D8296
3-Deazaadenosine
Synonym(s):
4-Amino-1-(β-D-ribofuranosyl)-1H-imidazo(4,5)-pyridine
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About This Item
Empirical Formula (Hill Notation):
C11H14N4O4
CAS Number:
Molecular Weight:
266.25
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
51111800
MDL number:
Form:
powder
Quality level:
form
powder
Quality Level
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)
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 inhibitor of leukocyte adhesion to TNF-treated endothelial cells.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Articles
Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.