D8296
3-Deazaadenosine
别名:
4-Amino-1-(β-D-ribofuranosyl)-1H-imidazo(4,5)-pyridine
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关于此项目
经验公式（希尔记法）:
C11H14N4O4
化学文摘社编号:
分子量:
266.25
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
51111800
MDL number:
Form:
powder
Quality level:
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)
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.
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
法规信息
涉药品监管产品
此项目有
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
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
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
3-Deaza-adenosine and inhibition of HIV.
C W Flexner et al.
Lancet (London, England), 339(8790), 438-438 (1992-02-15)
商品
Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.
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