Formation of the carboxamidine precursor of cyanuric acid from guanine oxidative lesion dehydro-guanidinohydantoin

Irvoas, Joris; Trzcionka, Jérôme; Pratviel, Geneviève

doi:10.1016/j.bmc.2014.07.010

Cited by 3 publications

(2 citation statements)

References 41 publications

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“…It has been described that cyanuric acid is also produced from guanine after DNA lesions caused by oxidative stress. In particular, hydrogen peroxide may oxidize guanine forming a carboxamidine derivative, which is a precursor of cyanuric acid (Irvoas et al, 2014).…”

Section: Differential Quantitative Proteomicmentioning

confidence: 99%

Role of the Dihydrodipicolinate Synthase DapA1 on Iron Homeostasis During Cyanide Assimilation by the Alkaliphilic Bacterium Pseudomonas pseudoalcaligenes CECT5344

et al. 2020

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Section: Differential Quantitative Proteomicmentioning

confidence: 99%

Role of the Dihydrodipicolinate Synthase DapA1 on Iron Homeostasis During Cyanide Assimilation by the Alkaliphilic Bacterium Pseudomonas pseudoalcaligenes CECT5344

et al. 2020

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“…Most studies characterized products in DNA models, e.g., nucleosides. Two-electron oxidation of dG yields 8-oxo-7,8-dihydro-2′-deoxyguanosine (dOG) and 5-carboxamido-5-formamido-2-iminohydantoin-2′-deoxyribonucleoside (d2Ih), ,− while four-electron oxidation of dG yields two diastereomers of spiroiminodihydantoin-2′-deoxyribonucleoside (dSp), two diastereomers of 5-guanidinohydantoin-2′-deoxyribonucleoside (dGh), and 2,5-diaminoimidazolone-2′-deoxyribonucleoside (dIz) that readily hydrolyzes to 2,2,4-triamino-2 H -oxazol-5-one-2′-deoxyribonucleoside (dZ). ,− The six-electron oxidation of dG yields dehydroguanidinohydantoin-2′-deoxynucleoside (dGh ox ), a compound of limited stability that ultimately decomposes to a ribosyl-urea lesion. ,− Another product that is formed during certain oxidations, but is not formally oxidized, is 2,6-diamino-4-hydroxy-5-formamidopyrimidine-2′-deoxyribonucleoside (Fapy·dG), a ring-opened hydrolysis product of dG (Scheme ). , The same products have been observed in oxidations of rG. , Many of these lesions resulting from dG oxidation have been observed in genomic samples of biological origin, − except d2Ih and dGh ox , whose cellular existence is awaiting confirmation. In cellular RNA samples, rOG is the only lesion that has been characterized thus far .…”

Section: Introductionmentioning

confidence: 99%

Rates of Chemical Cleavage of DNA and RNA Oligomers Containing Guanine Oxidation Products

Fleming

Alshykhly

Zhu

et al. 2015

Chem. Res. Toxicol.

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The nucleobase guanine in DNA (dG) and RNA (rG) has the lowest standard reduction potential of the bases, rendering it a major site of oxidative damage in these polymers. Mapping the sites at which oxidation occurs in an oligomer via chemical reagents utilizes hot piperidine for cleaving oxidized DNA and aniline (pH 4.5) for cleaving oxidized RNA. In the present studies, a series of time-dependent cleavages of DNA and RNA strands containing various guanine lesions were examined to determine the strand scission rate constants. The guanine base lesions 8-oxo-7,8-dihydroguanine (OG), spiroiminodihydantoin (Sp), 5-guanidinohydantoin (Gh), 2,2,4-triamino-2H-oxazol-5-one (Z), and 5-carboxamido-5-formamido-2-iminohydantoin (2Ih) were evaluated in piperidine-treated DNA and aniline-treated RNA. These data identified wide variability in the chemical lability of the lesions studied in both DNA and RNA. Further, the rate constants for cleaving lesions in RNA were generally found to be significantly smaller than for lesions in DNA. The OG nucleotides were poorly cleaved in DNA and RNA; Sp nucleotides were slowly cleaved in DNA and did not cleave significantly in RNA; Gh and Z nucleotides cleaved in both DNA and RNA at intermediate rates; and 2Ih oligonucleotides cleaved relatively quickly in both DNA and RNA. The data are compared and contrasted with respect to future experimental design.

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Ozonation products of zidovudine and thymidine in oxidative water treatment

et al. 2021

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Ozonation is an advanced treatment technology that is increasingly used for the removal of organic micropollutants from wastewater and drinking water. However, reaction of organic compounds with ozone can also result in the formation of toxic transformation products. In the present study, the degradation of the antiviral drug zidovudine during ozonation was investigated. To obtain further insights into the reaction mechanisms and pathways, results of zidovudine were compared with the transformation of the naturally occurring derivative thymidine. Kinetic experiments were accompanied by elucidation of formed transformation products using lab-scale batch experiments and subsequent liquid chromatography – high resolution mass spectrometry (LC-HRMS) analysis. Degradation rate constants for zidovudine with ozone in the presence of t -BuOH as radical scavenger varied between 2.8 ∙ 10 4 M −1 s −1 (pH 7) and 3.2 ∙ 10 4 M −1 s −1 (pH 3). The structural difference of zidovudine to thymidine is the exchange of the OH-moiety by the azide function at position 3’. In contrast to inorganic azide, no reaction with ozone was observed for the organic bound azide. In total, nine transformation products (TPs) were identified for both zidovudine and thymidine. Their formation can be attributed to the attack of ozone at the C–C-double bond of the pyrimidine-base. As a result of rearrangements, the primary ozonide decomposed in three pathways forming two different TPs, including hydroperoxide TPs. Rearrangement reactions followed by hydrolysis and subsequent release of H 2 O 2 further revealed a cascade of TPs containing amide moieties. In addition, a formyl amide riboside and a urea riboside were identified as TPs indicating that oxidations of amide groups occur during ozonation processes.

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Formation of the carboxamidine precursor of cyanuric acid from guanine oxidative lesion dehydro-guanidinohydantoin

Cited by 3 publications

References 41 publications

Role of the Dihydrodipicolinate Synthase DapA1 on Iron Homeostasis During Cyanide Assimilation by the Alkaliphilic Bacterium Pseudomonas pseudoalcaligenes CECT5344

Role of the Dihydrodipicolinate Synthase DapA1 on Iron Homeostasis During Cyanide Assimilation by the Alkaliphilic Bacterium Pseudomonas pseudoalcaligenes CECT5344

Rates of Chemical Cleavage of DNA and RNA Oligomers Containing Guanine Oxidation Products

Ozonation products of zidovudine and thymidine in oxidative water treatment

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