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D8296

Sigma-Aldrich

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:
6736-58-9
Molecular Weight:
266.25
MDL number:
MFCD00153951
UNSPSC Code:
51111800
PubChem Substance ID:
24278391
NACRES:
NA.77

form

powder

Quality Level

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)

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Lydia A Afman et al.
Brain research. Developmental brain research, 158(1-2), 59-65 (2005-07-06)
Periconceptional folic acid supplementation can reduce the occurrence of neural tube defects. A low folate status will result in reduced remethylation of homocysteine (Hcy) to methionine and, subsequently, in a rise of Hcy levels. Indeed, elevated Hcy concentrations have been
Diane M Hill et al.
Clinical chemistry, 48(11), 2017-2022 (2002-10-31)
The accuracy of homocysteine (Hcy) results is currently compromised by the requirement to separate the plasma within 1 h of sample collection. We studied the effect of temperature on the stability of plasma Hcy over a 72-h time course in
Ruediger C Braun-Dullaeus et al.
Shock (Augusta, Ga.), 19(3), 245-251 (2003-03-13)
Severe sepsis is accompanied by a profound depression of myocardial contractility. Leukocyte adhesion with subsequent local excess nitric oxide and reactive oxygen species production play major roles for this deleterious effect. We hypothesized that 3-deazaadenosine (c3Ado), an adenosine analogue with
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
Sachi Sunaga et al.
Biochemical and biophysical research communications, 572, 178-184 (2021-08-11)
Cell competition is a phenomenon that eliminates unfit cells from cell society, a function vital for maintaining cellular and organismal homeostasis. We previously showed that Madin-Darby canine kidney (MDCK) epithelial cells expressing the active form of the transcriptional coactivator Yes-associated
View All Related Papers

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