Synthesis and mass spectroscopy kinetics of a novel ternary copper(II) complex with cytotoxic activity against cancer cells

Barceló‐Oliver, Miquel; Garcı́a-Raso, Ángel; Terrón, Àngel; Molins, Elı́es; Prieto, Marı́a José; Moreno, Virtudes; Martínez, J. Larrauri; Lladó, Victoria; López, Iván; Gutiérrez, Antonio; Escribá, Pablo V.

doi:10.1016/j.jinorgbio.2006.12.008

Cited by 70 publications

(36 citation statements)

References 34 publications

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“…217 In addition, COMET assay in peripheral blood lymphocytes and HeLa cells suggested a potential DNA damage that seemed related to the nature of the substituents on the chelate structure. 217 Escriba`et al 218 have described the synthesis, structural characterization, and biological activity of a ternary copper(II) complex with phen and an amino acid conjugated with orthoiodohippurate (10a), which generated [Cu(phen) 2 ] 1 in aqueous solution without the addition of any external reductant, possibly by an intramolecular redox process in the presence of oxygen. (10a) was able to cleave pBR322 plasmidic DNA confirming the nuclease effect.…”

Section: (Mal)]mentioning

confidence: 99%

“…Moreover, tested on A549 human nonsmall lung adenocarcinoma cells, it induced a marked growth inhibition and apoptosis at nanomolar concentration. 218 The molecular mechanisms underlying this inhibitory effect was studied by flow cytometry analyses that revealed that (10a) induced a marked decrease in the number of cells in phases G1, S, and G2/M and an increase in the number of apoptotic cells. 218 The induction of apoptosis was confirmed by microscopic analyses of treated cells and by determination of poly ADP-ribose polymerase (PARP) fragmentation through immunoblotting.…”

Section: (Mal)]mentioning

confidence: 99%

“…218 The molecular mechanisms underlying this inhibitory effect was studied by flow cytometry analyses that revealed that (10a) induced a marked decrease in the number of cells in phases G1, S, and G2/M and an increase in the number of apoptotic cells. 218 The induction of apoptosis was confirmed by microscopic analyses of treated cells and by determination of poly ADP-ribose polymerase (PARP) fragmentation through immunoblotting. Moreover, treatment with the same concentrations of (10a) did not affect adipocyte survival attesting an useful selectivity against cancer cells (Scheme 10).…”

Section: (Mal)]mentioning

confidence: 99%

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Copper in diseases and treatments, and copper‐based anticancer strategies

Tisato¹,

Marzano

Porchia³

et al. 2009

Medicinal Research Reviews

652

420

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Copper is found in all living organisms and is a crucial trace element in redox chemistry, growth and development. It is important for the function of several enzymes and proteins involved in energy metabolism, respiration, and DNA synthesis, notably cytochrome oxidase, superoxide dismutase, ascorbate oxidase, and tyrosinase. The major functions of copper-biological molecules involve oxidation-reduction reactions in which they react directly with molecular oxygen to produce free radicals. Therefore, copper requires tightly regulated homeostatic mechanisms to ensure adequate supplies without any toxic effects. Overload or deficiency of copper is associated, respectively, with Wilson disease (WD) and Menkes disease (MD), which are of genetic origin. Researches on Menkes and Wilson disorders have provided useful insights in the field of copper homeostasis and in particular into the understanding of intracellular trafficking and distribution of copper at molecular levels. Therapies based on metal supplementation with copper histidine or removal of copper excess by means of specific copper chelators are currently effective in treating MD and WD, respectively. Copper chelation therapy is now attracting much attention for the investigation and treatment of various neurodegenerative disorders such as Alzheimer, Parkinson and CreutzfeldtJakob. An excess of copper appears to be an essential co-factor for angiogenesis. Moreover, elevated levels of copper have been found in many types of human cancers, including prostate, breast, colon, lung, and brain. On these basis, the employment of copper chelators has been reported to be of therapeutic value in the treatment of several types of cancers as anti-angiogenic molecules. More recently, mixtures of copper chelators with copper salts have been found to act as efficient proteasome inhibitors and apoptosis inducers, specifically in cancer cells. Moreover, following the worldwide success of platinum(II) compounds in cancer chemotherapy, several families of individual copper complexes have been studied as potential antitumor agents. These investigations, revealing the occurrence of mechanisms of action quite different from platinum drugs, head toward the development of new anticancer metallodrugs with improved specificity and decreased toxic side effects.

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Section: (Mal)]mentioning

confidence: 99%

Section: (Mal)]mentioning

confidence: 99%

Section: (Mal)]mentioning

confidence: 99%

See 1 more Smart Citation

Copper in diseases and treatments, and copper‐based anticancer strategies

Tisato¹,

Marzano

Porchia³

et al. 2009

Medicinal Research Reviews

652

420

View full text Add to dashboard Cite

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“…16 It also plays important roles in multiple systems, including the nervous system, cardiovascular system, and immune system. 17 Also, recent intensive research has revealed that Cu provides good antibacterial, [18][19][20] osteogenic, 20 and antineoplastic properties, 21 which is potentially advantageous for the treatment of orthopedic diseases. Unfortunately, Cu is not directly used as an implant material in clinical applications, except for in female intrauterine devices, 22 due to its inflammatory property and cytotoxicity.…”

Section: Introductionmentioning

confidence: 99%

Nano-copper-bearing stainless steel promotes fracture healing by accelerating the callus evolution process

Wang¹,

Li²,

Ren³

et al. 2017

IJN

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Treatment for fractures requires internal fixation devices, which are mainly produced from stainless steel or titanium alloy without biological functions. Therefore, we developed a novel nano-copper-bearing stainless steel with nano-sized copper-precipitation (317L-Cu SS). Based on previous studies, this work explores the effect of 317L-Cu SS on fracture healing; that is, proliferation, osteogenic differentiation, osteogenesis-related gene expression, and lysyl oxidase activity of human bone mesenchymal stem cells were detected in vitro. Sprague–Dawley rats were used to build an animal fracture model, and fracture healing and callus evolution were investigated by radiology (X-ray and micro-CT), histology (H&E, Masson, and safranin O/fast green staining), and histomorphometry. Further, the Cu 2+ content and Runx2 level in the callus were determined, and local mechanical test of the fracture was performed to assess the healing quality. Our results revealed that 317L-Cu SS did not affect the proliferation of human bone mesenchymal stem cells, but promoted osteogenic differentiation and the expression of osteogenesis-related genes. In addition, 317L-Cu SS upregulated the lysyl oxidase activity. The X-ray and micro-CT results showed that the callus evolution efficiency and fracture healing speed were superior for 317L-Cu SS. Histological staining displayed large amounts of fibrous tissues at 3 weeks, and cartilage and new bone at 6 weeks. Further, histomorphometric analysis indicated that the callus possessed higher osteogenic efficiency at 6 weeks, and a high Cu 2+ content and increased Runx2 expression were observed in the callus for 317L-Cu SS. Besides, the mechanical strength of the fracture site was much better than that of the control group. Overall, we conclude that 317L-Cu SS possesses the ability to increase Cu 2+ content and promote osteogenesis in the callus, which could accelerate the callus evolution process and bone formation to provide faster and better fracture healing.

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“…Appearance of this peak in the spectra of both the ligand and its Cu (II) complex indicates that the secondary amine at the extreme end of the structure is free from complexation. However, the spectrum of the ligand shows sharp absorption at1640.cm -1 which is due to azomethine -C=N-, this absorption seems to shift to a lower frequency in the spectra of the complex which indicates the involvement -C=N-nitrogen in the coordination to metal ion 5,6 . Assignment of the proposed coordination site is further supported by the appearance of medium bands at 554cm-1 which could be attributed to ½(M-N) and 624cm-1 for (M-O) 7,3 .…”

Section: Infra Red Spectramentioning

confidence: 94%

Influence of Steric Hindrance on The Antioxidant Activity of Some Schiff Base Ligands And Their Copper(II) Complexes

Salga¹,

Sada²,

Mustapha³

2014

Orient J Chem

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Herein we report the synthesis, characterization and antioxidant activity of the Schiff base ligands (E)-4-bromo-2-((2-piperazine-1-yl)ethylimino)methylphenol and 2,2'-(1E,1E')-cyclohexane-1,2-diylbis(azan-1-yl-1-ylidene))bismethan-1-yl-1-ylidene)bis (4-bromophenol) and their complexes of copper (II) ion. Antioxidant activities of the copper complexes were studied by ferric reducing antioxidant power (FRAP) assay according to the procedure reported by Benzie and Strain 1 which considered the reduction of ferric tripyridyl triazine complex to a ferrous complex at low pH by monitoring the change in absorption at 593nm. The overall results showed an increased in antioxidant activity with the increase in steric crowd. Similarly, the ligands show high activity than the complexes.

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Synthesis and mass spectroscopy kinetics of a novel ternary copper(II) complex with cytotoxic activity against cancer cells

Cited by 70 publications

References 34 publications

Copper in diseases and treatments, and copper‐based anticancer strategies

Copper in diseases and treatments, and copper‐based anticancer strategies

Nano-copper-bearing stainless steel promotes fracture healing by accelerating the callus evolution process

Influence of Steric Hindrance on The Antioxidant Activity of Some Schiff Base Ligands And Their Copper(II) Complexes

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