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Chemical Compound Review:

Oksaden 6-amino-7,9-dihydropurin-8-one

Synonyms: Oxaden, Oxyadenine, SureCN42335, SureCN42336, SureCN48258, ...

Trzeciak, A.R. et al., Jenner, A. et al., Miller, P.S. et al., Tuo, J. et al., Proteggente, A.R. et al., et al.

Jenner, England, Aruoma, Halliwell,

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Disease relevance of Oxaden

The cockayne syndrome group B gene product is involved in cellular repair of 8-hydroxyadenine in DNA [1].
Genetic effects of oxidative DNA damage: comparative mutagenesis of 7,8-dihydro-8-oxoguanine and 7,8-dihydro-8-oxoadenine in Escherichia coli [2].
Using liquid chromatography/mass spectrometry and gas chromatography/mass spectrometry, we show increased levels of oxidative DNA base lesions, 8-hydroxyguanine (8-oxoG), 8-hydroxyadenine (8-oxoA) and 5-hydroxycytosine (5OHC) over the baseline in PC-3 and DU-145 prostate cancer cells following exposure to ionizing radiation and a repair period [3].

High impact information on Oxaden

The present study investigated the role of the CSB protein in cellular repair of 8-hydroxyadenine (8-OH-Ade), another abundant lesion in oxidatively damaged DNA [1].
8-Hydroxyadenine (7,8-dihydro-8-oxoadenine) induces misincorporation in in vitro DNA synthesis and mutations in NIH 3T3 cells [4].
Adenine residues in DNA are oxidized under the action of ionizing radiation at the C-8 position to give 7,8-dihydro-8-oxoadenine [5].
Levels of 8-hydroxyguanine, 8-hydroxyadenine and 5-hydroxycytosine measured in hydrolysed calf thymus DNA by the improved procedures described here were comparable with those reported previously by HPLC with electrochemical detection and by GC-MS with prepurification to remove undamaged base [6].
The stability of triplexes with 7,8-dihydro-8-oxoadenine, unlike those with 5-methylcytosine, is not substantially diminished upon raising the pH to 7 [7].

Chemical compound and disease context of Oxaden

Primary fibroblasts of Cockayne syndrome patients are defective in cellular repair of 8-hydroxyguanine and 8-hydroxyadenine resulting from oxidative stress [8].

Biological context of Oxaden

Recognition of a guanine-cytosine base pair by 8-oxoadenine [9].
Of the three types of DNA damage only 8-oxoadenine was without effect on AP-1 binding [10].
1. Abnormal amounts of adenine, 8-hydroxyadenine and 2,8-dihydroxyadenine are found in the urine of homozygotes for APRTase deficiency and are diagnostic of this condition [11].

Associations of Oxaden with other chemical compounds

It appears that the keto form of 8-oxoadenine can potentially form two hydrogen bonds with the N-7 and O-6 atoms of G of the G.C base pair, when the 8-oxoadenine is in the syn conformation and in contrast to cytosine does not require protonation of the base [9].
Decreasing derivatization temperature to 23 degrees C lowered levels of 8-hydroxyguanine, 8-hydroxyadenine, 5-hydroxycytosine and 5-(hydroxymethyl)uracil measured by GC-MS in hydrolysed calf thymus DNA [6].
Significant gender differences in levels of modified DNA bases such as 2,6-diamino-4-hydroxy-5-formamidopyrimidine (FAPy guanine), 8-hydroxyadenine (8OHA) and 5-hydroxycytosine (5OHC), measured by gas chromatography-mass spectrometry (GC/MS), were observed [12].
We now report that Ku enables the Werner exonuclease to digest through regions of DNA containing 8-oxoadenine and 8-oxoguanine modifications, lesions that have previously been shown to block the exonuclease activity of WRN alone [13].

Analytical, diagnostic and therapeutic context of Oxaden

Radioimmunoassay of 7,8-dihydro-8-oxoadenine (8-hydroxyadenine) [14].

References

The cockayne syndrome group B gene product is involved in cellular repair of 8-hydroxyadenine in DNA. Tuo, J., Jaruga, P., Rodriguez, H., Dizdaroglu, M., Bohr, V.A. J. Biol. Chem. (2002) [Pubmed]
Genetic effects of oxidative DNA damage: comparative mutagenesis of 7,8-dihydro-8-oxoguanine and 7,8-dihydro-8-oxoadenine in Escherichia coli. Wood, M.L., Esteve, A., Morningstar, M.L., Kuziemko, G.M., Essigmann, J.M. Nucleic Acids Res. (1992) [Pubmed]
Cellular repair of oxidatively induced DNA base lesions is defective in prostate cancer cell lines, PC-3 and DU-145. Trzeciak, A.R., Nyaga, S.G., Jaruga, P., Lohani, A., Dizdaroglu, M., Evans, M.K. Carcinogenesis (2004) [Pubmed]
8-Hydroxyadenine (7,8-dihydro-8-oxoadenine) induces misincorporation in in vitro DNA synthesis and mutations in NIH 3T3 cells. Kamiya, H., Miura, H., Murata-Kamiya, N., Ishikawa, H., Sakaguchi, T., Inoue, H., Sasaki, T., Masutani, C., Hanaoka, F., Nishimura, S. Nucleic Acids Res. (1995) [Pubmed]
Structure and in vitro replication of DNA templates containing 7,8-dihydro-8-oxoadenine. Guschlbauer, W., Duplaa, A.M., Guy, A., Téoule, R., Fazakerley, G.V. Nucleic Acids Res. (1991) [Pubmed]
Measurement of oxidative DNA damage by gas chromatography-mass spectrometry: ethanethiol prevents artifactual generation of oxidized DNA bases. Jenner, A., England, T.G., Aruoma, O.I., Halliwell, B. Biochem. J. (1998) [Pubmed]
7,8-Dihydro-8-oxoadenine as a replacement for cytosine in the third strand of triple helices. Triplex formation without hypochromicity. Jetter, M.C., Hobbs, F.W. Biochemistry (1993) [Pubmed]
Primary fibroblasts of Cockayne syndrome patients are defective in cellular repair of 8-hydroxyguanine and 8-hydroxyadenine resulting from oxidative stress. Tuo, J., Jaruga, P., Rodriguez, H., Bohr, V.A., Dizdaroglu, M. FASEB J. (2003) [Pubmed]
Recognition of a guanine-cytosine base pair by 8-oxoadenine. Miller, P.S., Bhan, P., Cushman, C.D., Trapane, T.L. Biochemistry (1992) [Pubmed]
The effect of DNA damage on the formation of protein/DNA complexes. Parsian, A.J., Funk, M.C., Tao, T.Y., Hunt, C.R. Mutat. Res. (2002) [Pubmed]
Purine excretion in complete adenine phosphoribosyltransferase deficiency: effect of diet and allopurinol therapy. Simmonds, H.A., Van Acker, K.J., Cameron, J.S., McBurney, A. Adv. Exp. Med. Biol. (1977) [Pubmed]
Gender differences in steady-state levels of oxidative damage to DNA in healthy individuals. Proteggente, A.R., England, T.G., Rehman, A., Rice-Evans, C.A., Halliwell, B. Free Radic. Res. (2002) [Pubmed]
A functional interaction of Ku with Werner exonuclease facilitates digestion of damaged DNA. Orren, D.K., Machwe, A., Karmakar, P., Piotrowski, J., Cooper, M.P., Bohr, V.A. Nucleic Acids Res. (2001) [Pubmed]
Radioimmunoassay of 7,8-dihydro-8-oxoadenine (8-hydroxyadenine). West, G.J., West, I.W., Ward, J.F. Int. J. Radiat. Biol. Relat. Stud. Phys. Chem. Med. (1982) [Pubmed]

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