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D8296

Sigma-Aldrich

3-Deazaadenosine

Synonyme(s) :

4-Amino-1-(β-D-ribofuranosyl)-1H-imidazo(4,5)-pyridine

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About This Item

Formule empirique (notation de Hill):
C11H14N4O4
Numéro CAS:
6736-58-9
Poids moléculaire :
266.25
Numéro MDL:
MFCD00153951
Code UNSPSC :
51111800
ID de substance PubChem :
24278391
Nomenclature NACRES :
NA.77

Forme

powder

Niveau de qualité

200

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

DBZQFUNLCALWDY-PNHWDRBUSA-N

Informations sur le gène

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

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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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
Mary C Long et al.
The Journal of antimicrobial chemotherapy, 59(1), 118-121 (2006-11-07)
Analyse a series of halogenated 3-deaza-adenosine analogues for efficacy against Mycobacterium tuberculosis H37Ra and determine if adenosine (Ado) kinase plays a role in the mechanism of action of these compounds. The MIC as determined by microdilution broth assay provided a
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
3-Deaza-adenosine and inhibition of HIV.
C W Flexner et al.
Lancet (London, England), 339(8790), 438-438 (1992-02-15)
Horst Fingerhuth et al.
The Journal of heart and lung transplantation : the official publication of the International Society for Heart Transplantation, 23(8), 970-978 (2004-08-18)
In the initial phase after cardiac transplantation, mononuclear cells infiltrate the graft, initiating a relevant impulse for rejection. 3-Deazaadenosine (c3Ado), an analog of adenosine, has proven anti-inflammatory properties both in vitro and in vivo. We hypothesized that c3Ado can serve
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