Bis(2‐methylbenzimidazolyl)amine‐Derived Copper Complexes and Their Antineoplastic Activity

Solano, Laura A. Rodríguez; Aguiñiga, Itzen; Ortiz, Manuel López; Tiburcio, Reynaldo; Luviano, Axel; Regla, Ignacio; Santiago‐Osorio, Edelmiro; Ugalde‐Saldívar, Víctor M.; Toscano, Rubén A.; Castillo, Iván

doi:10.1002/ejic.201100301

Cited by 22 publications

(27 citation statements)

References 40 publications

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“…The S ? Cu LMCT is blueshifted relative to that reported for [L 4 CuCl]ClO 4 (411 nm, e = 408 M À1 cm À1 ) possibly due to electronic delocalization of the arylthioether donor orbital involved in the transition in L 4 [16].…”

Section: Copper Complexescontrasting

confidence: 56%

Synthesis, spectroscopic, and structural characterization of mixed thioether–benzimidazole copper complexes

et al. 2015

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Section: Copper Complexescontrasting

confidence: 56%

Synthesis, spectroscopic, and structural characterization of mixed thioether–benzimidazole copper complexes

et al. 2015

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“…The preparation of L 3' has previously been reported. [8] All the ligands were completely characterized (see the Experimental Section).…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…[7] Likewise, the reaction of CuA C H T U N G T R E N N U N G (ClO 4 ) 2 ·6 H 2 O with L 2 results in ligand oxidation with concomitant reduction of Cu 2 + to Cu + . Analysis of the 1 H NMR spectra obtained in the presence of 0.5, 1.0, 1.5, and 2.0 equivalents of Cu 2 + allowed the identification of the oxidation products 2,4-dimethA C H T U N G T R E N N U N G ylthiophenol, the corresponding disulfide, and (1), CuÀS3 2.246(1), CuÀN1 2.217(4); selected bond angles [8]: S1ÀCuÀS2 100.29(4), S1ÀCuÀS3 133.81(5), S2ÀCuÀS3 125.77(5), S1ÀCuÀN1 83.07 (9), S2ÀCuÀN1 91.09 (9), S3ÀCuÀN1 92.04 (9). bis (2,4-dimethylphenylthio)methane (see Figure S1 in the Supporting Information), based on a comparison with the spectra of authentic samples.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…To further investigate the redox properties of methylene-bridged thioethers, we have synthesized related sulfur-containing ligands that incorporate the biologically relevant benzimidazole as mimics of the ubiquitous histidine residues in the active sites of copper-containing metalloenzymes. [8] A combined experimental and theoretical study of the effect of thioether ligands on the electrochemical properties of their copper complexes based on the systematic variation of the number of sulfur (thioether) and nitrogen (benzimidazole) donors was undertaken. The results obtained, including the isolated and fully characterized oxidative decomposition products of two of the ligands, allowed us to postulate a mechanism for the reactions observed.…”

Section: Introductionmentioning

confidence: 99%

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Copper Versus Thioether‐Centered Oxidation: Mechanistic Insights into the Non‐Innocent Redox Behavior of Tripodal Benzimidazolylaminothioether Ligands

Martínez‐Alanis¹,

Sánchez-Eguía²,

Ugalde‐Saldívar³

et al. 2013

Chemistry A European J

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A series of Cu(+) complexes with ligands that feature varying numbers of benzimidazole/thioether donors and methylene or ethylene linkers between the central nitrogen atom and the thioether sulfur atoms have been spectroscopically and electrochemically characterized. Cyclic voltammetry measurements indicated that the highest Cu(2+)/Cu(+) redox potentials correspond to sulfur-rich coordination environments, with values decreasing as the thioether donors are replaced by nitrogen-donating benzimidazoles. Both Cu(2+) and Cu(+) complexes were studied by DFT. Their electronic properties were determined by analyzing their frontier orbitals, relative energies, and the contributions to the orbitals involved in redox processes, which revealed that the HOMOs of the more sulfur-rich copper complexes, particularly those with methylene linkers (-N-CH2-S-), show significant aromatic thioether character. Thus, the theoretically predicted initial oxidation at the sulfur atom of the methylene-bridged ligands agrees with the experimentally determined oxidation waves in the voltammograms of the NS3- and N2S2-type ligands as being ligand-based, as opposed to the copper-based processes of the ethylene-bridged Cu(+) complexes. The electrochemical and theoretical results are consistent with our previously reported mechanistic proposal for Cu(2+)-promoted oxidative C-S bond cleavage, which in this work resulted in the isolation and complete characterization (including by X-ray crystallography) of the decomposition products of two ligands employed, further supporting the novel reactivity pathway invoked. The combined results raise the possibility that the reactions of copper-thioether complexes in chemical and biochemical systems occur with redox participation of the sulfur atom.

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“…The significant antitumor activity of copper(II) complexes, e.g. containing ligands based on benzimidazole and thiosemicarbazone derivatives, has been reported . Thus copper‐based complexes are regarded as potential anticancer agents among non‐platinum compounds.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic and Antimicrobial Properties of Copper(II) Complexes of Pyridine and Benzimidazole Derivatives

Kalinowska-Lis

Szabłowska-Gadomska

Lisowska

et al. 2017

Zeitschrift anorg allge chemie

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The cytotoxic and antimicrobial activity of a series of six copper(II) complexes with phosphate and hydroxymethyl derivatives of pyridine and benzimidazole were investigated. The complexes and the corresponding free ligands were tested against Staphylococcus aureus ATCC 6538, Staphylococcus epidermidis ATCC 12228, Pseudomonas aeruginosa ATCC 15442, Escherichia coli ATCC 25922, Proteus hauseri ATCC 13315, and Candida albicans ATCC 10231. Among the tested copper(II) complexes, compounds 2 and 5 containing 1H‐benzimidazol‐2‐ylmethyl diethyl phosphate and 2‐(hydroxymethyl)benzimidazole as ligands, respectively, were most active and limited the growth of S. aureus, E. coli, and C. albicans by 30–60 % according to concentration and microorganism. The in vitro cytotoxic activity of the CuII complexes and free ligands towards cancerous B16 (murine melanoma) and non‐cancerous 10T1/2 (murine fibroblasts) cell lines was determined. The 10T1/2 cells were treated with the compounds at concentrations equal to IC50 values for B16 cells. In spite of the use of relatively high concentrations of the complexes, the viability of 10T1/2 cells was very high, ca. 80 % in some cases. Stability of the CuII complexes was evaluated in water solutions by UV/Vis spectroscopy. The copper(II) complex of 4‐(hydroxymethyl)pyridine was synthesized and identified.

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Bis(2‐methylbenzimidazolyl)amine‐Derived Copper Complexes and Their Antineoplastic Activity

Cited by 22 publications

References 40 publications

Synthesis, spectroscopic, and structural characterization of mixed thioether–benzimidazole copper complexes

Synthesis, spectroscopic, and structural characterization of mixed thioether–benzimidazole copper complexes

Copper Versus Thioether‐Centered Oxidation: Mechanistic Insights into the Non‐Innocent Redox Behavior of Tripodal Benzimidazolylaminothioether Ligands

Cytotoxic and Antimicrobial Properties of Copper(II) Complexes of Pyridine and Benzimidazole Derivatives

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