5-Azacytidine

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Chemical Structure| 320-67-2 同义名 : 5-氮杂胞苷;阿托胞苷;阿扎胞苷（5-氮杂胞嘧啶核苷） ;Azacitidine;5-AzaC;Vidaza.;ladakamycin. US brand names: Mylosar;azacytidine;5AZC. 5-azacytidine;Abbreviations: 5AC;WR 183027;U 18496;NSC 103-627;NSC 102816;Mylosar;Antibiotic U 18496;Ladakamycin
CAS号 : 320-67-2
货号 : A386837
分子式 : C8H12N4O5
纯度 : 95%
分子量 : 244.205
MDL号 : MFCD00006539
存储条件：

Pure form Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

In solvent -20°C:3-6个月-80°C:12个月
溶解度 :

DMSO: 30 mg/mL(122.85 mM)，注意：DMSO长时间开封后，会吸水并导致溶解能力下降，请避免使用长期开封的DMSO

H2O: 25 mg/mL(102.37 mM)，配合低频超声，并水浴加热至45℃助溶
动物实验配方：

5% DMSO+30% PEG 300+water 10 mg/mL

生物活性
靶点

  • DNA Methyltransferase
描述 DNA methyltransferase enzymes (DNMTs) are responsible for the DNA methylation process which could catalyze the transfer of a methyl group from S-adenosyl methionine to the cytosine target nucleotide producing methylcytosine[5]. Azacytidine (5-AZ) is a DNMT inhibitor with IC50 value of 0.8 - 3 μmol/L on MM cells[6]. The K12-72.1 cells were treated with 5-AZ at both 5 and 10 μM, and the methylation status of the CpG sites in the promotor region of the gene PGP9.5 were measured by bisulfite sequencing. It was found that both concentrations could cause demethylation of the CpG sites and increased the expression of the gene PGP9.5. Moreover, after the treatment of 50 μM of 5-AZ on MCF10CA1a and MCF7 cells, the cell viability as measured by MTT assay decreased significantly compared with control[7]. The nude mice with SKOV3 xenografts were treated with 2 mg/kg 5-AZ thrice weekly for 10 weeks. The volume and weight per nodule were decreased after the treatment of 5-AZ, which indicated that the 5-AZ could inhibit growth of tumors[8].
作用机制 The 5-AZ could inhibit the DNA methylation through covalently binding to DNA methyltransferases, forming nucleoprotein adducts. Therefore, the number of active DNA methyltransferase enzymes in the cells are depletes[9].
细胞研究
细胞系 浓度 检测类型 检测时间 活动说明 数据源
92.1 0.5/1/2 μM Growth Inhibition Assay 7 d inhibits cell growth in a dose dependent manner 25146981
92.1 0.5/1 μM Function Assay 48 h decreases clonogenicity dose-dependently 25146981
92.1 0.5/1 μM Cell Viability Assay 5 d decreases radiation-induced cell viability inhibition 25146981
实验方案
1mg 5mg 10mg

1 mM

5 mM

10 mM

4.09mL

0.82mL

0.41mL

20.47mL

4.09mL

2.05mL

40.95mL

8.19mL

4.09mL
参考文献

[1]Christman JK. 5-Azacytidine and 5-aza-2'-deoxycytidine as inhibitors of DNA methylation: mechanistic studies and their implications for cancer therapy. Oncogene. 2002 Aug 12;21(35):5483-95.

[2]Creusot F, Acs G, et al. Inhibition of DNA methyltransferase and induction of Friend erythroleukemia cell differentiation by 5-azacytidine and 5-aza-2'-deoxycytidine. J Biol Chem. 1982 Feb 25;257(4):2041-8.

[3]Mahesh S, Saxena A, et al. Intratracheally administered 5-azacytidine is effective against orthotopic human lung cancer xenograft models and devoid of important systemic toxicity. Clin Lung Cancer. 2010;11(6):405-11.

[4]Heby O, Russell DH. Depression of polyamine synthesis in L1210 leukemic mice during treatment with a potent antileukemic agent, 5-azacytidine. Cancer Res. 1973;33(1):159-65.

[5]Holliday R, Pugh JE. DNA modification mechanisms and gene activity during development. Science. 1975 Jan 24;187(4173):226-32.

[6]Kiziltepe T, Hideshima T, Catley L, Raje N, Yasui H, Shiraishi N, Okawa Y, Ikeda H, Vallet S, Pozzi S, Ishitsuka K, Ocio EM, Chauhan D, Anderson KC. 5-Azacytidine, a DNA methyltransferase inhibitor, induces ATR-mediated DNA double-strand break responses, apoptosis, and synergistic cytotoxicity with doxorubicin and bortezomib against multiple myeloma cells. Mol Cancer Ther. 2007 Jun;6(6):1718-27.

[7]Harman RM, Curtis TM, Argyle DJ, Coonrod SA, Van de Walle GR. A Comparative Study on the In Vitro Effects of the DNA Methyltransferase Inhibitor 5-Azacytidine (5-AzaC) in Breast/Mammary Cancer of Different Mammalian Species. J Mammary Gland Biol Neoplasia. 2016 Jun;21(1-2):51-66.

[8]Cao D, Li D, Huang Y, Ma Y, Zhang B, Zhao C, Deng S, Luo M, Yin T, Wei YQ, Wang W. 5-Azacytidine promotes invadopodia formation and tumor metastasis through the upregulation of PI3K in ovarian cancer cells. Oncotarget. 2017 Jun 20;8(36):60173-60187.

[9]Griffin PT, Niederhuth CE, Schmitz RJ. A Comparative Analysis of 5-Azacytidine- and Zebularine-Induced DNA Demethylation. G3 (Bethesda). 2016 Sep 8;6(9):2773-80.