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3-Deazaadenosine Catalog No.GC14713

S-Adenosylhomocysteine (SAH) hydrolase inhibitor

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1mg
$33.00
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5mg
$135.00
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10mg
$252.00
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Sample solution is provided at 25 µL, 10mM.

Quality Control

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Protocol

Cell experiment:

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:

[1]. Gordon RK, et al. Anti-HIV-1 activity of 3-deaza-adenosine analogs. Inhibition of S-adenosylhomocysteine hydrolase and nucleotide congeners. Eur J Biochem. 2003 Sep;270(17):3507-17.
[2]. Jeong SY, et al. 3-deazaadenosine, a S-adenosylhomocysteine hydrolase inhibitor, has dual effects on NF-kappaB regulation. Inhibition of NF-kappaB transcriptional activity and promotion of IkappaBalpha degradation. J Biol Chem. 1999 Jul 2;274(27):18981-8.
[3]. Sedding DG, et al. 3-Deazaadenosine prevents smooth muscle cell proliferation and neointima formation by interfering with Ras signaling. Circ Res. 2009 May 22;104(10):1192-200.

Chemical Properties

Cas No. 6736-58-9 SDF
Chemical Name (2R,3R,4S,5R)-2-(4-amino-1H-imidazo[4,5-c]pyridin-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
Canonical SMILES NC1=C2C(N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)=CC=N1
Formula C11H14N4O4 M.Wt 266.25
Solubility ≥ 26.6mg/mL in DMSO Storage Store at -20°C
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request
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Background

Ki: 3.9 μM

3-Deazaadenosine is an inhibitor of S-Adenosylhomocysteine (SAH) hydrolase.

S-Adenosylhomocysteine (SAH) hydrolase can catalyze the reversible hydrolysis of SAH to adenosine and homocysteine. The inhibition of SAH hydrolase result in the intracellular accumulation of SAH, elevating the ratio of SAH to S-adenosylmethionine (SAM) and also inhibiting SAM-dependent methyltransferases.

In vitro: 3-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 vivo: In 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 × 105pfu/g virus. Treatment with 3-aeazaadenosine at 2.2 mg/kg initiated on day 3 resulted in 40% survival [1].

Clinical trial: Up to now, 3-deazaadenosine is still in the preclinical development stage.

Reference:
[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).