Electrochemical and enzymic oxidation of guanosine and 8-hydroxyguanosine and the effects of oxidation products in mice

Goyal, Rajendra N.; Jain, Nidhi; Garg, Dinesh

doi:10.1016/s0302-4598(96)05182-3

Cited by 79 publications

(88 citation statements)

References 17 publications

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“…While on mCILE a big and welldefined oxidation peak (Ia) appeared with the oxidation peak potential as 1.254 V and the oxidation peak current as 73.46 nA on the first positive sweep (Figure 2b). Based on the electro-oxidation mechanism of guanine or guanosine with the similar molecular structure, 16,20 this oxidation peak can be attributed to the oxidation of dGTP to a free radical moiety and further form a diimine specie. In the reverse sweep two cathodic peaks of Ic (0.943 V) and IIc (0.756 V) appeared.…”

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

confidence: 99%

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

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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.

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

confidence: 99%

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

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“…Processes I a and I' a have been previously described [8] to merge into a single peak at high concentrations of guanosine, thus, they were studied together. From those and posterior investigations [9], authors proposed that the electrochemical oxidation of guanosine is globally a 4 e À , 4 H þ electrochemical reaction leading to the generation of a diimine species via radical intermediate species. The ring opening because of nucleophilic attack to the unstable diimine causes the formation of several final products in solution such as 5-guanidinohydantoin.…”

Section: Oxidation Of Guanosinementioning

confidence: 99%

“…It has been shown that the electrochemical oxidation of guanosine also proceeds through the 8-oxoderivative, thus, the study of the electrogenerated products can provide valuable information to understand the oxidative stress in biological systems. In the past, only oxidation products of guanosine in acid and neutral solution [8,9] have been investigated using electrochemistry. Nevertheless, De-losSantos-Alvarez et al have recently described the existence of products stabilized by adsorption on the surface of pyrolytic graphite electrodes (PGE) [10].…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Oxidation of Guanosine and Xanthosine at Physiological pH: Further Evidences of a Convergent Mechanism for the Oxidation of Purine Nucleosides

González‐Fernández

de‐los‐Santos‐Álvarez

Lobo-Castañón

et al. 2008

Electroanalysis

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The electrochemical oxidation of guanosine and xanthosine, which only differ in the presence of an oxygen atom at C2 position instead of an amine group, is studied on pyrolytic graphite electrodes at different electrolysis time scales in solutions of physiological pH. The oxidation products adsorbed on the electrode surface were electrochemical characterized in terms of variation of the formal potential with pH and catalytic activity towards the oxidation of NADH. The results were compared with those previously described for the oxidation of guanosine and adenosine in alkaline solutions. A common oxidation product is described, the oxidized form of 9-b-d-ribofuranosyluric acid, which is proposed as the point of convergence in the oxidation routes of all three purine nucleosides.

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“…The second and minor oxidized oligonucleotide was observed to have a value of m/z = 918.7 amu and was attributed to a spiroiminodihydantoin lesion, 3 (Scheme 1). [21,[51][52][53][54][55][56][57] These two 8-oxoG oxidation products are well known from the literature. The control experiment of riboflavin oxidation performed in D 2 O showed the same yield of oligonucleotide oxidation.…”

Section: àmentioning

confidence: 99%

Guanine Oxidation by Electron Transfer: One‐ versus Two‐Electron Oxidation Mechanism

et al. 2006

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The degeneracy of the guanine radical cation, which is formed in DNA by oxidation of guanine by electron transfer, was studied by a detailed analysis of the oxidation products of guanine on oligonucleotide duplexes and by labeling experiments. It was shown that imidazolone, the major product of guanine oxidation, is formed through a one-electron oxidation process and incorporates one oxygen atom from O2. The formation of 8-oxo-7,8-dihydroguanine by a two-electron oxidation process was a minor pathway. The two-electron oxidation mechanism was also evidenced by the formation of a tris(hydroxymethyl)aminomethane adduct.

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Electrochemical and enzymic oxidation of guanosine and 8-hydroxyguanosine and the effects of oxidation products in mice

Cited by 79 publications

References 17 publications

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

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

Electrochemical Oxidation of Guanosine and Xanthosine at Physiological pH: Further Evidences of a Convergent Mechanism for the Oxidation of Purine Nucleosides

Guanine Oxidation by Electron Transfer: One‐ versus Two‐Electron Oxidation Mechanism

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