Synthesis, coordination properties and biological activity of vanadium complexes with hydrazone Schiff base ligands

Szklarzewicz, Janusz; Jurowska, Anna; Matoga, Dariusz; Kruczała, Krzysztof; Kazek, Grzegorz; Mordyl, Barbara; Sapa, Jacek; Papież, Monika

doi:10.1016/j.poly.2020.114589

Cited by 39 publications

(25 citation statements)

References 21 publications

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“…All this may indicate that the biological activity of 3 is similar to that of BMOV, as both types of complex decompose after injection into simple VO 2+ ions. Complex 2, being more stable, is more effective due to its only partial decomposition, supporting the observed fact that the type of L ligand influences the biological activity and in some cases V(IV) complexes with ONO ligands are threefold more effective than BMOV and human insulin [23].…”

Section: Discussionsupporting

confidence: 62%

“…Usually, in our previous investigations with vanadium complexes based on Schiff base ligands, oxidation of V(IV) to V(V) when co-ligand (for example, phen) was not used [22,23,25,27,28] was observed. In this part of the investigation, the oxidovanadium(IV) complexes (1, 9, 11, 12, 18, 23) were obtained, among others, for which there was no change in the oxidation state and for which a stabilizing ligand for the V(IV) oxidation state was not used in the synthesis.…”

Section: General Remarks On the Synthesismentioning

confidence: 99%

“…We present herein the synthesis and physicochemical characterization of vanadium(IV,V) complex with tridentate ONO hydrazone Schiff base ligands, now extended to those based on 5-nitrosalicylaldehyde, 5-methoxysalicylaldehyde, and 5-sulfosalicylaldehyde with a set of hydrazides used by us previously [20][21][22][23][24][25][26][27][28]. As shown earlier, for tridentate contrary to bidentate ligands, a huge change of biological activity is observed, indicating that complexes in unchanged form (or at least with ONO ligand still coordinated to vanadium) pass into cells.…”

Section: Introductionmentioning

confidence: 99%

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Characterization and antidiabetic activity of salicylhydrazone Schiff base vanadium(IV) and (V) complexes

et al. 2020

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Twenty-four oxidovanadium(IV,V) complexes with tridentate Schiff base ligands based on 5-nitrosalicylaldehyde, 5-methoxysalicylaldehyde, or 5-sulfosalicylaldehyde and respective hydrazide were isolated, and characterized using physicochemical and spectroscopic methods. Three of them were structurally characterized by single-crystal X-ray structure determination. The biological activity studies included inhibition of human tyrosine phosphatases, studies on myocyte C2C12, adipocyte 3T3-L1, and human hepatocyte HepG2 cell lines, glucose uptake in myocytes and adipocytes, and cytotoxicity tests. The complexes that were unstable in solutions showed biological activity typical of other V(IV) complexes, while the stable one showed much higher, ligand-dependent, activity.

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Section: Discussionsupporting

confidence: 62%

Section: General Remarks On the Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Characterization and antidiabetic activity of salicylhydrazone Schiff base vanadium(IV) and (V) complexes

et al. 2020

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“…[ 28 ] Also, trinuclear VO 2+ ‐ and VO 3+ ‐complexes of arylhydrazone derivatives have been reported as peroxidase mimicking potential by Pessoa et al [ 29 ] Vanadium (III–V)–Schiff base hydrazone complexes, which are derived from phenylacetic acid, documented a valuable inhibiting reactivity of human tyrosine phosphatases through cytotoxicity investigation. [ 30 ] Furthermore, the insulin‐like action of some synthesized VO‐aroylhydrazone chelates was studied in some normal and streptozotocin‐diabetic mice. [ 31 ] Moreover, dioxidovanadium (V)–nicotinoylhydrazone complexes showed high antidiabetic activity, which has also been intensively studied.…”

Section: Introductionmentioning

confidence: 99%

Two ionic oxo‐vanadate and dioxo‐molybdate complexes of dinitro‐aroylhydrazone derivative: Effective catalysts for epoxidation reactions, biological activity, ctDNA binding, density functional theory, andin silicoinvestigations

Adam

Shaaban

El‐Metwaly

2022

Applied Organom Chemis

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To meet the ecological demand for synthesis of ecofriendly metalated organic compounds, two new green dinitro‐aroylhydrazone derivatives (HLZNa) were used for the synthesis of vanadate(IV) and cis‐molybdate(VI) complexes (VOLZNa and MoO2LZNa). The N,O‐bidentate ligand and its M‐pincer chelates were characterized using various spectroscopic tools. Infrared spectra exhibited a high shift of the CH=N band with the disappearance of the O–H band of HLZNa after its coordination with V4+ and Mo6+ in VOLZNa and MoO2LZNa, respectively. 1H NMR spectra supported this observation for HLZNa compared with that of MoO2LZNa for the spectral signal of CH=N and O–H groups. In the UV–Vis. spectra, VOLZNa showed an additional spectral band at 741 nm for the d → d transition, which accomplished such complexation. Catalytically, VOLZNa exhibited slightly more catalytic action, with 92% yield after 2 h, compared with the MoO2LZNa catalyst (4 h with 92% yield) in the oxygenation of 1,2‐cyclooctene, that is, the epoxidation, at 90 °C. A strong reversible electrochemical behavior of VOLZNa (V4+/V5+redox couple) enhanced the catalytic action of VOLZNa over MoO2LZNa, which is supported by spectroscopic analysis. The biological behavior of HLZNa, VOLZNa, and MoO2LZNa was examined through their binding ability to ctDNA via UV–Vis. spectroscopy and hydrodynamic measurements. Spectroscopically, the derived binding constant of VOLZNa and MoO2LZNa (Kb = 4.45 and 5.01 × 108 mol−1 dm3, respectively) was higher than that of the free ligand (HLZNa, 2.88 × 108 mol−1 dm3), which is attributed to their reactivity toward ctDNA. Also, the Gibbs free energy values ( ∆Gb≠) for such an interaction illustrated their high potential against ctDNA over their ligand (−31.14, −32.22, and −32.52 kJ/mol for HLZNa, VOLZNa, and MoO2LZNa, respectively). The metal ions (V4+ and Mo6+) in VOLZNa and MoO2LZNa, respectively, improved their antioxidant, antimicrobial, and antitumor activities over the free ligand. The structures of the current compounds were further elucidated using the DFT/B3LYP method, which confirmed the mode of bonding depending on the distribution of the coordinating functional groups. Some physical parameters were estimated to evaluate the probability of these compounds' reactivity biologically and catalytically. The catalytic role of the MoO2LZNa complex was confirmed computationally. The in vitro obtains regarding the antimicrobial activity of the M‐chelates were tested using in silico approaches. The outcomes reflected the high conformity of VOLZNa as an effective antimicrobial reagent.

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“…Accordingly, the hydrazonic chelators and their chelated compounds have been intensely utilized in coordination chemistry because of their chelating capabilities, physiological activities, and broad range of applications in several fields like analytical, clinical, biological, pharmacological, industrial chemistry, biomedical chemical, and wastewater remediation. [4][5][6][7] In this respect, various hydrazonic chelators and their chelated compounds have been stated to have important biological and pharmacological activities involving antimalarial, [8] enzyme inhibitors, [9][10][11][12] antimicrobial, antifungal, antibacterial, [13][14][15] antitrypanosome, [16] anticancer, [17,18] antidiabetic, [19,20] antitumor, [6,21,22] antiinflammatory, [10,23] antiviral, [10,24] and antioxidant. [25,26] Also, some acyl-hydrazone derivatives have been utilized in the Alzheimer's disease treatment, radical scavenging, and myeloperoxidase/acetylcholinesterase inhibition.…”

Section: Introductionmentioning

confidence: 99%

Structure investigation, density functional theory, and biostudy of synthesized dihydrazone incorporating isatin moiety and its homo‐bimetallic complexes

Shakdofa

Saleem

Shakdofa

2021

Applied Organom Chemis

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Seven homo-bimetallic complexes derived from 3-(-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)methylene)hydrazono)indolin-2-one with Fe 3+ , Co 2+ , Cu 2+ , and UO 2 2+ have been prepared and structurally investigated using elemental and thermo-gravimetric analyses and spectral, magnetic, and molar conductivity measurements. This structural investigation leads us to conclude that the bis-hydrazone has behaved as neutral tetradentate chelator chelated to the Fe 3+ , Co 2+ , Cu 2+ , and UO 2 2+ ions via the carbonyl and azomethine groups adopting distorted octahedral structure for Fe 3+ , Co 2+ , and Cu 2+ complexes (2-5), whereas the Cu 2+ complexes (6-7) have square planar structures. The structural characterization of bis-hydrazone and its chelated compounds has been supported by density functional theory calculations. The optimized geometry, global reactivity descriptors, and lowest unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO) of the molecules have been calculated in accordance with the density functional theory (DFT)-Beckee3eLeeeYangeParr (B3LYP) technique and 6e311G(d,p) basis set. The molecular electrostatic potential image was also drawn by the DFT-B3LYP technique and 6e311G(d,p) basis set to envision the charge distribution and chemical reactivity on the molecules. The bioeffect of bis-hydrazone and its chelated compounds was assessed against bacterial strains Bacillus subtilis, Escherichia coli, as well as fungal strains Canadian albicans and Aspergillus niger. The observed data imply encouraging bioeffect of some of these complexes in comparing with the free bis-hydrazone or amphotericin B (AmB) against all fungal C. albicans and A. niger.

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Synthesis, coordination properties and biological activity of vanadium complexes with hydrazone Schiff base ligands

Cited by 39 publications

References 21 publications

Characterization and antidiabetic activity of salicylhydrazone Schiff base vanadium(IV) and (V) complexes

Characterization and antidiabetic activity of salicylhydrazone Schiff base vanadium(IV) and (V) complexes

Two ionic oxo‐vanadate and dioxo‐molybdate complexes of dinitro‐aroylhydrazone derivative: Effective catalysts for epoxidation reactions, biological activity, ctDNA binding, density functional theory, andin silicoinvestigations

Structure investigation, density functional theory, and biostudy of synthesized dihydrazone incorporating isatin moiety and its homo‐bimetallic complexes

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