2'-Deoxyguanosine

Deoxyguanosine(2'-Deoxyguanosine) is composed of the purine nucleoside guanine linked by its N9 nitrogen to the C1 carbon of deoxyribose.

References:
[1]. Deoxyguanosine, From Wikipedia

Erratum: Gu, S. et al. Error-Free Bypass of 7,8-dihydro-8-oxo-2'-deoxyguanosine by DNA Polymerase of Pseudomonas aeruginosa Phage PaP1. Genes 2017, 8, 18.[Pubmed:28273830]

Genes (Basel). 2017 Mar 3;8(3). pii: genes8030091.

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Gas-Phase Conformations and N-Glycosidic Bond Stabilities of Sodium Cationized 2'-Deoxyguanosine and Guanosine: Sodium Cations Preferentially Bind to the Guanine Residue.[Pubmed:28355483]

J Phys Chem B. 2017 Apr 27;121(16):4048-4060.

2'-Deoxyguanosine (dGuo) and guanosine (Guo) are fundamental building blocks of DNA and RNA nucleic acids. In order to understand the effects of sodium cationization on the gas-phase conformations and stabilities of dGuo and Guo, infrared multiple photon dissociation (IRMPD) action spectroscopy experiments and complementary electronic structure calculations are performed. The measured IRMPD spectra of [dGuo+Na](+) and [Guo+Na](+) are compared to calculated IR spectra predicted for the stable low-energy structures computed for these species to determine the most favorable sodium cation binding sites, identify the structures populated in the experiments, and elucidate the influence of the 2'-hydroxyl substituent on the structures and IRMPD spectral features. These results are compared with those from a previous IRMPD study of the protonated guanine nucleosides to elucidate the differences between sodium cationization and protonation on structure. Energy-resolved collision-induced dissociation (ER-CID) experiments and survival yield analyses of protonated and sodium cationized dGuo and Guo are performed to compare the effects of these cations toward activating the N-glycosidic bonds of these nucleosides. For both [dGuo+Na](+) and [Guo+Na](+), the gas-phase structures populated in the experiments are found to involve bidentate binding of the sodium cation to the O6 and N7 atoms of guanine, forming a 5-membered chelation ring, with guanine found in both anti and syn orientations and C2'-endo ((2)T3 or (3)T2) puckering of the sugar. The ER-CID results, IRMPD yields and the computed C1'-N9 bond lengths indicate that sodium cationization activates the N-glycosidic bond less effectively than protonation for both dGuo and Guo. The 2'-hydroxyl substituent of Guo is found to impact the preferred structures very little except that it enables a 2'OH...3'OH hydrogen bond to be formed, and stabilizes the N-glycosidic bond relative to that of dGuo in both the sodium cationized and protonated complexes.

MTH1, an 8-oxo-2'-deoxyguanosine triphosphatase, and MYH, a DNA glycosylase, cooperate to inhibit mutations induced by chronic exposure to oxidative stress of ionising radiation.[Pubmed:28340109]

Mutagenesis. 2017 May 1;32(3):389-396.

Our previous results showed that in addition to the immediate interaction of ionising radiation with DNA (direct and indirect effect), low-dose and chronic low-dose rate of irradiation induce endogenous oxidative stress. During oxidative stress, free radicals react with DNA, nucleoside triphosphates (dNTPs), proteins and lipids, and modify their structures. The MYH and MTH1 genes play important roles in preventing mutations induced by 8-hydroxy-guanine, which is an oxidised product of guanine. In this study, we used short-hairpin RNA to permanently knockdown MYH and MTH1 proteins in human lymphoblastoid TK6 cells. Knockdown and wild-type cells were chronically exposed to low dose rates of gamma-radiation (between 1.4 and 30 mGy/h). The cells were also subjected to acute doses delivered at a high-dose rate. Growth rate, extracellular 8-hydroxy-2'-deoxyguanosine, clonogenic cell survival and mutant frequencies were analysed in all cell types. A reduced level of cell growth and survival as well as increased mutant frequencies were observed in cells lacking both MYH and MTH1 proteins as compared to cells lacking only MYH and wild-type cells. To sum up, our results suggest that low-dose rates elevate oxidative stress. MTH1 together with MYH plays an important role in protection against mutations induced by modified dNTPs during chronic oxidative stress. In addition, we found no dose-rate effect at the level of mutations in the wild-type TK6 and MYH-KD cells. Our data interestingly indicate a dose-rate threshold for mutation induction in MTH1/MYH double knockdown cells.

Urinary 8-Oxo-7,8-Dihydro-2'-Deoxyguanosine in Tunisian Electric Steel Foundry Workers Exposed to Polycyclic Aromatic Hydrocarbons.[Pubmed:28355448]

Ann Work Expo Health. 2017 Apr 1;61(3):333-343.

In this study, urinary 8-oxo-7,8-dihydro-2'-deoxyguanosine (8-oxodG), as biomarker of oxidative DNA damage, was evaluated in Tunisian electric steel foundry workers and was associated with polycyclic aromatic hydrocarbon (PAH) exposure. Ninety-three healthy male workers were enrolled in the study; 8-oxodG was assessed by liquid chromatography-triple quadrupole mass spectrometry. Exposure to PAHs was evaluated by measuring 16 urinary PAHs (U-PAHs) and 8 monohydroxylated metabolites (OHPAHs). The median 8-oxodG level for all subjects was 3.20 microg l-1 (1.85 microg g-1 creatinine). No correlation between 8-oxodG and 1-hydroxypyrene or any other OHPAH was found. Significant linear correlations between 8-oxodG and some U-PAHs were found, particularly urinary acenaphthylene (r = 0.249), phenanthrene (r = 0.327), anthracene (r = 0.357), fluoranthene (r = 0.248), and pyrene (r = 0.244). Multiple regression analyses confirmed that urinary phenanthrene, anthracene, and naphthalene (the latter with a non-linear relationship) were predictors of 8-oxodG; job title, but not smoking, was a determinant of 8-oxodG; the variance explained by these models was up to 20%. The oxidative DNA damage assessed by urinary 8-oxodG was moderate and in the range of values reported in other occupational fields or in the general population. The results of this study indicate that the investigated biomarkers of PAH exposure were only minor contributors to urinary 8-oxodG.

2'-Deoxyguanosine (Deoxyguanosine) is composed of the purine nucleoside guanine linked by its N9 nitrogen to the C1 carbon of deoxyribose.

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