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    Azacitidine
    Azacitidine

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V0404
    CAS #: 320-67-2Purity ≥98%

    Description: 5-Azacytidine (also known as 5-AzaC), a pyrimidine nucleoside compound belonging to a class of cytosine analogues, is a DNA methyl transferase (DNMT) inhibitor that exerts potent cytotoxicity against multiple myeloma (MM) cells, including MM.1S, MM.1R, RPMI-8266, RPMI-LR5, RPMI-Dox40 and Patient-derived MM, with the half maximal inhibition concentration IC50 values of 1.5 μmol/L, 0.7 μmol/L, 1.1 μmol/L, 2.5 μmol/L, 3.2 μmol/L and 1.5 μmol/L respectively.

    References: Oncogene. 2002 Aug 12;21(35):5483-95; J Biol Chem. 1982 Feb 25;257(4):2041-8.

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    Molecular Weight (MW)244.2
    FormulaC8H12N4O5
    CAS No.320-67-2
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 48 mg/mL (196.6 mM)
    Water:<1 mg/mL
    Ethanol:<1 mg/mL
    Solubility (In vivo)30% propylene glycol, 5% Tween 80, 65% D5W: 30 mg/mL
    Synonyms

    Synonym: Vidaza; Abbreviations: 5AC; 5AZC. 5-azacytidine; azacytidine; U-18496; U 18496; U18496; ladakamycin. US brand names: Mylosar; 

    IUPAC/Chemical Name: 4-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1H)-one

    InChi Key: NMUSYJAQQFHJEW-KVTDHHQDSA-N

    InChi Code: InChI=1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1

    SMILES Code: O=C1N([[email protected]@H]2O[[email protected]](CO)[[email protected]@H](O)[[email protected]]2O)C=NC(N)=N1 


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    In Vitro

    In vitro activity: Azacitidine is widely used to demonstrate the correlation between loss of methylation in specifc gene regions and activation of the associated genes. After incorporation into DNA, Azacitidine inhibits DNA methyltransferase noncompetitively, causing a block in cytosine methylation in newly replicated DNA but not in resting, nondividing cells. Azacitidine induces differentiation of Friend Erythroleukemia Cell C3H10T1/2 with myotube formation. Azacitidine can be activated to the nucleoside triphosphate and incorporate into both DNA and RNA, leading to inhibition of DNA, RNA and protein synthesis in normal eukaryotic cells and in cancer cell lines, which could finally leads to cell death. Azacitidine also inhibits the incorporation of purine metabolites into macromolecules. Azacitidine inhibits the L1210 cells growth with IC50 and of 0.019 μg/mL.


    Kinase Assay: A crude cell-free extract is isolated from LI 210 cells in culture by suspension of the cells in a given volume of 0.05mol/LTris-HCl buffer, pH 7.4, and sonic extraction with a Biosonik at 70% maximal output for 30 sec. The supernatant is collected after centrifugation at 105,000 × g for 60 min (4°C) in a Model L Spinco ultracentrifuge. The final protein concentration of the cell-free extracts is approximately 3 mg/mL. The extracts are used as the source of enzymes. Ribonucleotide reductase activity is measured. A unit of enzyme is defined as the amount that catalyzed dCMP synthesis at a rate of 1 mμmole/hr. The assay systems for the measurement of pyrimidine nucleoside (CR) and deoxynucleoside (TdR, CdR) kinases are essentially those described by Chu and Fischer. However, reactions are terminated by heating for 2 min in a boiling water bath, and the phosphorylated derivatives are isolated according to the method of Bach. Fifty-jul aliquots are applied to 1-inch discs of diethylaminoethyl paper, which are then placed in counting vials and eluted with 0.5 mL of 0.5 mol/LPCA. After 1 hr, 12 mL of Diotol are added, and the radioactivity is determined.


    Cell Assay: 5 mL of L1210 cells (5 × 103 cells/mL) are incubated with Azacitidine at 37 ℃ for 3 days. Cell number is determined twice a day for 3 days by means of a Model A Coulter counter.

    In VivoAzacitidine inhibits polynucleotide synthesis in leukemic BDF1 mice. Azacitidine (3 mg/kg, i.p.) increases the mean survival time in leukemic BDF1 mice inoculated with Ll210 ascites tumor cells. Azacitidine markedly suppresses all enzymes activity in the polyamine-biosynthetic pathway, including ornithine decarboxylase activity. putrescine-dependent S-adenosyl-L-methionine decarboxylase activity, and spermidine-dependent S-adenosyl-L-methionine decarboxylase activity. Azacitidine also inhibits the accumulations of polyamines in leukemic mice.
    Animal modelBDF1 mice bearing lymphoid leukemia L1210
    Formulation & DosageDissolved in 0.85% NaCl solution; 3 mg/kg;  i.p. injection
    References

    Oncogene. 2002 Aug 12;21(35):5483-95; J Biol Chem. 1982 Feb 25;257(4):2041-8.


    These protocols are for reference only. InvivoChem does not independently validate these methods.

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