docking and cytotoxicity studies