New transition metal complexes of 2,4-dihydroxybenzaldehyde benzoylhydrazone Schiff base (H2dhbh): Synthesis, spectroscopic characterization, DNA binding/cleavage and antioxidant activity

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A series of new complexes of oxovanadium(IV) [VO(L)(B)] and ruthenium(II) [Ru(CO)(PPh3)2(L)] (1.1- 1.3, 2.1–2.3) (H2L = dehydroacetic acid Schiff base of S‐methyldithiocarbazate, H2smdha (1) or S‐benzyldithiocarbazate, H2sbdha (2); B = 2,2′‐bipyridine (bpy) or 1,10‐phenanthroline (phen)) have been synthesized. The structure of these complexes was authenticated using elemental analyses and spectroscopic techniques, and their magnetic properties and electrochemical behaviour were studied. The molecular structures of oxovanadium(IV) complexes [VO(smdha)(bpy)]⋅CH2Cl2 (1.1) and [VO(sbdha)(phen)]⋅2H2O (2.2) were confirmed using single‐crystal X‐ray crystallography. Analytical data showed that the ligands 1 and 2 are chelated to the metal centres in a bi‐negative tridentate fashion through azomethine N, thiol S and deprotonated hydroxyl group. The antioxidant activity of the synthesized compounds was tested against 2,2‐diphenyl‐1‐picrylhydrazyl) radical, which showed that the complexes demonstrate a better scavenging activity than their corresponding ligands. The cupric ion reducing antioxidant capacity method was also employed and the total equivalent antioxidant capacity values were found to be higher for the oxovandium(IV) complexes. DNA binding affinity of the compounds was determined using UV–visible and fluorescence spectra, revealing an intercalation binding mode. Higher cytotoxicity for the complexes compared to their ligands was found against human liver hepatocellular carcinoma (HepG2) and breast adenocarcinoma (MCF7) cell lines using MTT assay.

Section: Resultssupporting

confidence: 82%

Section: Resultssupporting

confidence: 76%

Section: Resultsmentioning

confidence: 76%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 3 more Smart Citations

Oxovanadium(IV) and ruthenium(II) carbonyl complexes of ONS‐donor ligands derived from dehydroacetic acid and dithiocarbazate: Synthesis, characterization, antioxidant activity, DNA binding and in vitro cytotoxicity

Sarhan

Elsayed

Mashaly

et al. 2018

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Mononuclear Co(III), Ni(II) and Cu(II) complexes of 2‐(2,4‐dichlorobenzamido)‐N'‐(3,5‐di‐tert‐butyl‐2‐hydroxybenzylidene)benzohydrazide: Structural insight and biological assay

Chimmalagi

Kendur

Patil

et al. 2018

A series of mononuclear metal complexes of Co(III), Ni(II) and Cu(II) with 2-(2,4-dichlorobenzamido)-N′-(3,5-di-tert-butyl-2-hydroxybenzylidene)benzohydrazide (LH 3 ) have been synthesized and characterized using various physico-chemical, spectroscopic and single crystal X-ray diffraction techniques. Structural studies of [Co(LH)(LH 2 )]·H 2 O (4) revealed the presence of both amido and imidol tautomeric forms of LH 3 , resulting in a distorted octahedral geometry around the Co(III) ion. [Ni(LH)(H 2 O)]·H 2 O (5) and [Cu(LH)(H 2 O)]·H 2 O (6) are isomorphous structures and crystallize in the monoclinic P2 1 /c space group. The crystal structures of 4, 5 and 6 are stabilized by hydrogen bonds formed by the enclathrated water molecules, C-H···π and π···π interactions. Complexes along with the ligand (LH 3 ) were screened for their in vivo anti-inflammatory activity (carrageenan-induced rat paw edema method) and in vitro antioxidant activity (DPPH free radical scavenging assay). Metal complexes have shown significant anti-inflammatory and antioxidant potential.KEYWORDS anti-inflammatory activity, antioxidant activity, crystal structure, di-tert-butyl phenylhydrazone, isomorphous metal complexes

Novel metal complexes of 3‐acetylcoumarin‐2‐hydrazinobenzothiazole Schiff base: Design, structural characterizations, DNA binding, DFT calculations, molecular docking and biological studies

Elsayed

El‐Gharabawy

Butler

et al. 2020

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Five new Cu (II), Zn (II), Pd (II), Ru (III) and Ag(I) complexes, derived from the 3‐acetylcoumarin‐2‐hydrazinobenzothiazole Schiff base (Hachbt), have been synthesized and characterized. The structures were established with the aid of elemental analyses (C, H, N), FT‐IR, 1H‐NMR, ESR, UV–visible and ESI‐mass spectra. The complexes were also investigated by magnetic susceptibility, thermal gravimetric analysis (TG‐DTA) and cyclic voltammetry measurements. The results suggest that the Schiff base ligand behaves in two different ways: neutral mono/bidentate or mono‐negative bi/tridentate. The calf thymus DNA (CT DNA) binding affinities of Hachbt and its complexes have been examined by UV–visible spectroscopy. The antifungal activity of the compounds was also screened against two fungal species of wood‐decay basidiomycetes using the agar dilution method. Different complexes caused a reduction in the fungal colony diameters at a media concentration of 100 μg/ml. The best antifungal activity was observed for the Pd (II) and Ag(I) complexes with a 60% and 79% reduction, respectively. The effect of the complexes on the ability of the same fungi to decolorize poly‐R dye on agar plates was also tested. All of the complexes showed an enhanced effect on the decolorization ability and the Cu (II) and Ru (III) complexes exhibited the strongest effect at a media concentration of 5 μg/ml. Theoretical studies were performed for all the complexes using the DFT/B3LYP/6–31 + g(d) basis set for calculations on the ligand atoms and LAN2DZ for the Pd (II) complex. The optimized geometries were found to be in a good agreement with the proposed structures. The molecular docking calculations show that the binding affinity of the Pd (II) complex is −309.170‐309.2 kcal/mol, which suggests complexation with the DNA minor groove.