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Chemical Compound Review

SureCN114651     2-amino-9-[(2R,3R,4S,5R)-3,4- dihydroxy-5...

Synonyms: SureCN437750, SureCN529666, CCRIS 8242, AG-J-04337, CHEMBL1688964, ...
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Disease relevance of NSC 90393


Psychiatry related information on NSC 90393


High impact information on NSC 90393

  • RESULTS: After ER-1 cells were treated for 1 month with EGF, levels of intracellular peroxide and 8-hydroxyguanosine in the DNA of treated cells were higher than those in the DNA of control cells, and treated ER-1 cells were more tumorigenic and metastatic in vivo and more invasive in vitro than untreated control cells (all P<.001) [8].
  • Structural basis for the dual coding potential of 8-oxoguanosine by a high-fidelity DNA polymerase [9].
  • Estimates commonly rely on measurements of 8-oxo-2'-deoxyguanosine (oxo8dG), an adduct that occurs in DNA and is also excreted in urine after DNA repair [10].
  • We hypothesized that 8-hydroxyguanosine could be involved and found elevations in 5 of 15 (33%) MSS CRC cell lines analyzed [1].
  • A significant age-related increase (P = 0.05) in steady-state levels of oxidative DNA damage was observed, as monitored by 8-oxo-2'-deoxyguanosine levels [11].

Chemical compound and disease context of NSC 90393


Biological context of NSC 90393


Anatomical context of NSC 90393


Associations of NSC 90393 with other chemical compounds


Gene context of NSC 90393

  • Oxidized hydroethidine, 8-hydroxyguanosine immunoreactivity, and nitrotyrosine immunoreactivity were increased in the Sod2 -/+ mice compared with the Wt mice after 3-NP treatment (P < 0.001) [23].
  • We postulated that DNA repair enzymes such as 8-oxoguanosine DNA glycosylase (OGG1) are involved in the PD process [24].
  • Double immunofluorescence analysis revealed that subcellular localization of 8-hydroxyguanosine immunoreactivity was overlapping with eNOS phosphorylated at Ser-114 in human MSCs providing evidence that phosphorylation at this residue is linked to the generation of superoxide anions [25].
  • As a function of age, 8OHG immunoreactivity increased significantly in the teens and twenties (p < 0.04), while Abeta burden only increased after age 30 (p < 0.0001) [26].
  • Recently, we demonstrated a significant increase of an oxidized nucleoside derived from RNA, 8-hydroxyguanosine (8OHG), and an oxidized amino acid, nitrotyrosine in vulnerable neurons of patients with Alzheimer disease (AD) [27].

Analytical, diagnostic and therapeutic context of NSC 90393


  1. 8-Hydroxyguanosine repair is defective in some microsatellite stable colorectal cancer cells. Parker, A.R., O'Meally, R.N., Oliver, D.H., Hua, L., Nelson, W.G., DeWeese, T.L., Eshleman, J.R. Cancer Res. (2002) [Pubmed]
  2. Oxidative DNA damage in diabetes mellitus: its association with diabetic complications. Hinokio, Y., Suzuki, S., Hirai, M., Chiba, M., Hirai, A., Toyota, T. Diabetologia (1999) [Pubmed]
  3. Higher activity of 8-oxo-2'-deoxyguanosine 5'-triphosphate pyrophosphohydrolase (8-oxo-dGTPase) coincides with lower background levels of 8-oxo-2'-deoxyguanosine in DNA of fetal compared with maternal mouse organs. Bialkowski, K., Bialkowska, A., Anderson, L.M., Kasprzak, K.S. Free Radic. Biol. Med. (1999) [Pubmed]
  4. Persistent oxidative stress in colorectal carcinoma patients. Gackowski, D., Banaszkiewicz, Z., Rozalski, R., Jawien, A., Olinski, R. Int. J. Cancer (2002) [Pubmed]
  5. Urinary thymine dimers and 8-oxo-2'-deoxyguanosine in psoriasis. Ahmad, J., Cooke, M.S., Hussieni, A., Evans, M.D., Patel, K., Burd, R.M., Bleiker, T.O., Hutchinson, P.E., Lunec, J. FEBS Lett. (1999) [Pubmed]
  6. Neuronal RNA oxidation is a prominent feature of familial Alzheimer's disease. Nunomura, A., Chiba, S., Lippa, C.F., Cras, P., Kalaria, R.N., Takeda, A., Honda, K., Smith, M.A., Perry, G. Neurobiol. Dis. (2004) [Pubmed]
  7. Neuronal RNA oxidation is a prominent feature of dementia with Lewy bodies. Nunomura, A., Chiba, S., Kosaka, K., Takeda, A., Castellani, R.J., Smith, M.A., Perry, G. Neuroreport (2002) [Pubmed]
  8. Increased oxidative DNA damage in mammary tumor cells by continuous epidermal growth factor stimulation. Hamada, J., Nakata, D., Nakae, D., Kobayashi, Y., Akai, H., Konishi, Y., Okada, F., Shibata, T., Hosokawa, M., Moriuchi, T. J. Natl. Cancer Inst. (2001) [Pubmed]
  9. Structural basis for the dual coding potential of 8-oxoguanosine by a high-fidelity DNA polymerase. Brieba, L.G., Eichman, B.F., Kokoska, R.J., Doublié, S., Kunkel, T.A., Ellenberger, T. EMBO J. (2004) [Pubmed]
  10. DNA oxidation matters: the HPLC-electrochemical detection assay of 8-oxo-deoxyguanosine and 8-oxo-guanine. Helbock, H.J., Beckman, K.B., Shigenaga, M.K., Walter, P.B., Woodall, A.A., Yeo, H.C., Ames, B.N. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  11. Oxidative stress in the aging rat heart is reversed by dietary supplementation with (R)-(alpha)-lipoic acid. Suh, J.H., Shigeno, E.T., Morrow, J.D., Cox, B., Rocha, A.E., Frei, B., Hagen, T.M. FASEB J. (2001) [Pubmed]
  12. Herpes simplex virus type 1 latency in the murine nervous system is associated with oxidative damage to neurons. Valyi-Nagy, T., Olson, S.J., Valyi-Nagy, K., Montine, T.J., Dermody, T.S. Virology (2000) [Pubmed]
  13. Base pair stability of 8-chloro- and 8-iodo-2'-deoxyguanosine opposite 2'-deoxycytidine: implications regarding the bioactivity of 8-oxo-2'-deoxyguanosine. Hamm, M.L., Rajguru, S., Downs, A.M., Cholera, R. J. Am. Chem. Soc. (2005) [Pubmed]
  14. A novel assay of 8-oxo-2'-deoxyguanosine 5'-triphosphate pyrophosphohydrolase (8-oxo-dGTPase) activity in cultured cells and its use for evaluation of cadmium(II) inhibition of this activity. Bialkowski, K., Kasprzak, K.S. Nucleic Acids Res. (1998) [Pubmed]
  15. Oxidative damage in tissues of rats exposed to cigarette smoke. Park, E.M., Park, Y.M., Gwak, Y.S. Free Radic. Biol. Med. (1998) [Pubmed]
  16. Activity of the antimutagenic enzyme 8-oxo-2'-deoxyguanosine 5'-triphosphate pyrophosphohydrolase (8-oxo-dGTPase) in cultured chinese hamster ovary cells: effects of cell cycle, proliferation rate, and population density. Bialkowski, K., Kasprzak, K.S. Free Radic. Biol. Med. (2000) [Pubmed]
  17. Parkinson's disease is associated with oxidative damage to cytoplasmic DNA and RNA in substantia nigra neurons. Zhang, J., Perry, G., Smith, M.A., Robertson, D., Olson, S.J., Graham, D.G., Montine, T.J. Am. J. Pathol. (1999) [Pubmed]
  18. Two pathways for chromium(VI)-induced DNA damage in 14 day chick embryos: Cr-DNA binding in liver and 8-oxo-2'-deoxyguanosine in red blood cells. Misra, M., Alcedo, J.A., Wetterhahn, K.E. Carcinogenesis (1994) [Pubmed]
  19. An oxidized purine nucleoside triphosphatase, MTH1, suppresses cell death caused by oxidative stress. Yoshimura, D., Sakumi, K., Ohno, M., Sakai, Y., Furuichi, M., Iwai, S., Nakabeppu, Y. J. Biol. Chem. (2003) [Pubmed]
  20. Redox ribonucleosides. Isolation and characterization of 5-hydroxyuridine, 8-hydroxyguanosine, and 8-hydroxyadenosine from Torula yeast RNA. Yanagawa, H., Ogawa, Y., Ueno, M. J. Biol. Chem. (1992) [Pubmed]
  21. Measurement of 8-oxo-2'-deoxyguanosine and 8-oxo-2'-deoxyadenosine in DNA and human urine by high performance liquid chromatography-electrospray tandem mass spectrometry. Weimann, A., Belling, D., Poulsen, H.E. Free Radic. Biol. Med. (2001) [Pubmed]
  22. N2-methyl-8-oxoguanine: a tRNA urinary metabolite--role of xanthine oxidase. Helbock, H.J., Thompson, J., Yeo, H., Ames, B.N. Free Radic. Biol. Med. (1996) [Pubmed]
  23. Involvement of superoxide in excitotoxicity and DNA fragmentation in striatal vulnerability in mice after treatment with the mitochondrial toxin, 3-nitropropionic acid. Kim, G.W., Chan, P.H. J. Cereb. Blood Flow Metab. (2002) [Pubmed]
  24. Expression of 8-oxoguanine DNA glycosylase (OGG1) in Parkinson's disease and related neurodegenerative disorders. Fukae, J., Takanashi, M., Kubo, S., Nishioka, K., Nakabeppu, Y., Mori, H., Mizuno, Y., Hattori, N. Acta Neuropathol. (2005) [Pubmed]
  25. Phospho-eNOS Ser-114 in human mesenchymal stem cells: constitutive phosphorylation, nuclear localization and upregulation during mitosis. Klinz, F.J., Schmidt, A., Schinköthe, T., Arnhold, S., Desai, B., Popken, F., Brixius, K., Schwinger, R., Mehlhorn, U., Staib, P., Addicks, K., Bloch, W. Eur. J. Cell Biol. (2005) [Pubmed]
  26. Neuronal oxidative stress precedes amyloid-beta deposition in Down syndrome. Nunomura, A., Perry, G., Pappolla, M.A., Friedland, R.P., Hirai, K., Chiba, S., Smith, M.A. J. Neuropathol. Exp. Neurol. (2000) [Pubmed]
  27. Oxidative damage is the earliest event in Alzheimer disease. Nunomura, A., Perry, G., Aliev, G., Hirai, K., Takeda, A., Balraj, E.K., Jones, P.K., Ghanbari, H., Wataya, T., Shimohama, S., Chiba, S., Atwood, C.S., Petersen, R.B., Smith, M.A. J. Neuropathol. Exp. Neurol. (2001) [Pubmed]
  28. In vitro evolution of the hammerhead ribozyme to a purine-specific ribozyme using mutagenic PCR with two nucleotide analogues. Kore, A.R., Vaish, N.K., Morris, J.A., Eckstein, F. J. Mol. Biol. (2000) [Pubmed]
  29. Modulation of hOGG1 DNA repair enzyme in human cultured cells in response to pro-oxidant and antioxidant challenge. Mistry, P., Herbert, K.E. Free Radic. Biol. Med. (2003) [Pubmed]
  30. Time-course of mitochondrial gene expressions in mice brains: implications for mitochondrial dysfunction, oxidative damage, and cytochrome c in aging. Manczak, M., Jung, Y., Park, B.S., Partovi, D., Reddy, P.H. J. Neurochem. (2005) [Pubmed]
  31. Studies on genotoxic effects of iron overload and alcohol in an animal model of hepatocarcinogenesis. Stål, P., Olsson, J., Svoboda, P., Hultcrantz, R., Harms-Ringdahl, M., Eriksson, L.C. J. Hepatol. (1997) [Pubmed]
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