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Chemical Structure| 320-67-2 Chemical Structure| 320-67-2

Structure of 5-Azacytidine
CAS No.: 320-67-2

Chemical Structure| 320-67-2

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5-Azacytidine is a nucleoside analogue of cytidine that specifically inhibits DNA methylation by trapping DNA methyltransferases.

Synonyms: Azacitidine; 5-AzaC; WR 183027

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Product Citations

Product Citations

Boyao Zhang ; George-Eugen Maftei ; Bartosz Bartmanski ; Michael Zimmermann ;

Abstract: Organic carcinogens, in particular DNA-reactive compounds, contribute to the irreversible initiation step of tumorigenesis through introduction of genomic instability. Although carcinogen bioactivation and detoxification by human enzymes has been extensively studied, carcinogen biotransformation by human-associated bacteria, the microbiota, has not yet been systematically investigated. We tested the biotransformation of 68 mutagenic carcinogens by 34 bacterial species representative for the upper and lower human gastrointestinal tract and found that the majority (41) of the tested carcinogens undergo bacterial biotransformation. To assess the functional consequences of microbial carcinogen metabolism, we developed a pipeline to couple gut bacterial carcinogen biotransformation assays with Ames mutagenicity testing and liver biotransformation experiments. This revealed a bidirectional crosstalk between gut microbiota and host carcinogen metabolism, which we validated in gnotobiotic mouse models. Overall, the systematic assessment of gut microbiota carcinogen biotransformation and its interplay with host metabolism highlights the gut microbiome as an important modulator of exposome-induced tumorigenesis.

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Product Details of 5-Azacytidine

CAS No. :320-67-2
Formula : C8H12N4O5
M.W : 244.20
SMILES Code : OC[C@@H]1[C@H]([C@H]([C@H](N2C(N=C(N=C2)N)=O)O1)O)O
Synonyms :
Azacitidine; 5-AzaC; WR 183027
MDL No. :MFCD00006539

Safety of 5-Azacytidine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335-H351-H361
Precautionary Statements:P261-P305+P351+P338

Related Pathways of 5-Azacytidine

epigenetics
DNA

Isoform Comparison

Biological Activity

Target
  • DNA Methyltransferase

Protocol

Bio Calculators
Preparing Stock Solutions 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

References

[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.

 

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