CAS Number4294-16-0
SynonymsBAP 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; Benzyladenosine; 6-Benzylaminopurine Ribosiden; EINECS 224-298-9; N-(Phenylmethyl)adenosine; (-)-N6-(benzyl)adenosine; MFCD00005740
Molecular FormulaC17H19N5O4
Molecular Weight357.364
Purity98.00%
Density1.6±0.1 g/cm3
Boiling Point689.3±65.0 °C at 760 mmHg
Melting Point184-186 °C
Appearancewhite solid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 4294-16-0 |
| Catalog No. | 2A-9030735 |
| Chinese Name | N6-苄基腺苷 |
| Synonyms | 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; Benzyladenosine; 6-Benzylaminopurine Ribosiden; EINECS 224-298-9; N-(Phenylmethyl)adenosine; (-)-N6-(benzyl)adenosine; MFCD00005740 |
| Molecular Formula | C17H19N5O4 |
| Molecular Weight | 357.364 |
| Purity | 98.00 |
| Density | 1.6±0.1 g/cm3 |
| Boiling Point | 689.3±65.0 °C at 760 mmHg |
| Melting Point | 184-186 °C |
| Appearance | white solid |
| Storage Condition | Store airtight in a cool, dry warehouse. |
| Application | N6 benzyladenosine is an adenosine receptor agonist with cellular activity. N6 benzyladenosine arrests the cell cycle in the G0/G1 phase and induces apoptosis. N6 benzyladenosine also has inhibitory e |
| SMILES | OCC1OC(n2cnc3c(NCc4ccccc4)ncnc32)C(O)C1O |
| InChI | InChI=1S/C17H19N5O4/c23-7-11-13(24)14(25)17(26-11)22-9-21-12-15(19-8-20-16(12)22)18-6-10-4-2-1-3-5-10/h1-5,8-9,11,13-14,17,23-25H,6-7H2,(H,18,19,20) |
| InChI Key | MRPKNNSABYPGBF-LSCFUAHRSA-N |
| Hazard Symbols | transportation |
| Bioactivity | 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. Chemical & Physical Properties 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 InChIKey MRPKNNSABYPGBF-LSCFUAHRSA-N SMILES OCC1OC(n2cnc3c(NCc4ccccc4)ncnc32)C(O)C1O Storage condition 2-8°C |
| Use of | Properties Name n6-benzyladenosine Synonym More Synonyms N-Benzyladenosine Biological Activity Related Catalog Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Research Areas >> Inflammation/Immunology Signaling Pathways >> GPCR/G Protein >> Adenosine Receptor 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. [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. Chemical & Physical Properties Molecular Formula C17H19N5O4 Exact Mass 357.143707 PSA 125.55000 Index of Refraction 1.763 InChIKey MRPKNNSABYPGBF-LSCFUAHRSA-N |
| Transport Info | Product name: Purity: 99.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: No dangerous goods IMDG Code: No dangerous goods International Air Transport Dangerous Regulations: No dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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