5-Azacytidine

5-Azacytidine (Azacitidine; 5-AzaC; Ladakamycin) is a nucleoside analogue of cytidine that specifically inhibits DNA methylation. 5-Azacytidine is incorporated into DNA to covalently trap DNA methyltransferases and contributes to reverse epigenetic changes[1][2]. 5-Azacytidine induces cell autophagy[4].

Product Specifications

CAS Number

[320-67-2]

Product Name Alternative

Azacitidine; 5-AzaC; Ladakamycin

UNSPSC

12352005

Hazard Statement

H302, H341, H350, H360, H372, H410

Target

Antibiotic; Autophagy; Bacterial; DNA Methyltransferase; Nucleoside Antimetabolite/Analog; Organoid

Type

Reference compound

Related Pathways

Anti-infection; Autophagy; Cell Cycle/DNA Damage; Epigenetics; Stem Cell/Wnt

Applications

Cancer-programmed cell death

Field of Research

Cancer; Infection

Assay Protocol

https://www.medchemexpress.com/5-Azacytidine.html

Purity

99.94

Solubility

DMSO : 250 mg/mL (ultrasonic) |H2O : 25 mg/mL (ultrasonic; warming; heat to 60°C)

Smiles

OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C(N=C(N)N=C2)=O)O1

Molecular Formula

C8H12N4O5

Molecular Weight

244.20

Precautions

H302, H341, H350, H360, H372, H410

References & Citations

[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, et al. Inhibition of DNA methyltransferase and induction of Friend erythroleukemia cell differentiation by 5-azacytidineand 5-aza-2'-deoxycytidine. J Biol Chem. 1982 Feb 25;257 (4) :2041-8.|[3]Li LH, et al. Cytotoxicity and mode of action of 5-azacytidine on L1210 leukemia. Cancer Res. 1970 Nov;30 (11) :2760-9.|[4]Marycz K, et al. 5-Azacytidine and Resveratrol Enhance Chondrogenic Differentiation of Metabolic Syndrome-Derived Mesenchymal Stem Cells by Modulating Autophagy.Oxid Med Cell Longev. 2019 May 12;2019:1523140.