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.

Physicochemical Properties

Molecular Formula	C10H11N5O4
Molecular Weight	265.23
Exact Mass	265.081
CAS #	34240-05-6
Related CAS #	34240-05-6
PubChem CID	99920
Appearance	White to off-white oil
LogP	-1.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	6
Heavy Atom Count	19
Complexity	331
Defined Atom Stereocenter Count	0
SMILES	OCC(OC(N1C=NC2=C(N=CN=C12)N)C=O)C=O
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)

Biological Activity

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.

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.