Synthesis, characterization, DNA interaction, apoptosis and molecular docking of Cu(II) and Mn(II) complexes with <i>endo</i>‐norbornene‐<i>cis</i>‐5,6‐dicarboxylic acid

Gao, Enjun; Ding, Yuqing; Sun, Na; Zhang, Shaozhong; Zhan, Yang; Zhu, Mingchang

doi:10.1002/aoc.3575

Cited by 10 publications

(4 citation statements)

References 39 publications

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“…Electron absorption spectrum is one of the most important techniques for detecting the pattern of binding of DNA to metal complexes . Hypochromism and bathchromism are shown in the UV absorption spectroscopy when a complex binds to DNA through intercalation, due to the coupling π orbital is partially filled by electrons resulting in hypochromism . It seems that the degree of color reduction in the ultraviolet band is generally consistent with the intensity of the intercalation interaction .…”

Section: Resultsmentioning

confidence: 99%

Structure and cytotoxicity of zinc (II) and cobalt (II) complexes based on 1,3,5‐tris(1‐imidazolyl) benzene

Zhu

Zhao

Peng

et al. 2019

Applied Organom Chemis

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Three novel complexes, [Zn (tib)2·(H2O)2]·(NO3)2 (1), [Co (tib)2]·2NO3 (2) and [Co2(tib)2(btc)]·H2O (3) [H4btc = 1,2,4,5‐benzenetetracarboxylic acid; H2tib = 1,3,5‐tris(1‐imidazolyl)benzene], were synthesized and characterized by single‐crystal X‐ray, IR and elemental analysis. The interaction of these complexes with FS‐DNA (fish sperm DNA) was monitored, and binding constants were determined using UV/Vis, which revealed that they have the ability to bind to FS‐DNA. DNA‐binding constants (K) for the three complexes were 2.2 × 104 m−1, 0.7 × 104 m−1 and 0.09 × 104 m−1, respectively. The interaction capacity of the complexes with FS‐DNA has been investigated by fluorescence spectroscopy. Stern–Volmer quenching plot values for complexes 1, 2 and 3 were 0.3784, 0.1028 and 0.076, respectively. The viscosity measurement suggested that complexes 1, 2 and 3 interact with DNA in an intercalation mode. In addition, anti‐cancer activities of these complexes investigated through MTT assays in vitro indicated that the complexes showed good cytotoxic activity against cancer cell lines. Cytotoxic activity of test complexes against two different cancer cell lines (HeLa and KB cells) showed significant cancer cell inhibition rates. Flow cytometry experiments and morphological apoptosis studies showed that the complexes induced apoptosis of HeLa tumor cell lines. Finally, a further molecular docking technique was employed to confirm the binding of the complexes toward the molecular target DNA.

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Section: Resultsmentioning

confidence: 99%

Structure and cytotoxicity of zinc (II) and cobalt (II) complexes based on 1,3,5‐tris(1‐imidazolyl) benzene

Zhu

Zhao

Peng

et al. 2019

Applied Organom Chemis

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“…Evaluating the results, we find that the cytotoxicity of the complexes has an apparent dependence on ligand and metal. Many articles have reported that the types of metal can make a great difference to crystal properties …”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization, DNA binding, apoptosis and molecular docking of three Mn(II), Zn(II) and Cu(II) complexes with terpyridine‐based carboxylic acid

Gao

Feng

et al. 2017

Applied Organom Chemis

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A series of novel cytotoxic compounds, [Mn(cpt)2], [Zn(tpt)(H2O)2]⋅DMA⋅2(H2O) and [Cu(tpt)]⋅DMA (cpt = 4′‐(4‐carboxyphenyl)‐2,2′:6′,2″‐terpyridine, tpt = 4‐(2,4,6‐tricarboxylphenyl)‐2,2′:6′,2″‐terpyridine, DMA = (CH3)2NH), were isolated and characterized. The structures of these complexes were characterized using single‐crystal X‐ray diffraction. The mode and extent of binding between fish sperm DNA and the complexes were investigated using fluorescence spectroscopy and molecular docking. These results indicate the ability of the complexes to bind to DNA with different binding affinities. The binding of the Zn(II) complex with DNA is stronger than that of the corresponding Cu(II) analogue, which is expected due to the z* effect and geometry. The ability of these complexes to cleave pBR322 plasmid DNA was demonstrated using gel electrophoresis assay, showing that the complexes have effective DNA cleavage activity. In addition, the cytotoxic effects of these complexes were examined on HeLa cells (human cervix epithelia carcinoma cells) in vitro. The three complexes exhibit different cytotoxic effects and decent cancer cell inhibitory rate. This means that the structures and type of metal have a great influence on the activity of these novel complexes.

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“…The interaction of a given drug with DNA, in turn, can occur through the major or minor grooves with the formation of covalent bonds or by DNA degradation by reactive oxygen species (ROS) [6][7][8][9][10][11][12][13]. Coordination compounds of Cu and Mn containing phenanthroline (phen) derived ligands have been extensively studied due to the ability to degrade DNA either by intercalation and/or oxidative mechanisms [13][14][15][16][17][18]. A series of copper complexes containing tetracoordinating bis-phenanthroline ligands, named clip-phen (1,3-bis((1,10-phenanthrolin-2-yl)oxy)propan-2-amine), was developed by Pitié et al and showed antitumor properties [14,[19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

Magnetic nanoparticles as a support for a copper (II) complex with nuclease activity

Silva

Romo

Abreu

et al. 2018

Journal of Inorganic Biochemistry

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Magnetic nanoparticles have been extensively explored for the development of platforms for drug delivery and imaging probes. In this work, we have used a modular capping strategy to produce magnetic gold-coated FeO (FeO@Au) nanoparticles, which have been decorated with a copper (II) complex containing a thioether derivative of clip-phen (FeO@Au@Cu), where the complex [Cu(2CP-Bz-SMe)] has affinity to bind DNA and proven nuclease activity (2CP-Bz-SMe=1,3-bis((1,10-phenanthrolin-2-yl)oxy)-N-(4-(methylthio)benzylidene)propan-2-imine). The functionalization of FeO@Au with the copper complex occurs through the sulfur atom of the thioether moiety, as indicated by Raman scattering on surface. The magnetic measurements showed the nanomaterial FeO@Au@Cu is still magnetic although the gold shell and the functionalization with the copper complex have diminished the magnetization due to the dilution of the magnetic core. The nuclease assays performed with FeO@Au@Cu indicate that the nuclease activity of the nanomaterial toward the plasmid DNA involves an oxidative pathway in which HO species is involved as intermediate in a Fenton-like reaction. Based on the electron paramagnetic resonance spectra (a = 15.07 G, a = 14.99 G), such nuclease activity is assigned, essentially, to the HO species indicating that the radical production property of [Cu(2CP-Bz-SMe)] is successfully transferred to the core-shell gold-coated FeO magnetic nanoparticles. To the best of our knowledge, this is the first study reporting nuclease activity due to the reactive oxygen species generated by a copper complex immobilized on a gold-coated magnetic nanoparticle.

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Synthesis, characterization, DNA interaction, apoptosis and molecular docking of Cu(II) and Mn(II) complexes with endo‐norbornene‐cis‐5,6‐dicarboxylic acid

Cited by 10 publications

References 39 publications

Structure and cytotoxicity of zinc (II) and cobalt (II) complexes based on 1,3,5‐tris(1‐imidazolyl) benzene

Structure and cytotoxicity of zinc (II) and cobalt (II) complexes based on 1,3,5‐tris(1‐imidazolyl) benzene

Synthesis, characterization, DNA binding, apoptosis and molecular docking of three Mn(II), Zn(II) and Cu(II) complexes with terpyridine‐based carboxylic acid

Magnetic nanoparticles as a support for a copper (II) complex with nuclease activity

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