D8296
3-Deazaadenosine
Sinónimos:
4-Amino-1-(β-D-ribofuranosyl)-1H-imidazo(4,5)-pyridine
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Acerca de este artículo
Fórmula empírica (notación de Hill):
C11H14N4O4
Número CAS:
Peso molecular:
266.25
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
51111800
MDL number:
Form:
powder
Quality level:
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Permítanos ayudarleInChI
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)
Categorías relacionadas
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.
Clase de almacenamiento
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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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
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
Janusz M Bujnicki et al.
Proteins, 52(4), 624-632 (2003-08-12)
S-adenosylhomocysteine hydrolase (SAHH) is a key regulator of S-adenosylmethionine-dependent methylation reactions and an interesting pharmacologic target. We cloned the SAHH gene from Plasmodium falciparum (PfSAHH), with an amino acid sequence agreeing with that of the PlasmoDB genomic database. Even though
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
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