Synthesis, structure and biological evaluation of mixed ligand oxidovanadium(<scp>iv</scp>) complexes incorporating 2-(arylazo)phenolates

Lima, Sudhir; Banerjee, Atanu; Mohanty, Monalisa; Sahu, Gurunath; Kausar, Chahat; Patra, Samir Kumar; Garribba, Eugenio; Kaminsky, Werner; Dinda, Rupam

doi:10.1039/c9nj01910c

Cited by 24 publications

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“…In continuation of our previous work on the synthesis, characterization, and biological studies of vanadium(V/IV) complexes [8,13,[31][32][33][34][35][36][37][38][39][40][41][42][43][44][45], here we report a new mononuclear dioxidovanadium(V) (1) as well as an oxido-bridged dinuclear oxidovanadium(V) (2) complex, each with a tridentate ONO donor Schiff base ligand derived from 2,4-dihydroxybenzaldehyde and 2-amino-4-nitrophenol. Considering the therapeutic potential of the synthesized polyphenolic ligand molecule [27,30,46], corresponding oxidovanadium(V) complexes were synthesized to further investigate their pharmacological activities such as DNA interaction and anticancer activities.…”

Section: Introductionmentioning

confidence: 60%

“…Crystal data and refinement details are given in Table 5. The interaction of the ligand and its respective oxidovanadium(V) complexes (1 and 2) with CT-DNA was investigated by the absorption titration method with a Shimadzu spectrophotometer (UV-2450) [39,40,42,51]. The absorption titration of DNA was conducted by using a fixed concentration of metal complex (25 µM) in 50 mM Tris-HCl buffer (pH = 7.4), with gradual increases in concentration of the CT-DNA from 0 to 100 µM.…”

Section: Single-crystal X-ray Crystallographymentioning

confidence: 99%

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Study of DNA Interaction and Cytotoxicity Activity of Oxidovanadium(V) Complexes with ONO Donor Schiff Base Ligands

2021

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Two new oxidovanadium(V) complexes, (HNEt3)[VVO2L] (1) and [(VVOL)2μ-O] (2), have been synthesized using a tridentate Schiff base ligand H2L [where H2L = 4-((E)-(2-hydroxy-5-nitrophenylimino)methyl)benzene-1,3-diol] and VO(acac)2 as starting metal precursor. The ligand and corresponding metal complexes are characterized by physicochemical (elemental analysis), spectroscopic (FT-IR, UV–Vis, and NMR), and spectrometric (ESI–MS) methods. X-ray crystallographic analysis indicates the anion in salt 1 features a distorted square-pyramidal geometry for the vanadium(V) center defined by imine-N, two phenoxide-O, and two oxido-O atoms. The interaction of the compounds with CT–DNA was studied through UV–Vis absorption titration and circular dichroism methods. The results indicated that complexes showed enhanced binding affinity towards DNA compared to the ligand molecule. Finally, the in vitro cytotoxicity studies of H2L, 1, and 2 were evaluated against colon cancer (HT-29) and mouse embryonic fibroblast (NIH-3T3) cell lines by MTT assay. The results demonstrated that the compounds manifested a cytotoxic potential comparable with clinically referred drugs and caused cell death by apoptosis.

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Section: Introductionmentioning

confidence: 60%

Section: Single-crystal X-ray Crystallographymentioning

confidence: 99%

Study of DNA Interaction and Cytotoxicity Activity of Oxidovanadium(V) Complexes with ONO Donor Schiff Base Ligands

2021

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“…Vanadium complexes (vanadocene dichloride, Cp 2 V IV Cl 2 ) were first studied for their anticancer activity in the treatment of Ehrlich ascites tumor in the 1983. − Later on Metvan, [V IV O(4,7-Me 2 phen) 2 (SO 4 )] (4,7-Me 2 phen = 4,7-dimethyl-1,10-phenanthroline), was reported to be a promising anticancer drug against various cancer cell lines, including cisplatin-resistant testicular and ovarian cancer . Gradually, a great deal of attention has been paid toward the study of anticancer activities of several oxidovanadium complexes having O- and N-donor ligands and their underlying molecular and biochemical mechanisms, such as the (i) species or form of the complex in which they are delivered to the target organs, as the ligand-exchange and redox chemistry of vanadium complexes under biologically relevant conditions is generally complicated, (ii) regulation of metabolic pathways such as the disruption of cellular metabolism and alterations of some cellular signal transduction pathways, (iii) the mechanism of action and binding to biomolecules, and (iv) the chemical nature of the ligands that may confer better selectivity and potency to the biological efficacy of the vanadium complexes. − Even our group has contributed various oxovanadium(V/IV) complexes bearing ONO donor ligands with substantial anticancer activity against various human cancer cells. − …”

Section: Introductionmentioning

confidence: 99%

Water-Soluble Dioxidovanadium(V) Complexes of Aroylhydrazones: DNA/BSA Interactions, Hydrophobicity, and Cell-Selective Anticancer Potential

et al. 2021

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Five new anionic aqueous dioxidovanadium(V) complexes, [{VO2L1,2}A(H2O) n ]α (1–5), with the aroylhydrazone ligands pyridine-4-carboxylic acid (3-ethoxy-2-hydroxybenzylidene)hydrazide (H2L1) and furan-2-carboxylic acid (3-ethoxy-2-hydroxybenzylidene)hydrazide (H2L2) incorporating different alkali metals (A = Na+, K+, Cs+) as countercation were synthesized and characterized by various physicochemical techniques. The solution-phase stabilities of 1–5 were determined by time-dependent NMR and UV–vis, and also the octanol/water partition coefficients were obtained by spectroscopic techniques. X-ray crystallography of 2–4 confirmed the presence of vanadium(V) centers coordinated by two cis-oxido-O atoms and the O, N, and O atoms of a dianionic tridentate ligand. To evaluate the biological behavior, all complexes were screened for their DNA/protein binding propensity through spectroscopic experiments. Finally, a cytotoxicity study of 1–5 was performed against colon (HT-29), breast (MCF-7), and cervical (HeLa) cancer cell lines and a noncancerous NIH-3T3 cell line. The cytotoxicity was cell-selective, being more active against HT-29 than against other cells. In addition, the role of hydrophobicity in the cytotoxicity was explained in that an optimal hydrophobicity is essential for high cytotoxicity. Moreover, the results of wound-healing assays indicated antimigration in case of HT-29 cells. Remarkably, 1 with an IC50 value of 5.42 ± 0.15 μM showed greater activity in comparison to cisplatin against the HT-29 cell line.

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“…29 The exponential progress in the medicinal chemistry of biologically relevant vanadium complexes for therapeutic applications is evident from numerous reports. 30–33…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and biological properties of oxidovanadium(IV) complexes of acetylsalicylhydroxamic acid (N-acetyloxy-2-hydroxybenzamide) as potential antimicrobials

Priya

Kumar

Sharma

2020

Journal of Chemical Research

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New oxidovanadium(IV) complexes of composition [VO(AcSHA)2] 1 and [VO(acac)(AcSHA)] 2 are synthesized by reactions of VOSO4.5H2O and [VO(acac)2] with acetylsalicylhydroxamic acid AcSH2A (C6H4(OH)(CONHOCOCH3)) in a 1:2 molar ratio in absolute ethanol. The compounds are characterized by the Fourier-transform infrared spectroscopy, ultraviolet–visible spectroscopy, electron spin resonance, and mass spectrometry along with elemental analyses, molar conductivity, and magnetic moment measurements. The infrared spectra of the complexes suggest bonding through carbonyl and phenolic oxygen atoms (O,O coordination). The magnetic moment, electron spin resonance, and mass spectra of the complexes indicate that both exist as monomers, and a distorted square pyramidal geometry around vanadium is proposed. The thermal behavior of the complexes is studied by thermogravimetry and differential thermal analysis techniques under an N2 atmosphere, yielding VO2 as the decomposition product. The in vitro antimicrobial assays against pathogenic Gram-positive bacteria, Gram-negative bacteria, and fungi (minimum inhibitory concentration method) show the appreciable antimicrobial potential relative to the respective standard drugs, tetracycline hydrochloride, and fluconazole.

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Synthesis, structure and biological evaluation of mixed ligand oxidovanadium(iv) complexes incorporating 2-(arylazo)phenolates

Abstract: Synthesis and characterization of mixed ligand oxidovanadium(iv) complexes [VIVO(L1–4)(LNN)] incorporating arylazo ligands: evaluation of DNA/BSA interaction and cytotoxicity activity.

Cited by 24 publications

References 134 publications

Study of DNA Interaction and Cytotoxicity Activity of Oxidovanadium(V) Complexes with ONO Donor Schiff Base Ligands

Study of DNA Interaction and Cytotoxicity Activity of Oxidovanadium(V) Complexes with ONO Donor Schiff Base Ligands

Water-Soluble Dioxidovanadium(V) Complexes of Aroylhydrazones: DNA/BSA Interactions, Hydrophobicity, and Cell-Selective Anticancer Potential

Synthesis, characterization, and biological properties of oxidovanadium(IV) complexes of acetylsalicylhydroxamic acid (N-acetyloxy-2-hydroxybenzamide) as potential antimicrobials

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