Time‐Dependent Cytotoxic Properties of Terpyridine‐Based Copper Complexes

Grau, Jordi Mas; Caubet, Amparo; Roubeau, Olivier; Montpeyó, David; Lorenzo, Júlia; Gámez, Patrick

doi:10.1002/cbic.202000154

Cited by 18 publications

(16 citation statements)

References 62 publications

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“…Previous studies have shown that the toxicity of Cu(II) 2,2´:6´,2´´-terpyridine complexes within a cellular model is highly increased upon incubation for several days. [33] Therefore, the complexes were incubated for 44 h and, after this time, the cell viability assessed. The complexes 7-9, 11-12 Several compounds were further characterised by single crystal X-ray diffraction studies.…”

Section: Biological Evaluationmentioning

confidence: 99%

“…[29,30] As a class of compounds with particular interest, complexes of the type [Cu(2,2´:6´,2´´terpyridine)(Cl)2] have been studied. The terminal extension of the ligand with piperidine, bis(2-pyridylmethyl)amine [31,32], naphthalene [33], anthracene [34] as well as diverse substituted phenyl groups [35] including their multinuclear complexes have generated cytotoxic agents against various cancer cell lines. Worthy of note, the naphthalene derivative with a labile nitrate and water molecule instead of chloride ligands, was also found to be cytotoxic against cancerous cells.…”

Section: Introductionmentioning

confidence: 99%

“…This study indicated that these compounds strongly interact with DNA and trigger cell death by apoptosis. [33] The compounds reported in our work were synthesised by complexation of the functionalised 2,2´:6´,2´´-terpyridine derivative with CuCl2 or CuNO3 . xH2O.…”

Section: Introductionmentioning

confidence: 99%

“…These results are very encouraging as this compound is 82-times more cytotoxic in A549 cells and 242-times more cytotoxic in its drug resistant version A549R than the clinically approved drug cisplatin. Recent studies have demonstrated that structurally related Cu(II) 2,2´:6´,2´´-terpyridine complexes trigger cell death by necrosis or apoptosis [33].…”

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confidence: 99%

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Highly cytotoxic copper(II) terpyridine complexes as anticancer drug candidates

Karges

Xiong

Blacque

et al. 2021

Inorganica Chimica Acta

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Cancer is one of the deadliest diseases worldwide. Chemotherapy remains one of the frequently applied treatment modalities in the clinics. However, as the currently applied agents are associated with severe side effects, scientists are searching for novel chemotherapeutic drugs.Within the last decades, Cu(II) polypyridine complexes have received increasing attention as potential anticancer drug candidates. Herein, the biological activity of terminally functionalised mono-and bis-coordinated Cu(II)-2,2´:6´,2´´-terpyridine complexes have been investigated.The bis-coordinated compounds were found to have a cytotoxic effect in the nanomolar range in human adenocarcinomic alveolar basal epithelial cells. Promisingly, the complexes were equally active in the corresponding cisplatin resistant cell line, indicating that they could potentially be useful for the treatment of drug resistant tumours. HIGHLIGHTS-Synthesis of terminally functionalised Cu(II) polypyridine of the type [Cu(2,2´:6´,2´´terpyridine)(Cl)2] and [Cu(2,2´:6´,2´´-terpyridine)2][NO3]2.-Single crystal X-ray analysis of metal complexes.-Biological evaluation revealed cytotoxicity of lead compounds in the nanomolar range against human adenocarcinomic alveolar basal epithelial cells.-Effective in drug resistant cancer cell line.

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Section: Biological Evaluationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Highly cytotoxic copper(II) terpyridine complexes as anticancer drug candidates

Karges

Xiong

Blacque

et al. 2021

Inorganica Chimica Acta

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“…In this context, a number of copper(II) and palladium(II) compounds have been investigated as potential DNA binders and/or cleavers [17,18,[23][24][25]. In a previous study, we investigated the DNA-interacting and cytotoxic properties of a dinuclear [Cu(L)Cl 2 ] 2 complex, where L is a Schiff base ligand, namely (E)-phenyl-N-((pyridin-2-yl)methylene)methanamine [26].…”

Section: Introductionmentioning

confidence: 99%

DNA-interacting properties of two analogous square-planar cis-chlorido complexes: copper versus palladium

et al. 2021

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Two square-planar coordination compounds, namely [Cu(CPYA)Cl2] (1) and [Pd(CPYA)Cl2] (2), were prepared from the ligand 4-chloro-N-(pyridin-2-ylmethyl)aniline (CPYA) and two chloride salts, and were fully characterized, including by X-ray diffraction. Spectroscopic, electrophoretic and AFM studies revealed that the two isostructural compounds were interacting differently with DNA. In both cases, the initial interaction involves electrostatic contacts of the CPYA ligand in the minor groove (as suggested by molecular docking), but subsequent strong binding occurs with the palladium(II) complex 2, whereas the binding with the copper complex 1 is weaker and concentration dependent. The strong binding of 2 eventually leads to the cleavage of the double strand and the redox activity of 1 allows to oxidatively cleave the biomolecule. Graphic abstract

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Spectroscopic and electrochemical investigation of ternary Cu (II) complex interaction with calf thymus DNA

Mostafa

Abdelaziz

Qutb

et al. 2023

Applied Organom Chemis

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Aiming to design unique metallic drugs with significant therapeutic activity, in this work, mixed ligand Cu (II) complex involving 2,2′‐bipyridine and phenylalanine [Cu (bpy) (phenala.)Cl].2H2O has been fabricated and characterized using IR spectroscopy. The interaction of Cu (II) complex with CT‐DNA molecules was examined through UV–vis absorption titration plots, thermal denaturation experiments, viscosity measurements, and electrochemical studies. Cyclic voltammetry, electrochemical impedance spectroscopy, and chronoamperometry measurements have been exploited to elucidate their binding style. The negative potential shift in ΔE and E1/2 values as well as the increased current density of Cu (II)/Cu(I) redox couple suggested the promoted rate of electron transfer process in presence of CT‐DNA molecules in the examined solution. Some kinetic parameters were also estimated such as the diffusion coefficient, the exchange current density, and Tafel slope values. Based on the results of these binding experiments, a groove and/or electrostatic interaction mode was expected. The antimicrobial activity of the studied Cu (II) complex was screened against a series of bacteria and fungi. An outstanding performance was shown when treating different Gram‐positive and Gram‐negative bacteria types. Moreover, an enhanced cytotoxicity behavior toward some human tumor cell lines, including MCF7, HEPG2, and HFB4, was detected with respective IC50 values of 43.02, 51.21, and >200 μM when incubated with Cu (II) complex for 72 h. These results suggest the application of [Cu (bpy) (phenala.)Cl].2H2O complex as a chemotherapeutic agent with a promising output in the drug discovery field.

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Time‐Dependent Cytotoxic Properties of Terpyridine‐Based Copper Complexes

Cited by 18 publications

References 62 publications

Highly cytotoxic copper(II) terpyridine complexes as anticancer drug candidates

Highly cytotoxic copper(II) terpyridine complexes as anticancer drug candidates

DNA-interacting properties of two analogous square-planar cis-chlorido complexes: copper versus palladium

Spectroscopic and electrochemical investigation of ternary Cu (II) complex interaction with calf thymus DNA

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