| Synonyms |
3-Deaza-Adenosine hydrochloride; 3-Deaza-rA Hcl; 1-(β-D-Ribofuranosyl)-1H-imidazo[4,5-c]pyridin-4-amine hydrochloride (1:1); 1H-Imidazo[4,5-c]pyridin-4-amine, 1-β-D-ribofuranosyl-, hydrochloride (1:1) |
| IUPAC Name |
(2R,3R,4S,5R)-2-(4-aminoimidazo[4,5-c]pyridin-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol;hydrochloride |
| Molecular Weight |
302.71 |
| Molecular Formula |
C11H15ClN4O4 |
| Canonical SMILES |
C1=CN=C(C2=C1N(C=N2)C3C(C(C(O3)CO)O)O)N.Cl |
| InChI |
InChI=1S/C11H14N4O4.ClH/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);1H/t6-,8-,9-,11-;/m1./s1 |
| InChIKey |
WQRKYGAAEYXMKZ-RPWKAPHTSA-N |
| Purity |
≥97% by HPLC |
| Solubility |
Soluble in DMSO |
| Appearance |
Crystalline solid |
| Shelf Life |
>3 years if stored properly |
| Storage |
Store at 2-8°C |
| Complexity |
334 |
| Exact Mass |
302.0781827 |
| In Vitro |
3-Deazaadenosine is an inhibitor of S-adenosylhomocysteine hydrolase, with a Ki of 3.9 µM. It shows anti-HIV effect, and inhibits p24 antigen in peripheral blood mononuclear (PBMCs) cells infected with HIV-1 isolates with IC50s of 0.15 and 0.20 µM, respectively. In addition, 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. 3-Deazaadenosine can inhibit 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. |
| Target |
IC50: 0.15 (HIV-1, A012 isolate), 0.20 µM (HIV-1, A018 isolate)
Ki: 3.9 µM (S-adenosylhomocysteine hydrolase) |
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