3-Deazaadenosine
Modify Date: 2024-01-02 22:45:06
3-Deazaadenosine structure
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Common Name | 3-Deazaadenosine | ||
|---|---|---|---|---|
| CAS Number | 6736-58-9 | Molecular Weight | 266.253 | |
| Density | 1.9±0.1 g/cm3 | Boiling Point | 665.7±65.0 °C at 760 mmHg | |
| Molecular Formula | C11H14N4O4 | Melting Point | 228-229ºC | |
| MSDS | USA | Flash Point | 356.4±34.3 °C | |
Use of 3-Deazaadenosine3-Deazaadenosine is an inhibitor of S-adenosylhomocysteine hydrolase, with a Ki of 3.9 µM; 3-Deazaadenosine has anti-inflammatory, anti-proliferative and anti-HIV activity. |
| Name | Adenosine, 3-deaza |
|---|---|
| Synonym | More Synonyms |
| Description | 3-Deazaadenosine is an inhibitor of S-adenosylhomocysteine hydrolase, with a Ki of 3.9 µM; 3-Deazaadenosine has anti-inflammatory, anti-proliferative and anti-HIV activity. |
|---|---|
| Related Catalog | |
| Target |
IC50: 0.15 (HIV-1, A012 isolate), 0.20 µM (HIV-1, A018 isolate)[1] Ki: 3.9 µM (S-adenosylhomocysteine hydrolase)[1] |
| In Vitro | 3-Deazaadenosine is an inhibitor of S-adenosylhomocysteine hydrolase, with a Ki of 3.9 µM. 3-Deazaadenosine shows anti-HIV effect, and inhibits p24 antigen in peripheral blood mononuclear (PBMCs) cells infected with HIV-1 isolates (A012 and A018) with IC50s of 0.15 and 0.20 µM, respectively[1]. 3-Deazaadenosine (1-100 µM) inhibits LPS-induced expression of TNF-α mRNA, increases DNA binding activity of NF-κB, and causes proteolytic degradation of IκBα, but Not IκBβ in RAW 264.7 cells. 3-Deazaadenosine (100 µM) enhances nuclear translocation of NF-κB, but blocks LPS-induced NF-κB transcriptional activity, and such inhibition is augmented by the addition of homocysteine[2]. 3-Deazaadenosine (50, 100 µM) dose-dependently inhibits the phosphorylation of Raf and ERK, protein-dependent kinase 1, protein kinase B (Akt), and forkhead transcription factor FoxO1a. 3-Deazaadenosine (50 µM) suppresses vascular smooth muscle cell (VSMC) proliferation via interfering with Ras signaling[3]. |
| Cell Assay | The HIV-1 strains A012 and A018 are used in the assay. Inhibition of p24 antigen is measured. Briefly, PHA-stimulated peripheral blood mononuclear (PBMCs) are incubated with either HIV-1 strain for 1 h at 37°C at 200-fold the 50% tissue culture infectious dose (TCID50) of the virus stock per 2 × 105 PBMC cells. The TCID50 is defined as the amount of virus stock at which 50% of the inoculated wells are positive. Cells are then grown in microtiter plates with different drug concentrations at 2 × 105 cells per well. On day 4, cells are resuspended and split 1:3 with fresh media and 3-Deazaadenosine. Supernatant p24 antigen is determined on day 7 by ELISA[1]. |
| References |
| Density | 1.9±0.1 g/cm3 |
|---|---|
| Boiling Point | 665.7±65.0 °C at 760 mmHg |
| Melting Point | 228-229ºC |
| Molecular Formula | C11H14N4O4 |
| Molecular Weight | 266.253 |
| Flash Point | 356.4±34.3 °C |
| Exact Mass | 266.101501 |
| PSA | 126.65000 |
| LogP | 0.18 |
| Vapour Pressure | 0.0±2.1 mmHg at 25°C |
| Index of Refraction | 1.834 |
| Storage condition | 2-8°C |
| Water Solubility | H2O: 10 mg/mL with heating to 60 °C |
| Personal Protective Equipment | Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter |
|---|---|
| Safety Phrases | 24/25 |
| RIDADR | UN 2811 |
| WGK Germany | 3 |
| Packaging Group | II |
| Hazard Class | 6.1(a) |
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Disruption of choline methyl group donation for phosphatidylethanolamine methylation in hepatocarcinoma cells.
J. Biol. Chem. 277(19) , 17217-25, (2002) Despite being widely hypothesized, the actual contribution of choline as a methyl source for phosphatidylethanolamine (PE) methylation has never been demonstrated, mainly due to the inability of conve... |
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Activation of caspase-8 in 3-deazaadenosine-induced apoptosis of U-937 cells occurs downstream of caspase-3 and caspase-9 without Fas receptor-ligand interaction.
Exp. Mol. Med. 33(4) , 284-92, (2001) 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... |
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Identification of A-minor tertiary interactions within a bacterial group I intron active site by 3-deazaadenosine interference mapping.
Biochemistry 41(33) , 10426-38, (2002) The A-minor motifs appear to be the most ubiquitous helix packing elements within RNA tertiary structures. These motifs have been identified throughout the ribosome and almost every other tertiary-fol... |
| 1H-Imidazo[4,5-c]pyridine, 4-amino-1-β-D-ribofuranosyl- |
| C3-Ado |
| 3-Deaza-D-adenosine |
| 3-DEAZAADENOSINE |
| 1-(β-D-Ribofuranosyl)-1H-imidazo[4,5-c]pyridin-4-amine |
| 1H-Imidazo[4,5-c]pyridin-4-amine, 1-β-D-ribofuranosyl- |