8-Aminoadenosine

• CAT Number: R002667
• CAS Number: 3868-33-5
• Molecular Formula: C10H14N6O4
• Molecular Weight: 282.26
• Purity: ≥95%
• Synonyms: (2R,3R,4S,5R)-2-(6,8-diaminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• InChI: 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
• InChIKey: DVGWFQILDUEEGX-UUOKFMHZSA-N
• SMILES: C1=NC(=C2C(=N1)N(C(=N2)N)C3C(C(C(O3)CO)O)O)N

8-Aminoadenosine (8-NH2-Ado), a RNA-directed nucleoside analogue, reduces cellular ATP levels and inhibits mRNA synthesis. 8-Aminoadenosine blocks Akt/mTOR signaling and induces autophagy and apoptosis in a p53-independent manner. 8-Aminoadenosine has antitumor activity[1][2][3].
8-Aminoadenosine (8-NH2-Ado; 0.1-10 μM; for 48 h) has IC50s of 1.5 μM and 8.88 μM in MM.1S and U266 cells, respectively[1].
8-Aminoadenosine (10 μM; for 24 h) induces significant apoptotic death of MCF-7 cells in p53-independent pathway. 8-Aminoadenosine causes PARP cleavage in MCF-7 cells[2].
8-Aminoadenosine (3 μM; 0.5-4 h) induces autophagy in the MM.1S cell line[1].
8-Aminoadenosine (3 μM; 2-16 h) causes a greater drop in ATP levels in the MM.1S cells[1].
8-Aminoadenosine (3 μM; 5 h) causes a 50% reduction in glucose consumption in MM.1S cells[1].
8-Aminoadenosine (3 μM; 5 h) indicates a time-dependent decrease in GLUT1 expression at 5 h, whereas at 24 h there was a down-regulation of both transporters (GLUT1 and GLUT4) in MM.1S cells[1].
8-Aminoadenosine inhibits cell proliferation, activated cell death, and does not activate transcription of the p53 target gene p21 or increase protein levels of either p53 or p21[1].
The toxic effects of 8-Aminoadenosine require adenosine kinase activity to convert 8-Aminoadenosine to 8-NH2-ATP in adenosine kinase-deficient cells[1].

Reference

[1]. Mala Shanmugam, et al. Targeting glucose consumption and autophagy in myeloma with the novel nucleoside analogue 8-aminoadenosine. J Biol Chem. 2009 Sep 25;284(39):26816-30.
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[2]. Alla Polotskaia, et al. 8-Amino-adenosine activates p53-independent cell death of metastatic breast cancers. Mol Cancer Ther. 2012 Nov;11(11):2495-504.
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[3]. Jennifer Ann Frey, et al. 8-Amino-adenosine inhibits multiple mechanisms of transcription. Mol Cancer Ther. 2010 Jan;9(1):236-45.
 [Content Brief]