4294-16-0

4294-16-0 structure

Name: N-Benzyladenosine
Chemical Name: n6-benzyladenosine
CAS Number: 4294-16-0
Molecular Formula: C₁₇H₁₉N₅O₄
Molecular Weight: 357.364
Catalog: Biochemical Nucleoside drugs Nucleoside intermediate
Create Date: 2018-05-01 08:00:00
Modify Date: 2024-01-02 12:56:37
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].

Name	n6-benzyladenosine
Synonyms	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

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.

Density	1.6±0.1 g/cm3
Boiling Point	689.3±65.0 °C at 760 mmHg
Melting Point	184-186 °C
Molecular Formula	C₁₇H₁₉N₅O₄
Molecular Weight	357.364
Flash Point	370.7±34.3 °C
Exact Mass	357.143707
PSA	125.55000
LogP	1.04
Vapour Pressure	0.0±2.3 mmHg at 25°C
Index of Refraction	1.763
Storage condition	2-8°C

Hazard Codes	Xn
Risk Phrases	20/21/22-36/37/38
Safety Phrases	S22-S24/25
WGK Germany	3

Precursor 8
2004-06-0 100-46-9 58-63-9 3287-99-8
100-52-7 58-61-7 3181-38-2 932-90-1
DownStream 7
58-61-7 34408-14-5 78188-38-2 2946-39-6
1214-39-7 18646-11-2 13484-66-7

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