Comparative study of the catalytic oxidation of catechols by copper(II) complexes of tripodal ligands

Malachowski, Mitchell R.; Huynh, Hong B.; Tomlinson, Laura; Kelly, Richard S.; Furbee, James W.

doi:10.1039/dt9950000031

Cited by 122 publications

(60 citation statements)

References 36 publications

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“…Similar trends have been observed for dinuclear and mononuclear copper complexes and their reactivity toward catechol oxidation (41,42). Dinuclear copper complexes routinely show significantly higher catechol oxidation rates.…”

Section: Resultssupporting

confidence: 64%

Catecholase Activity Associated with Copper-S100B

et al. 2003

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This study addresses the spectroscopic properties and reactivity associated with the copperloaded form of S100B isolated from bovine brain. Copper(II)-S100B displays EPR features typical of a type II copper center and is shown here to exhibit catecholase activity, the two-electron oxidation of catechols. The steady-state kinetics associated with the oxidation of several catecholamines has been probed in order to further characterize this activity. The evidence provided indicates that the catecholase chemistry is copper initiated. Superoxide dismutase has no effect on the rates of catecholamine oxidation catalyzed by Cu-S100B, establishing that superoxide is not produced during this reaction, ruling out an autoxidative mechanism. Addition of catalase to the Cu-S100B reaction with catechols reduces the amount of oxygen consumed by 50%, demonstrating that peroxide is released during this reaction. The release of peroxide is mechanistically distinct from the type III dinuclear copper proteins, catechol oxidase and tyrosinase.

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Section: Resultssupporting

confidence: 64%

Catecholase Activity Associated with Copper-S100B

et al. 2003

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“…15 The catecholase activity has been determined in vitro for many mononuclear and dinuclear copper(II) complexes. 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.…”

Section: Introductionmentioning

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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“…9,22,23 This pathway is supported by the identification of H 2 O 2 through iodometric titration and the isolation of 3,5-DTBQ. The isolated product was characterised by …”

Section: Resultsmentioning

confidence: 87%

Kinetic study of the Catecholase activities of a tetranuclearCu(I) complex in different Solvents

2018

IJCTR

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:The structure of [Cu 4 (μ 3 -Cl) 4 (PPh 3 ) 4 (1) reveals a four coordinate system around the metal ions and1 behaves as an effective catalyst towards the oxidation of 3,5-di-tertbutylcatechol in methanol and DMF to the corresponding quinone in the presence of oxygen. The reaction follows Michaelis-Menten enzymatic reaction kinetics with turnover numbers (Kcat), 2.06 and 1.51 h -1 in methanol and DMF respectively.

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Comparative study of the catalytic oxidation of catechols by copper(II) complexes of tripodal ligands

Cited by 122 publications

References 36 publications

Catecholase Activity Associated with Copper-S100B

Catecholase Activity Associated with Copper-S100B

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

Kinetic study of the Catecholase activities of a tetranuclearCu(I) complex in different Solvents

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