3-Deazaadenosine hydrochloride

SKU: orb1310056

Description

3-Deazaadenosine hydrochloride is a potent inhibitor of S-adenosylhomocysteine hydrolase (Ki: 3.9 µM). This activity underpins its observed anti-inflammatory, anti-proliferative, and anti-HIV effects, making it a valuable research tool for studying epigenetic regulation and viral replication in both cellular and animal models.

Research Area

Infectious Disease & Virology, Protein Biochemistry

Images & Validation

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Key Properties

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CAS Number	86583-19-9
MW	302.71
Purity	99.99%
Formula	C₁₁H₁₅ClN₄O₄
SMILES	Cl.Nc1nccc2n(cnc12)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
Target	HIV Protease
Solubility	H2O:20 mg/mL (66.07 mM);DMSO:127.5 mg/mL (421.2 mM)

Bioactivity

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Target IC50	HIV-1 (A018 isolate):0.20 µM \|S-adenosylhomocysteine hydrolase:(ki)3.9 µM \|HIV-1 (A012 isolate):0.15
In Vitro	3-Deazaadenosine exhibits antiviral properties specifically against HIV, by inhibiting the p24 antigen in HIV-1 infected peripheral blood mononuclear (PBMCs) cells (A012 and A018 isolates, IC50s: 0.15 and 0.20 μM) . Furthermore, it modulates inflammatory responses by suppressing LPS-induced TNF-α mRNA expression and altering NF-κB pathway activity in RAW 264.7 cells. This includes inhibition of NF-κB transcriptional activity, which is enhanced by homocysteine, and proteolytic degradation of IκBα (not IκBβ), despite increasing NF-κB's DNA binding activity and promoting its nuclear translocation . Additionally, at concentrations of 50 and 100 μM, 3-Deazaadenosine impedes the phosphorylation of several key signaling molecules, including Raf, ERK, protein-dependent kinase 1, protein kinase B (Akt), and forkhead transcription factor FoxO1a. At 50 μM, it also inhibits the proliferation of vascular smooth muscle cells (VSMC) by interfering with Ras signaling pathways, showcasing its potential for cardiovascular applications . Read more...
Cell Research	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 × 10^5 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 × 10^5 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 . Read more...

Storage & Handling

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Storage	Powder: -20°C for 3 years \| In solvent: -80°C for 1 year \| Shipping with blue ice/Shipping at ambient temperature.
Expiration Date	12 months from date of receipt.
Disclaimer	For research use only

Alternative Names

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S-adenosylhomocysteine hydrolase, 3-Deazaadenosine, 3Deazaadenosine hydrochloride, 3-Deazaadenosine Hydrochloride, 3 Deazaadenosine hydrochloride, inhibit, Human immunodeficiency virus, Inhibitor, HIV Protease, HIV, HIVProtease, HIV-1, A012 isolate, HIV-1, A018 isolate

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Compound Identifiers

PubChem CID

134828261 ↗

Key Properties

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No computed properties available.

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