In vitro anticancer activity of 4(3H)-quinazolinone derived Schiff base and its Cu(II), Zn(II) and Cd(II) complexes: Preparation, X-ray structural, spectral characterization and theoretical investigations

Ashok, Ubale Panchsheela; Kollur, Shiva Prasad; Arun, Bansode Prakash; Sanjay, Chavan; Suresh, Karhale Shrikrishna; Anil, Nishad; Baburao, Helavi Vasant; Markad, Datta; Castro, Joaquín Ortega; Frau, Juan; Flores-Holgúın, Norma

doi:10.1016/j.ica.2020.119846

Cited by 17 publications

(7 citation statements)

References 46 publications

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“…It was found that they are able to suppress proliferation of cancer cells mainly by generating ROS or inducing cell cycle arrest, leading to apoptosis. However, when redox activity is prevented, then the metal complex may act as a DNA intercalator [27][28][29][30][31]. Since the cytotoxicity of transition-metal complexes appears to be the result of multiple mechanisms, copper complexes with various heterocyclic Schiff base ligands have been studied.…”

Section: Introductionmentioning

confidence: 99%

Enhancement of the Cytotoxicity of Quinazolinone Schiff Base Derivatives with Copper Coordination

Gurgul,

Hricovíniová,

Mazuryk

et al. 2023

Inorganics

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Two copper(II) complexes (Cu-L1, Cu-L2) derived from 2,3-substituted quinazolinone Schiff base ligands (L1, L2) were prepared to examine their anticancer activity. Compounds were characterized using various spectroscopic methods (FTIR, NMR, UV-vis) and quantum-chemical calculations. The biological effects of Cu(II) complexes bearing quinazolinone scaffolds were evaluated on two cancers’ cell lines (breast—MCF-7 and lung—A549), as well as on untransformed cells (keratinocytes—HaCaT). Copper complexes were highly cytotoxic, with IC50 in the low micromolar range, while the quinazoline ligands L1 and L2 remained inactive in inhibiting cell proliferation. Antioxidant activity was investigated in the model systems using DPPH and FRAP assays. The Cu-L1 and Cu-L2 complexes exhibited enhanced DPPH free radical scavenging efficiency compared to the L1 and L2 ligands, but their reducing ability was comparable to that of the free ligands. Evaluation of oxidative stress in vitro carried out by staining cells with various ROS-specific indicators showed reduced production of superoxide anion radical and hydrogen peroxide after treatment of cells with copper complexes. Such a negative impact on ROS formation in cells can lead to cellular redox imbalance and consequent cell death, among others, by inducing apoptosis and/or necrosis, depending on the copper complex used. We hypothesize that the high cytotoxic activity of the investigated copper complexes is apparently the result of multiple mechanisms of action, and the imbalance in the cellular antioxidant system partly contributes to the overall cytotoxic effect.

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Section: Introductionmentioning

confidence: 99%

Enhancement of the Cytotoxicity of Quinazolinone Schiff Base Derivatives with Copper Coordination

Gurgul,

Hricovíniová,

Mazuryk

et al. 2023

Inorganics

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“…The applications of Schiff bases for the synthesis of privileged frameworks are of prime significance in diversity-oriented synthesis and medicinal chemistry, among others. The phenolato ligands of metal complexes show highly potent in vitro anticancer activities [6,7].…”

Section: Introductionmentioning

confidence: 99%

Preparation, Spectroscopic Characterization, Theoretical Investigations, and In Vitro Anticancer Activity of Cd(II), Ni(II), Zn(II), and Cu(II) Complexes of 4(3H)-Quinazolinone-Derived Schiff Base

et al. 2020

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Herein, we report the synthesis and characterization of a new Schiff base ligand 3-[[(E)-(3-hydroxyphenyl)-methylidene]amino]-2-methyl-quinazolin-4(3H)-one (HAMQ) and its Cd(II), Ni(II), Zn(II), and Cu(II) complexes (C1–C4). The ligand HAMQ was synthesized by reacting 3-hydroxybenzaldehyde and 3-amino-2-methyl-4(3H)-quinazolinone in a 1:1 molar ratio. The structure of the ligand and its complexes (C1–C4) were evaluated using ultraviolet (UV)–visible (Vis) light spectroscopy, 1H-NMR, Fourier-transform infrared (FT-IR) spectroscopy, MS, elemental analysis, conductance data, and thermogravimetric analysis (TGA). The characterization results suggested that the bidentate ligand, HAMQ, coordinated to the metal center through the lactum oxygen and the azomethine nitrogen. Moreover, all the metal complexes were analyzed using powder X-ray diffraction studies, which revealed that all of them belong to a triclinic crystal system. The research was supplemented by density functional theory (DFT) studies on the IR and UV–Vis spectra, as well as the chemical reactivity of the HAMQ and its four metallic derivatives making use of conceptual density functional theory (CDFT) by means of KID (Koopmans in DFT) methodology. The synthesized complexes displayed significant in vitro anticancer activity against human cancer cell lines (HeLa and HCT-115).

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“…The bidentate quinolin-4(3 H )-one based Schiff base ligand L 11 and its 1,10-phenanthroline zinc complex 11 ( Figure 7 ) have been screened for their in vitro cytotoxic activity against the human breast cancer MCF-7 cell line [ 116 ]. Even if the antiproliferative activity of metal complexes is often due to the synergistic effect produced by the metal core and the ligands, the free ligand L 11 resulted inactive against MCF-7 cells.…”

Section: 22′-bipyridine and 110-phenanthroline Systemsmentioning

confidence: 99%

“…In fact, complex 11 exhibited interesting anticancer activity against MCF-7 cells (GI 50 = 0.016 μM) even at lower GI 50 value than the reference drug doxorubicin (GI 50 = 0.018 μM) ( Table 3 ). In addition, the cells treated with 11 displayed a bead like shape, indicating cellular shrinkage, vacuolated cytoplasm, small nuclei and membrionic blebbing that are typical features of apoptosis [ 116 ].…”

Section: 22′-bipyridine and 110-phenanthroline Systemsmentioning

confidence: 99%

Zinc Complexes with Nitrogen Donor Ligands as Anticancer Agents

et al. 2020

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The search for anticancer metal-based drugs alternative to platinum derivatives could not exclude zinc derivatives due to the importance of this metal for the correct functioning of the human body. Zinc, the second most abundant trace element in the human body, is one of the most important micro-elements essential for human physiology. Its ubiquity in thousands of proteins and enzymes is related to its chemical features, in particular its lack of redox activity and its ability to support different coordination geometries and to promote fast ligands exchange. Analogously to other trace elements, the impairment of its homeostasis can lead to various diseases and in some cases can be also related to cancer development. However, in addition to its physiological role, zinc can have beneficial therapeutic and preventive effects on infectious diseases and, compared to other metal-based drugs, Zn(II) complexes generally exert lower toxicity and offer few side effects. Zinc derivatives have been proposed as antitumor agents and, among the great number of zinc coordination complexes which have been described so far, this review focuses on the design, synthesis and biological studies of zinc complexes comprising N-donor ligands and that have been reported within the last five years.

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In vitro anticancer activity of 4(3H)-quinazolinone derived Schiff base and its Cu(II), Zn(II) and Cd(II) complexes: Preparation, X-ray structural, spectral characterization and theoretical investigations

Cited by 17 publications

References 46 publications

Enhancement of the Cytotoxicity of Quinazolinone Schiff Base Derivatives with Copper Coordination

Enhancement of the Cytotoxicity of Quinazolinone Schiff Base Derivatives with Copper Coordination

Preparation, Spectroscopic Characterization, Theoretical Investigations, and In Vitro Anticancer Activity of Cd(II), Ni(II), Zn(II), and Cu(II) Complexes of 4(3H)-Quinazolinone-Derived Schiff Base

Zinc Complexes with Nitrogen Donor Ligands as Anticancer Agents

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