Synthesis, characterization and catecholase-mimetic activity of mononuclear copper(II) aspirinate complexes

Abuhijleh, A. Latif; Woods, Clifton; Bogas, Ekaterini; Guenniou, Gaelle Le

doi:10.1016/s0020-1693(00)83851-7

Cited by 59 publications

(31 citation statements)

References 25 publications

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“…5) show that in this case the copper(II) ion is in a trans square-planar arrangement to the nitrogen atom of two pyridine molecules and to one carboxylate oxygen atom from each of two indomethacin anions [14]. The values of gH = 2.287 and A H = 178 G and the appearance of five superhyperfine lines in the g• region due to the interactions of the paramagnetic electron with two equivalent nitrogen nuclei (IN= 1) confirm the existence of CuN202 chromophore (aN= 15 G).…”

Section: Resultsmentioning

confidence: 95%

ESR study of Cu(II)-indomethacin and its pyridine and DMF adducts

et al. 1994

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Abstraet.Powder ESR spectra of [Cu2([nd)4](H20)2 at room temperature show the presence of copper acetate like dimers charactedzed by a slrong antiferromagnetie exchange interaction (J~--338 cm J). Two different monomeric speeies were evidenced in 40%Py+60%DMF solution absorbed on NaY zeolite: the Cu(Ind)2(DMF)2 with ah elongated tetragonal-octahedral symmetry and the Cu(Ind)2(Py) 2 with a CuN202 chromophore in a trans square-planar arrangement. Only one monomeric species Cu(Ind)2(Py)2 was identified in 20%Py+80%DMF and 20%Py+80%Chloroform sotutions. The Cu(Py)42 § species of CuN 4 chromophore occurs in pyridine Cu(II)-indomethacin solution suggesting a decomposition of the solvit compound.

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Section: Resultsmentioning

confidence: 95%

ESR study of Cu(II)-indomethacin and its pyridine and DMF adducts

et al. 1994

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“…Specialized research groups have developed μ-hidroxo, μ-carboxylato or μ-imidazole dinuclear copper(II) compounds with the aim of mimicking the active site of the catechol oxidase enzyme, [12][13][14][15][18][19][20][21][22][23][24][25][26][27][28][29] and the mechanism of the catalytic cycle has been proposed for some complexes. Catecholase activity has been also determined for a few mononuclear and dinuclear copper(II)-NSAIDs complexes, [30][31][32] but the mechanism of the catalytic oxidation remains unclear.Fenoprofen, 2-(3-phenoxyphenyl)propionic acid or α-methyl-3-phenoxybenzeneacetic acid (Scheme 1) is an antipyretic, analgesic and non steroidal anti-inflammatory drug (NSAID). It belongs to the group of compounds commonly referred as the 2-arylpropionic acids.…”

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confidence: 99%

Significant anti-inflammatory properties of a copper(II) fenoprofenate complex compared with its parent drug: Physical and chemical characterization of the complex

Agotegaray¹,

Boeris²,

Quinzani³

2010

J. Braz. Chem. Soc.

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A síntese, a caracterização físico-química, as propriedades anti-inflamatórias e a atividade mimética de catecolase do complexo de cobre(II) com a droga anti-inflamatória non-esteroidal Fenoprofeno [ácido 2-(3-fenóxifenil)propiônico] com fórmula [Cu 2 (fen) 2 (dmf) 2 ] (fen = ânion do fenoprofenato, dmf = N,N-dimetilformamida) foram investigadas. Os resultados da análise espectroscópica (espectros de FTIR e EPR) e dados de análise termogravimétrica e térmica diferencial obtidos para o complexo sólido estão de acordo com a sua estrutura dinuclear. Os espectros eletrônicos do produto são igualmente apresentados e discutidos neste trabalho. O complexo foi testado para as suas propriedades anti-inflamatórias em comparação com a droga de referência, o sal de cálcio do Fenoprofeno. A administração oral do composto binuclear inibiu o desenvolvimento do edema induzido por carragenana em ratos; esta inibição foi mais significativa do que a obtida com a droga de referência. O estudo cinético da atividade mimética da catecolase foi realizado espectrofotometricamente, monitorando-se a transformação oxidativa do 3,5-di-terc-butilcatecol na o-quinona correspondente. Os parâmetros cinéticos foram determinados pelo emprego do modelo de Michaelis-Menten, que demonstrou que o novo complexo mimetiza a atividade da catecol oxidase.The synthesis, physicochemical characterization, anti-inflammatory properties and catecholase mimetic activity of the dinuclear complex of copper(II) with the non-steroidal anti-inflammatory drug Fenoprofen [2-(3-phenoxyphenyl)propionic acid] with formula [Cu 2 (fen) 4 (dmf) 2 ] (fen = fenoprofenate anion, dmf = N,N-dimethylformamide) have been investigated. Results of spectroscopic analysis (FTIR and EPR) as well as thermogravimetric and differential thermal analysis data obtained for the solid complex are in good agreement with its dinuclear structure. Electronic spectra of the product are also reported and discussed. The complex was tested for anti-inflammatory properties in comparison to the parent drug, Fenoprofen calcium salt. Oral administration of the dinuclear compound inhibited development of carrageenan-induced oedema in mice; this inhibition was higher than that observed for the parent drug. The kinetic study of the catecholase mimetic activity was carried out spectrophotometrically by monitoring the oxidative transformation of 3,5-di-tert-butylcatechol into the corresponding light-absorbing o-quinone. Kinetic parameters were determined employing the Michaelis-Menten model, showing that the new complex presents catechol oxidase mimetic activity.Keywords: copper(II), Fenoprofen, anti-inflammatory properties, catecholase activity IntroductionThe proposed curative properties of copper(II) carboxylate-based non-steroidal anti-inflammatory drugs (NSAIDs) have led to the development of numerous mononuclear and dinuclear copper(II) complexes of NSAIDs with enhanced anti-inflammatory activity.1,2 The elevation of total blood copper levels during acute as well as chronic inflammatory states has been re...

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“…The gH = 2.285 and A n = 177.6 G parameters characteristic of the second species show that in this case the copper(II) ion is bonded in a trans square-planar arrangement to the nitrogen atom of two pyridine molecules and to orte carboxylate oxygen atorn from each of two aspirinate anions [6]. The existence of the CuN20 2 chromophore is confirmed by the appearance of nitrogen superhyperfine lines in the g• region of the spectra (Fig.…”

Section: Resultsmentioning

confidence: 71%

“…Pyridine adducts and other mononuclear adducts of Cu(II)-aspirinate with nitrogen donors have recently been reported to have superoxide dismutase activity [6,12]. UV-Vis, IR, ESR, and X-ray data are consistent with the presence in these mononuclear complexes of the CuO2N 2 co-ordination center or chromophore in a trans square-planar arrangement [12][13][14].…”

Section: Introducfionmentioning

confidence: 93%

“…Copper(II) complexes of aspirin and other salicylic derivates have been found to be more potent and desirable drugs than the ligands themselves [1][2][3]. In addition, these metal complexes exhibit a variety of pharmacological effects such as antiulcer, antidiabetic, anticancer, anticonvulsant and radiation recovery activities [1][2][3][4][5][6].…”

Section: Introducfionmentioning

confidence: 99%

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ESR study of some solvent effects of the Cu(II)-aspirinate complex

et al. 1995

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Powder ESR spectra of the [Cu2(Asp)4](H20)z complex show the existence of Cu(II) aeetate like dimers characterized by a strong antiferromagnetic exchange interaction (J =-288 cm l), In pyridine-dimethylformamide solutiotas the monomeric species prevait. Two different monomeric species, the Cu(DMF)4 of planar-distorted tetrahedral (Td) symmetry and the Cu(Asp)2(DMF) 2 with elongated tetrahedral-octahedral symmetry were evidenced in DMF solution adsorbed on NaY zeolite. In 40 % Py + 60 % DMF solution two monomeric species were also identified. These are Cu(Asp)2(DMF)z and Cu(AsP)2(Py)2, the last species having a CuN202 chromophore in a trans squareplanar arrangement. In py¡ Cu(lI)-aspirinate solution only the Cu(Py)4 monomeric species of CuN 4 chromophore was evidenced.

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Synthesis, characterization and catecholase-mimetic activity of mononuclear copper(II) aspirinate complexes

Cited by 59 publications

References 25 publications

ESR study of Cu(II)-indomethacin and its pyridine and DMF adducts

ESR study of Cu(II)-indomethacin and its pyridine and DMF adducts

Significant anti-inflammatory properties of a copper(II) fenoprofenate complex compared with its parent drug: Physical and chemical characterization of the complex

ESR study of some solvent effects of the Cu(II)-aspirinate complex

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