Synthesis, structure and properties of unsymmetrical μ-alkoxo-dicopper(II) complexes: biological relevance to phosphodiester and DNA cleavage and cytotoxic activity

Rossi, Liane M.; Neves, Ademir; Bortoluzzi, Adaı́lton J.; Hörner, Rosmari; Szpoganicz, Bruno; Terenzi, Hernán; Mangrich, Antônio S.; Pereira-Maia, Elene C.; Castellano, Eduardo E.; Haase, W.

doi:10.1016/j.ica.2004.10.027

Cited by 72 publications

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“…[1][2][3][4][5][6][7][8][9] The development of functional models of metalloenzymes for catalyst oxidation reactions is a subject of great interest. [10][11][12][13][14][15][16] Neves et al [17][18][19][20][21][22][23][24][25] have extensively synthesized and characterized model complexes to mimic the active site of the different enzymes (e.g., catechol oxidase, peroxidase, galactose oxidase, catalase, purple acid phosphatase). The majority of O 2 -reactive copper models have been based on the binuclear-Cu catechol oxidase.…”

Section: Introductionmentioning

confidence: 99%

“…Amine, pyridyl, pyrazolyl and imidazole nitrogen-type donor ligands with bi-, tri-and tetradentate ligands have been successfully used to stabilize Cu:O 2 intermediates at low temperature and in aprotic solvents. 10,[16][17][18][19][20] Many biomimetic catalysts of catechol oxidase have been reported in the literature. 10,[16][17][18][19][20] However, very few report their uses in biomimetic sensors.…”

Section: Introductionmentioning

confidence: 99%

“…10,[16][17][18][19][20] Many biomimetic catalysts of catechol oxidase have been reported in the literature. 10,[16][17][18][19][20] However, very few report their uses in biomimetic sensors. 12,13,26 Biomimetic catechol oxidase catalysts have been shown to be efficient catalysts for the oxidation of phenolic substrates to quinones.…”

Section: Introductionmentioning

confidence: 99%

“…6, 2008 (2-hydroxy-3,5-di-tert-butylbenzyl)]-1,3-propanediamine-2-ol (H 3 L) was obtained in good yield using epichlorohydrin, which is widely used as a convenient precursor for the synthesis of unsymmetric ligands containing the central skeleton 1,3-diaminopropan-2-ol. 20,21,24 The H 3 L ligand's structure was confirmed through 1 H NMR spectroscopy and prepared in order to synthesize dinuclear copper(II) complexes in which the molecular spacer alkoxo oxygen atom holds the two metal centers in close proximity and the fifth and sixth coordination positions are available for the coordination of exogenous ligands.The H 3 L ligand reacts in methanolic solution with Cu(CH 3 COO) 2 .H 2 O (stoichiometry 1:2) and addition of NaClO 4 results in the formation of the dinuclear complex [Cu 2 II (HL)(μ-CH 3 COO)](ClO 4 ). This complex was confirmed and characterized through IR, elemental and X-ray crystallographic analysis.…”

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Determination of catechin in green tea using a catechol oxidase biomimetic sensor

Fernandes

Osório

Anjos

et al. 2008

J. Braz. Chem. Soc.

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Um sensor biomimético catecol oxidase, baseado em um novo complexo cobre(II) foi desenvolvido para determinação de catequina em chá verde e os resultados comparados com os obtidos por eletroforese capilar. O complexo dinuclear de cobre(II) [Cu 2 (HL)(µ-CH 3 COO)] (ClO 4 ), contendo o ligante N,N-[bis-(2-piridilmetil)]-N',N'-[(2-hidroxibenzil)(2-hidroxi-3,5-di-tert-butilbenzil)]-1,3-propanodiamino-2-ol (H 3 L), foi sintetizado e caracterizado por IV, 1 H RMN e análise elementar. As melhores condições para otimização do sensor biomimético foram estabelecidas por voltametria de onda quadrada. O melhor desempenho desse sensor foi obtido em 75:15:10% (m/m/m) de pó de grafite:nujol:complexo de cobre(II), tampão fosfato 0,05 mol L -1 (pH 7,5) e freqüência, amplitude de potencial, incremento em 30 Hz, 80 mV, 3,3 mV, respectivamente. A curva analítica foi linear na faixa de concentração 4,95 × 10 -6 a 3,27 × 10 -5 mol L -1 (r=0,9993) com limite de detecção de 2,8 × 10 -7 mol L -1 . Esse sensor biomimético demonstrou longo tempo de estabilidade (9 meses; 800 determinações) e reprodutibilidade com um desvio padrão relativo de 3,5%. A recuperação da catequina em amostras de chá verde variou de 93,8 a 106,9% e a determinação, comparada com a obtida usando eletroforese capilar, mostrou-se aceitável a um nível de confiança de 95%.A catechol oxidase biomimetic sensor, based on a novel copper(II) complex, was developed for the determination of catechin in green tea and the results were compared with those obtained by capillary electrophoresis. The dinuclear copper(II) complex, [Cu 2 (HL)(µ-CH 3 COO)](ClO 4 ), containing the ligand N,N-[bis-(2-pyridylmethyl)]-N',N'-[(2-hydroxybenzyl)(2-hydroxy-3,5-ditert-butylbenzyl)]-1,3-propanediamine-2-ol (H 3 L), was synthesized and characterized by IR, 1 H NMR and elemental analysis. The best conditions for the optimization of the biomimetic sensor were established by square wave voltammetry. The best performance for this sensor was obtained in 75:15:10% (m/m/m) of the graphite powder:nujol:copper(II) complex, 0.05 mol L -1 phosphate buffer solution (pH 7.5) and frequency, pulse amplitude, scan increment at 30 Hz, 80 mV, 3.3 mV, respectively. The analytical curve was linear in the concentration range 4.95 × 10 -6 to 3.27 × 10 -5 mol L -1 (r = 0.9993) with a detection limit of 2.8 × 10 -7 mol L -1 . This biomimetic sensor demonstrated long-term stability (9 months; 800 determinations) and reproducibility with a relative standard deviation of 3.5%. The recovery of catechin from green tea samples ranged from 93.8 to 106.9% and the determination, compared with that obtained using capillary electrophoresis, was found to be acceptable at the 95% confidence level.Keywords: catechin, green tea, biomimetic sensor, square wave voltammetry IntroductionTea is one of the most consumed beverages in the world and was firstly used in China for its medicinal properties 5000 years ago. Recent epidemiological studies have shown that the consumption of tea may help to prevent cancers in humans because the tea l...

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Determination of catechin in green tea using a catechol oxidase biomimetic sensor

Fernandes

Osório

Anjos

et al. 2008

J. Braz. Chem. Soc.

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“…3 Thus, copper complexes are known to be promising reagents for the cleavage of nucleic acids. 4 Moreover, organic copper complexes based on a quinoline ring system have also been investigated as potential and selective proteasome inhibitors in human cancer cells, as well as their biological activity toward the cell viability was verified, focusing in the capability of inducing the apoptotic process. 5 On the other hand, zinc is an essential element for humans and plays an important role in biochemical and nutritional processes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structure and physicochemical properties of zinc and copper complexes based on sulfonamides containing 8-aminoquinoline ligands

Silva¹,

Sousa²,

Joussef³

et al. 2008

Quím. Nova

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Recebido em 10/8/07; aceito em 14/11/07; publicado na web em 8/7/08 Sulfonamides obtained by reaction of 8-aminoquinoline with 4-nitrobenzenesulfonylchloride and 2,4,6-triisopropylbenzenesulfonyl chloride were used to synthesize coordination compounds with Cu II and Zn II with a ML 2 composition. Determination of the crystal structures of the resulting zinc and copper complexes by X-ray diffraction show a distorted tetrahedral environment for the [Cu(qnbsa) 2 ], [Cu(qibsa) 2 ] and [Zn(qibsa) 2 ] complexes in which the sulfonamide group acts as a bidentate ligand through the nitrogen atoms from the sulfonamidate and quinoline groups. The complex [Zn(qnbsa) 2 ] crystallizes with a water molecule from the solvent and the Zn is five-coordinated and shows a bipyramidal-trigonal geometry. The electrochemical and electronic spectroscopy properties of the copper complexes are also discussed.

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Heteroleptic Schiff base complexes containing terpyridine as chemical nucleases and their biological potential: A study of DNA binding and cleaving, antimicrobial and cytotoxic tendencies

Utthra¹,

Kumaravel²,

Senthilkumar

et al. 2016

Applied Organom Chemis

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Amidst the very many metallodrugs for the treatment of cancer regularly reported, the development of the next generation of compounds with an aim of overcoming the shortcomings by enhancing biological activity and cytotoxicity but exhibiting low toxicity is essential. Herein we report such octahedral metal(II) complexes (1-12) containing triazole-derived Schiff base as the scaffold. The complexes were synthesized and characterized by means of elemental analysis and various spectroscopic techniques. The complexes were subjected to various investigations that involved their interaction with calf thymus DNA and supercoiled pBR322 DNA.In vitro antimicrobial studies were also conducted in addition to the use of spectrophotometric, spectrofluorometric, cyclic voltammetric and hydrodynamic techniques. Although all complexes showed activity, complex 9 revealed excellent DNA proclivity, DNA cleaving tendencies and antimicrobial efficacy. All copper (II) complexes were evaluated for their antiproliferative activity against a panel of human cancer cell lines (HeLa, Hep-2, MCF-7 and NHDF). Complexes 1-12 showed activity against all the cell lines with low toxicity towards normal cell line, and the activity of complex 9 towards Hep-2 was prominent. The effect of the ligand system on the complexes is also discussed along with the importance of tuning the ligand system.

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Synthesis, structure and properties of unsymmetrical μ-alkoxo-dicopper(II) complexes: biological relevance to phosphodiester and DNA cleavage and cytotoxic activity

Cited by 72 publications

References 58 publications

Determination of catechin in green tea using a catechol oxidase biomimetic sensor

Determination of catechin in green tea using a catechol oxidase biomimetic sensor

Synthesis, structure and physicochemical properties of zinc and copper complexes based on sulfonamides containing 8-aminoquinoline ligands

Heteroleptic Schiff base complexes containing terpyridine as chemical nucleases and their biological potential: A study of DNA binding and cleaving, antimicrobial and cytotoxic tendencies

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