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:
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
SMILES string
Nc1nccc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O
InChI key
DBZQFUNLCALWDY-PNHWDRBUSA-N
form
powder
storage temp.
2-8°C
Quality Level
Gene Information
rat ... Adora1(29290), Adora2a(25369), Adora3(25370)
Related Categories
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)
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Y J Cha et al.
Experimental & molecular medicine, 33(4), 284-292 (2002-01-25)
3-Deazaadenosine (DZA), a cellular methylation blocker was reported to induce the caspase-3-like activities-dependent apoptosis in U-937 cells. In this study, we analyzed the activation pathway of the caspase cascade involved in the DZA-induced apoptosis using specific inhibitors of caspases. In
Cynthia J DeLong et al.
The Journal of biological chemistry, 277(19), 17217-17225 (2002-02-28)
Despite being widely hypothesized, the actual contribution of choline as a methyl source for phosphatidylethanolamine (PE) methylation has never been demonstrated, mainly due to the inability of conventional methods to distinguish the products from that of the CDP-choline pathway. Using
Juliane K Soukup et al.
Biochemistry, 41(33), 10426-10438 (2002-08-14)
The A-minor motifs appear to be the most ubiquitous helix packing elements within RNA tertiary structures. These motifs have been identified throughout the ribosome and almost every other tertiary-folded RNA for which structural information is available. These motifs utilize the
3-Deaza-adenosine and inhibition of HIV.
C W Flexner et al.
Lancet (London, England), 339(8790), 438-438 (1992-02-15)
C H Jurgensen et al.
Journal of immunology (Baltimore, Md. : 1950), 144(2), 653-661 (1990-01-15)
Previous reports demonstrate that cultured human umbilical vein endothelial cells (HEC) treated with TNF and other inflammatory mediators show an increased capacity to adhere human neutrophils. This increase is associated with the up-regulation of intercellular adhesion molecule 1 (ICAM-1) and
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