N-Benzyladenosine

Names

[ Name ]:
N-Benzyladenosine

[Synonym ]:
Adenosine, N-(phenylmethyl)-
Adenosine, N-benzyl-
BAP RIBOSE
(2S,3R,4S,5R)-2-(6-(benzylamino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
N6-BENZYL-D-ADENOSINE
BAP RIBOSIDE
N-Benzyladenosine
6-BENZYLADENOSINE
N6-Benzyladenosine
(4S,2R,3R,5R)-2-hydroxymethyl-5-[6-(benzylamino)-purin-9-yl]-tetrahydrofuran-3,4-diol
Adenosine, N- (phenylmethyl)-
Benzyladenosine
6-Benzylaminopurine Ribosiden
EINECS 224-298-9
N-(Phenylmethyl)adenosine
(-)-N6-(benzyl)adenosine
MFCD00005740

Biological Activity

[Description]:

N6-Benzyladenosine is an adenosine receptor agonist, has a cytoactive activity. N6-Benzyladenosine arrests cell cycle at G0/G1 phase and induces cell apoptosis. N6-Benzyladenosine also exerts inhibitory effect on T. gondii adenosine kinase and glioma[1]-[5].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

Signaling Pathways >> GPCR/G Protein >> Adenosine Receptor

[In Vitro]

N6-benzyladenosine suppresses the clonogenic activity and the growth of different neoplastic cells[2]. N6-benzyladenosine results cell morphology alteration and actin cytoskeleton disorganization in T24 cell[2]. N6-benzyladenosine (10 μM; 24 h) is a potent inductor of apoptosis, and belongs to apoptotic systems with distinct caspase-3 and caspase-9 activation[3]. N6-benzyladenosine (0-100 μM; 24 h) induces chromatin condensation, formation of apoptotic bodies, and cleavage of DNA to nucleosomal fragments in a dose-dependent manner[3]. N6-benzyladenosine acts as a selective anti-toxoplasma agent with binding affinity to T. gondii adenosine kinase (apparent Km =179.8 μM), over human adenosine kinase[4]. N6-benzyladenosine (0-50 μM) shows weak inhibition against adenosine kinase deficient (TgAKS3) strains of Toxoplasma gondii[4]. N6-benzyladenosine (compound 2) (0.3-20 μM) exerts anti-glioma activity by interfering with the mevalonate pathway and inhibiting FPPS (Farnesyl pyrophosphate synthase) [5]. Apoptosis Analysis[3] Cell Line: HL-60 Concentration: 10 μM Incubation Time: 24 hours Result: Induced cell apoptosis by increasing caspase-3 (DEVDase) as well as caspase-9 (LEHDase) activity, indicating an apoptotic systems with distinct caspase-3/9 activation. Apoptosis Analysis[5] Cell Line: U87MG human glioma cell line. Concentration: 0.3, 0.6, 1.2, 2.5, 5, 10, 20 μM Incubation Time: 48 hours Result: Inhibited glioma growth by interfering with the mevalonate pathway and inhibiting FPPS.

[References]

[1]. Kaminek M, et al. Cytokinin activities of N6-benzyladenosine derivatives hydroxylated on the side-chain phenyl ring. Journal of Plant Growth Regulation. 1987. 6(2):113.

[2]. Castiglioni S, et al. N6-isopentenyladenosine and its analogue N6-benzyladenosine induce cell cycle arrest and apoptosis in bladder carcinoma T24 cells. Anticancer Agents Med Chem. 2013 May;13(4):672-8.

[3]. Mlejnek P. Caspase inhibition and N6-benzyladenosine-induced apoptosis in HL-60 cells. J Cell Biochem. 2001;83(4):678-89.

[4]. Kim YA, et al. Synthesis, biological evaluation and molecular modeling studies of N6-benzyladenosine analogues as potential anti-toxoplasma agents. Biochem Pharmacol. 2007 May 15;73(10):1558-72.

[5]. Grimaldi M, et al. NMR for screening and a biochemical assay: Identification of new FPPS inhibitors exerting anticancer activity. Bioorg Chem. 2020 May;98:103449.