Electrochemistry of potentially bioreductive alkylating quinones

Driebergen, R. J.; Moret, Ed E.; Janssen, Lambert H.M.; Blauw, J.S.; Holthuis, J.J.M.; Kelder, S.J. Postma; Verboom, Willem; Reinhoudt, David N.; Linden, Willem J. van der

doi:10.1016/0003-2670(92)85179-a

Cited by 30 publications

(10 citation statements)

References 30 publications

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“…The formal redox potential, E°' = À0.420 V (vs. SCE), is in good agreement with the values reported for other structurally close 2-amino-1,4-naphthoquinones, ranging between À0.419 and À0.476 V (vs. SCE, at pH 7) [37] depending on the investigated compound. These values are significantly more negative than that of the unsubstituted 1,4-naphthoquinone (E°' = À0.190 V vs. SCE [37]), because the electron-donating properties of the amino group of 2-amino-1,4-naphthoquinones makes them more difficult to reduce [37,38]. The electron donor character of the nitrogen is influ- …”

Section: Behaviour In Buffered Solutionsupporting

confidence: 82%

Electrochemical investigations of dissolved and surface immobilised 2-amino-1,4-naphthoquinones in aqueous solutions

Bouffier

Lister

Higgins

et al. 2012

Journal of Electroanalytical Chemistry

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Section: Behaviour In Buffered Solutionsupporting

confidence: 82%

Electrochemical investigations of dissolved and surface immobilised 2-amino-1,4-naphthoquinones in aqueous solutions

Bouffier

Lister

Higgins

et al. 2012

Journal of Electroanalytical Chemistry

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“…Quantitative structureelectrochemistry relationships of aziridinylquinones (5) were established by Driebergen and coworkers. 33 There is a wealth of prior experience in correlating polarographic data with Hammett and related substituent constants. This correlation can be used to extend limited experimental measurements and predict redox properties of a much wider range of compounds with considerable reliability.…”

Section: Correlation Of Electrochemical Data and Structural Parametersmentioning

confidence: 99%

“…70-80 mV change in redox potential leads to 10 fold change in the reduction rate. Two hypoxic active nitrobenzyloxycarbonyl derivatives of 1,2-bis (methylsulfonyl)-1-(2-chloroethyl) hydrazines (33) were studied by pulse polarography in different pH values and appear to be reduced more easily under acidic conditions than under neutral conditions (Scheme 10). 61 While the potency of the bioreductive quinones varies with their redox potential, the direction and magnitude of the oxic/hypoxic differential cannot yet be predicted from the structures.…”

Section: Generalitiesmentioning

confidence: 99%

Some Applications of Electrochemistry in Biomedical Chemistry. Emphasis on the Correlation of Electrochemical and Bioactive Properties

Abreu¹,

Ferraz²,

Goulart³

2002

J. Braz. Chem. Soc.

153

124

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Essa revisão resume alguns dos aspectos mais relevantes na correlação entre processos e parâmetros eletroquímicos e atividades biológicas, relacionadas, principalmente, a doenças tropicais e câncer. Apesar da gama de possibilidades e da complexidade da química celular/tecidual/extracelular, é possível racionalizar o papel da eletroquímica em poucas bases teóricas, principalmente: transferência eletrônica -estresse oxidativo, geração eletroquímica in situ de agentes tóxicos diferentes das espécies oxigenadas reativas, interação com endobióticos, com ênfase particular em alquilação biorredutiva e substituição de endobióticos com função em reações de oxi-redução biológicas. O uso de métodos eletroquímicos para a obtenção de mecanismos de ação de drogas e na análise de eventos celulares é também apresentado. Nessas correlações, métodos e/ou parâmetros eletroquímicos exercem papel relevante, porém, não absoluto.This review summarises some of the more relevant achievements in the correlation between electrochemical processes and parameters and bioactive properties, mainly related to cancer and tropical diseases. Despite the broad range of possibilities and the complexity of cell/tissue/extracell chemistry, it is possible to rationalise the role of electrochemistry in few basic theoretical frameworks, mainly, the one based on electron transfer-oxidative stress and in situ generation of toxic species, other than the reactive oxygen species; interaction with endobiotics, with emphasis on bioreductive alkylation and replacement of endobiotics with function in biological redox reactions. The use of electrochemical methods to obtain relevant informations about drugs' mechanism of action and analysis of cellular events is also presented. Electrochemical methods and/or parameters play essential but not absolute roles.

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“…Some examples are quantitative structure-reactivity relationships (QSRRs) [1], quantitative structure-chromatography relationships (QSCRs) [2,3], quantitative structure-toxicity relationships (QSTRs) [4], quantitative structure-electrochemistry relationships (QSERs) [5][6][7], quantitative structure-biodegradability relationships (QSBRs) [8,9] and etc.…”

Section: Introductionmentioning

confidence: 99%