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Chemical Compound Review:

AG-H-00151 4-amino-1,6- dihydropyrimidine-2,5-dione

Synonyms: ANW-67254, AC1L2QGR, AC1Q6DBB, AK-89493, CTK5E1430, ...

Wagner, J.R. et al., Lipinski, L.J. et al., Matsubara, M. et al., Eide, L. et al., D'Ham, C. et al., et al.

Wagner, Blount, Weinfeld,

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Disease relevance of 5-Hydroxycytosine

Excision of 5,6-dihydroxy-5,6-dihydrothymine, 5,6-dihydrothymine, and 5-hydroxycytosine from defined sequence oligonucleotides by Escherichia coli endonuclease III and Fpg proteins: kinetic and mechanistic aspects [1].
A new nitrogen base 5-hydroxycytosine in phage N-17 DNA [2].
Genotoxicity of ribo- and deoxyribonucleosides of 8-hydroxyguanine, 5-hydroxycytosine, and 2-hydroxyadenine: induction of SCE in human lymphocytes and mutagenicity in Salmonella typhimurium TA 100 [3].

High impact information on 5-Hydroxycytosine

Conversely, 5-hydroxycytosine was removed efficiently only by Ntg2 [4].
Another oxidative lesion, 5-hydroxycytosine, also enhanced top1 cleavage by 2-fold when incorporated at the +1 position of the scissile strand [5].
We also show a correlation between severely defective incision of TG and 5OHC and reduced levels of NTH1 in PC-3 mitochondria [6].
The results indicated that endonuclease III induced the release of 5-hydroxyhydantoin (1), 5-hydroxyuracil (2), cis-uracil 5,6-glycol (3), 5-hydroxycytosine (4), trans-uracil 5,6-glycol (5), and trans-1-carbamoyl-2-oxo-4,5-dihydroxyimidazolidine (8) [7].
The excision of 5-hydroxyuracil (2) and 5-hydroxycytosine (4) lesions was studied in greater detail by enzymatic digestion and HPLC coupled to electrochemical (EC) detection which determines the amounts of these products in DNA [7].

Biological context of 5-Hydroxycytosine

To further elucidate this effect, we have introduced mutations in the helix-hairpin-helix domain of hNTH1 (K212S, P211R, +G212, and DeltaP211), and measured the kinetics of 5-hydroxycytosine removal of the mutants relative to wild type [8].

Anatomical context of 5-Hydroxycytosine

Using gas chromatography/isotope dilution mass spectrometry, we have detected induction of the oxidative DNA lesions 5-hydroxycytosine (5-OH-Cyt), 2,6-diamino-4-hydroxy-5-formamidopyrimidine (FapyGua) and 4, 6-diamino-5-formamidopyrimidine (FapyAde) in cultured cells irradiated with FL [9].

Associations of 5-Hydroxycytosine with other chemical compounds

In this case, products of cytosine oxidation such as 5-hydroxycytosine, which are the substrate for endonuclease III and endonuclease VIII, were the principal mutagenic lesions [10].
The sequence context-dependent mispairing of 5-hydroxycytosine and 5-hydroxyuridine in vitro [11].
Integration of the present results and the structural data elucidates how hSMUG1 accepts uracil, hoU, hmU and fU as substrates, but not other oxidized pyrimidines such as 5-hydroxycytosine, 5-formylcytosine and thymine glycol, and intact pyrimidines such as thymine and cytosine [12].

References

Excision of 5,6-dihydroxy-5,6-dihydrothymine, 5,6-dihydrothymine, and 5-hydroxycytosine from defined sequence oligonucleotides by Escherichia coli endonuclease III and Fpg proteins: kinetic and mechanistic aspects. D'Ham, C., Romieu, A., Jaquinod, M., Gasparutto, D., Cadet, J. Biochemistry (1999) [Pubmed]
A new nitrogen base 5-hydroxycytosine in phage N-17 DNA. Kchromov, I.S., Sorotchkina, V.V., Nigmatullin, T.G., Tikchonenko, T.I. FEBS Lett. (1980) [Pubmed]
Genotoxicity of ribo- and deoxyribonucleosides of 8-hydroxyguanine, 5-hydroxycytosine, and 2-hydroxyadenine: induction of SCE in human lymphocytes and mutagenicity in Salmonella typhimurium TA 100. Arashidani, K., Iwamoto-Tanaka, N., Muraoka, M., Kasai, H. Mutat. Res. (1998) [Pubmed]
The Saccharomyces cerevisiae homologues of endonuclease III from Escherichia coli, Ntg1 and Ntg2, are both required for efficient repair of spontaneous and induced oxidative DNA damage in yeast. Alseth, I., Eide, L., Pirovano, M., Rognes, T., Seeberg, E., Bjørås, M. Mol. Cell. Biol. (1999) [Pubmed]
Induction of reversible complexes between eukaryotic DNA topoisomerase I and DNA-containing oxidative base damages. 7, 8-dihydro-8-oxoguanine and 5-hydroxycytosine. Pourquier, P., Ueng, L.M., Fertala, J., Wang, D., Park, H.J., Essigmann, J.M., Bjornsti, M.A., Pommier, Y. J. Biol. Chem. (1999) [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]
Excision of oxidative cytosine modifications from gamma-irradiated DNA by Escherichia coli endonuclease III and human whole-cell extracts. Wagner, J.R., Blount, B.C., Weinfeld, M. Anal. Biochem. (1996) [Pubmed]
Human endonuclease III acts preferentially on DNA damage opposite guanine residues in DNA. Eide, L., Luna, L., Gustad, E.C., Henderson, P.T., Essigmann, J.M., Demple, B., Seeberg, E. Biochemistry (2001) [Pubmed]
Repair of oxidative DNA base lesions induced by fluorescent light is defective in xeroderma pigmentosum group A cells. Lipinski, L.J., Hoehr, N., Mazur, S.J., Dianov, G.L., Sentürker, S., Dizdaroglu, M., Bohr, V.A. Nucleic Acids Res. (1999) [Pubmed]
Spontaneous and osmium tetroxide-induced mutagenesis in an Escherichia coli strain deficient in both endonuclease III and endonuclease VIII. Najrana, T., Saito, Y., Uraki, F., Kubo, K., Yamamoto, K. Mutagenesis (2000) [Pubmed]
The sequence context-dependent mispairing of 5-hydroxycytosine and 5-hydroxyuridine in vitro. Purmal, A.A., Lampman, G.W., Kow, Y.W., Wallace, S.S. Ann. N. Y. Acad. Sci. (1994) [Pubmed]
Mutational analysis of the damage-recognition and catalytic mechanism of human SMUG1 DNA glycosylase. Matsubara, M., Tanaka, T., Terato, H., Ohmae, E., Izumi, S., Katayanagi, K., Ide, H. Nucleic Acids Res. (2004) [Pubmed]

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