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Adenosine Dialdehyde (ADOX)

Alias: Adenosine dialdehyde
Cat No.:V3152 Purity: ≥98%
Adenosine Dialdehyde (also named as ADOX), an adenosine analog, is an inhibitor of the S-adenosylmethionine-dependent methyltransferase with an IC50 of 40 nM.
Adenosine Dialdehyde (ADOX)
Adenosine Dialdehyde (ADOX) Chemical Structure CAS No.: 34240-05-6
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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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Adenosine Dialdehyde (also named as ADOX), an adenosine analog, is an inhibitor of the S-adenosylmethionine-dependent methyltransferase with an IC50 of 40 nM. Adenosine dialdehyde functions as a cell-incorporated indirect inhibitor. S-adenosyl-L-homo cystein (Adoicy), a product inhibitor of methyltransferases that use S-adenosyl-L-methionine (AdoMet) as the methyl group donor, can accumulate as a result of ADOX's inhibition of S-adenosyl-L-homocystein hydrolase. p53 was reactivated and p53 target genes were induced as a result of ADOX's inhibition of the Tax-activated NF-κB pathway.

Biological Activity I Assay Protocols (From Reference)
Targets
AdoHcy hydrolase ( IC50 = 40 nM )
ln Vitro

Adenosine dialdehyde (AdOx) is an indirect inhibitor that cells have the ability to absorb. The accumulation of S-adenosyl-L-homo cystein (Adoicy), a product inhibitor of methyltransferases that use S-adenosyl-L-methionine (AdoMet) as the methyl group donor, is caused by AdOx's inhibition of S-adenosyl-L-homocystein hydrolase[2]. AdOx caused p53 to reactivate and p53 target genes to be induced by blocking the Tax-activated NF-κB pathway. By stabilizing the NF-κB inhibitor IκBα, AdOx treatment led to the degradation of the IκB kinase complex and the inhibition of NF-κB, as revealed by an analysis of the NF-κB pathway. AdOx caused cell death and G2/M cell cycle arrest in HTLV-1-transformed lymphocytes, but not in control cells[4].

ln Vivo
AdOx, when given by steady state infusion, does not suppress hematopoiesis and has a strong inhibitory effect on the in situ growth of established murine neuroblastoma (MNB) tumors. It also extends the life span of tumor-bearing mice. AdOx given intraperitoneally at a dose of 20 mg/kg/day until death inhibits the replication of L1210 leukemia cells and increases life span by about 40%[3].
Cell Assay
Hela cells are cultured in MEM medium with 10% fetal bovine serum supplement in an incubator with 5% CO2 at 37 °C. AdOx treatment of cells was carried out for varied lengths of time. Following cell harvesting, the cells are rinsed in phosphate-buffered saline and then resuspended in buffer A, which contains complete protease inhibitor cocktail, 5% glycerol, 1 mM sodium EGTA, 1 mM dithiothreitol, and 0.5% Triton X-100.
Animal Protocol
Formulated in DMSO (3.3%, v/v), ethanol (50%, v/v) and saline (46.7%, v/v); 1.5 to 2.5 mg/kg/day; s.c.
Murine Neuroblastoma Tumor Model
References

[1]. J. Med. Chem. 1988, 31, 9, 1798–1804

[2]. J Biochem . 2004 Sep;136(3):371-6.

[3]. Cancer Res . 1987 Jul 15;47(14):3656-61.

[4]. J Virol. 2008 Jan; 82(1): 49–59.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H11N5O4
Molecular Weight
265.23
Exact Mass
265.08
CAS #
34240-05-6
Related CAS #
34240-05-6
Appearance
Oil
SMILES
C1=NC(=C2C(=N1)N(C=N2)C(C=O)OC(CO)C=O)N
InChi Key
ILMNSCQOSGKTNZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H11N5O4/c11-9-8-10(13-4-12-9)15(5-14-8)7(3-18)19-6(1-16)2-17/h1,3-7,17H,2H2,(H2,11,12,13)
Chemical Name
2-[1-(6-aminopurin-9-yl)-2-oxoethoxy]-3-hydroxypropanal
Synonyms
Adenosine dialdehyde
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

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: 10~19 mg/mL (37.7~71.6 mM)
Water: ~3 mg/mL (11.3 mM)
Ethanol: < 1mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (7.84 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 (7.84 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.7703 mL 18.8516 mL 37.7031 mL
5 mM 0.7541 mL 3.7703 mL 7.5406 mL
10 mM 0.3770 mL 1.8852 mL 3.7703 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.

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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?
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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:
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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
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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.

Biological Data
  • AdOx inhibits transcriptional activity of HTLV-1 LTR and Tax transcription. J Virol. 2008 Jan; 82(1): 49–59.
  • AdOx inhibits the growth of HTLV-1-transformed cell lines. J Virol. 2008 Jan; 82(1): 49–59.
  • AdOx induces the G2/M checkpoint and induces apoptosis in HTLV-1-transformed cell lines. J Virol. 2008 Jan; 82(1): 49–59.
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