Synthesis, crystallographic characterization and electrochemical property of a copper(II) complex of the anticancer agent elesclomol

Vo, Nha Huu; Xia, Zhiqiang; Hanko, Jason A.; Yun, T.S.; Bloom, Steve; Shen, Jianhua; Koya, Keizo; Sun, Lijun; Chen, Shoujun

doi:10.1016/j.jinorgbio.2013.10.005

Cited by 15 publications

(9 citation statements)

References 17 publications

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“…The redox imbalance could be targeted by chelate formation coupled Cu(II) reduction in the proliferating tissue. Indeed, the reversible one-electron reduction of Cu(II) does occur, as exemplified by the thiosemicarbazone complex of Cu(II) in the elesclomol [ 330 , 331 ] (Table 3 ).…”

Section: Introductionmentioning

confidence: 99%

Copper signalling: causes and consequences

Kardos¹,

Héja²,

Simon³

et al. 2018

Cell Commun Signal

163

140

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Copper-containing enzymes perform fundamental functions by activating dioxygen (O2) and therefore allowing chemical energy-transfer for aerobic metabolism. The copper-dependence of O2 transport, metabolism and production of signalling molecules are supported by molecular systems that regulate and preserve tightly-bound static and weakly-bound dynamic cellular copper pools. Disruption of the reducing intracellular environment, characterized by glutathione shortage and ambient Cu(II) abundance drives oxidative stress and interferes with the bidirectional, copper-dependent communication between neurons and astrocytes, eventually leading to various brain disease forms. A deeper understanding of of the regulatory effects of copper on neuro-glia coupling via polyamine metabolism may reveal novel copper signalling functions and new directions for therapeutic intervention in brain disorders associated with aberrant copper metabolism.

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Section: Introductionmentioning

confidence: 99%

Copper signalling: causes and consequences

Kardos¹,

Héja²,

Simon³

et al. 2018

Cell Commun Signal

163

140

View full text Add to dashboard Cite

show abstract

“…In the voltammogram of the complex, a redox couple at 0.10 V and 0.065 V with the peak currents of 1.56 and 2.58 μA, respectively were observed which can be assigned to Cu II/I . 32,33 Once again, increasing the potential scan rate shifted the first peak (oxidation) towards more positive potentials and shifted the second one (reduction) towards more negative potentials. Generally, cytotoxic effect of the complex is more than those of the other tested compounds.…”

Section: Electrochemical Studiesmentioning

confidence: 90%

Synthesis, characterization, X-ray crystal structure, electrochemical evaluation and anti-cancer studies of a mixed ligand Cu(II) complex of (E)-N′-((2-hydroxynaphthalen-1-yl)methylene)acetohydrazide

et al. 2015

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A ternary mixed ligand Cu(II) complex, [Cu(L)(Phen)], was prepared from the reaction of (E)-N-((2-hydroxynaphthalen-1-yl)methylene)acetohydrazide [HL], Cu(NO 3) 2 .3H 2 O and 1,10-Phenanthroline in 1:1:1 molar ratio. This complex was fully characterized using spectroscopic and physicochemical methods. The structure of the complex was determined by single crystal X-ray diffraction. The Cu(II) center is coordinated by two oxygen and one nitrogen donors of L 2− and nitrogen atoms of the heterocyclic group. Electrochemical studies of the Cu(II) complex showed shifts in the ligand peaks as well as the appearance of new peaks after complexation. The electrochemical behavior of the Cu(II) complex was also studied using cyclic voltammetry. According to biochemical investigation (MCF-7 cells viability), anticancer activity of [Cu(L)(Phen)] was higher than those of Cu(NO 3) 2 .3H 2 O, HL and 1,10-Phenanthroline.

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“…Actually, such a strategy has already been applied successfully. For example, elesclomol (N′ 1 ,N′ 3 -dimethyl-N′ 1 ,N′ 3 -di(phenylcarbonothio-yl)malonohydrazide) is a potential novel anticancer agent (that has been evaluated in late-stage clinical trials), 72 whose apoptotic properties arise from its coordination to intracellular copper(II) ions that ultimately leads to generation of harmful reactive oxygen species (ROS). 73,74 Accordingly, cytotoxicity assays have been carried out with the free ligands as well.…”

Section: Articlementioning

confidence: 99%

Highly cytotoxic DNA-interacting copper(ii) coordination compounds

et al. 2014

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Four new Schiff-base ligands have been designed and prepared by condensation reaction between hydrazine derivatives (i.e. 2-hydrazinopyridine or 2-hydrazinoquinoline) and mono- or dialdehyde (3-tert-butyl-2-hydroxybenzaldehyde and 5-tert-butyl-2-hydroxyisophthalaldehyde, respectively). Six copper(II) coordination compounds of various nuclearities have been obtained from these ligands, which are formulated as [Cu(L1)Cl](CH3OH) (1), [Cu(L2)NO3] (2), [Cu2(L3)(ClO4)2(CH3O)(CH3OH)](CH3OH) (3), [Cu2(L4)(ClO4)(OH)(CH3OH)](ClO4) (4), [Cu8(L3)4(NO3)4(OH)5](NO3)3(CH3OH)5(H2O)8 (5) and [Cu3(HL2')4Cl6](CH3OH)6 (6), as revealed by single-crystal X-ray studies. Their DNA-interacting abilities have been investigated using different characterization techniques, which suggest that the metal complexes act as efficient DNA binders. Moreover, cytotoxicity assays with several cancer cell lines show that some of them are very active, as evidenced by the sub-micromolar IC50 values achieved in some cases.

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Synthesis, crystallographic characterization and electrochemical property of a copper(II) complex of the anticancer agent elesclomol

Cited by 15 publications

References 17 publications

Copper signalling: causes and consequences

Copper signalling: causes and consequences

Synthesis, characterization, X-ray crystal structure, electrochemical evaluation and anti-cancer studies of a mixed ligand Cu(II) complex of (E)-N′-((2-hydroxynaphthalen-1-yl)methylene)acetohydrazide

Highly cytotoxic DNA-interacting copper(ii) coordination compounds

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