| Size | Price | Stock | Qty |
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| 1g |
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| Other Sizes |
| Targets |
The (2S,3R,5S) stereoisomer is considered an inactive isomer with no specific biological target, designed for use as an experimental control rather than for receptor or enzyme targeting. In contrast, the active isomer 7-Deaza-2'-deoxy-7-iodoadenosine can be incorporated into DNA and RNA, where it interacts with DNA/RNA polymerases and other nucleic acid-processing enzymes. The iodine atom at the 7-position enhances interaction with various enzymes and proteins, potentially leading to inhibition of viral replication and cancer cell growth.
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| ln Vitro |
The (2S,3R,5S) stereoisomer shows no specific biological activity in vitro, serving as a negative control for experiments using the active isomer 7-Deaza-2'-deoxy-7-iodoadenosine. The active isomer functions through incorporation into nucleic acids, where it can disrupt normal cellular processes, alter DNA duplex stability, and potentially inhibit viral replication and cancer cell growth. The 7-deaza modification influences base pairing and stacking interactions, making these compounds useful for studying nucleic acid structure and function.
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| ln Vivo |
In vivo activity has not been characterized for this inactive stereoisomer as it is used solely as a control compound. The active isomer 7-Deaza-2'-deoxy-7-iodoadenosine has been investigated in cellular systems for its effects on nucleic acid metabolism and viral replication. The 7-deazaadenine modification alters the biophysical properties of oligonucleotides, including duplex stability, which can be studied in cellular contexts but does not represent therapeutic activity.
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| Enzyme Assay |
Cell-free nucleic acid incorporation protocol: Oligonucleotides containing the active isomer are synthesized and hybridized with complementary strands. Thermal melting experiments are performed to determine duplex stability (Tm). For enzyme studies, DNA polymerases or reverse transcriptases are incubated with modified oligonucleotide templates and substrates, and incorporation efficiency is measured by gel electrophoresis or radioactive labeling. The inactive stereoisomer serves as a control to confirm stereospecificity of enzymatic recognition.
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| Cell Assay |
Cell-based control experiments using the inactive isomer typically involve treating cells (e.g., cancer cell lines or virus-infected cells) with both the active and inactive isomers at comparable concentrations (typically 1-100 microM). Cells are incubated for 24-72 hours, and viability is assessed by MTT assay. The inactive isomer should show no significant effect compared to vehicle control, while the active isomer may inhibit proliferation or viral replication. This validates the stereospecificity of observed biological effects.
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| Animal Protocol |
In vivo animal studies are not conducted with this inactive stereoisomer, as it is designed exclusively as a negative control compound. For the active isomer, typical protocols involve administration to tumor-bearing mice via intravenous or intraperitoneal injection to assess antitumor efficacy. Pharmacodynamic endpoints include tumor volume measurement and analysis of oligonucleotide incorporation into tumor DNA. However, these studies use the active isomer, not the (2S,3R,5S) stereoisomer.
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| ADME/Pharmacokinetics |
Pharmacokinetic studies are not performed for this inactive stereoisomer. For nucleoside analogues in general, absorption, distribution, metabolism, and excretion would be characterized if a compound were under drug development. This compound is not a drug candidate; it is a research tool for control experiments. The active isomer shows typical nucleoside analog PK properties with cellular uptake via nucleoside transporters, intracellular phosphorylation, and incorporation into nucleic acids.
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| Toxicity/Toxicokinetics |
No toxicity studies have been performed for this inactive stereoisomer as it is used only as a laboratory control at low concentrations in cell culture. It is not administered to animals or humans. Standard laboratory safety precautions for handling nucleoside analogues are recommended, including avoiding inhalation and skin contact. The iodine atom may confer photolability, requiring protection from light during handling.
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| References |
[1]. Frank Seela, et al. Oligonucleotides Containing 7‐Deazaadenines: The Influence of the 7‐Substituent Chain Length and Charge on the Duplex Stability. Research Article
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| Additional Infomation |
(2S,3R,5S)-7-Deaza-2'-deoxy-7-iodoadenosine is not a drug and has no clinical applications or regulatory approval. It is a research-grade chemical used exclusively as a negative control for experiments involving the active isomer 7-Deaza-2'-deoxy-7-iodoadenosine (CAS# 166247-63-8). The active isomer is a modified nucleoside containing 7-deazaadenine, used in studies of nucleic acid structure, oligonucleotide therapeutics, antiviral drug development, and DNA polymerase substrate specificity. The inactive isomer has no biological activity.
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| Molecular Formula |
C11H13IN4O3
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|---|---|
| Molecular Weight |
376.150394201279
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| Exact Mass |
376.003
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| CAS # |
908130-61-0
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| Related CAS # |
7-Deaza-2'-deoxy-7-iodoadenosine;166247-63-8
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| PubChem CID |
16080018
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| Appearance |
White to off-white solid powder
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| Density |
2.4±0.1 g/cm3
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| Boiling Point |
657.4±55.0 °C at 760 mmHg
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| Flash Point |
351.4±31.5 °C
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| Vapour Pressure |
0.0±2.1 mmHg at 25°C
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| Index of Refraction |
1.882
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| LogP |
0.97
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
19
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| Complexity |
337
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| Defined Atom Stereocenter Count |
3
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| SMILES |
IC1C2C(=NC=NC=2N([C@@H]2C[C@@H](O)[C@H](CO)O2)C=1)N
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| InChi Key |
LIIIRHQRQZIIRT-CSMHCCOUSA-N
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| InChi Code |
InChI=1S/C11H13IN4O3/c12-5-2-16(8-1-6(18)7(3-17)19-8)11-9(5)10(13)14-4-15-11/h2,4,6-8,17-18H,1,3H2,(H2,13,14,15)/t6-,7+,8+/m1/s1
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| Chemical Name |
(2S,3R,5S)-5-(4-amino-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)oxolan-3-ol
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6585 mL | 13.2926 mL | 26.5851 mL | |
| 5 mM | 0.5317 mL | 2.6585 mL | 5.3170 mL | |
| 10 mM | 0.2659 mL | 1.3293 mL | 2.6585 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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