3131-60-0

Usage

General Description

White crystalline powder.

Air & Water Reactions

6-AZACYTIDINE may be light and air sensitive.

Reactivity Profile

6-AZACYTIDINE is an aminoalcohol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Fire Hazard

Flash point data for 6-AZACYTIDINE are not available. 6-AZACYTIDINE is probably combustible.

Safety Profile

Mildly toxic by intraperitonealroute. An experimental teratogen. Other experimentalreproductive effects. Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C8H12N4O5/c9-4-1-10-12(8(16)11-4)7-6(15)5(14)3(2-13)17-7/h1,3,5-7,13-15H,2H2,(H2,9,11,16)/t3-,5+,6+,7+/m0/s1

Upstream product

• 20757-62-4 5-amino-2-(tri-O-acetyl-β-D-ribofuranosyl)-2H-[1,2,4]triazin-3-one 
• 2169-64-4 2',3',5'-tri-O-acetyl-6-azauridine 
• 54-25-1 6-Azauridine 
• 257297-86-2 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(3-oxo-5-[1,2,4]triazol-1-yl-3H-[1,2,4]triazin-2-yl)-tetrahydro-furan-3-yl ester 
• 28708-32-9 1,2,3,5-tetra-O-acetyl-D-ribofuranose 
• 20757-62-4 2',3',5'-tri-O-acetyl-6-azacytidine 

Relevant academic research and scientific papers

Synthesis and Comparative Study of Anti-Adenoviral Activity of 6-Azacytidine and Its Analogues

This paper presents the results of synthesis and study of cytotoxicity and the anti-adenoviral activity of new N4-derivatives of 6-azacytidine and its α-L-glycopyranosyl analogues obtained by the simplified one-pot version of the silyl condensation method. The resulting acylated 4-methylmercapto-1,2,4-triazin-3(2H)-one glycosides then underwent the amination and/or ammonolysis to provide 6-azacytidine glycoside analogues (2-6, 12, 15, 17) and compounds with modifications at both base and sugar fragments (11, 15). The evaluation of cytotoxicity and antiviral activity of new compounds against AdV5 showed high selectivity indexes for N4-methyl-6-azacytidine (2) and N,O-tetraacetyl-6-azacytidine (8). High anti-adenoviral activity of N4-methyl-6-azacytidine as well as very low cytotoxicity may suggest its further investigation as potential compound for the therapy of AdV infection.

6-Azacytidine - Compound with wide spectrum of antiviral activity

6-Acytidine demonstrates activity against adenoviruses types 1, 2, 5. It inhibit synthesis of viral DNA and proteins. 6-AC shows antiherpetic and antiinfluenza action during experimental infection in mice. 6-AC is prospective for drug development as an antiviral substance with a wide spectrum of activity.

Biochemical detection of cytidine protonation within RNA

Perturbation of active site functional group pK(a)s is an important strategy employed by protein enzymes to achieve catalysis. There is increasing evidence to indicate that RNAs also utilize functional group pK(a) perturbation for folding and reactivity. One of the best candidates for a functionally relevant pK(a) perturbation is the N3 of C (pK(a) 4.2), which could be sufficiently raised to allow protonation near physiological pH. Here we report the synthesis and use of a series of α-phosphorothioate tagged cytidine analogues whose altered N3 pK(a)s make it possible to efficiently detect functionally relevant protonation events by nucleotide analogue interference mapping. 6-Azacytidine (n6CαS) and 5-fluorocytidine (f5CαS) both have enhanced acidity at the N3 position (pK(a) 2.6 and 2.3, respectively) but leave the hydrogen bonding face of C otherwise unaffected. In contrast, pseudoisocytidine (ΨiCαS) is a charge neutral analogue that mimics the hydrogen bonding character of protonated C. To test the utility of these analogues, we characterized the C300+-G97-C277 mutant form of the Tetrahymena group I intron, which is predicted to require C300 protonation for ribozyme folding and reactivity. At neutral to alkaline pHs, C300 was the only site of n6CαS and f5Cαs interference within the intron, yet both interferences were rescued at acidic pH. Furthermore, ΨiCαS substitution at C300 resulted in enhanced activity at alkaline pHs, consistent with the presence of an N3 proton under the pH conditions studied. Interference mapping with these analogues provides an efficient and sensitive means to identify every site within an RNA where cytidine protonation is important for RNA function and may make it possible to identify C's that participate in general acid/base catalysis within ribozyme active sites.