Synthesis, DNA binding, antibacterial and anticancer properties of two novel water-soluble copper(II) complexes containing gluconate

Cai, Dai-Hong; Zhang, Chun‐Lian; Liu, Qi-Yan; He, Liangmei; Liu, Yun-Jun; Xiong, Yong; Le, Xueyi

doi:10.1016/j.ejmech.2021.113182

Cited by 40 publications

(22 citation statements)

References 60 publications

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“…Cell death was independent of caspase activation or PARP cleavage, strongly suggesting that the plasma membrane (and perhaps other cellular membranes) was the key target of the combinations. These findings are in line with the recently demonstrated efficacy of the combination of Cu (II)-containing compounds and ascorbate in inducing cell cycle perturbation and death via oxidative damage of biomacromolecules [ 19 ].…”

Section: Discussionsupporting

confidence: 84%

“…Copper’s unique sensitivity to the electrochemical status makes it particularly advantageous in situations where the biological effects are mechanistically dependent on reactive oxygen species (ROS) [ 15 , 16 , 17 , 18 , 19 ]. These studies have highlighted the opportunity of using Cu-containing compounds alone or in combinations with conventional and novel agents.…”

Section: Introductionmentioning

confidence: 99%

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Copper-Containing Nanoparticles and Organic Complexes: Metal Reduction Triggers Rapid Cell Death via Oxidative Burst

Tsymbal

Moiseeva

Agadzhanian

et al. 2021

IJMS

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Copper-containing agents are promising antitumor pharmaceuticals due to the ability of the metal ion to react with biomolecules. In the current study, we demonstrate that inorganic Cu2+ in the form of oxide nanoparticles (NPs) or salts, as well as Cu ions in the context of organic complexes (oxidation states +1, +1.5 and +2), acquire significant cytotoxic potency (2–3 orders of magnitude determined by IC50 values) in combinations with N-acetylcysteine (NAC), cysteine, or ascorbate. In contrast, other divalent cations (Zn, Fe, Mo, and Co) evoked no cytotoxicity with these combinations. CuO NPs (0.1–1 µg/mL) together with 1 mM NAC triggered the formation of reactive oxygen species (ROS) within 2–6 h concomitantly with perturbation of the plasma membrane and caspase-independent cell death. Furthermore, NAC potently sensitized HCT116 colon carcinoma cells to Cu–organic complexes in which the metal ion coordinated with 5-(2-pyridylmethylene)-2-methylthio-imidazol-4-one or was present in the coordination sphere of the porphyrin macrocycle. The sensitization effect was detectable in a panel of mammalian tumor cell lines including the sublines with the determinants of chemotherapeutic drug resistance. The components of the combination were non-toxic if added separately. Electrochemical studies revealed that Cu cations underwent a stepwise reduction in the presence of NAC or ascorbate. This mechanism explains differential efficacy of individual Cu–organic compounds in cell sensitization depending on the availability of Cu ions for reduction. In the presence of oxygen, Cu+1 complexes can generate a superoxide anion in a Fenton-like reaction Cu+1L + O2 → O2−.+ Cu+2L, where L is the organic ligand. Studies on artificial lipid membranes showed that NAC interacted with negatively charged phospholipids, an effect that can facilitate the penetration of CuO NPs across the membranes. Thus, electrochemical modification of Cu ions and subsequent ROS generation, as well as direct interaction with membranes, represent the mechanisms of irreversible membrane damage and cell death in response to metal reduction in inorganic and organic Cu-containing compounds.

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Section: Discussionsupporting

confidence: 84%

Section: Introductionmentioning

confidence: 99%

Copper-Containing Nanoparticles and Organic Complexes: Metal Reduction Triggers Rapid Cell Death via Oxidative Burst

Tsymbal

Moiseeva

Agadzhanian

et al. 2021

IJMS

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“…5,6 Therefore, developing the most potent drug to prevent the development of cancer is warranted. Most of the reported anticancer metallodrugs rely on metals like Pt, Cu, Ru, and Ir, 7–15 whereas only a few reports are available on using relatively abundant metals like Mn, Co, and Ni. 16–19…”

Section: Introductionmentioning

confidence: 99%

“…Other investigators have demonstrated in vitro the anti-tumor effect of many metal coordinate complexes against different types of cancer cells. 11–17,33,34 Most of these studies mentioned the effect of metal complexes on the viability/growth inhibition of the tumor cells with minimal details on the cell death caused by the complexes. However, none of those studies were supported by both comparative long-term and short-term anti-tumor assays.…”

Section: Introductionmentioning

confidence: 99%

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In vitroandIn silicoanticancer activities of Mn(ii), Co(ii), and Ni(ii) complexes: synthesis, characterization, crystal structures, and DFT studies

et al. 2022

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Copper(II) Complexes Derived from Schiff Bases Containing 4‐Methylbenzylamine as a Core Unit: Cytotoxicity, pBR322‐DNA Studies, Biological Assays, and Quantum Chemical Parameters

Shankar,

Rambabu,

et al. 2023

Chemistry & Biodiversity

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Bivalent copper complexes, [Cu(SB 1 ) 2 ] 1 (SB 1 = (2-(4-methylbenzylimino)methyl)-5-methylphenol, [Cu(SB 2 ) 2 ] 2 (SB 2 = (2-(4methylbenzylimino)methyl)-4-bromolphenol), and [Cu(SB 3 ) 2 ] 3 (SB 3 = (2-(4-methylbenzylimino)methyl)-4,6-dibromophenol) were synthesized using the Schiff bases prepared from 4methylbenzylamine (p-tolylmethanamine). These were characterized using a variety of spectro-analytical methods. For all copper complexes, a square planar geometry was determined through spectral analyses. Utilizing molecular orbital energies, the stability of the copper complexes was calculated from quantum chemical characteristics. The kinetic and thermal degradation parameters were calculated from the thermo-grams. Studies on DNA binding interactions, such as UV absorption and emission, have shown that the manner of DNA binding is intercalative, and the binding constant (K b ) order is 3 > 2 > 1. Under oxidative and photolytic techniques, the copper complexes outperform the parent Schiff bases in their ability to cleave double-stranded pBR322 DNA. When tested for cytotoxicity on the KB3 and MCF7 cell lines, complexes displayed greater activity than their parent ligands. Studies on the complexes' in-vitro antibacterial and antioxidant activity showed that they are significantly more powerful than the parent ligands.

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Synthesis, DNA binding, antibacterial and anticancer properties of two novel water-soluble copper(II) complexes containing gluconate

Cited by 40 publications

References 60 publications

Copper-Containing Nanoparticles and Organic Complexes: Metal Reduction Triggers Rapid Cell Death via Oxidative Burst

Copper-Containing Nanoparticles and Organic Complexes: Metal Reduction Triggers Rapid Cell Death via Oxidative Burst

In vitroandIn silicoanticancer activities of Mn(ii), Co(ii), and Ni(ii) complexes: synthesis, characterization, crystal structures, and DFT studies

Copper(II) Complexes Derived from Schiff Bases Containing 4‐Methylbenzylamine as a Core Unit: Cytotoxicity, pBR322‐DNA Studies, Biological Assays, and Quantum Chemical Parameters

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