Cu(<scp>ii</scp>), Mn(<scp>ii</scp>) and Zn(<scp>ii</scp>) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity

Stevanović, Nevena; Zlatar, Matija; Novaković, Irena; Pevec, Andrej; Radanović, Dušanka; Matić, Ivana Z.; Crnogorac, Marija Đorđić; Stanojković, Tatjana; Vujčić, Miroslava; Gruden, Maja; Sladić, Dušan; Anđelković, Katarina; Turel, Iztok; Čobeljić, Božidar

doi:10.1039/d1dt03169d

Cited by 15 publications

(21 citation statements)

References 81 publications

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“…The 1 H NMR spectrum of ligand L1 and complex 2 displayed the characteristic singlet peaks centered at 11.5 and 11.8 ppm, which were attributed to the imine proton (NH) of the hydrazide unit (H 8 ) and the indole ring (H 6 ), respectively. However, in the 1 H spectrum of complex 2 , the disappearance of the peak at 11.5 ppm suggested the coordination of ligand L1 (possibly in the enolic form) via deprotonation . The diagnostic azomethine (−HCN) singlet peak observed at 8.52 ppm (H1) in the spectrum of L1 was found deshielded and shifted to 8.75 ppm in the spectrum complex 2 , thereby confirming its coordination with the Zn(II) ion.…”

Section: Results and Discussionmentioning

confidence: 95%

“…However, in complex 2 , these diagnostic peaks were found shifted and appeared at 177 and 145 ppm, respectively, thereby validating the coordination of carbonyl oxygen and azomethine nitrogen of L1 with the Zn(II) ion. 28 In addition, the corresponding spectra of L1 and complex 2 displayed signature peaks of aromatic carbons in the region 110–140 ppm.…”

Section: Results and Discussionmentioning

confidence: 99%

“… 23 Furthermore, all other bond parameters (bond angles and bond lengths) are also found within the range of reported hydrazide Schiff bases ( Table S2 ). 28 …”

Section: Results and Discussionmentioning

confidence: 99%

“…DMSO solvent was used as a control. The antibacterial activity of compounds was confirmed by calculating the MIC values using the broth dilution method containing the concentrations of 2, 5, 10, and 15 mM in DMSO . These measurements were carried out in triplicate for each compound, and their average values are reported.…”

Section: Antibacterial Activitymentioning

confidence: 99%

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Syntheses, Structural Characterization, and Cytotoxicity Assessment of Novel Mn(II) and Zn(II) Complexes of Aroyl-Hydrazone Schiff Base Ligand

2023

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This work describes the syntheses, structural characterization, and biological profile of Mn(II)- and Zn(II)-based complexes 1 and 2 derived from the aroyl-hydrazone Schiff base ligand (L1). The synthesized compounds were thoroughly characterized by elemental analysis, Fourier transform infrared spectroscopy (FTIR), UV–vis, electron paramagnetic resonance (EPR), nuclear magnetic resonance (NMR), and single-crystal X-ray diffraction (s-XRD). Density functional theory (DFT) studies of complexes 1 and 2 were performed to ascertain the structural and electronic properties. Hirshfeld surface analysis was used to investigate different intermolecular interactions that define the stability of crystal lattice structures. To ascertain the therapeutic potential of complexes 1 and 2, in vitro interaction studies were carried out with ct-DNA and bovine serum albumin (BSA) using analytical and multispectroscopic techniques, and the results showed more avid binding of complex 2 than complex 1 and L1. The antioxidant potential of complexes 1 and 2 was examined against the 2,2-diphenyl picrylhydrazyl (DPPH) free radical, which revealed better antioxidant ability of the Mn(II) complex. Moreover, the antibacterial activity of synthesized complexes 1 and 2 was tested against Gram-positive and Gram-negative bacteria in which complex 2 demonstrated more effective bactericidal activity than L1 and complex 1 toward Gram-positive bacteria. Furthermore, the in vitro cytotoxicity assessment of L1 and complexes 1 and 2 was carried out against MDA-MB-231 (triple negative breast cancer) and A549 (lung) cancer cell lines. The cytotoxic results revealed that the polymeric Zn(II) complex exhibited better and selective cytotoxicity against the A549 cancer cell line as was evidenced by its low IC50 value.

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Section: Results and Discussionmentioning

confidence: 95%

Section: Results and Discussionmentioning

confidence: 99%

“… 23 Furthermore, all other bond parameters (bond angles and bond lengths) are also found within the range of reported hydrazide Schiff bases ( Table S2 ). 28 …”

Section: Results and Discussionmentioning

confidence: 99%

Section: Antibacterial Activitymentioning

confidence: 99%

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Syntheses, Structural Characterization, and Cytotoxicity Assessment of Novel Mn(II) and Zn(II) Complexes of Aroyl-Hydrazone Schiff Base Ligand

2023

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“…In previous biological studies Cu(II) complex with N,N,N-trimethyl-2-oxo-2-(2-(1-(thiazol-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride showed moderate antibacterial activity against all tested bacterial strains (best activity towards Escherichia coli strain and very weak selectivity towards Gram-negative bacteria) and moderate antifungal activity. 19 Also, this complex exhibited high radical-scavenging activity which is not surprising given the existence of a redox-active Cu 2+ in structure. Another significant feature is the pronounced cytotoxic activity against tested human cancer cell lines.…”

Section: Introductionmentioning

confidence: 81%

Evaluation of antitumor potential of Cu(II) complex with hydrazone of 2-acetylthiazole and Girard’s t reagent

Stevanović

Jevtovic²,

Mitić³

et al. 2022

JSCS

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In this paper, the previously synthesized Cu(II) complex ([CuL1(N3) (CH3OH)]BF4) with N,N,N-trimethyl-2-oxo-2-(2-(1-(thiazol-2-yl)ethylidene)- hydrazinyl)ethan-1-aminium chloride, has been characterized and its biological activity has been studied in detail. The Cu(II) complex consists of ligand coordinated in a deprotonated, formally neutral zwitter-ionic form, via NNO atoms, one azido ligand and one methanol molecule. The Cu(II) complex was selected due to results of the cytotoxic activity, the brine shrimp test and DPPH radical scavenging activity, which were previously performed. The effects of Cu(II) complex on cell cycle phase distribution of cervical adenocarcinoma HeLa cells were investigated in order to examine the mechanisms of its anticancer activity. The measurement of intracellular ROS levels in HeLa and HaCaT cell lines were evaluated in order to explore their possible generation and the role in cytotoxic activity. The possible anti-invasive and anti-angiogenic properties of Cu(II) complex were evaluated. DNA binding experiments, including fluorescence displacement study and DNA cleavage experiments, were performed in order to obtain information on the type of DNA-metal complex interactions.

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Synthesis, characterization, crystal structure, thermal and redox behaviour and antiproliferative studies of morpholine‐based two copper(II) compounds

Mandal

Nandi

Acharya

et al. 2023

Applied Organom Chemis

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Two novel copper(II) complexes, [Cu(L)(Cl) 2 ](H 2 O) (1) and [Cu(L)(N 3 ) 2 ] (2), have been synthesized from a morpholine-based N,N,N donor tridentate Schiff base ligand, (E)-N-(2-morpholinoethyl)-1-phenyl-1-(pyridin-2-yl)methanimine (L). Ligand (L) and its stabilized complexes, 1 and 2, have been comprehensively characterized by different physical and spectroscopic techniques. Solidstate single-crystal X-ray structures of both 1 and 2 have been determined. Powder X-ray diffraction studies on the bulk samples of 1 and 2 have been executed to demonstrate that the synthesized bulk materials retain their solidphase purity as that exists in the single crystals. Cyclic voltammetric experiments have been done to demonstrate the redox behaviour of 1 and 2. UV-vis spectra of the copper(II) complexes with variation in time were accrued to probe that both 1 and 2 retain their stability in solution. Thermogravimetric analysis (TGA) has been performed to collate the thermal stability of 1 along with its possible thermal degradation behaviour. Room temperature magnetic moments of 1 and 2 have been determined. Cytotoxic activity of 1 and 2 has been screened against non-small human lung cancer cell, A549.

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Cu(ii), Mn(ii) and Zn(ii) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity

Cited by 15 publications

References 81 publications

Syntheses, Structural Characterization, and Cytotoxicity Assessment of Novel Mn(II) and Zn(II) Complexes of Aroyl-Hydrazone Schiff Base Ligand

Syntheses, Structural Characterization, and Cytotoxicity Assessment of Novel Mn(II) and Zn(II) Complexes of Aroyl-Hydrazone Schiff Base Ligand

Evaluation of antitumor potential of Cu(II) complex with hydrazone of 2-acetylthiazole and Girard’s t reagent

Synthesis, characterization, crystal structure, thermal and redox behaviour and antiproliferative studies of morpholine‐based two copper(II) compounds

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