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
Molecular Formula | C11H14N4O4 |
Molecular Weight | 266.2533 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/1653773Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19372464
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1653773
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2966 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2002459 |
360.0 µM [Ki] | ||
Target ID: CHEMBL2664 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6283083 |
4.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Adenosine analogues as substrates and inhibitors of S-adenosylhomocysteine hydrolase. | 1981 Jan 6 |
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Broad-spectrum antiviral activity of the carbocyclic analog of 3-deazaadenosine. | 1983 Mar |
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Broad-spectrum antiviral activity of adenosine analogues. | 1984 Jun |
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Structure-activity relationship of novel oligopeptide antiviral and antitumor agents related to netropsin and distamycin. | 1986 Jul |
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Inhibitory effect of selected antiviral compounds on measles (SSPE) virus replication in vitro. | 1989 Sep |
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3-Deaza-adenosine and inhibition of HIV. | 1992 Feb 15 |
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Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives. | 1992 Nov 27 |
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Inhibitory activity of S-adenosylhomocysteine hydrolase inhibitors against human cytomegalovirus replication. | 1993 Jul |
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Anti-human immunodeficiency virus 1 (HIV-1) activities of 3-deazaadenosine analogs: increased potency against 3'-azido-3'-deoxythymidine-resistant HIV-1 strains. | 1995 Jan 3 |
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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 Nov 11 |
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Extracellular ATP and adenosine cause apoptosis of pulmonary artery endothelial cells. | 1997 Aug |
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Characterization of glycine N-methyltransferase from rabbit liver. | 2004 Jun |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19372464
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.
Substance Class |
Chemical
Created
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admin
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Edited
Fri Dec 15 15:05:48 GMT 2023
by
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Fri Dec 15 15:05:48 GMT 2023
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Record UNII |
037V4520IY
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Record Status |
Validated (UNII)
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Record Version |
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