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Chemical Compound Review:

CCRIS 8238 4-amino-5-hydroxy-1-[4- hydroxy-5...

Synonyms: AC1L3XRS, LS-59073, CTK8J0055, ZINC02388311, AR-1G0449, ...

Morin, B. et al., Hatahet, Z. et al., Suen, W. et al., Loeb, L.A. et al., Tremblay, S. et al., et al.

Arimoto-Kobayashi, Anma, Yoshinaga, Douki, Cadet, Hayatsu, Loeb, Mullins,

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Disease relevance of 5-Hydroxy-2'-deoxycytidine

This glycol was observed to decompose with a half-life of 50 min at 37 degrees C in buffered neutral solutions and preferentially undergo dehydration to 5-hydroxy-2'-deoxycytidine [1].
New substrates for old enzymes. 5-Hydroxy-2'-deoxycytidine and 5-hydroxy-2'-deoxyuridine are substrates for Escherichia coli endonuclease III and formamidopyrimidine DNA N-glycosylase, while 5-hydroxy-2'-deoxyuridine is a substrate for uracil DNA N-glycosylase [2].
In the presence of 5-hydroxydeoxycytidine, there was a loss of viral replication after sequential passages of HIV in human CEM cells (Loeb LA, et al.: Proc Natl Acad Sci USA 1999;96:14921497) [3].

High impact information on 5-Hydroxy-2'-deoxycytidine

Oxidative DNA damage was estimated by the analysis of 5-hydroxy-2'-deoxycytidine (oh(5)dCyd) and 8-oxo-7,8-dihydro-2'-deoxyguanosine (oxo(8)dGuo) [4].
The formation of two oxidation products of DNA, 8-oxo-7,8-dihydro-2'-deoxyguanosine (8oxodG) and 5-hydroxy-2'-deoxycytidine (5OHdC), were studied with a novel HPLC using gradient elution and an electrochemical detection method, which allowed the detection of both DNA modifications in a single experiment [5].
Formation of 5-hydroxy-2'-deoxycytidine in calf thymus DNA treated with NPYR plus UVA was also observed [6].

Analytical, diagnostic and therapeutic context of 5-Hydroxy-2'-deoxycytidine

UV resonance Raman spectroscopy was used to detect and estimate the frequency of the unfavored imino tautomer of the transition mutagen 5-hydroxy-2'-deoxycytidine (HO5dCyt) in its anionic form [7].

References

2'-Deoxycytidine glycols, a missing link in the free radical-mediated oxidation of DNA. Tremblay, S., Douki, T., Cadet, J., Wagner, J.R. J. Biol. Chem. (1999) [Pubmed]
New substrates for old enzymes. 5-Hydroxy-2'-deoxycytidine and 5-hydroxy-2'-deoxyuridine are substrates for Escherichia coli endonuclease III and formamidopyrimidine DNA N-glycosylase, while 5-hydroxy-2'-deoxyuridine is a substrate for uracil DNA N-glycosylase. Hatahet, Z., Kow, Y.W., Purmal, A.A., Cunningham, R.P., Wallace, S.S. J. Biol. Chem. (1994) [Pubmed]
Lethal mutagenesis of HIV by mutagenic ribonucleoside analogs. Loeb, L.A., Mullins, J.I. AIDS Res. Hum. Retroviruses (2000) [Pubmed]
Ascorbate and H2O2 induced oxidative DNA damage in Jurkat cells. Rivière, J., Ravanat, J.L., Wagner, J.R. Free Radic. Biol. Med. (2006) [Pubmed]
The protein oxidation product 3,4-dihydroxyphenylalanine (DOPA) mediates oxidative DNA damage. Morin, B., Davies, M.J., Dean, R.T. Biochem. J. (1998) [Pubmed]
Oxidative damage and induced mutations in m13mp2 phage DNA exposed to N-nitrosopyrrolidine with UVA radiation. Arimoto-Kobayashi, S., Anma, N., Yoshinaga, Y., Douki, T., Cadet, J., Hayatsu, H. Mutagenesis (2000) [Pubmed]
Identification by UV resonance Raman spectroscopy of an imino tautomer of 5-hydroxy-2'-deoxycytidine, a powerful base analog transition mutagen with a much higher unfavored tautomer frequency than that of the natural residue 2'-deoxycytidine. Suen, W., Spiro, T.G., Sowers, L.C., Fresco, J.R. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]

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