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Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agents
Open accessAbstract
The C-8 position of deoxyguanosine (dGuo) was hydroxylated by ascorbic acid in the presence of oxygen (O2) in 0.1 M phosphate buffer (pH 6.8) at 37 degrees C. Addition of hydrogen peroxide (H2O2) remarkably enhanced this hydroxylation. The Udenfriend system [ascorbic acid, FeII, ethylenediaminetetraacetic acid (EDTA) and O2] was also effective for hydroxylation of dGuo in high yield. Guanine residues in DNA were also hydroxylated by ascorbic acid. Other reducing agents, such as hydroxylamine, hydrazine, dihydroxymaleic acid, sodium bisulfite and acetol, were also effective for the hydroxylation reaction, as were metal-EDTA complexes (FeII-, SnII-, TiIII-, CuI-EDTA). An OH radical seemed to be involved in this hydroxylation reaction in most of the above hydroxylating systems, but another reaction mechanism may also be involved, particularly when dGuo is hydroxylated by ascorbic acid alone or ascorbic acid plus H2O2. The possible biological significance of the hydroxylation of guanine residues in DNA in relation to mutagenesis and carcinogenesis is discussed.
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Citations
Cited by
Instability and decay of the primary structure of DNA
Lindahl, T. (1993) · Nature · doi:10.1038/362709a0 · Cited by 5,679
Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG
Shibutani, S., Takeshita, M., & Grollman, A. P. (1991) · Nature · doi:10.1038/349431a0 · Cited by 2,224
Mechanisms of DNA damage, repair, and mutagenesis
Chatterjee, N., & Walker, G. C. (2017) · Environmental and Molecular Mutagenesis · doi:10.1002/em.22087 · Cited by 2,039
“8-oxo-guanine pairs incorrectly with adenine instead of cytosine, thereby adding to the overall mutational load, and is further oxidized to other deleterious secondary DNA lesions because of its low oxidation potential [Kasai and Nishimura, 1984; Cheng et al., 1992; Cadet et al., 1999, 2010].”
8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G-T and A-C substitutions.
Cheng, K. C., Cahill, D. S., Kasai, H., Nishimura, S., & Loeb, L. A. (1992) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)48474-8 · Cited by 1,844
Self-citationPersistent oxidative stress in cancer
Toyokuni, S., Okamoto, K., Yodoi, J., & Hiai, H. (1995) · FEBS Letters · doi:10.1016/0014-5793(94)01368-b · Cited by 1,219
Metadata
- Authors
- Kasai, H., & Nishimura, S.
- Venue
- Nucleic Acids Research
- Publisher
- Oxford University Press (OUP)
- Published
- 1984
- Volume
- 12
- Issue
- 4
- Pages
- 2137-2145
- ISSN
- 0305-1048 (ISSN-L)
- 1362-4962
- OpenAlex
- W2024755124
- Cited by
- 945
- References
- 0
- FWCI
- 9.47
- Type
- journal article
- Language
- en
- Open access
- green
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- Kasai, H., & Nishimura, S. (1984). Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agents. Nucleic Acids Research. https://doi.org/10.1093/nar/12.4.2137
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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