Description
Key facts
CAS number:320-67-2,
Purity:>98%,
Form:SolidSee storage information,
Molecular weight:244.2 Da,
Molecular formula:C8H12N4O5,
PubChem:9444,
Nature:Synthetic,
Solubility:Soluble in water to 50 mMSoluble in DMSO to 100 mM,
Biochemical name:Azacitidine,
Biological description:Potent DNA methyltransferase 1 (DNMT1) inhibitor (IC50 = 0.2 μM). Incorporated into DNA, inhibits DNMT1 activity to induce DNA hypomethylation. Interferes with protein synthesis. Shows anti-metabolic and anti-cancer activities in vitro. Active in vivo. At high doses the compound can have effects on other DNA methyltransferases.,
Canonical smiles:C1=NC(=NC(=O)N1C2C(C(C(O2)CO)O)O)N,
Isomeric smiles:C1=NC(=NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)N,
InChi: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,
InChiKey:NMUSYJAQQFHJEW-KVTDHHQDSA-N,
IUPAC Name:4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
Properties and Storage Information:
Shipped at conditions-Ambient - Can Ship with Ice, Appropriate short-term storage conditions-Ambient, Appropriate long-term storage conditions-Ambient, Storage information-The product can be stored for up to 12 months
Supplementary Information:
This supplementary information is collated from multiple sources and compiled automatically.
GAPDH also known as Glyceraldehyde-3-phosphate dehydrogenase is a multifunctional enzyme with a mass of approximately 36 kDa. It is widely expressed across various tissues where it primarily participates in glycolysis by catalyzing the sixth step converting glyceraldehyde-3-phosphate to 13-bisphosphoglycerate. The Glucocorticoid Receptor also called NR3C1 is a nuclear receptor involved in gene expression regulation and is predominantly found in the cytoplasm before ligand binding. GADD34 a growth arrest and DNA damage-inducible protein plays a role in stress responses. DNA methyltransferase 1 (Dnmt1) is important for maintenance methylation; it has a structural mass around 183 kDa and is expressed mainly in proliferating cells. Atad5 is involved in DNA replication while LVV hemorphin 7 a peptide appears in extracellular spaces. The Androgen Receptor and Estrogen Related Receptor alpha are nuclear receptors that bind to androgens and estrogen respectively. ROR gamma and Nrf2 are transcription factors where Nrf2 acts as a cellular defense regulator while IDH1 is an enzyme involved in the citric acid cycle.
Biological function summary
Several of these proteins participate in various essential processes. GAPDH is known for its central role in metabolism but also engages in cellular processes like apoptosis and gene expression. The Glucocorticoid and Androgen Receptors as part of the nuclear receptor family regulate genes that control development metabolism and immune response. Dnmt1 maintains DNA methylation patterns across cell divisions influenced by inhibitors such as 5-azacytidine widely studied for cancer treatments. Estrogen Related Receptor alpha although not directly binding estrogen influences metabolic pathways. ROR gamma impacts immune system function whereas Nrf2 orchestrates the antioxidative response by regulating genes involved in redox homeostasis.
Pathways
GAPDH integrates into the glycolytic pathway influencing energy yield and apoptosis through interactions with Bcl-2 dependent networks. The Glucocorticoid Receptor integrates into the inflammatory signaling pathways modulating responses to external stimuli and stress. Dnmt1 is critical in the epigenetic pathway particularly in DNA methylation wherein it recruits other proteins to maintain genomic DNA methylation status. Nrf2 participates in the oxidative stress response pathway working alongside proteins like Keap1 in cellular defense. IDH1 is an important component of the tricarboxylic acid (TCA) cycle linking to metabolic enzymes influencing bioenergetics and macromolecule synthesis.
Dnmt1 plays a significant role in cancer impacting tumorigenic processes through DNA methylation changes sometimes targeted by demethylating agents like 5-azacytidine. Aberrant Dnmt1 activity can connect to oncogenes and tumor suppressors like p53. The Glucocorticoid Receptor has implications in inflammatory diseases and disorders including rheumatoid arthritis and asthma due to its regulatory function on inflammation and immune response. Nrf2's dysfunction is associated with neurodegenerative diseases due to oxidative stress connecting it to antioxidant response elements. IDH1 mutations significantly feature in gliomas and acute myeloid leukemia contributing to oncogenic metabolism alteration.
