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

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Chemical Compound Review:

CCRIS 6742 5-amino-2-[(2R,3R,4S,5R)-3,4- dihydroxy-5...

Synonyms: AG-F-04123, LS-7205, NSC 524767, AC1L22MJ, 6-Azacytidine, ...

Doerksen, T. et al., Hancock, M.C. et al., Walker, C. et al., Landolph, J.R. et al., Mitra, C. et al., et al.

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Disease relevance of NSC 524767

6-azacytidine demonstrates activity against adenoviruses types 1, 2, 5 [1].

High impact information on NSC 524767

Exposure to 5-azacytidine, which decreases methylation of DNA and may thereby activate gene transcription, increased the incidence of anchorage-independent growth 20 times; whereas treatment with 6-azacytidine had no effect [2].
In addition, the hypomethylating agent 5-azadeoxycytidine also transformed primary rat tracheal epithelial cells, whereas 6-azacytidine, a cytosine analogue which does not induce DNA hypomethylation, did not [3].
In an assay for mutation to ouabain resistance in 10T 1/2 cells, which detects base substitution mutations but not frameshift mutations, 5-AzaCR and 6-azacytidine were not significantly mutagenic [4].
Although neither 6-azacytidine nor 4 wk of 5-azacytidine treatment affected male reproductive organ weights or sperm counts, 11 wk of 5-azacytidine resulted in dose-dependent reductions in testis and epididymal weights and sperm counts [5].
N4-amino-acid derivatives of 6-azacytidine: structure-activity relationship [6].

Associations of NSC 524767 with other chemical compounds

The X-ray crystallographic conformations of 6-azauridine and 6-azacytidine have been attributed to intermolecular hydrogen bonding and crystal packing forces [7].

References

6-azacytidine--compound with wide spectrum of antiviral activity. Alexeeva, I., Dyachenko, N., Nosach, L., Zhovnovataya, V., Rybalko, S., Lozitskaya, R., Fedchuk, A., Lozitsky, V., Gridina, T., Shalamay, A., Palchikovskaja, L., Povnitsa, O. Nucleosides Nucleotides Nucleic Acids (2001) [Pubmed]
Phenotypic variability in anchorage-independent growth by a human breast tumor cell line. Hancock, M.C., Smith, H.S. J. Natl. Cancer Inst. (1984) [Pubmed]
In vitro transformation of primary rat tracheal epithelial cells by 5-azacytidine. Walker, C., Nettesheim, P. Cancer Res. (1986) [Pubmed]
Mutagenicity of 5-azacytidine and related nucleosides in C3H/10T 1/2 clone 8 and V79 cells. Landolph, J.R., Jones, P.A. Cancer Res. (1982) [Pubmed]
Developmental exposure of male germ cells to 5-azacytidine results in abnormal preimplantation development in rats. Doerksen, T., Trasler, J.M. Biol. Reprod. (1996) [Pubmed]
N4-amino-acid derivatives of 6-azacytidine: structure-activity relationship. Alexeeva, I., Palchikovskaya, L., Shalamay, A., Nosach, L., Zhovnovataya, V., Povnitsa, O., Dyachenko, N. Acta Biochim. Pol. (2000) [Pubmed]
Molecular orbital studies on nucleoside analogs. II. Conformation of 6-azapyrimidine nucleosides. Mitra, C., Saran, A. Biochim. Biophys. Acta (1978) [Pubmed]

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