Ni(<scp>ii</scp>) complex with bishydrazone ligand: synthesis, characterization, DNA binding studies and pro-apoptotic and pro-differentiation induction in human cancerous cell lines

Filipović, Nenad R.; Bjelogrlić, Snežana K.; Todorović, Tamara R.; Blagojević, Vladimir A.; Muller, Christian D.; Marinković, Aleksandar D.; Vujčić, Miroslava; Janović, Barbara; Malešević, Aleksandar; Begović, Nebojša; Senćanski, Milan; Minić, Duško

doi:10.1039/c6ra24604d

Cited by 16 publications

(11 citation statements)

References 106 publications

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“…While more than a half of MCF-7 cells in the samples subjected to 1 at 10 μM were found as double-stained, CDDP at 75 and 100 μM guided only one third of those cells toward advanced stages of apoptotic death. Relying on results presented here and those we previously reported [116][117][118][119], 1 showed superior activity on both cell lines in respect to CDDP or other compounds investigated on CSCs.…”

Section: Superior Pro-apoptotic Activity Of 1 As Compared To Cddpsupporting

confidence: 81%

“…In general, covalent interactions include coordination to DNA base, sugar and phosphate moieties, as well as their nuclease activity. In the case of non-covalent interactions, metal complexes the most frequently interact with DNA via minor groove, and by intercalation [119]. Detection of interactions of DNA with potential drugs includes variety of conclusive electrochemical and spectroscopic methods [151,152].…”

Section: Dna Binding Studiesmentioning

confidence: 99%

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A novel binuclear hydrazone-based Cd(II) complex is a strong pro-apoptotic inducer with significant activity against 2D and 3D pancreatic cancer stem cells

Bjelogrlić

Todorović

Cvijetić

et al. 2019

Journal of Inorganic Biochemistry

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A novel binuclear Cd complex (1) with hydrazone-based ligand was prepared and characterized by spectroscopy and single crystal X-ray diffraction techniques. Complex 1 reveals a strong pro-apoptotic activity in both human, mammary adenocarcinoma cells (MCF-7) and pancreatic AsPC-1 cancer stem cells (CSCs). While apoptosis undergoes mostly caspase-independent, 1 stimulates the activation of intrinsic pathway with noteworthy down regulation of caspase-8 activity in respect to non-treated controls. Distribution of cells over mitotic division indicates that 1 caused DNA damage in both cell lines, which is confirmed in DNA interaction studies. Compared to 1, cisplatin (CDDP) does not achieve cell death in 2D cultured AsPC-1 cells, while induces different pattern of cell cycle changes and caspase activation in 2D cultured MCF-7 cells, implying that these two compounds do not share similar mechanism of action. Additionally, 1 acts as a powerful inducer of mitochondrial superoxide production with dissipated trans-membrane potential in the majority of the treated cells already after 6 h of incubation. On 3D tumors, 1 displays a superior activity against CSC model, and at 100 μM induces disintegration of spheroids within 2 days of incubation. Fluorescence spectroscopy, along with molecular docking show that compound 1 binds to the minor groove of DNA. Compound 1 binds to the human serum albumin (HSA) showing that the HSA can effectively transport and store 1 in the human body. Thus, our current study strongly supports further investigations on antitumor activity of 1 as a drug candidate for the treatment of highly resistant pancreatic cancer.

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Section: Superior Pro-apoptotic Activity Of 1 As Compared To Cddpsupporting

confidence: 81%

Section: Dna Binding Studiesmentioning

confidence: 99%

A novel binuclear hydrazone-based Cd(II) complex is a strong pro-apoptotic inducer with significant activity against 2D and 3D pancreatic cancer stem cells

Bjelogrlić

Todorović

Cvijetić

et al. 2019

Journal of Inorganic Biochemistry

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“…Morphological features of apoptotic and viable HeLa cells stained with Annexin V‐FITC and propidium iodide were observed from confocal fluorescence images of HeLa cells [ 59,60 ] . The result is depicted in Figure 8.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization, DNA binding, cytotoxicity and molecular docking properties of three novel butterfly‐like complexes with nitrogen‐containing heterocyclic ligands

Gao

Zhu

et al. 2020

Applied Organom Chemis

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Three novel complexes, namely [Nd·L1·HCOO·(H2O)4] (1), [Pr·L1·HCOO·(H2O)4] (2) and [In·L2·Cl·(H2O)2] (3) (L1 = 1,1‐bis(5‐(pyrazin‐2‐yl)‐1,2,4‐triazol‐3‐yl)methane, L2 = 1,1‐bis(5‐(pyrazin‐2‐yl)‐1,2,4‐triazol‐3‐yl)ketone), were synthesized and characterized. The molecular structures of 1–3 were confirmed using single‐crystal X‐ray diffraction. All three obtained complexes are zero‐dimensional and connected to each other by hydrogen bonds. In 1 and 2 the metal is surrounded by nine donors and 3 has seven coordination sites. The interaction of 1–3 with calf thymus DNA (CT‐DNA) was explored using UV absorption spectra and fluorescence spectra. The intrinsic binding constants of 1–3 with CT‐DNA are about 1.9 × 104, 1.4 × 104 and 1.1 × 104, respectively. Stern–Volmer quenching plots of 1–3 have slopes of 0.1508, 0.134 and 0.1205, respectively. The ability of these complexes to cleave pBR322 plasmid DNA was demonstrated using gel electrophoresis assay. Apoptosis studies of the three novel complexes showed a significant inhibitory effect on HeLa cells. Furthermore, MTT assays were used to evaluate the anticancer activity of the three complexes. The cytotoxicity study indicated that complex 1 possesses a higher inhibitory rate of HeLa cells than the other complexes. Especially, the efficacy of 1 was shown to be the highest for cisplatin at 24 h. A further molecular docking technique was introduced to understand the binding of the complexes toward the target DNA.

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“…Vibrational spectroscopy plays a major role in the identification of the functional groups of organic compounds and investigation of the molecular reaction kinetics and conformations . PED was evaluated as previously reported . It is worthy to mention that PED could explain the detailed vibrational assignments of the complexes.…”

Section: Spectroscopic Characterization Of (1) and (2)mentioning

confidence: 98%

Polymorphism of Palladium(II) Complexes : Crystal Structure Determination, Luminescence Properties, Hirshfeld Surface Analyses and DFT/TD‐DFT Studies

et al. 2019

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Two luminescent polymorphs based on a new Pd(II) complex [Pd(mtzt)2(en)] (mtzt=1‐methyl‐1H‐1,2,3,4‐tetrazole‐5‐thiol and en=ethylenediamine) have been synthesized and characterized by FTIR, UV/Vis, elemental analysis,1HNMR and single‐crystal X‐ray diﬀraction analysis. The X‐ray structural analysis indicated that in the structures of these polymorphs Pd(II) cation is four‐coordinated in a distorted square planer configuration by two tetrazole rings in the cis‐positions, two nitrogen atoms of chelated ethylenediamine ligand. The dihedral angles between the planes of the tetrazole rings of polymorphs (1) and (2) are 72.01 and 77.70°, respectively. Moreover, in these polymorphs, intermolecular interactions C−H…N, C−H…S, and N−H…N hydrogen bonds, are effective in the stabilization of the crystal structures. The present study reports a detailed analysis of Hirshfeld surfaces, facilitating a comparison of intermolecular interactions in the supramolecular structure. The geometries of polymorphs (1) and (2) are optimized with B3LYP−D3/TZVP method, and analyzed with natural bond orbital (NBO), then their UV/Vis spectra are calculated with time‐dependent density functional theory (TD‐DFT) method. The IR spectroscopy was performed using VEDA4 software and compared with the experimental values. Quantum chemical parameters are: such as EHOMO, ELUMO, energy gap, chemical hardness (η), and dipole moment (μ), and the frontier molecular orbital properties.

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Ni(ii) complex with bishydrazone ligand: synthesis, characterization, DNA binding studies and pro-apoptotic and pro-differentiation induction in human cancerous cell lines

Abstract: A new Ni(ii) complex, [Ni(L)(H2O)] (1), with diethyl 3,3′-(2,2′-(1,1′-(pyridine-2,6-diyl)bis(ethan-1-yl-1-ylidene))bis(hydrazin-1-yl-2-ylidene))bis(3-oxopropanoate) ligand (H2L) was synthesized as a potential chemotherapeutic agent.

Cited by 16 publications

References 106 publications

A novel binuclear hydrazone-based Cd(II) complex is a strong pro-apoptotic inducer with significant activity against 2D and 3D pancreatic cancer stem cells

A novel binuclear hydrazone-based Cd(II) complex is a strong pro-apoptotic inducer with significant activity against 2D and 3D pancreatic cancer stem cells

Synthesis, characterization, DNA binding, cytotoxicity and molecular docking properties of three novel butterfly‐like complexes with nitrogen‐containing heterocyclic ligands

Polymorphism of Palladium(II) Complexes : Crystal Structure Determination, Luminescence Properties, Hirshfeld Surface Analyses and DFT/TD‐DFT Studies

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