Synthesis of nickel(II) complexes of isatin thiosemicarbazone derivatives: <i>in vitro</i> anti-cancer, DNA binding, and cleavage activities

Ali, Amna Qasem; Teoh, Siang Guan; Eltayeb, Naser Eltaher; Ahamed, Mohamed B. Khadeer; Majid, Ams Abdul

doi:10.1080/00958972.2014.959943

Cited by 21 publications

(8 citation statements)

References 52 publications

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“…However, the complex alone is less effective in cleaving DNA than when it is associated with H 2 O 2 . In this way, we propose that complex II binds to minor groove of DNA and triggers breaks through a redox mechanism as reported by several authors [52][53][54][55][56][57][58].…”

Section: Cleavage Of Plasmid Dna By Complex IIsupporting

confidence: 54%

“…Ali et al also observed that Ni II complexes can degrade pBR322 plasmid through oxidative cleavage in the presence of H 2 O 2 inducing formation of hydroxyl radical species. The authors also observed that the addition of hydroxyl radical scavenger, like DMSO, completely inhibits DNA cleavage activity of the studied complexes [52]. According to these authors, Fenton-type or Haber-Weisstype reactions can explain how this oxidative break occurs.…”

Section: Cleavage Of Plasmid Dna By Complex IImentioning

confidence: 85%

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Obtenção de complexos de Pt(II) e Pd(II) derivados de 1,3,4-oxadiazol-2-(3H)-tiona e 5-amino-1,3,4-tiadiazol-2-tiol: potencial antitumoral de dois complexos de Pt(II) contendo 1,10-fenantrolina

Souza¹

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Metal-based drugs have been developed in order to minimize side effects and/or to overcome intrinsic or acquired resistance to antitumor drugs available in medical clinics. In this sense, we are also looking for new pharmacological agents capable of curing or at least prolonging the survival of patients with tumors classified as incurable until then. Considering the need for rational production of new antitumor agents, this work describes the synthesis and structural characterization of new complexes of Pt (II) and Pd (II) of the type [M(L1)2(L2)2] (L1 = derived from 5-alkyl-1,3,4-oxadiazole-2-thione (5-alkyl-odztH) and L2 = triphenylphosphine) and of the type [M(L1)2L2] (L1 = derived from 5-alkyl-odztH or 5-amino-1,3,4-thiadiazole-2-thiol (5amino-tdztH) and L2 = 1,10-phenanthroline). The platinum and palladium complexes were characterized by elemental analysis, conductivity measurements, high-resolution electrospray ionization mass spectrometry (HRESIMS), infrared spectroscopy (FT-IR) and multinuclear NMR spectroscopy. Three complexes of the type [Pt(L1)2(PPh3)2] and one complex of the type [Pt(L1)2fen] had their crystalline structures determined by single-crystal X-ray diffraction. In all the complexes, the metal ion was coordinated with the two L1 ligands via a sulfur atom, in which two triphenylphosphine molecules or one phenanthroline molecule completes its coordination sphere. The molar conductivity values of 1.0 × 10 −3 mol L −1 solutions confirm that the complexes are non-electrolytes. The cytotoxic activity of the [Pt(heptyl-odzt)2fen] and [Pt(nonyl-odzt)2fen] complexes was evaluated in two tumor-cell lines (MCF-7 and MDA-MB-231), with the complex [Pt(5-nonil-odztH) 2 fen] being more active in both, since their IC50 values were lower. DNA interaction studies for both complexes reveled Kb values on the order of 10 4 M −1 , with no variation observed in positive or negative bands of circular dichroism (CD) spectra. In turn, in the fluorescence spectra of the Hoechst-DNA system, an observed reduction in fluorescence intensity indicated that these complexes interact with DNA through the minor groove.

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Section: Cleavage Of Plasmid Dna By Complex IIsupporting

confidence: 54%

Section: Cleavage Of Plasmid Dna By Complex IImentioning

confidence: 85%

Obtenção de complexos de Pt(II) e Pd(II) derivados de 1,3,4-oxadiazol-2-(3H)-tiona e 5-amino-1,3,4-tiadiazol-2-tiol: potencial antitumoral de dois complexos de Pt(II) contendo 1,10-fenantrolina

Souza¹

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“…The metal to ligand charge transfer bands are found at 350–400 and 400–450 nm. [ 56 ] The lower wavelength band is assigned to S → M(II) transitions, which are quite common in the electronic spectra of metal chelates of thiosemicarbazones, [ 57 ] and the higher wavelength band is associated with N → M(II) transitions. It has been shown that the phenolate compounds show a broadening line with a tail running across the visible part of the spectrum resulting from phenolate to metal charge transfer that overlaps on the high wavelength side of S → M(II) transitions.…”

Section: Resultsmentioning

confidence: 99%

“…[56] The lower wavelength band is assigned to S ! M(II) transitions, which are quite common in the electronic spectra of metal chelates of thiosemicarbazones, [57] and the higher wavelength band is associated with N ! M(II) transitions.…”

Section: T a B L Ementioning

confidence: 99%

Synthesis, spectroscopic, electrochemical characterization, density functional theory (DFT), time dependent density functional theory (TD‐DFT), and antibacterial studies of some Co(II), Ni(II), and Cu(II) chelates of (E)‐4‐(1,5‐dimethyl‐3‐oxo‐2‐phenyl‐2,3‐dihydro‐1H‐pyrazol‐4‐yl)‐1‐(3‐hydroxynaphthalen‐2‐yl)methylene) thiosemicarbazide Schiff base ligand

El‐Sawaf

Abdel‐Monem

Azzam

2020

Applied Organom Chemis

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In this study, mononuclear Co(II), Ni(II), and Cu(II) chelates of the potentially tridentate O, N, S donor ligand (E)-4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-1-(3-hydroxynaphthalen-2-yl)methylene) thiosemicarbazide (H 2 L) were synthesized and characterized by elemental analyses, conductivity measurements, Fourier transform infrared spectroscopy, UV-visible spectroscopy, magnetic susceptibility, electron spin resonance (ESR) spectral analysis, thermal thermogravimetric analyses, cyclic voltammetry, and theoretical density functional theory (DFT) and time dependent density functional theory (TD-DFT) studies. The potential donors O (phenolic) and N (azomethine) are found in a syn configuration due to a strong intramolecular hydrogen bond [O-H …. N(1)] as shown in the 1 H NMR spectrum of the free ligand. In addition, analytical results revealed the formation of the metal chelates in a ligand-to-metal molar ratio of 1:1. The organic ligand (H 2 L) coordinated to the metal center through azomethine nitrogen, phenolate oxygen, and thione/thiolate sulfur groups with the formation of a five-and six-membered rings. The magnetic and spectral results supported the formation of tetrahedral geometry around the Co(II) and Ni(II) centers, while Cu(II) centers were assumed to have a square planar geometry. The time dependent density functional theory (TD-DFT) calculation outputs were used to expect and explain the experimental bathochromic and hypsochromic shifts resulting from the ligand chelation. The antibacterial activity of the compounds under study was evaluated in vitro against Staphylococcus aureus and Escherichia coli demonstrating Gram-positive and Gram-negative bacteria, respectively. It was found that among synthesized compounds, Cu(II) chelate 5 showed the most inhibitory activity against both Gram-positive and Gram-negative

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“…9,10 The coordination also can be tridentate by incorporating the Oxygen of the carbonyl group in the Isatin. 11,12 Isatin derived Schiff bases and their complexes are known to have antibacterial and antifungal activity. 13,14 Furthermore, the Schiff bases of isatin were also reported to possess cytotoxic and anticonvulsant Isatin-derived schiff bases with S-dithiocarbazate ester and their complexes are increasingly important for antibacterial activity, so new Hg complexes were prepared with benzyl 2-(2oxoindolin-3-ylidene) hydrazinecarbodithioate (BHT) and diphosphines (dppm, dppe, dppp and dppb) or amines (bipy, phen).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Antibacterial Activity of some Hg(II) Complexes with Mixed Benzyl 2-(2-oxoindolin-3-ylidene) Hydrazinecarbodithioate and Phosphines or Amines Ligands

2021

TJNPR

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activity. 15,16 The anticancer evaluation of a substantial number of metal complexes containing isatin-based ligands has been described as antitumor compounds, especially Mg(II), Co(II), Ni(II), and Cu(II) complexes, with different coordination geometries and reactivities. 17 Materials and MethodsAll the chemicals, reagents and solvents for the synthesis of compounds were supplied and used without more purification. The melting point of the prepared complexes was recorded on Automatic (SMP30) melting point apparatus. The molar conductivity of 10 -3 M freshly DMSO solution of prepared complexes was measured using (Starter 3100c) digital conductivity meter at 25 o C. Microanalyses for carbon, hydrogen, nitrogen and sulfur were carried out using an Elementar vario El III CHN elemental analyzer. The IR spectra of the prepared complexes as KBr pellets were recorded using a Shimadzu FT-IR 8400S spectrophotometer (400-4000 cm -1 ). NMR spectra were acquired on a Bruker 400 MHz spectrometer in DMSO-d6 as a solvent. The isolates of the pathological bacteria that were used in the research obtained from the laboratories of the Department of Life Sciences in the College of Education for Pure Sciences at the University of Tikrit. Preparation of benzyl 2-(2-oxoindolin-3-ylidene)hydrazinecarbodithioate (BHT) ligandThe benzyl 2-(2-oxoindolin-3-ylidene)hydrazinecarbodithioate (BHT) Prepared by two steps: First step: Preparation of S-Benzyldithiocarbazate (SBDTC). This compound was synthesized as previously reported, 18 the melting point was 124 o C where it was at 124-125 o C in the literature. 19 Second step: To the hot solution of S-benzyldithiocarbazate, SBDTC (1.36g, 0.01 mol) in ethanol (35 mL), an equimolar amount of isatin

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Synthesis of nickel(II) complexes of isatin thiosemicarbazone derivatives: in vitro anti-cancer, DNA binding, and cleavage activities

Cited by 21 publications

References 52 publications

Obtenção de complexos de Pt(II) e Pd(II) derivados de 1,3,4-oxadiazol-2-(3H)-tiona e 5-amino-1,3,4-tiadiazol-2-tiol: potencial antitumoral de dois complexos de Pt(II) contendo 1,10-fenantrolina

Obtenção de complexos de Pt(II) e Pd(II) derivados de 1,3,4-oxadiazol-2-(3H)-tiona e 5-amino-1,3,4-tiadiazol-2-tiol: potencial antitumoral de dois complexos de Pt(II) contendo 1,10-fenantrolina

Synthesis, Characterization and Antibacterial Activity of some Hg(II) Complexes with Mixed Benzyl 2-(2-oxoindolin-3-ylidene) Hydrazinecarbodithioate and Phosphines or Amines Ligands

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