Novel copper(II) coordination polymer containing the drugs nalidixic acid and 8-hydroxyquinoline: Evaluation of the structural, magnetic, electronic, and antitumor properties

Carvalho, Alexandre B. de; Souza, Ívina P. de; Andrade, Lídia M.; Binatti, Ildefonso; Pedroso, Emerson F.; Oliveira, Willian X. C.; Pereira-Maia, Elene C.; Silva-Caldeira, Priscila Pereira

doi:10.1016/j.poly.2018.09.046

Cited by 23 publications

(11 citation statements)

References 52 publications

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“…Stock solutions of the compounds were prepared in dimethyl sulfoxide ( dmso )/H 2 O. The final concentration of dmso in the cytotoxicity experiments was below 0.5%, which is well tolerated by K562 cells and allowed sufficient solubility of the ligand dppb.…”

Section: Methodsmentioning

confidence: 99%

“…To study the interaction of the prepared dicopper complex with DNA, spectroscopic titration was performed using a method reported previously . The stock solution of calf thymus DNA (CT‐DNA) was prepared with a buffer (50 m m Tris–HCl/50 m m KCl, pH 7.2) and the DNA concentration was determined by UV absorbance at 260 nm using ε = 6600 m −1 cm −1 .…”

Section: Methodsmentioning

confidence: 99%

“…Furthermore, there is a unique contribution in the literature involving a copper(II) complex in a closed conformation employing benzimidazole as ligand . Considering our interest in the investigation of the antitumoral properties of metal complexes bearing biorelevant organic molecules as ligands, we prepared a new dinuclear copper(II) complex with two pyridine benzimidazole molecules as ligands in a ring‐like conformation [Cu( dppb )( acn )(ClO 4 )] 2 (ClO 4 ) 2 ·4 acn ( 1 ). This work reports the synthesis, characterization, crystal structure, theoretical studies, assessment of DNA binding, and cytotoxic activity of this dinuclear copper(II) complex toward the chronic myelogenous leukemia cell line.…”

Section: Introductionmentioning

confidence: 99%

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Dinuclear copper(II) complex with a benzimidazole derivative: Crystal structure, theoretical calculations, and cytotoxic activity

Cassemiro

Santos

Oliveira

et al. 2020

Applied Organom Chemis

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This work describes a facile synthesis of 5,6‐dimethyl‐2‐(pyridin‐2‐yl)‐1‐[(pyridin‐2‐yl)methyl]‐1H‐benzimidazole (dppb) and the preparation of a dinuclear copper(II) complex bearing this ligand in a ring‐like conformation of formula [Cu(dppb)(acn)ClO4]2(ClO4)2·4acn (1), where acn represents acetonitrile. The crystal structure of the complex was determined by single‐crystal X‐ray diffraction experiment, which showed that dppb acts as a bridge in 1 due to its bidentate–monodentate μ‐κ2NN′:κN″coordination mode, and the coordination sphere of each metal center is completed by one acn molecule and one perchlorate ion. The structure of dinuclear copper(II) complex is symmetric and the two square–pyramidal copper(II) centers are separated by 5.381(1) Å. The geometry optimization, electronic structure, and vibrational spectrum of the [Cu(dppb)(acn)ClO4]22+ cation were calculated using the density functional theory method. The geometrical parameters obtained theoretically were remarkably similar to those observed in the crystal structure of 1 and the calculated vibrational frequencies are in satisfactory coherence with experimental data. In solution, the prepared complex can bind to DNA (Kb = 1.43 × 105 M−1) and inhibit the growth of a human chronic myelogenous leukemia cell line (K562) in a concentration‐dependent manner; importantly, it is almost four times more active than the corresponding free benzimidazole.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Dinuclear copper(II) complex with a benzimidazole derivative: Crystal structure, theoretical calculations, and cytotoxic activity

Cassemiro

Santos

Oliveira

et al. 2020

Applied Organom Chemis

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“…Moreover, extended organic ligands based on the quinoline core have been applied in the development of luminescent coordination polymers, which represents an efficient strategy, albeit, often requiring multi-step preparation of organic ligand systems [ 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 ]. Alternatively, simple quinolinate ligands could be incorporated into mixed-ligand CPs as co-ligands, an approach which has the challenge of designing and controlling the self-assembly of multicomponent supramolecular systems [ 35 ], therefore it is not surprising that this approach has been explored to a lesser extent and only a few examples of well-defined functional quinolinate-based CPs [ 36 , 37 , 38 ], including materials with valuable luminescent properties [ 39 , 40 ], are reported.…”

Section: Introductionmentioning

confidence: 99%

From a Well-Defined Organozinc Precursor to Diverse Luminescent Coordination Polymers Based on Zn(II)-Quinolinate Building Units Interconnected by Mixed Ligand Systems

et al. 2021

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Introduction of photoactive building blocks into mixed-ligand coordination polymers appears to be a promising way to produce new advanced luminescent materials. However, rational design and self-assembly of the multi-component supramolecular systems is challenging from both a conceptual and synthetic perspective. Here, we report exploratory studies that investigate the potential of [Zn(q)2]2[tBuZn(OH)]2 complex (q = deprotonated 8-hydroxyquinoline) as an organozinc precursor as well as a mixed-ligand synthetic strategy for the preparation of new luminescent coordination polymers (CPs). As a result we present three new 2D mixed-ligand Zn(II)-quinolinate coordination polymers which are based on various zinc quinolinate secondary building units interconnected by two different organic linker types, i.e., deprotonated 4,4′-oxybisbenzoic acid (H2obc) as a flexible dicarboxylate linker and/or selected bipyridines (bipy). Remarkably, using the title organozinc precursors in a combination with H2obc and 4,4′-bipyridine, a novel molecular zinc quinolinate building unit, [Zn4(q)6(bipy)2(obc)2], was obtained which self-assembled into a chain-type hydrogen-bonded network. The application of the organometallic precursor allowed for its direct reaction with the selected ligands at ambient temperature, avoiding the use of both solvothermal conditions and additional base reagents. In turn, the reaction involving Zn(NO3)2, as a classical inorganic precursor, in a combination with H2obc and bipy led to a novel 1D coordination polymer [Zn2(q)2(NO3)2(bipy)]. While the presence of H2obc was essential for the formation of this coordination polymer, this ditopic linker was not incorporated into the isolated product, which indicates its templating behavior. The reported compounds were characterized by single-crystal and powder X-ray diffraction, elemental analysis as well as UV-Vis and photoluminescence spectroscopy.

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“…Coordination polymers (CPs) have developed rapidly and attracted a great deal of interest due to their widespread biological activities and potential applications, such as antioxidant, anticancer, antimicrobial, DNA binding, serum albumin interaction, and so on (Wu et al, 2014; de Carvalho et al, 2018;Liu et al, 2011;Metlushka et al, 2016;Li et al, 2015). It has been reported that the bioactivity of CPs synthesized by coordination of organic compounds with metal ions is usually enhanced (Belicchi Ferrari et al, 2002;Senthil Raja et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure and biological properties of Cd and Zn coordination polymers based on a flexible tripodal ligand

Wang

Ling

et al. 2019

Acta Crystallogr C

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Two new coordination polymers, namely poly[[hexathiocyanatotetrakis{μ3‐2,4,6‐trimethyl‐1,3,5‐tris[(triazol‐1‐yl)methyl]benzene}tricadmium(II)] 3.5‐hydrate], {[Cd3(SCN)6(C18H21N9)4]·3.5H2O}n (1), and poly[[hexathiocyanatotetrakis{μ3‐2,4,6‐trimethyl‐1,3,5‐tris[(triazol‐1‐yl)methyl]benzene}trizinc(II)] 3.5‐hydrate], {[Zn3(SCN)6(C18H21N9)4]·3.5H2O}n (2), have been synthesized under hydrothermal conditions and characterized by elemental analysis, IR spectroscopy and single‐crystal X‐ray diffraction analysis. From the X‐ray analysis, it is noteworthy that polymers 1 and 2 are isostructural, with their three‐dimensional structures composed of three kinds of four‐connection metal ions and two kinds of three‐connection 2,4,6‐trimethyl‐1,3,5‐tris[(triazol‐1‐yl)methyl]benzene (TTTMB) ligand nodes. Each metal ion is six‐coordinated in a slightly distorted octahedral geometry. The antioxidant activity against DPPH (2,2‐diphenyl‐1‐picrylhydrazyl) and the antidiabetic activity against α‐amylase of the synthesized compounds were evaluated in vitro. The results of the DPPH free‐radical scavenging assay showed that polymers 1 and 2 exhibited strong antioxidant effects, with IC50 values of 3.81 and 2.56 mg ml−1, respectively. The IC50 value in the antidiabetic studies of polymer 1 was 3.94 mg ml−1, while polymer 2 exhibited no antidiabetic activity. Polymers 1 and 2 revealed different inhibitory activities on DPPH and α‐amylase, which indicated that the metal ions play important roles in the biological activity of coordination polymers. In addition, the solid‐state photoluminescence properties and thermal stability of 1 and 2 have been investigated.

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Novel copper(II) coordination polymer containing the drugs nalidixic acid and 8-hydroxyquinoline: Evaluation of the structural, magnetic, electronic, and antitumor properties

Cited by 23 publications

References 52 publications

Dinuclear copper(II) complex with a benzimidazole derivative: Crystal structure, theoretical calculations, and cytotoxic activity

Dinuclear copper(II) complex with a benzimidazole derivative: Crystal structure, theoretical calculations, and cytotoxic activity

From a Well-Defined Organozinc Precursor to Diverse Luminescent Coordination Polymers Based on Zn(II)-Quinolinate Building Units Interconnected by Mixed Ligand Systems

Synthesis, crystal structure and biological properties of Cd and Zn coordination polymers based on a flexible tripodal ligand

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