D8296

3-Deazaadenosine

• Synonym(s): 4-Amino-1-(β-D-ribofuranosyl)-1H-imidazo(4,5)-pyridine
• Empirical Formula (Hill Notation): C₁₁H₁₄N₄O₄
• CAS Number: 6736-58-9
• Molecular Weight: 266.25
• NACRES: NA.77
• PubChem Substance ID: 24278391
• UNSPSC Code: 51111800
• MDL number: MFCD00153951
• Form: powder

Properties

• form: powder
• Quality Segment: 200
• storage temp.: 2-8°C
• SMILES string: Nc1nccc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O
• InChI: 1S/C11H14N4O4/c12-10-7-5(1-2-13-10)15(4-14-7)11-9(18)8(17)6(3-16)19-11/h1-2,4,6,8-9,11,16-18H,3H2,(H2,12,13)/t6-,8-,9-,11-/m1/s1
• InChI key: DBZQFUNLCALWDY-PNHWDRBUSA-N
• Gene Information: rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

Description

Application

3-Deazaadenosine has been used as a methylation inhibitor:

• to study the effect of m6A modification on suppressor of cytokine signaling 2 (SOCS2) expression in colon cancer cells
• to study its effects on the expression of influenza A virus (IAV) proteins in human lung epithelial cell line
• to evaluate its effects on the replication of SV40 virus in BSC40 cells

Biochem/physiol Actions

3-Deazaadenosine (DZA), an analog of adenosine, acts as a blocker of S-adenosylhomocysteine (SAH)-hydrolase, a regulator of cellular methyltransferase activity. It has been observed in inhibiting some of the factors involved in atherosclerosis and restenosis. DZA inhibits lymphocyte-mediated tumor cell lysis, macrophage phagocytosis, microfilament disorganization, monocyte, and neutrophil chemotaxis. It also inhibits histamine release by basophils, superoxide anion generation, and macrophage lysosomal secretion. DZA possesses anti-inflammatory, anti-human immunodeficiency virus (HIV) properties and inhibitory effects of cytokine expression that include interleukin-1β (IL-1β), tumor necrosis factor-α (TNF-α), and nuclear factor-κB (NF-κB) transcription activity.

Possesses antiviral activity[1] inhibitor of leukocyte adhesion to TNF-treated endothelial cells.[2]

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)