Investigations of electron-transfer reactions and the redox mechanism of 2′-deoxyguanosine-5′-monophosphate using electrochemical techniques

Goyal, Rajendra N.; Sondhi, Sham M.; Lahoti, Anand M.

doi:10.1039/b415452p

Cited by 18 publications

(22 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…8-oxo-dGMP is one of the major oxidative DNA lesions [1 -3] and a frequently studied biomarker for oxidative damage in vivo [34 -36]. It has also been reported as an electrochemical generated oxidation product of dGMP in several studies based on CV measurements [11,12,37]. As discussed in detail for 8-oxo-dGMP, the fragmentation pattern of further oxidation products of dGMP was analyzed.…”

Section: Oxidation Of Nucleotides By Ec/esi-msmentioning

confidence: 99%

“…A comparison of the oxidation peaks of different nucleotides by differential pulse voltammetry shows that guanosine 5'-monophosphate (GMP) requires the lowest oxidation potential of all four nucleotides [9]. The products generated upon oxidation have been studied by spectrometric techniques [11]. Additionally, stable oxidation products have been isolated and further characterized by nuclear magnetic resonance (NMR) as well as by gas chromatography (GC) after derivatization into volatile products [10].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

On‐Line Electrochemistry/Electrospray Ionization Mass Spectrometry (EC/ESI‐MS) for the Generation and Identification of Nucleotide Oxidation Products

et al. 2010

View full text Add to dashboard Cite

The oxidation behavior of DNA and RNA nucleotides is studied by an on-line set-up consisting of an electrochemical thin-layer cell (EC) directly coupled to electrospray ionization mass spectrometry (ESI-MS). This set-up allows the generation of nucleotide oxidation products in the electrochemical cell at increasing potentials. Moreover, the products are determined directly, without isolation or derivatization steps, by electrospray ionization time of flight mass spectrometry (ESI-ToF/MS). The dependence of the mass spectra on the applied potential is displayed as mass voltammograms. An advanced set-up, consisting of the electrochemical cell coupled to electrospray ionization tandem mass spectrometry (EC/ESI-MS/MS) allows further structure elucidation based on fragmentation experiments. The electrochemical conversion is performed using a boron doped diamond (BDD) working electrode, which is known to generate hydroxyl radicals at high potentials. The capability of the EC-MS system to generate highly relevant oxidation products which also occur upon oxidative damage in vivo is demonstrated in this study by the formation of well known biomarkers for DNA damage, including 2'-deoxy-8-oxo-guanosine 5'-monophosphate.

show abstract

Section: Oxidation Of Nucleotides By Ec/esi-msmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

On‐Line Electrochemistry/Electrospray Ionization Mass Spectrometry (EC/ESI‐MS) for the Generation and Identification of Nucleotide Oxidation Products

et al. 2010

View full text Add to dashboard Cite

show abstract

“…In the continuous (second) sweep to the positive direction another two oxidation peaks IIa (0.879 V) and IIIa (0.447 V) appeared. The phenomena was very similar to the electrooxidation of GTP, 7 guanoside-5'-monophosphate (GMP) 8 or 2'-deoxyguanosine-5'-monophosphate (dGMP) 19 on the pyrolytic graphite electrode. Goyal et al had widely investigated the oxidation mechanisms of purine based and their nucleosides or nucleotides on the solid electrode with different methods such as cyclic voltammetry, spectral studies, bulk electrolysis and related techniques.…”

Section: Cyclic Voltamograms Of 2'-deoxyguanosin-5'-triphosphatementioning

confidence: 64%

“…Due to the presence of IL in the electrode, the electrochemical response was increased, which was ascribed to the electrocatalytic ability of mCILE. Compared with early reports about electrooxidation of dGMP 19 or GTP 7 on the pyrolytic graphite electrode, the initial oxidation peak (Ia) appeared on the cyclic voltamogram was contributed to the one electron and one proton oxidation step of guanine group to give a free radical moiety, which was occurred from the CH group at position 8. The free radical formed could give a diimine species or take place different following chemical reactions with different kinds of oxidation products formed.…”

Section: Discussionmentioning

confidence: 99%

“…The results were similar to the reports of electrooxidation dGMP. 19 The effect of scan rate on the redox peak potential (E p ) and peak current (I p ) were further investigated in the scan rate range from 10 to 400 mV s -1 . With the increase of scan rate the oxidation peak potentials shifted towards more positive directions and the reduction peak potentials moved towards more negative directions.…”

Section: Cyclic Voltamograms Of 2'-deoxyguanosin-5'-triphosphatementioning

confidence: 99%

See 1 more Smart Citation

Electrochemical Oxidation of 2’-deoxyguanosine-5’-triphosphate on Ionic Liquid Modified Carbon Paste Microelectrode and its Sensitive Detection

Gao¹,

Duan²,

Xu³

et al. 2011

Croat. Chem. Acta

View full text Add to dashboard Cite

Abstract. Electrochemical oxidation of 2'-deoxyguanosine-5'-triphosphate (dGTP) was investigated on the ionic liquid modified carbon paste microelectrode by cyclic voltammetry in this paper. The carbon ionic liquid microelectrode (mCILE) was prepared with ionic liquid 1-ethyl-3-methylimidazolium ethylsulfate ([Emim][EtOSO 3 ]) as the modifier. Then the electrochemical process of dGTP on the mCILE was recorded with the electrochemical parameters calculated and the oxidation mechanism discussed. Under the optimal conditions differential pulse voltammetric peak current was proportional to the dGTP concentration in the range from 1.0× 10 -6 M to 7.0× 10 -4 M with the linear regression equation as log ( I pa / A) = 0.77 log(c / mol dm -3 ) -4.082 (γ = 0.999). The proposed method showed good selectivity and stability without the interferences of coexisting substances.

show abstract

Characterization of the Oxidative Behavior of Cyclic Nucleotides Using Electrochemistry–Mass Spectrometry

2014

View full text Add to dashboard Cite

The oxidative behavior of cyclic nucleotides, important intracellular second messengers, was investigated. Guanosine‐3′,5′‐cyclic monophosphate, adenosine‐3′,5′‐cyclic monophosphate and cytidine‐3′,5′‐cyclic monophosphate were subjected to electrochemical oxidation at different pH using boron doped diamond (BDD) and screen‐printed carbon (SPC) electrodes. While oxidation on SPC electrodes proceeds only via direct analyteelectrode electron transfer, BDD involves in addition the action of hydroxyl radicals, formed at the electrode surface. Generated oxidation products were analyzed by liquid chromatography coupled to high resolution mass spectrometry (LC‐MS). As an alternative electrochemically assisted injectioncapillary electrophoresismass spectrometry was used as a means for product generation and identification. The results obtained indicate that experimental conditions as well as the presence of the cyclic phosphate group influence the oxidative pathway of cyclic nucleotides. Simplicity of the experiment and the absence of complex biological matrices are the main advantages of electrochemistry over other techniques, employed for investigation of oxidative stress. Elucidation of oxidation products and reaction mechanism is an important aspect of therapeutic strategies of numerous severe diseases.

show abstract

Investigations of electron-transfer reactions and the redox mechanism of 2′-deoxyguanosine-5′-monophosphate using electrochemical techniques

Cited by 18 publications

References 42 publications

On‐Line Electrochemistry/Electrospray Ionization Mass Spectrometry (EC/ESI‐MS) for the Generation and Identification of Nucleotide Oxidation Products

On‐Line Electrochemistry/Electrospray Ionization Mass Spectrometry (EC/ESI‐MS) for the Generation and Identification of Nucleotide Oxidation Products

Electrochemical Oxidation of 2’-deoxyguanosine-5’-triphosphate on Ionic Liquid Modified Carbon Paste Microelectrode and its Sensitive Detection

Characterization of the Oxidative Behavior of Cyclic Nucleotides Using Electrochemistry–Mass Spectrometry

Contact Info

Product

Resources

About