3-DEAZAADENOSINE

3-DEAZAADENOSINE Basic information
Product Name:3-DEAZAADENOSINE
Synonyms:3-DEAZAADENOSINE;4-AMINO-1-[BETA-D-RIBOFURANOSYL]-1H-IMIDAZO[4,5]-PYRIDINE;4-Amino-1-(D-ribofuranosyl)-1H-imidazo(4,5)-pyridine;1H-Imidazo4,5-cpyridin-4-amine, 1-.beta.-D-ribofuranosyl-;3-Deaza-D-adenosine;NSC 167897;(2R,3R,4S,5R)-2-(4-AMino-1H-iMidazo[4,5-c]pyridin-1-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diol;3-Deaza-rA
CAS:6736-58-9
MF:C11H14N4O4
MW:266.25
EINECS:
Product Categories:Bases & Related Reagents;Inhibitors;Nucleotides
Mol File:6736-58-9.mol
3-DEAZAADENOSINE Structure
3-DEAZAADENOSINE Chemical Properties
Melting point 228-229°C
Boiling point 665.7±65.0 °C(Predicted)
density 1.90±0.1 g/cm3 (20 ºC 760 Torr)
storage temp. Keep in dark place,Inert atmosphere,2-8°C
solubility H2O: 10 mg/mL with heating to 60 °C
pka13.24±0.70(Predicted)
form Solid
color White to Off-White
Safety Information
Safety Statements 24/25
RIDADR 2811
WGK Germany 3
HazardClass 6.1(a)
PackingGroup II
HS Code 29419090
MSDS Information
ProviderLanguage
SigmaAldrich English
3-DEAZAADENOSINE Usage And Synthesis
Description3-Deazaadenosine (3-DZA) is an inhibitor of SAH (Sadenosylhomocysteine) hydrolase (Ki = 3.9 μM). It has antiinflammatory properties, inhibiting leukocyte adhesion and chemotaxis, lymphocyte-mediated cytolysis, phagocytosis, degranulation, and NF-κB signaling. 3-DZA also has anti-viral and anti-bacterial activities.
Chemical PropertiesBright Yellow Solid
UsesPossesses antiviral activity. It is an inhibitor of leukocyte adhesion to TNF-treated endothelial cells.
Biochem/physiol ActionsPossesses antiviral activity inhibitor of leukocyte adhesion to TNF-treated endothelial cells.
in vitro3-deazaadenosine showed inhibitory values against the ebo-z viruses, ebo, and marburg virus in various cell lines of primate (sw13, vero 76, frhl, llc-mk2, mrc-5, vero e6) and mouse (balb/3t3 clone a31) origin. 3-deazaadenosine at 2 μg/ml could reduce viral replication by 3 logs in a dose-dependent manner. however, there was no further inhibition even with a 100-fold increase in concentration [1].
in vivoin vehicle control group, adult balb/c mice lethally infected with mouse-adapted ebola virus die 5-7 days after infection. in contrast, 3-deazaadenosine treatment initiated on day 0 or 1 led to a dose-dependent protection, with mortality completely prevented at doses around 0.7 mg/kg every 8 h. moreover, there was significant protection when 3-deazaadenosine treatment was begun on day 2, at which time, the spleen had an average titer of 2 × 106 pfu/g and the liver had 3 × 105 pfu/g virus. treatment with 3-aeazaadenosine at 2.2 mg/kg initiated on day 3 resulted in 40% survival [1].
references[1] huggins, z. x. zhang and m. bray. antiretroviral drug therapy of filovirus infections: s-adenosylhomocysteine hydrolase inhibitors inhibit ebola virus in vitro and in a lethal mouse model. journal of infectious diseases 179 (1), s240-s247 (1999).
3-DEAZAADENOSINE Preparation Products And Raw materials
5'-chloro-5'-deoxy-9-deazaadenosine carbocyclic 3-deazaadenosine 3-Deazaadenosine 5'-triphosphate 7-DEAZAADENOSINE 2-chloro-N(sup 6)-cyclopentyl-1-deazaadenosine 4-AMINO-6-CHLORO-1-B-D-RIBOFURANOSYLIMIDAZO[4,5-C]PYRIDINE 7-DEAZAADENOSINE-5'-TRIPHOSPHATE LITHIUM SALT 7-IODO-7-DEAZAADENOSINE,7-Iodo-7-deazaadenosine, 4-Amino-5-iodo-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 3-DEAZA-CADP-RIBOSE 2-AMINO-6-METHOXY-2'-DEOXY-7-DEAZAADENOSINE 4-AMINO-1-(2',3',5'-TRI-O-TERT-BUTYLDIMETHYLSILYL-B-D-RIBOFURANOSYL)-IMIDAZO[4,5-A]PYRIDINE 7-DEAZAADENOSINE-3',5'-CYCLIC MONOPHOSPHATE SODIUM SALT,7-deazaadenosine-3’,5’-cyclicmonophosphate(7-ch-camp),sodiumsal 3-DEAZAADENOSINE, [3H]- 9-deazaadenosine triphosphate 7-DEAZAADENOSINE, [3H]- 3-DEAZAADENOSINE 3-DEAZAADENOSINE, [8-3H] 7-IODO-2',3'-DIDEOXY-7-DEAZAADENOSINE

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