Correlation of electrochemical reduction of adenine nucleosides and nucleotides with structure and orientation in solution

Janik, Borivoj; Elving, Philip J.

doi:10.1021/ja00705a001

Cited by 121 publications

(20 citation statements)

References 10 publications

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“…2), the sample current is depressed below that of the background at potentials more positive than ca. -0.8 V. The similar background and sample curve patterns at pH 2.6 and 3.8 are analogous to the total ac polarograms at pH 2.5 [40]. The deep depression at -0.6 V indicates that maximal adsorption occurs near the pzc (ca.…”

Section: Ac Polarography : Quadrature Componentsupporting

confidence: 53%

Adsorption of adenine at the mercury/water interface. Effects of pH and ionic strength

Katz

Cummings

Elving

1979

Ber Bunsenges Phys Chem

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The adsorption of adenine at the mercury/aqueous solution interface has been examined by phase‐selective a. c. polarography. Surface charge, surface tension and adsorption isotherms have been derived from the capacity curves. At all pH, adenine molecules are adsorbed in a flat orientation due to specific π‐orbital interaction, which, in acidic media, predominates over electrostatic repulsion between protonated adenine and positively charged electrode. The extent of adsorption increases with pH in Mcllvaine buffer (pH 2.6 to 7.2); it is less in pH 9.0 carbonate buffer than in pH 7.2 Mcllvaine buffer. With increasingly negative electrode potential or charge, the surface excess of adenine steadily decreases; adenine is not adsorbed negative of ‐1.6V. There is neither potential‐ nor surface‐charge‐dependent reorientation beyond about ‐ 1.1 V; a concentration‐dependent‐reorientation occurs before monolayer coverage is complete. Adsorption can be described by a Frumkin isotherm with an interaction factor corresponding to attraction between adsorbed molecules for potentials positive of ‐0.7 V at pH 7.2 and ‐ 0.5 V at pH 9.0. Repulsion between adsorbed molecules at pH 3.8 implies that protonated adenine is present on the surface. The standard free energy of adsorption varies from ‐ 29 to ‐ 38 kJ/mol.

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Section: Ac Polarography : Quadrature Componentsupporting

confidence: 53%

Adsorption of adenine at the mercury/water interface. Effects of pH and ionic strength

Katz

Cummings

Elving

1979

Ber Bunsenges Phys Chem

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“…We suppose that the stacking interaction is a key factor affecting the reduction process. This is supported by the finding that the stacking energy of cytosine moieties is lower than that of adenine ones [29,30].…”

Section: Resultsmentioning

confidence: 68%

Application of Elimination Voltammetry to the Resolution of Adenine and Cytosine Signals in Oligonucleotides. I. Homo‐oligodeoxynucleotides dA₉ and dC₉

2003

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Elimination voltammetry with linear scan (EVLS) has been applied to the resolution of reduction signals of adenine and cytosine in short synthetic homo-oligodeoxynucleotides (dA 9 and dC 9 ). In comparison with the common electrochemical methods (linear sweep, differential pulse, and square-wave voltammetry) EVLS enables one to resolve the overlapped signals by using the function which eliminates the charging and kinetic currents (I c , I k ) and conserves the diffusion current (I d ). For the adsorbed electroactive substance, this elimination function gives a good readable peak-counterpeak which has successfully been utilized to the analysis of overlapped reduction signals of adenine and cytosine on hanging mercury drop electrode (HMDE). The height and potential of signals studied were affected by the dC 9 /dA 9 ratio, the time of accumulation, the stirring speed during the adsorption, and pH. Our results showed that EVLS in connection with the adsorption procedure is a useful tool for qualitative and quantitative studies of short oligonucleotides.

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“…Adenine, one of the important purine bases, plays a vital role in many biological processes. Its electirochemical nature was investigated by different electroanalytical techniques [19][20][21][22][23][24][25][26][27][28][29][30]. Extensive studies were carried out for the adsorption and reduction of adenine at mercury electrodes [20-2S].…”

Section: Introductionmentioning

confidence: 99%

Synergistic electrochemical and chemical modification of carbon paste electrodes for open‐circuit preconcentration and voltammetric determination of trace adenine

1995

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A new concept of electrode modification is presented, consisting of chemically assisted electrochemical oxidative pretreatment of the electrode surface. If carbon paste electrodes (CPEs) are polarized at +1.75V (vs Ag/AgCl) in a dilute alkaline medium (1 x lo-' mol/L) containing 0.1 mol/L NaN03 for 61) s, they exhibit a unique ability to preconcentrate adenine, an important biological substance. that served as a model compound. In this work, a thorough study has been performed to explore the new pretreatment procedure, but also its analytical application for trace adenine determination was optimized. During the pretreatment of a CPE, a specific oxide layer is formed due to a synergistic effect of a combined anodic and chemical oxidation process, in which the presence of sodium nitrate plays a crucial role. In a subsequent step under open-circuit conditions, adenine is oxidized by the oxide layer, and the resulting oxidation product is strongly adsorbed onto the electrode surface. After medium exchange, the adsorbed oxidation product of adenine is reduced at -0.5 V (vs. Ag/AgCl) and the voltammetric current response can be utilized for analytical purposes. Applying 10 min accumulation and square-wave voltammetric operation, the detection limit of 20pg/L (1.5 x lo-' mol/L) of adenine in a sample solution was acquired. The voltammetric behavior of adenine at plain and pretreated CPEs is also presented and discussed.

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Correlation of electrochemical reduction of adenine nucleosides and nucleotides with structure and orientation in solution

Cited by 121 publications

References 10 publications

Adsorption of adenine at the mercury/water interface. Effects of pH and ionic strength

Adsorption of adenine at the mercury/water interface. Effects of pH and ionic strength

Application of Elimination Voltammetry to the Resolution of Adenine and Cytosine Signals in Oligonucleotides. I. Homo‐oligodeoxynucleotides dA₉ and dC₉

Synergistic electrochemical and chemical modification of carbon paste electrodes for open‐circuit preconcentration and voltammetric determination of trace adenine

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Correlation of electrochemical reduction of adenine nucleosides and nucleotides with structure and orientation in solution

Cited by 121 publications

References 10 publications

Adsorption of adenine at the mercury/water interface. Effects of pH and ionic strength

Adsorption of adenine at the mercury/water interface. Effects of pH and ionic strength

Application of Elimination Voltammetry to the Resolution of Adenine and Cytosine Signals in Oligonucleotides. I. Homo‐oligodeoxynucleotides dA9 and dC9

Synergistic electrochemical and chemical modification of carbon paste electrodes for open‐circuit preconcentration and voltammetric determination of trace adenine

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About

Application of Elimination Voltammetry to the Resolution of Adenine and Cytosine Signals in Oligonucleotides. I. Homo‐oligodeoxynucleotides dA₉ and dC₉