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2-Aminoadenosine (2-aminoadenine nucleoside; 2,6-diaminopurine riboside)

Cat No.:V55265 Purity: ≥98%
2-Aminoadenosine is an adenine nucleoside analogue.
2-Aminoadenosine (2-aminoadenine nucleoside; 2,6-diaminopurine riboside)
2-Aminoadenosine (2-aminoadenine nucleoside; 2,6-diaminopurine riboside) Chemical Structure CAS No.: 2096-10-8
Product category: Nucleoside Antimetabolite/Analog
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
2-Aminoadenosine is an adenine nucleoside analogue. Adenosine analogs mostly work as smooth muscle vasodilators and also have been found to suppress cancer progression. Its popular products include Adenosine phosphate, Acadesine, Clofarabine, Fludarabine phosphate and Vidarabine .
2-Aminoadenosine (CAS 2096-10-8) is a purine nucleoside analog also known as 2,6-diaminopurine riboside. Its molecular formula is C10H14N6O4 with a molecular weight of 282.26 g/mol. This compound is a modified form of adenosine that serves as an inhibitor or substrate of adenosine kinase. It inhibits DNA polymerase and RNA polymerase activities, thereby inhibiting the growth of certain cancer cells.
Biological Activity I Assay Protocols (From Reference)
Targets
2-Aminoadenosine targets adenosine kinase, serving as either an inhibitor or substrate of this enzyme. The compound also inhibits DNA polymerase and RNA polymerase activities. By inhibiting these polymerases, the compound interferes with DNA and RNA synthesis, leading to inhibition of cancer cell growth.
ln Vitro
In cell-free biochemical systems, 2-Aminoadenosine inhibits DNA polymerase and RNA polymerase activities. The compound serves as a substrate for adenosine kinase from M. tuberculosis. These activities demonstrate the compound's direct effects on nucleic acid synthesis enzymes and adenosine metabolism.
ln Vivo
In cell-based assays, 2-Aminoadenosine has been shown to inhibit the growth of certain cancer cells in vitro. The compound's mechanism of action involves inhibition of DNA and RNA synthesis through polymerase inhibition. The compound is used to study adenosine receptor activity and has potential applications in drug development, particularly in neurological disorders and cancer therapy.
Enzyme Assay
The cell-free assay for DNA polymerase inhibition involves measuring the incorporation of radiolabeled nucleotides into DNA in the presence of the compound. The reaction contains purified DNA polymerase, template DNA, dNTPs, and the inhibitor at various concentrations. The RNA polymerase inhibition assay is performed similarly using RNA polymerase and NTPs. The IC50 values are determined from dose-response curves.
Cell Assay
Cell-based assays for anti-cancer activity involve culturing cancer cell lines and treating them with 2-Aminoadenosine at concentrations ranging from 0.1 to 100 μM. Cells are incubated for 24-72 hours, and cell viability is assessed using MTT or CCK-8 assays. The effect on DNA and RNA synthesis can be measured by incorporation of labeled precursors. The compound's effects on adenosine receptor signaling can be assessed in appropriate cell models.
Animal Protocol
There is no established animal experimental protocol for 2-Aminoadenosine specifically. As an adenosine analog with anti-cancer activity, the compound could potentially be evaluated in animal models of cancer. Typical protocols for nucleoside analogs involve administration to tumor-bearing mice via intraperitoneal or intravenous routes.
ADME/Pharmacokinetics
Pharmacokinetic properties of 2-Aminoadenosine have not been extensively reported. As a small molecule with molecular weight of 282.26 g/mol, the compound would be expected to have reasonable bioavailability and tissue penetration. The presence of the additional amino group may affect the compound's metabolism and distribution. Further pharmacokinetic studies would be required.
Toxicity/Toxicokinetics
Toxicity data for 2-Aminoadenosine are not well documented. As a nucleoside analog that inhibits DNA and RNA synthesis, the compound may have toxicity toward rapidly dividing cells, which could translate to bone marrow suppression and gastrointestinal toxicity. Standard toxicity studies would be required to determine the safety profile.
References

[1]. Potential and promising anticancer drugs from adenosine and its analogs. Drug Discov Today. 2021 Jun;26(6):1490-1500.

Additional Infomation
2-Aminoadenosine is a purine nucleoside.
2-Aminoadenosine is a research compound used to study adenosine kinase activity, adenosine receptor signaling, and nucleic acid synthesis inhibition. The compound inhibits DNA polymerase and RNA polymerase activities and has been shown to inhibit the growth of certain cancer cells in vitro. It has potential applications in drug development for neurological disorders and cancer therapy. It is not an approved pharmaceutical and has no clinical trial history. This product is intended for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H14N6O4
Molecular Weight
282.26
Exact Mass
282.107
CAS #
2096-10-8
PubChem CID
72200
Appearance
White to off-white solid powder
Density
2.3±0.1 g/cm3
Boiling Point
798.5±70.0 °C at 760 mmHg
Melting Point
241-243°C (dec.)
Flash Point
436.7±35.7 °C
Vapour Pressure
0.0±3.0 mmHg at 25°C
Index of Refraction
1.986
LogP
-1.08
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
2
Heavy Atom Count
20
Complexity
363
Defined Atom Stereocenter Count
4
SMILES
C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N)N
InChi Key
ZDTFMPXQUSBYRL-UUOKFMHZSA-N
InChi Code
InChI=1S/C10H14N6O4/c11-7-4-8(15-10(12)14-7)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H4,11,12,14,15)/t3-,5-,6-,9-/m1/s1
Chemical Name
(2R,3R,4S,5R)-2-(2,6-diaminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
HS Tariff Code
2934.99.9001
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)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~354.28 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.86 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 25.0 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: ≥ 2.5 mg/mL (8.86 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 25.0 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.5428 mL 17.7142 mL 35.4283 mL
5 mM 0.7086 mL 3.5428 mL 7.0857 mL
10 mM 0.3543 mL 1.7714 mL 3.5428 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.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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