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Azacitidine

CAS No.: 320-67-2

  • Molecular Formula: C₈H₁₂N₄O₅
  • Molecular Weight: 244.2 g/mol

Chemical type

  • Nucleoside analog (cytidine analog)
[1]
  • DNA methyltransferase inhibitor
[2]

Key properties

  • DNA methylation inhibitor
  • Induces hypomethylation by replacing cytosine during DNA replication
  • Covalently binds to DNA methyltransferases (DNMTs)
  • Concentration-dependent effects: enhances antioxidant enzyme activity at low levels (e.g., 50 µM), promotes secondary metabolite accumulation at higher levels (e.g., 200 µM)
  • Can cause physiological stress like leaf yellowing at excessive concentrations
[1]
  • Induces DNA demethylation
  • Inhibits DNA methyltransferases (DNMTs)
  • Promotes gene reactivation
[2]
  • Epigenetic regulator to modulate gene expression in plants
  • Promotes biosynthesis of secondary metabolites like patchoulol and pogostone
  • Alleviates environmental stresses (e.g., salt, aluminum) in plants
  • Induces traits like embryogenesis, flowering, and stress tolerance in research
[1]
  • Pharmacological tool to study DNA demethylation
  • Investigates effects on beige adipocyte differentiation and function
  • Enhances thermogenic gene expression (e.g., Ucp1, Cox7a1)
  • Increases mitochondrial function and fatty acid uptake
[2]

Classification by use

  • Chemicals used in epigenetic modulation
  • Chemicals used in plant secondary metabolism enhancement
  • Chemicals used in stress tolerance induction
[1]
  • Chemicals used in epigenetic research
  • Chemicals used in metabolic disease research (obesity, type 2 diabetes)
[2]

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  1. [Cite:1] 5-AzaC promotes the synthesis of patchoulol and pogostone in Pogostemon cablin by regulating DNA methylation, Scientia Horticulturae, Volume 351, September 2025, 114410
  2. [Cite:2] DNA methyltransferase inhibition by 5-azacytidine promotes thermogenic programming in beige adipocytes, Biochemical and Biophysical Research Communications, Volume 774, 8 August 2025, 152094