Vanadium complexes with salicylaldehyde-based Schiff base ligands—structure, properties and biological activity

Szklarzewicz, Janusz; Jurowska, Anna; Hodorowicz, Maciej; Gryboś, Ryszard; Kruczała, Krzysztof; Głuch‐Lutwin, Monika; Kazek, Grzegorz

doi:10.1080/00958972.2020.1755036

Cited by 27 publications

(20 citation statements)

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“…0.014 Å compared with 4. The V=O bond distance in 4, 10, and 16 is shorter than that observed in V(IV) analogs (1.604, 1.606, 1.593, 1.598, and 1.594 Å), and similar shortening is observed also for the V-O L (L = Schiff base ligand) bond [21,22]. In contrast, the V-N L distance is longer in V(V) compared with V(IV) complexes (bond distances 2.046, 2.058, 2.039, 2.038, and 2.031 Å) [21,22].…”

Section: Description Of the Structuressupporting

confidence: 59%

“…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: Description Of the Structuressupporting

confidence: 59%

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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“…By convention, the color red depicts negative potential (electron‐rich), whereas colors towards blue represent positive potential (electron‐poor). [ 4,5 ]…”

Section: Resultsmentioning

confidence: 99%

Synthesis, structural elucidation, biological screening, and density functional theory calculations of Cu(II), Ni(II), Mn(II), and Co(II) complexes of 20 Z‐N‐((Z)‐2‐(6‐nitrobenzo[d]thiazol‐2‐ylimino)‐1,2‐diphenylethylidene)‐5‐nitrobenzo[d]thiazol‐2‐amine Schiff base ligand

Shekhar

Sharma

Okolie

et al. 2022

Applied Organom Chemis

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The emerging Schiff base‐derived metal complexes are the building blocks for biomedical applications. Herein, novel Schiff base N,N′‐[(1Z,2Z)‐1,2‐diphenylethane‐1,2‐diylidene]bis(6‐nitro‐1,3‐thiazol‐2‐amine) and corresponding Cu(II), Ni(II), Mn(II), and Co(II) metal complexes were successfully synthesized and characterized. The characterization of ligand and corresponding metal complexes was carried out by employing elemental analysis, 1H and 13C nuclear magnetic resonance (NMR) spectroscopy, mass spectroscopy, Fourier transform infrared spectroscopy (FTIR) analysis, molar conductance, magnetic susceptibility measurements, electronic spectra, electronic paramagnetic resonance (EPR) and density functional theory (DFT) studies. DFT calculations at B3LYP/6‐311+G** level of theory have been executed to examine the equilibrium geometry of the ligand and metal complexes. Furthermore, total energy, highest‐occupied molecular orbital (HOMO) and lowest‐unoccupied molecular orbital (LUMO), and Mulliken atomic charges were reckoned. Tetrahedral geometry was observed in the case of the Ni(II) complex, and octahedral geometries were discerned for Cu(II), Mn(II), and Co(II), complexes. Docking studies were performed against the newly synthesized analogs with the active site of Escherichia coli (PDB ID: 3t88), Staphylococcus aureus (PDB ID: 3q8u), Candida Albicans (PDB ID: 3qlw), and Aspergillus flavus (PDB ID: 4ynt) receptors to recognize the interactions between complexes and identify their probable binding sites. Synthesized analogs were examined for in vitro antimicrobial activity employing both minimum inhibitory concentration and disk diffusion method against the aforementioned pathogens. The result for these pathogens suggested metal compounds evince higher activity in comparison to the free ligand.

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“…Schiff base oxidovanadium(IV/V) complexes with such donor systems have been preferred due to the excellent anticancer, antidiabetic, and antimicrobial activities exhibited by them. [ 16,33–35 ] In this context, two of our previous works reported ONS donor‐based oxovanadium(V) and O 2 N 2 donor‐based oxovanadium(IV) complexes that have shown excellent in vitro anticancer activity against breast cancer cells (MCF‐7) and glucose uptake inducing ability, respectively. [ 36,37 ] Also, it is expected that introducing noninnocent ligand systems such as catechol and bha to such coordination compounds would show increased potency for improved therapeutic activity behavior owing to the redox active nature of such coligands.…”

Section: Introductionmentioning

confidence: 99%

Oxidovanadium(IV/V) complexes bound with a ONS donor backbone: The search for therapeutic versatility in one class of compounds

Kongot

Chaudhary

Pooja

et al. 2021

Applied Organom Chemis

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Among the multifarious approaches to treat health challenges such as microbial infections, cancers, and diabetes, metallotherapy is a very significant one. Many transition metal‐based candidates have been previously developed that displayed promising therapeutic interests. Vanadium is one such biologically important transition metal, and in the present work, we have developed potent bioactive vanadium complexes, namely, [{VVO(hpdbal‐smdt)}2μ‐O] (1), [VVO(hpdbal‐smdt)(bha)] (2), [VVO(hpdbal‐smdt)(cat)] (3), [VIVO(hpdbal‐smdt)(phen)] (4), and [VIVO(hpdbal‐smdt)(bipy)] (5), which were synthesized using a ONS donor‐based ligand, H2hpdbal‐smdt (H2L), and [VO(acac)2] alongside secondary ligands, benzohydroxamic acid (bha), catechol (cat), 1,10‐phenanthroline (phen), and 2,2′‐bipyridyl (bipy), respectively. The complexes were mainly characterized using electron paramagnetic resonance (EPR), 1H‐NMR, 13C‐NMR, and infrared (IR) spectroscopy techniques. The ligand was additionally characterized using a single‐crystal X‐ray diffraction (XRD) technique. The compounds were tested for their therapeutic versatility, namely, glucose uptake activity, free radical scavenging activity, and growth inhibitory action towards resilient microbial strains and liver cancer cells. The oxo‐bridged dinuclear vanadium complex (1) showed promising growth inhibitory activity against Pseudomonas aeruginosa bacterial species. Secondary ligand tethered compound (2) displayed notable toxicity against the human liver cancer cells. All complexes induced glucose uptake by the insulin‐resistant cells and exhibited moderate to high antioxidant potential. pH titration and interaction study of these complexes with bovine serum albumin were conducted to investigate solution stability and protein binding properties.

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Vanadium complexes with salicylaldehyde-based Schiff base ligands—structure, properties and biological activity

Cited by 27 publications

References 50 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

Synthesis, structural elucidation, biological screening, and density functional theory calculations of Cu(II), Ni(II), Mn(II), and Co(II) complexes of 20 Z‐N‐((Z)‐2‐(6‐nitrobenzo[d]thiazol‐2‐ylimino)‐1,2‐diphenylethylidene)‐5‐nitrobenzo[d]thiazol‐2‐amine Schiff base ligand

Oxidovanadium(IV/V) complexes bound with a ONS donor backbone: The search for therapeutic versatility in one class of compounds

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