Oxidation chemistry of 2′-deoxyadenosine at pyrolytic graphite electrode

Goyal, Rajendra N.; Dhawan, Aikta

doi:10.1016/j.bioelechem.2006.03.003

Cited by 9 publications

(17 citation statements)

References 26 publications

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“…In the anodic scan, dA gives a single peak A ox at a potential of +1.39 V (Figure and Figure S1 in the Supporting Information showing the voltammograms in bigger size and better resolution) i. e. at the same potential as A residues in the DNA oligonucleotides . Oxidation of dA at PGE in phosphate buffers has previously been well described in a wide pH range . It has been found that dA oxidation occurs in adsorbed state and involves 6e − and 6H + , with the electrode reaction coupled to irreversible follow‐up chemical step(s).…”

Section: Resultscontrasting

confidence: 99%

“…This could be attributed either to a different surface pretreatment (sand paper‐polished surface used in could have more graphite edges than the surface peeled by adhesive tape, resulting in higher background discharge currents for the former). Another reason could be related to the background electrolyte composition (blank acetate buffer with dA present only at the electrode surface in our case, in contrast to phosphate buffer containing 0.5 mM dA in the bulk ).…”

Section: Resultscontrasting

confidence: 51%

“…Finally, for E v ≤+0.9 V (“safely” before the first G ox ), the peak G red remained fully developed and no additional reduction peaks of oxidized dG have been observed (Figure and S3). Appearance of multiple reduction signals of oxidized dG, which can be controlled by E v placement, supports the hypothesis of the complex dG oxidation involving radical intermediates and multiple different products, including base‐linked polymers as has been shown with guanosine and dA .…”

Section: Resultsmentioning

confidence: 99%

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Electrochemical Reduction and Oxidation of Six Natural 2′‐Deoxynucleosides at a Pyrolytic Graphite Electrode in the Presence or Absence of Ambient Oxygen

2019

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Recently we have demonstrated that pyrolytic graphite electrodes (PGE) offer a broad analytically useful potential window, ranging from about −2.0 V to +1.6 V vs. Ag|AgCl|3 M KCl, which enables to use the PGE not only for anodic measurements, but also for direct reduction of nucleobases in DNA oligonucleotides. In this follow‐up study, we have focused on the electrochemical behavior of four 2′‐deoxynucleosides derived from adenine, guanine, cytosine, thymine, uracil, and 5‐methyl cytosine on the PGE. On one hand we have obtained analogous primary redox responses as previously with the oligonucleotides. On the other hand, significant differences were observed, particularly when considering secondary responses involving products of the primary conversions, suggesting involvement of different mechanisms. Further we have found that presence of the ambient oxygen in the electrolyte does not dramatically affect the redox signals of the nucleosides. This finding is in contrast with DNA responses measured at the mercury‐based electrodes, where deaeration prior to the measurements was necessary. We demonstrate that all studied nucleosides can be analyzed using a simple ex situ (medium exchange) procedure.

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Section: Resultscontrasting

confidence: 99%

Section: Resultscontrasting

confidence: 51%

Section: Resultsmentioning

confidence: 99%

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Electrochemical Reduction and Oxidation of Six Natural 2′‐Deoxynucleosides at a Pyrolytic Graphite Electrode in the Presence or Absence of Ambient Oxygen

2019

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“…The hydrolysis followed by ring cleavage then gives number of pH dependent products as reported in literature [38,39]. The method is a promising alternative to the commonly reported chromatographic methods on account of its rapidity, good recovery, reliability and low detection limit.…”

Section: Discussionmentioning

confidence: 92%

“…The electrooxidation of adenine and 2'-deoxyadenosine has been studied earlier and it has been suggested that primary electrode reaction occurs by a loss of 6e À , 6H þ at pH 7.2 as illustrated in Scheme 1 [38,39]. [a] The RSD was < 3.1% for n ¼ 3.…”

Section: Discussionmentioning

confidence: 99%

Voltammetric Determination of 2′‐Deoxyadenosine and Adenine in Urine of Patients with Hepatocellular Carcinoma Using Fullerene‐C₆₀‐modified Glassy Carbon Electrode

2009

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A fullerene-C 60 -modified glassy carbon electrode has been examined for the simultaneous determination of 2'-deoxyadenosine (2'-dAdo) and adenine in human blood and urine using Osteryoung square-wave voltammetry (OSWV) at pH 7.2. Compared to bare glassy carbon electrode (GCE), the modified electrode displays a shift of the oxidation potential in the negative direction with significant increase in the peak current for both the analytes. At modified electrode well-defined anodic peaks at potential of 1248 mV and 994 mV are observed for 2'-dAdo and adenine respectively. Linear calibration curves were obtained within the concentration range 10 nM to 100 mM for both the compounds in 0.1 M phosphate buffer solution (PBS) with the limit of detection 0.8 Â 10 À8 M and 0.95 Â 10 À8M for 2'-dAdo and adenine respectively. The analytical utility of the present method is demonstrated by quantitative detection of 2'-dAdo and adenine in human urine of normal subjects as well as in patients with hepatocellular carcinoma. Interfering effect of some coexisting metabolites has also been reported.

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Electrochemical behaviour of 2,8-dihydroxyadenine at a glassy carbon electrode

Diculescu

Piedade

Oliveira-Brett

2007

Bioelectrochemistry

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The electrochemical behaviour of 2,8-dihydroxyadenine (2,8-DHA)- the main adenine oxidation product- has been investigated over a wide pH range at a glassy carbon electrode (GCE) using cyclic, differential pulse and square wave voltammetry. The oxidation of 2,8-DHA is a quasi-reversible process, pH dependent and occurs with the formation of a main oxidation product, P(2,8-DHA), that strongly adsorbs on the electrode surface. The reduction of 2,8-DHA also occurs and is a reversible process in the absence of molecular oxygen. In electrolytes with pH between 4 and 9 two consecutive reversible charge transfer reactions were identified. However, it was observed that O(2) interfered with the reductive electron transfer process of 2,8-DHA and that, in the presence of oxygen, the reduction of 2,8-DHA occurs at less negative potentials than in the absence of oxygen.

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Oxidation chemistry of 2′-deoxyadenosine at pyrolytic graphite electrode

Cited by 9 publications

References 26 publications

Electrochemical Reduction and Oxidation of Six Natural 2′‐Deoxynucleosides at a Pyrolytic Graphite Electrode in the Presence or Absence of Ambient Oxygen

Electrochemical Reduction and Oxidation of Six Natural 2′‐Deoxynucleosides at a Pyrolytic Graphite Electrode in the Presence or Absence of Ambient Oxygen

Voltammetric Determination of 2′‐Deoxyadenosine and Adenine in Urine of Patients with Hepatocellular Carcinoma Using Fullerene‐C₆₀‐modified Glassy Carbon Electrode

Electrochemical behaviour of 2,8-dihydroxyadenine at a glassy carbon electrode

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Oxidation chemistry of 2′-deoxyadenosine at pyrolytic graphite electrode

Cited by 9 publications

References 26 publications

Electrochemical Reduction and Oxidation of Six Natural 2′‐Deoxynucleosides at a Pyrolytic Graphite Electrode in the Presence or Absence of Ambient Oxygen

Electrochemical Reduction and Oxidation of Six Natural 2′‐Deoxynucleosides at a Pyrolytic Graphite Electrode in the Presence or Absence of Ambient Oxygen

Voltammetric Determination of 2′‐Deoxyadenosine and Adenine in Urine of Patients with Hepatocellular Carcinoma Using Fullerene‐C60‐modified Glassy Carbon Electrode

Electrochemical behaviour of 2,8-dihydroxyadenine at a glassy carbon electrode

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Voltammetric Determination of 2′‐Deoxyadenosine and Adenine in Urine of Patients with Hepatocellular Carcinoma Using Fullerene‐C₆₀‐modified Glassy Carbon Electrode