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Chemical Compound Review:

AC1L2Q0E (4S)-2-amino-4-hydroxy-9- [(4S,5R)-4...

Synonyms: 4-OH-8-O-2'dG, 137608-89-0, 4,8-Dihydro-4-hydroxy-8-oxo-2'-deoxyguanosine

Souza-Pinto, N.C. et al., Mozzherin, D.J. et al., Duthie, S.J. et al., Wheelhouse, N.M. et al., Babbar, N. et al., et al.

Eder, Wacker, Lutz, Nair, Fang, Bartsch, Beland, Schlatter, Lutz, Wheelhouse, Chan, Gillies, Caldwell, Ross, Harrison, Prost, Taddei, Hayakawa, Bouton, Cirinesi, Matic, Sekiguchi, Radman,

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Disease relevance of Guanosine, 2'-deoxy-4,8-dihydro-4-hydroxy-8-oxo-, (4R)-

The Escherichia coli MutT protein specifically hydrolyzes both 8-oxo-deoxyguanosine triphosphate (8-oxo-dGTP) and 8-oxo-guanosine triphosphate (8-oxo-rGTP), which are otherwise incorporated in DNA and RNA opposite template A [1].
Among the wide variety of DNA damage, 8-oxo-deoxyguanosine (8-oxo-dG) has received the most attention due to its mutagenicity and because of the possible correlation between its accumulation and pathological processes like cancer, degenerative diseases and aging [2].
The base substitution fidelity of HIV-1 reverse transcriptase on DNA and RNA templates probed with 8-oxo-deoxyguanosine triphosphate [3].
Supplementation with cranberry juice did not affect 8-oxo-deoxyguanosine in urine or endogenous or H(2)O(2)-induced DNA damage in lymphocytes.CONCLUSIONS: Cranberry juice consumption did not alter blood or cellular antioxidant status or several biomarkers of lipid status pertinent to heart disease [4].
Using a modified Comet assay, to measure DNA damage we have demonstrated that TNF-alpha causes the formation of 8-oxo-deoxyguanosine (8-oxodG), an established marker of oxidative DNA damage, and a lesion associated with chronic hepatitis in human livers [5].

High impact information on Guanosine, 2'-deoxy-4,8-dihydro-4-hydroxy-8-oxo-, (4R)-

Consistent with previous observations, proliferating cell nuclear antigen (PCNA) promotes DNA synthesis by calf thymus DNA polymerase delta (pol delta) past several chemically defined template lesions including model abasic sites, 8-oxo-deoxyguanosine (dG) and aminofluorene-dG (but not acetylaminofluorene-dG) [6].
Here, we show that TNF-alpha exposure results in increased production of reactive oxygen species (ROS), with a concomitant increase in the production of 8-oxo-deoxyguanosine, a marker for oxidative DNA damage, in human lung bronchial epithelial cells [7].
Age-associated increase in 8-oxo-deoxyguanosine glycosylase/AP lyase activity in rat mitochondria [2].
The role of the estrogen receptor in modulating DNA damage was further established in incubations with the ER antagonist tamoxifen, where decreases in 8-oxo-deoxyguanosine were observed [8].
Immunoperoxidase staining for 8-oxo-deoxyguanosine (8-oxo-dG) formation in RTS and normal human fibroblasts were compared to assess DNA damage [9].

Chemical compound and disease context of Guanosine, 2'-deoxy-4,8-dihydro-4-hydroxy-8-oxo-, (4R)-

Our results revealed that APAP produced ROS and significantly elevated the 8-oxo- deoxyguanosine (8-oxodG) levels in the nucleus of C6 glioma cells in a time and concentration dependent manner [10].

Biological context of Guanosine, 2'-deoxy-4,8-dihydro-4-hydroxy-8-oxo-, (4R)-

8-Oxo-deoxyguanosine (8-Oxo-dG) was also measured as direct oxidative stress marker [11].

Anatomical context of Guanosine, 2'-deoxy-4,8-dihydro-4-hydroxy-8-oxo-, (4R)-

During oxidative stress, 8-oxo-deoxyguanosine (8-oxodG) DNA adducts in the colon exceeded levels in the small intestine concomitant with increased ROS [12].

Associations of Guanosine, 2'-deoxy-4,8-dihydro-4-hydroxy-8-oxo-, (4R)- with other chemical compounds

DNA adducts of PAH and 4-aminobiphenyl and oxidative DNA damage (8-oxo-deoxyguanosine) are being measured in blood mononuclear cells and exfoliated oral and bladder cells from subjects on antioxidants or placebo [13].
Ethanol inhibits benzo[a]pyrene-DNA adduct removal and increases 8-oxo-deoxyguanosine formation in human mammary epithelial cells [14].

Analytical, diagnostic and therapeutic context of Guanosine, 2'-deoxy-4,8-dihydro-4-hydroxy-8-oxo-, (4R)-

Binary exposure of A549 cells to benzo[a]pyrene and UVC radiation yields enhanced DNA damage in the comet assay but no enhancement of 8-oxo-deoxyguanosine [15].

References

Counteraction by MutT protein of transcriptional errors caused by oxidative damage. Taddei, F., Hayakawa, H., Bouton, M., Cirinesi, A., Matic, I., Sekiguchi, M., Radman, M. Science (1997) [Pubmed]
Age-associated increase in 8-oxo-deoxyguanosine glycosylase/AP lyase activity in rat mitochondria. Souza-Pinto, N.C., Croteau, D.L., Hudson, E.K., Hansford, R.G., Bohr, V.A. Nucleic Acids Res. (1999) [Pubmed]
The base substitution fidelity of HIV-1 reverse transcriptase on DNA and RNA templates probed with 8-oxo-deoxyguanosine triphosphate. Bebenek, K., Boyer, J.C., Kunkel, T.A. Mutat. Res. (1999) [Pubmed]
The effects of cranberry juice consumption on antioxidant status and biomarkers relating to heart disease and cancer in healthy human volunteers. Duthie, S.J., Jenkinson, A.M., Crozier, A., Mullen, W., Pirie, L., Kyle, J., Yap, L.S., Christen, P., Duthie, G.G. European journal of nutrition. (2006) [Pubmed]
TNF-alpha induced DNA damage in primary murine hepatocytes. Wheelhouse, N.M., Chan, Y.S., Gillies, S.E., Caldwell, H., Ross, J.A., Harrison, D.J., Prost, S. Int. J. Mol. Med. (2003) [Pubmed]
Proliferating cell nuclear antigen promotes DNA synthesis past template lesions by mammalian DNA polymerase delta. Mozzherin, D.J., Shibutani, S., Tan, C.K., Downey, K.M., Fisher, P.A. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
Tumor Necrosis Factor-{alpha} Increases Reactive Oxygen Species by Inducing Spermine Oxidase in Human Lung Epithelial Cells: A Potential Mechanism for Inflammation-Induced Carcinogenesis. Babbar, N., Casero, R.A. Cancer Res. (2006) [Pubmed]
Oxidative DNA damage induced by equine estrogen metabolites: role of estrogen receptor alpha. Liu, X., Yao, J., Pisha, E., Yang, Y., Hua, Y., van Breemen, R.B., Bolton, J.L. Chem. Res. Toxicol. (2002) [Pubmed]
RECQL4-deficient cells are hypersensitive to oxidative stress/damage: Insights for osteosarcoma prevalence and heterogeneity in Rothmund-Thomson syndrome. Werner, S.R., Prahalad, A.K., Yang, J., Hock, J.M. Biochem. Biophys. Res. Commun. (2006) [Pubmed]
Acetoaminophen-induced accumulation of 8-oxodeoxyguanosine through reduction of Ogg1 DNA repair enzyme in C6 glioma cells. Wan, J., Bae, M.A., Song, B.J. Exp. Mol. Med. (2004) [Pubmed]
Oxidative stress related DNA adducts in the liver of female rats fed with sunflower-, rapeseed-, olive- or coconut oil supplemented diets. Eder, E., Wacker, M., Lutz, U., Nair, J., Fang, X., Bartsch, H., Beland, F.A., Schlatter, J., Lutz, W.K. Chem. Biol. Interact. (2006) [Pubmed]
Pro-oxidant environment of the colon compared to the small intestine may contribute to greater cancer susceptibility. Sanders, L.M., Henderson, C.E., Hong, M.Y., Barhoumi, R., Burghardt, R.C., Carroll, R.J., Turner, N.D., Chapkin, R.S., Lupton, J.R. Cancer Lett. (2004) [Pubmed]
DNA damage as an intermediate biomarker in intervention studies. Santella, R.M. Proc. Soc. Exp. Biol. Med. (1997) [Pubmed]
Ethanol inhibits benzo[a]pyrene-DNA adduct removal and increases 8-oxo-deoxyguanosine formation in human mammary epithelial cells. Singletary, K.W., Barnes, S.L., van Breemen, R.B. Cancer Lett. (2004) [Pubmed]
Binary exposure of A549 cells to benzo[a]pyrene and UVC radiation yields enhanced DNA damage in the comet assay but no enhancement of 8-oxo-deoxyguanosine. Misl'anová, C., Healey, K., White, K.L., Smith, E.C., Hardie, L.J., Dusinská, M., Wild, C.P., Routledge, M.N. Environ. Mol. Mutagen. (2003) [Pubmed]

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