Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C11H14N4O4 |
| Molecular Weight | 266.2533 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC=CC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O
InChI
InChIKey=DBZQFUNLCALWDY-PNHWDRBUSA-N
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
DescriptionCurator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19372464
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19372464
3-Deaza-adenosine (BW 91Y) is a potent inhibitor of adenosine deaminase and S-Adenosylhomocysteine (SAH) hydrolase, with potent antitumor activity against a range of leukemia cell lines. 3-Deaza-adenosine has anti-inflammatory properties, inhibiting leukocyte adhesion and chemotaxis, lymphocyte-mediated cytolysis, phagocytosis, degranulation, and NF-κB signaling. 3-Deaza-adenosine also has antiviral and antibacterial activities. 3-Deaza-adenosine has previously been shown to inhibit a variety of cellular functions, which could be critical for the development of atherosclerosis and restenosis. These include the thrombin-stimulated production of platelet-derived growth factor and the expression of endothelial leukocyte adhesion molecule-1 as well as cellular arachidonic acid and ROS production. Moreover, c3Ado prevents tumor necrosis factor (TNF)-alpha production, reduces TNF- alpha-induced macrophage adhesion to endothelial cells in vitro via the inhibition of ICAM-1 synthesis, and promotes monocyte apoptosis.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Evaluation of 3-deaza-adenosine analogues as ligands for adenosine kinase and inhibitors of Mycobacterium tuberculosis growth. | 2007-01 |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005-06 |
|
| Characterization of glycine N-methyltransferase from rabbit liver. | 2004-06 |
|
| Anti-HIV-1 activity of 3-deaza-adenosine analogs. Inhibition of S-adenosylhomocysteine hydrolase and nucleotide congeners. | 2003-09 |
|
| Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections. | 2001-04 |
|
| Induction of apoptosis in human leukemia cells by 3-deazaadenosine is mediated by caspase-3-like activity. | 2000-12-31 |
|
| Extracellular ATP and adenosine cause apoptosis of pulmonary artery endothelial cells. | 1997-08 |
|
| The role of phosphatidylethanolamine methylation in the secretion of very low density lipoproteins by cultured rat hepatocytes: rapid inhibition of phosphatidylethanolamine methylation by bezafibrate increases the density of apolipoprotein B48-containing lipoproteins. | 1996-11-11 |
|
| Anti-human immunodeficiency virus 1 (HIV-1) activities of 3-deazaadenosine analogs: increased potency against 3'-azido-3'-deoxythymidine-resistant HIV-1 strains. | 1995-01-03 |
|
| Inhibitory activity of S-adenosylhomocysteine hydrolase inhibitors against human cytomegalovirus replication. | 1993-07 |
|
| Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives. | 1992-11-27 |
|
| 3-Deaza-adenosine and inhibition of HIV. | 1992-02-15 |
|
| Inhibitory effect of selected antiviral compounds on arenavirus replication in vitro. | 1990-10-01 |
|
| Inhibitory effect of selected antiviral compounds on measles (SSPE) virus replication in vitro. | 1989-09 |
|
| Structure-activity relationship of novel oligopeptide antiviral and antitumor agents related to netropsin and distamycin. | 1986-07 |
|
| Broad-spectrum antiviral activity of adenosine analogues. | 1984-06 |
|
| Broad-spectrum antiviral activity of the carbocyclic analog of 3-deazaadenosine. | 1983-03 |
|
| Adenosine analogues as substrates and inhibitors of S-adenosylhomocysteine hydrolase. | 1981-01-06 |
Sample Use Guides
Human coronary artery smooth muscle cells (VSMCs; Clonetics, Verviers, Belgium) were grown in 500 mkL of supplemented growth medium containing 5% FCS (SmGM-2; Clonetics, Verviers, Belgium) in 24-well culture dishes. 10, 50 and 100 mkM of c3Ado (3-Deazaadenosine) were added to the growth medium. After 48 hours of incubation at 37°C/5% CO2, cells were trypsinized and counted using a hemocytometer.
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
23190
Created by
admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
|
PRIMARY | |||
|
167897
Created by
admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
|
PRIMARY | |||
|
DTXSID2040941
Created by
admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
|
PRIMARY | |||
|
037V4520IY
Created by
admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
|
PRIMARY | |||
|
6736-58-9
Created by
admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
|
PRIMARY | |||
|
DB04546
Created by
admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
|
PRIMARY |
SUBSTANCE RECORD
