A2385

5-Azacytidine

≥98% (HPLC), powder, DNA methyltransferase inhibitor

• Synonyme(s) : 5-Azacitidine, 4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, Ladakamycin
• Formule empirique (notation de Hill): C₈H₁₂N₄O₅
• Numéro CAS: 320-67-2
• Poids moléculaire : 244.20
• Numéro Beilstein : 620461
• Numéro CE : 206-280-2
• Numéro MDL: MFCD00006539
• Code UNSPSC : 12352200
• ID de substance PubChem : 24278211
• Nomenclature NACRES : NA.77

Propriétés

• product name: 5-Azacytidine, ≥98% (HPLC)
• Pureté: ≥98% (HPLC)
• Forme: powder
• Pf: 226-232 °C (dec.) (lit.)
• Spectre d'activité de l'antibiotique: viruses
• Mode d’action: DNA synthesis | interferes
• Auteur: Celgene
• Température de stockage: −20°C
• Chaîne SMILES: NC1=NC(=O)N(C=N1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O
• 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
• Clé InChI: NMUSYJAQQFHJEW-KVTDHHQDSA-N
• Informations sur le gène: human ... DNMT1(1786) , DNMT3A(1788) , DNMT3B(1789)

Description

Description générale

5-Azacytidine is a chemical analog of cytidine. It functions as a hypomethylating agent. 5-Azacytidine is used to treat myelodysplastic syndrome (MDS).

Chemical structure: nucleoside

Application

5-Azacytidine has been used:

• for cell induction
• to study its effects on bovine fetal mesenchymal stem cells (bfMSC)
• to study its effects on human bone marrow stromal cells (hBMSCs)
• to study its effects on and DNA methyltransferase 1 (DNMT1) and Ras protein activator like 1 (RASAL1) expression
• to interfere with DNA methylation and histone acetylation
• to determine its effects on the conversion of control fibroblasts
• for optical coherence tomography (OCT) and fluorescein angiography (FA)
• for the reactivation of Sal-like protein (SALL)3 expression

Actions biochimiques/physiologiques

5-Azacytidine (Aza-CR) acts as a potential chemotherapeutic regimen for acute myelogenous leukemia. This drug has an ability to selectively increase γ-globin synthesis. Therefore, 5-azacytidine is used in treating severe β-thalassemia. Aza-CR acts as a potential bacteriostatic, antitumor and mutagenic agent. In addition, it also exhibits various biological activity such as, immunosuppressive, antimitotic, radioprotective and virostatic effects.

A potent growth inhibitor and cytotoxic agent; inhibits DNA methyltransferase, an important regulatory mechanism of gene expression, gene activation and silencing.

Causes DNA demethylation or hemi-demethylation, creating openings that allow transcription factors to bind to DNA and reactivate tumor suppressor genes.

Caractéristiques et avantages

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound was developed by Celgene. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Informations sur la sécurité

• Pictogrammes: GHS08,GHS07,GHS09
• Mention d'avertissement: Danger
• Mentions de danger: H302,H341,H350,H360FD,H372,H410
• Conseils de prudence: P202 - P260 - P264 - P273 - P301 + P312 - P308 + P313
• Classification des risques: Acute Tox. 4 Oral - Aquatic Chronic 1 - Carc. 1A - Muta. 2 - Repr. 1B - STOT RE 1
• Code de la classe de stockage: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de danger pour l'eau (WGK): WGK 3
• Équipement de protection individuelle: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges