| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 100mg | |||
| Other Sizes |
| Targets |
HIV-1/2
Dideoxyadenosine acts as a chain-terminator of viral DNA by binding to reverse transcriptase. It effectively inhibits the replication of HIV-1, simian immunodeficiency virus (SIV), and murine sarcoma virus (MSV) across various cell lines. |
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| ln Vitro |
2',3'-Dideoxyadenosine suppresses HIV-1 and simian immunodeficiency virus (SIV) in MT-4 cells with EC50 values of 5.27 and 5.3 μM, respectively. In T-phase CEM cells, 2',3'-Dideoxyadenosine suppresses HIV-1 and HIV-2 with EC50 values of 4 μM and 8 μM, respectively. In Molt 4/C8 cells, 2',3'-Dideoxyadenosine suppresses HIV-1 and HIV-2 with EC50 values of 4 μM and 5.5 μM, respectively. HIV-1 and HIV-2 in C8166 cells are inhibited by 2',3'-Dideoxyadenosine, with EC50 values of 17 μM and 22 μM, respectively. With an EC50 of 24 μM, 2',3'-Dideoxyadenosine suppresses the murine sarcoma virus (MSV) in C3H/3T3 cells [1].
In vitro, dideoxyadenosine shows inhibition of HIV-1 replication. It is effective against HIV-1 and SIV in MT-4 cells with EC₅₀ values of 5.27 and 5.3 μM, respectively. It inhibits HIV-1 and HIV-2 in C8166 cells with EC₅₀ values of 17 μM and 22 μM. |
| ln Vivo |
In vivo, dideoxyadenosine is an inhibitor of HIV replication. Its principal side effect is nephrotoxicity. It has been studied for its antiretroviral activity and antiviral efficacy.
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| Enzyme Assay |
In vitro enzyme assays for dideoxyadenosine typically measure its ability to inhibit HIV reverse transcriptase. The enzyme is incubated with a template-primer and nucleotides in the presence of increasing concentrations of the compound. The incorporation of the chain-terminating nucleotide analog is measured. IC₅₀ values are calculated.
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| Cell Assay |
Antiviral activity of the test compounds[1]
CEM, MT-4, Molt 4/clone 8 and C8166 cells were suspended at 250 000–350 000 cells per ml of culture medium and infected with approximately 100 CCID50 (1 CCID50 being the 50% cell culture infective dose) of HIV-1(IIIB) or HIV-2(ROD). Then, 100 μl of the infected cell suspensions was added to 200-μl-microtiterplate wells containing 100 μl of an appropriate dilution of the test compounds (i.e., 250, 100, 20, 4, 0.8, 0.16, 0.032, 0.006, 0.001 μM). The inhibitory effect of the test compounds on HIV-1-induced syncytium formation in CEM, Molt 4 and C8166 cells was examined on day 4 post-infection, and their inhibitory effect on the viability of HIV-infected MT-4 cells was examined on day 5 post-infection, as described previously. The 50% effective concentration (EC50) was determined as the compound concentration required to inhibit syncytium formation (CEM, Molt 4, C8166) or to reduce cell viability (MT-4) by 50%. The 50% cytostatic concentration (CC50) was defined as the compound concentration required to reduce cell viability or cell proliferation by 50%[1]. Cell-based assays for dideoxyadenosine involve treating HIV-infected cell lines (e.g., MT-4 cells) with the compound and measuring viral replication. The compound's ability to inhibit HIV-1, SIV, and MSV replication is assessed. Cytotoxicity is also evaluated. |
| Animal Protocol |
In vivo animal studies for dideoxyadenosine are limited. The compound has been studied for its antiretroviral activity. Its nephrotoxicity has been observed as a principal side effect.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of dideoxyadenosine are characteristic of nucleoside analogs. The compound has a molecular weight of 235.24 g/mol and a molecular formula of C₁₀H₁₃N₅O₂. It is metabolized intracellularly to its active triphosphate form.
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| Toxicity/Toxicokinetics |
Toxicity Data
Mice (oral): LD50: 5 g/kg Mice (subcutaneous): LD50: 1320 mg/kg Dideoxyadenosine can cause nephrotoxicity. It should be handled with caution. The compound's toxicity profile is consistent with other nucleoside reverse transcriptase inhibitors. |
| References | |
| Additional Infomation |
2',3'-Dideoxyadenosine is a grayish-white powder. (NTP, 1992)
2',3'-Dideoxyadenosine is a purine 2',3'-dideoxyribonucleoside with adenine as its nucleobase. It is an EC 4.6.1.1 (adenylate cyclase) inhibitor and an EC 3.5.4.4 (adenylate deaminase) inhibitor. It is a purine 2',3'-dideoxyribonucleoside belonging to the adenosine class of compounds. Dideoxyadenosine is a prodrug form of didanoxin, a nucleoside reverse transcriptase inhibitor similar to adenosine. Dideoxynucleoside is a dideoxynucleoside compound in which the 3'-hydroxyl group of the sugar moiety is replaced by a hydrogen atom. This modification prevents the formation of phosphodiester bonds required for nucleic acid chain synthesis. This compound is an HIV replication inhibitor that terminates the viral DNA chain by binding to reverse transcriptase. Its main side effect is nephrotoxicity. In the body, dideoxyadenosine is rapidly metabolized into dideoxyinosine (ddI) by enzymatic deamination; ddI is then converted into dideoxyinosine monophosphate, and finally into dideoxyadenosine triphosphate, the latter of which is considered the active metabolite. Dideoxyadenosine is a nucleoside analog reverse transcriptase inhibitor. It is not approved for clinical use but serves as a valuable research tool for studying HIV replication and nucleoside analog development. |
| Molecular Formula |
C10H13N5O2
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|---|---|
| Molecular Weight |
235.25
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| Exact Mass |
235.106
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| Elemental Analysis |
C, 51.06; H, 5.57; N, 29.77; O, 13.60
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| CAS # |
4097-22-7
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| PubChem CID |
20039
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| Appearance |
White to off-white solid powder
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| Density |
1.8±0.1 g/cm3
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| Boiling Point |
539.1±60.0 °C at 760 mmHg
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| Melting Point |
181-184 °C(lit.)
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| Flash Point |
279.9±32.9 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.822
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| LogP |
-0.43
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
17
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| Complexity |
279
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| Defined Atom Stereocenter Count |
2
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| SMILES |
O1[C@]([H])(C([H])([H])O[H])C([H])([H])C([H])([H])[C@]1([H])N1C([H])=NC2=C(N([H])[H])N=C([H])N=C12
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| InChi Key |
WVXRAFOPTSTNLL-NKWVEPMBSA-N
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| InChi Code |
InChI=1S/C10H13N5O2/c11-9-8-10(13-4-12-9)15(5-14-8)7-2-1-6(3-16)17-7/h4-7,16H,1-3H2,(H2,11,12,13)/t6-,7+/m0/s1
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| Chemical Name |
[(2S,5R)-5-(6-aminopurin-9-yl)oxolan-2-yl]methanol
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| Synonyms |
Dideoxyadenosine; NSC-98700; 2',3'-Dideoxyadenosine; 4097-22-7; dideoxyadenosine; ADENOSINE, 2',3'-DIDEOXY-; ddAdo; ((2S,5R)-5-(6-Amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methanol; NSC-98700; NSC 98700; CCRIS 428; D2A; DDA; ddAdo; 2′,3′-Dideoxyadenosine ; NSC 98700
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O : ~100 mg/mL (~425.10 mM)
DMSO : ~100 mg/mL (~425.10 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (8.84 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (8.84 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (8.84 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 14.29 mg/mL (60.75 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C). |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.2508 mL | 21.2540 mL | 42.5080 mL | |
| 5 mM | 0.8502 mL | 4.2508 mL | 8.5016 mL | |
| 10 mM | 0.4251 mL | 2.1254 mL | 4.2508 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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