Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Editor

Personal info

View

About

Terms

Javascript disabled

Please enable Javascript support in your browser to use this application.

Instructions on how to enable JavaScript on different browsers can be found here: http://www.google.com/support/bin/answer.py?answer=23852.

[edit this page]

Chemical Compound Review:

deoxycytidine 4-amino-1-[(2R,4S,5R)-4- hydroxy-5...

Synonyms: dCYD, Desoxycytidin, Desoxycytidine, d-cytidine, deoxy-Cytidine, ...

Hirano, N. et al., Sabini, E. et al., Balzarini, J. et al., Kewn, S. et al., Lin, T.S. et al.

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of Cytosine deoxyriboside

The dose-limiting toxicity of ddC is severe neuropathy which may be caused by the inhibition of the synthesis of mitochondrial DNA. ddC has an IC50 value of 0.022 microM against host mitochondrial DNA synthesis [1].

High impact information on Cytosine deoxyriboside

Human deoxycytidine kinase (dCK) phosphorylates the natural deoxyribonucleosides deoxycytidine (dC), deoxyguanosine (dG) and deoxyadenosine (dA) and is an essential enzyme for the phosphorylation of numerous nucleoside analog prodrugs routinely used in cancer and antiviral chemotherapy [2].
Deoxycytidine (dCyd) and cytidine (Cyd) effectively blocked the intracellular phosphorylation of ddCyd: dCyd by competition with ddCyd for 2'-deoxycytidine kinase, and Cyd probably by competition with the higher nucleoside mono- and diphosphate kinases [3].
These results suggest that Endo IV preferentially recognizes short nucleotide sequences containing 5'-dTdCdA-3', which likely accounts for the limited digestion of ssDNA by the enzyme and may be responsible in part for the indispensability of a deficiency in denB for stable synthesis of dC-substituted T4 genomic DNA [4].
Characterization of Endo IV activity revealed that the enzyme catalyzed specific endonucleolytic cleavage of the 5' phosphodiester bond of dC in ssDNA with an efficiency markedly dependent on the surrounding nucleotide sequence [4].

Anatomical context of Cytosine deoxyriboside

Both deoxycytidine (dC) and 2',3'-dideoxycytidine (ddC) significantly inhibited 3TC phosphorylation (e.g. at dC 100 microM, no 3TCTP was detected in PBMCs; P < 0.001, whereas 66% of control 3TCTP production was observed in U937 cells; P < 0.01) [5].

References

Synthesis and biological evaluation of 2',3'-dideoxy-L-pyrimidine nucleosides as potential antiviral agents against human immunodeficiency virus (HIV) and hepatitis B virus (HBV). Lin, T.S., Luo, M.Z., Liu, M.C., Pai, S.B., Dutschman, G.E., Cheng, Y.C. J. Med. Chem. (1994) [Pubmed]
Structure of human dCK suggests strategies to improve anticancer and antiviral therapy. Sabini, E., Ort, S., Monnerjahn, C., Konrad, M., Lavie, A. Nat. Struct. Biol. (2003) [Pubmed]
2',3'-Dideoxycytidine: regulation of its metabolism and anti-retroviral potency by natural pyrimidine nucleosides and by inhibitors of pyrimidine nucleotide synthesis. Balzarini, J., Cooney, D.A., Dalal, M., Kang, G.J., Cupp, J.E., DeClercq, E., Broder, S., Johns, D.G. Mol. Pharmacol. (1987) [Pubmed]
Biochemical analysis of the substrate specificity and sequence preference of endonuclease IV from bacteriophage T4, a dC-specific endonuclease implicated in restriction of dC-substituted T4 DNA synthesis. Hirano, N., Ohshima, H., Takahashi, H. Nucleic Acids Res. (2006) [Pubmed]
Lamivudine (3TC) phosphorylation and drug interactions in vitro. Kewn, S., Veal, G.J., Hoggard, P.G., Barry, M.G., Back, D.J. Biochem. Pharmacol. (1997) [Pubmed]

Contributions to this collaborative article are from individual authors of WikiGenes or mined by the WikiGenes Data Mining Engine from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.About WikiGenes Open Access Licence Privacy Policy Terms of Use apsburg

The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.