8-Aminoadenosine (8-NH2-Ado) is an RNA-directed nucleoside analog that reduces cellular ATP levels and inhibits mRNA synthesis. 8-Aminoadenosine blocks Akt/mTOR signaling and induces p53-independent autophagy and apoptosis. 8-Aminoadenosine has anticancer effect.

Physicochemical Properties

Molecular Formula	C10H14N6O4
Molecular Weight	282.26
Exact Mass	282.108
CAS #	3868-33-5
PubChem CID	96851
Appearance	White to off-white solid powder
Density	2.25g/cm3
Boiling Point	747.1ºC at 760mmHg
Melting Point	180-185ºC dec.
Flash Point	405.6ºC
LogP	-1.4
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=NC(=C2C(=N1)N(C(=N2)N)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N
InChi Key	DVGWFQILDUEEGX-UUOKFMHZSA-N
InChi Code	InChI=1S/C10H14N6O4/c11-7-4-8(14-2-13-7)16(10(12)15-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,15)(H2,11,13,14)/t3-,5-,6-,9-/m1/s1
Chemical Name	(2R,3R,4S,5R)-2-(6,8-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
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	mTOR
ln Vitro	In MM.1S and U266 cells, 8-aminoadenosine (8-NH2-Ado; 0.1-10 μM; for 48 h) has IC50s of 1.5 μM and 8.88 μM, respectively[1]. 8-Aminoadenosine (10 μM; for 24 hours) significantly causes MCF-7 cells to undergo apoptosis through a p53-independent mechanism. In MCF-7 cells, 8-adenosine triggers PARP cleavage[2]. In the MM.1S cell line, 8-aminoadenosine (3 μM; 0.5–4 h) initiates autophagy[1]. In MM.1S cells, 8-adenosine (3 μM; 2–16 h) results in a higher decrease in ATP levels[1]. In MM.1S cells, 8-aminoadenosine (3 μM; 5 h) reduces glucose intake by 50%[1]. In MM.1S cells, 8-aminoadenosine (3 μM; 5 h) shows a time-dependent drop in GLUT1 expression at 5 h, while both transporters (GLUT1 and GLUT4) were down-regulated at 24 h[1]. In addition to inhibiting cell growth and activating cell death, 8-aminoadenosine does not enhance the levels of either p53 or p21 protein or stimulate transcription of the p53 target gene, p21[1]. In cells lacking adenosine kinase, the conversion of 8-Aminoadenosine to 8-NH2-ATP is necessary to counteract the harmful effects of 8-Aminoadenosine[1].
Cell Assay	Cell Viability Assay[1] Cell Types: MM.1S and U266 cells Tested Concentrations: 0.1, 0.3, 1, 3, 10 μM Incubation Duration: For 48 hrs (hours) Experimental Results: Had IC50s of 1.5 μM and 8.88 μM in MM.1S and U266 cells, respectively. Apoptosis Analysis[2] Cell Types: MCF-7 cells Tested Concentrations: 10 μM Incubation Duration: For 24 hrs (hours) Experimental Results: Induced significant apoptotic death. Apoptosis was not inhibited by knockdown of functional p53. Apoptosis Analysis[1] Cell Types: MM.1S cell line Tested Concentrations: 3 μM Incubation Duration: 0.5, 1, 1.5, 2, 2.5, 3, 3.5, 4 hrs (hours) Experimental Results: Induced the formation of LC3-II protein. Caused the appearance of a population with a high AVO content with 1 μM for 24 hrs (hours).
References	[1]. Targeting glucose consumption and autophagy in myeloma with the novel nucleoside analogue 8-aminoadenosine. J Biol Chem. 2009 Sep 25;284(39):26816-30. [2]. 8-Amino-adenosine activates p53-independent cell death of metastatic breast cancers. Mol Cancer Ther. 2012 Nov;11(11):2495-504. [3]. 8-Amino-adenosine inhibits multiple mechanisms of transcription. Mol Cancer Ther. 2010 Jan;9(1):236-45.

Solubility Data

Solubility (In Vitro)

DMSO : 83.33 mg/mL (295.22 mM)

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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (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.