4-AMINO-1-[BETA-D-RIBOFURANOSYL]-1H-IMIDAZO[4,5]-PYRIDINE

Name	3-Deazaadenosine
Synonyms	3dAdo Deaza-Ado NSC 167897 3-Deaza-rA 3-Deazaadenosine 3-DEAZAADENOSINE 3-Deaza-D-adenosine Adenosine, 3-deaza- 1-pentofuranosyl-1H-imidazo[4,5-c]pyridin-4-amine 4-Amino-1-(D-ribofuranosyl)-1H-imidazo(4,5)-pyridine 1H-Imidazo(4,5-c)pyridin-4-amine, 1-beta-D-ribofuranosyl- 4-AMINO-1-[BETA-D-RIBOFURANOSYL]-1H-IMIDAZO[4,5]-PYRIDINE 1H-Imidazo4,5-cpyridin-4-amine, 1-.beta.-D-ribofuranosyl- 1-(beta-D-ribofuranosyl)-1H-imidazo[4,5-c]pyridin-4-amine 1H-Imidazo(4,5-c)pyridine, 4-amino-1-beta-D-ribofuranosyl- (2R,3R,4S,5R)-2-(4-AMino-1H-iMidazo[4,5-c]pyridin-1-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diol
CAS	6736-58-9
InChI	InChI=1/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
Molar Mass	266.25
Density	1.90±0.1 g/cm3 (20 ºC 760 Torr)
Melting Point	228-229°C
Boling Point	665.7±65.0 °C(Predicted)
Flash Point	356.4°C
Solubility	H2O: 10mg/mL with heating to 60 °C
Vapor Presure	1.25E-18mmHg at 25°C
Appearance	Solid
Color	White to Off-White
pKa	13.24±0.70(Predicted)
Storage Condition	Keep in dark place,Inert atmosphere,2-8°C
Refractive Index	1.834
In vitro study	3-Deazaadenosine is an inhibitor of S-adenosylhomocysteine hydrolase, with a K i 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 IC 50 s of 0.15 and 0.20 µM, respectively. 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 (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.

Safety Description	24/25 - Avoid contact with skin and eyes.
UN IDs	2811
WGK Germany	3
HS Code	29419090
Hazard Class	6.1(a)
Packing Group	II

biological activity	3-Deazaadenosine is an S-adenosylhomocysteine hydrolase (S-adenosylhomocysteine hydroase) inhibitor, ki value is 3.9 μm; 3-Deazaadenosine has anti-inflammatory, anti-proliferative and anti-HIV activities.
Target	IC50: 0.15 (HIV-1, A012 isolate), 0.20 µm (HIV-1, A018 isolate) Ki: 3.9 µm (S-adenosylhomocysteine hydroase)

Last Update：2024-04-09 20:49:11

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