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Chemical Compound Review:

PubChem6331 4-amino-1-[(2R,3R,4S,5R)-3,4- dihydroxy-5...

Synonyms: CYT012, CHEMBL490033, SureCN207772, AG-C-92291, CHEBI:38190, ...

Webb, A.J. et al., Chong, Y. et al., Murakami, E. et al., Beres, J. et al., Ghoshal, K. et al., et al.

Ghoshal, Datta, Majumder, Bai, Kutay, Motiwala, Jacob,

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 CYTIDINE, 5-FLUORO-

Alterations in the maturation and structure of ribosomal precursor RNA in Novikoff hepatoma cells induced by 5-fluorocytidine [1].
In the L-3',3'-difluoro-2',3'-dideoxy nucleoside series, cytidine 16 and 5-fluorocytidine 18 analogues showed modest antiviral activity (EC(50) 11.5 and 8.8 microM, respectively) when evaluated against HIV-1 in human peripheral blood mononuclear (PBM) cells [2].
Both 5-fluorocytidine and 5-fluorocytidine 5'-monophosphate had marked antiviral activity (VR = 1.0-2.1) with the above viruses as well as with parainfluenza virus type 3 [3].
As other ribonucleosides including cytidine, uridine, adenosine, 2-deoxyuridine, and 2-deoxycytidine protected S. mutans from 5-fluorocytidine and 5-fluorouridine toxicity, it is likely that this transporter is involved in the uptake of these molecules [4].
Specific incorporation of 5-fluorocytidine into Escherichia coli RNA [5].

High impact information on CYTIDINE, 5-FLUORO-

Treatment of cells with other nucleoside analogs modified at C-5, 5-fluorodeoxyuridine and 5-fluorocytidine, did not induce the degradation of DNMT1 [6].
Whereas wild-type Dnmt3a and the ENV variants form covalent complexes with 5-fluorocytidine modified DNA, the PCN variant does not [7].
Inactivation of rnsA (ATPase) or rnsB (solute binding protein) resulted in strains resistant to 5-fluorocytidine and 5-fluorouridine (toxic ribonucleoside analogues) [4].
Investigating the effects of stereochemistry on incorporation and removal of 5-fluorocytidine analogs by mitochondrial DNA polymerase gamma: comparison of D- and L-D4FC-TP [8].
Mode of action of 5-fluorocytidine and 5-fluoro-2'-deoxycytidine in L5178Y cells in vitro [9].

Biological context of CYTIDINE, 5-FLUORO-

2. Two procedures were employed for methylation of 5-fluoro-1-methylcytosine and 5-fluorocytidine [10].

References

Alterations in the maturation and structure of ribosomal precursor RNA in Novikoff hepatoma cells induced by 5-fluorocytidine. Grosso, L.E., Pitot, H.C. Biochemistry (1984) [Pubmed]
l-2',3'-Didehydro-2',3'-dideoxy-3'-fluoronucleosides: synthesis, anti-HIV activity, chemical and enzymatic stability, and mechanism of resistance. Chong, Y., Gumina, G., Mathew, J.S., Schinazi, R.F., Chu, C.K. J. Med. Chem. (2003) [Pubmed]
Synthesis and antitumor and antiviral activities of a series of 1-beta-D-ribofuranosyl-5-halocytosine (5-halocytidine) cyclic 3',5'-monophosphates. Beres, J., Bentrude, W.G., Kruppa, G., McKernan, P.A., Robins, R.K. J. Med. Chem. (1985) [Pubmed]
A Member of the Second Carbohydrate Uptake Subfamily of ATP-Binding Cassette Transporters Is Responsible for Ribonucleoside Uptake in Streptococcus mutans. Webb, A.J., Hosie, A.H. J. Bacteriol. (2006) [Pubmed]
Specific incorporation of 5-fluorocytidine into Escherichia coli RNA. Kaiser, I.I., Kladianos, D.M., Frendewey, D.A. Biochim. Biophys. Acta (1985) [Pubmed]
5-Aza-deoxycytidine induces selective degradation of DNA methyltransferase 1 by a proteasomal pathway that requires the KEN box, bromo-adjacent homology domain, and nuclear localization signal. Ghoshal, K., Datta, J., Majumder, S., Bai, S., Kutay, H., Motiwala, T., Jacob, S.T. Mol. Cell. Biol. (2005) [Pubmed]
Catalytic mechanism of DNA-(cytosine-C5)-methyltransferases revisited: covalent intermediate formation is not essential for methyl group transfer by the murine Dnmt3a enzyme. Reither, S., Li, F., Gowher, H., Jeltsch, A. J. Mol. Biol. (2003) [Pubmed]
Investigating the effects of stereochemistry on incorporation and removal of 5-fluorocytidine analogs by mitochondrial DNA polymerase gamma: comparison of D- and L-D4FC-TP. Murakami, E., Ray, A.S., Schinazi, R.F., Anderson, K.S. Antiviral Res. (2004) [Pubmed]
Mode of action of 5-fluorocytidine and 5-fluoro-2'-deoxycytidine in L5178Y cells in vitro. Yoshida, M., Hoshi, A., Kuretani, K., Saneyoshi, M. Chem. Pharm. Bull. (1982) [Pubmed]
Methylation and tautomerism of 1-substituted 5-fluorocytosines. Kulikowski, T., Shugar, D. Acta Biochim. Pol. (1979) [Pubmed]

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