N6-Benzyladenosine (Synonyms: Benzyladenosine)

Name: N6-Benzyladenosine
Brand: MedChemExpress
SKU: HY-N7844
Rating: 4.5 (1 reviews)

Cat. No.: HY-N7844 Purity: 99.43%: FAQs
Data Sheet SDS COA Handling Instructions Technical Support

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^-.

For research use only. We do not sell to patients.

N6-Benzyladenosine Chemical Structure

CAS No. : 4294-16-0

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10 mM * 1 mL in DMSO ready for reconstitution	In-stock	Estimated Time of Arrival: December 31
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10 mM * 1 mL in DMSO	In-stock	Estimated Time of Arrival: December 31
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100 mg	In-stock	Estimated Time of Arrival: December 31
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Based on 1 publication(s) in Google Scholar

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Adenosine A₁ receptor (A₁R) Adenosine A_2A receptor (A_2AR) Adenosine A_2B receptor (A_2BR) Adenosine A₃ receptor (A₃R)

Biological Activity
Purity & Documentation
References
Customer Review

Description

Cellular Effect

Cell Line	Type	Value	Description	References
B16	IC₅₀	> 166.7 μM Compound: BAPR	Antitumor activity against mouse B16 cells after 72 hrs by Calcein AM assay Antitumor activity against mouse B16 cells after 72 hrs by Calcein AM assay	[PMID: 17418578]
Caco-2	GI₅₀	7.4 μM Compound: 19, BnA	Antitumor activity against human CaCo2 cells after 48 hrs by MTS assay Antitumor activity against human CaCo2 cells after 48 hrs by MTS assay	[PMID: 18588281]
CCRF-CEM	IC₅₀	1.4 μM Compound: BAPR	Antitumor activity against human CEM cells after 72 hrs by Calcein AM assay Antitumor activity against human CEM cells after 72 hrs by Calcein AM assay	[PMID: 17418578]
G-361	IC₅₀	> 166.7 μM Compound: BAPR	Antitumor activity against human G361 cells after 72 hrs by Calcein AM assay Antitumor activity against human G361 cells after 72 hrs by Calcein AM assay	[PMID: 17418578]
HL-60	IC₅₀	0.94 μM Compound: BAPR	Antitumor activity against human HL60 cells after 72 hrs by Calcein AM assay Antitumor activity against human HL60 cells after 72 hrs by Calcein AM assay	[PMID: 17418578]
HOS	IC₅₀	> 166.7 μM Compound: BAPR	Antitumor activity against human HOS cells after 72 hrs by Calcein AM assay Antitumor activity against human HOS cells after 72 hrs by Calcein AM assay	[PMID: 17418578]
HT-29	GI₅₀	22.3 μM Compound: 19, BnA	Antitumor activity against human HT29 cells after 48 hrs by MTS assay Antitumor activity against human HT29 cells after 48 hrs by MTS assay	[PMID: 18588281]
K562	GI₅₀	2.92 μM Compound: 19, BnA	Growth inhibition of 0.1 uM 1,4-dihydro-2-methyl-6-phenyl-4-(phenylethyl)-3,5-pyridine-dicarboxylic acid 3-ethyl-5-[(3-nitrophenyl) methyl] ester pretreated human K562 cells after 72 hrs by MTS assay Growth inhibition of 0.1 uM 1,4-dihydro-2-methyl-6-phenyl-4-(phenylethyl)-3,5-pyridine-dicarboxylic acid 3-ethyl-5-[(3-nitrophenyl) methyl] ester pretreated human K562 cells after 72 hrs by MTS assay	[PMID: 18588281]
K562	GI₅₀	2.92 μM Compound: 19, BnA	Growth inhibition of 1 uM 1,4-dihydro-2-methyl-6-phenyl-4-(phenylethyl)-3,5-pyridine-dicarboxylic acid 3-ethyl-5-[(3-nitrophenyl) methyl] ester pretreated human K562 cells after 72 hrs by MTS assay Growth inhibition of 1 uM 1,4-dihydro-2-methyl-6-phenyl-4-(phenylethyl)-3,5-pyridine-dicarboxylic acid 3-ethyl-5-[(3-nitrophenyl) methyl] ester pretreated human K562 cells after 72 hrs by MTS assay	[PMID: 18588281]
K562	GI₅₀	3.91 μM Compound: 19, BnA	Growth inhibition of 0.1 uM 1,4-dihydro-2-methyl-6-phenyl-4-(phenylethyl)-3,5-pyridine-dicarboxylic acid 3-ethyl-5-[(3-nitrophenyl) methyl] ester pretreated human K562 cells after 48 hrs by MTS assay Growth inhibition of 0.1 uM 1,4-dihydro-2-methyl-6-phenyl-4-(phenylethyl)-3,5-pyridine-dicarboxylic acid 3-ethyl-5-[(3-nitrophenyl) methyl] ester pretreated human K562 cells after 48 hrs by MTS assay	[PMID: 18588281]
K562	GI₅₀	4.17 μM Compound: 19, BnA	Growth inhibition of 1 uM 1,4-dihydro-2-methyl-6-phenyl-4-(phenylethyl)-3,5-pyridine-dicarboxylic acid 3-ethyl-5-[(3-nitrophenyl) methyl] ester pretreated human K562 cells after 48 hrs by MTS assay Growth inhibition of 1 uM 1,4-dihydro-2-methyl-6-phenyl-4-(phenylethyl)-3,5-pyridine-dicarboxylic acid 3-ethyl-5-[(3-nitrophenyl) methyl] ester pretreated human K562 cells after 48 hrs by MTS assay	[PMID: 18588281]
K562	GI₅₀	4.6 μM Compound: 19, BnA	Antitumor activity against human K562 cells after 48 hrs by MTS assay Antitumor activity against human K562 cells after 48 hrs by MTS assay	[PMID: 18588281]
K562	IC₅₀	5.5 μM Compound: BAPR	Antitumor activity against human K562 cells after 72 hrs by Calcein AM assay Antitumor activity against human K562 cells after 72 hrs by Calcein AM assay	[PMID: 17418578]
MCF7	GI₅₀	61 μM Compound: 19, BnA	Antitumor activity against human MCF7 cells after 48 hrs by MTS assay Antitumor activity against human MCF7 cells after 48 hrs by MTS assay	[PMID: 18588281]
NIH3T3	IC₅₀	39 μM Compound: BAPR	Cytotoxicity against mouse NIH 3T3 cells after 72 hrs by Calcein AM assay Cytotoxicity against mouse NIH 3T3 cells after 72 hrs by Calcein AM assay	[PMID: 17418578]
Platelet	IC₅₀	37.12 μM Compound: 2d	Inhibition of collagen-induced human platelet aggregation after 3 mins by light transmission aggregometry Inhibition of collagen-induced human platelet aggregation after 3 mins by light transmission aggregometry	[PMID: 25467153]
RD	EC₅₀	0.28 μM Compound: 23	Antiviral activity against Enterovirus 71 infected in human RD cells assessed as cell viability after 3 days by MTS assay Antiviral activity against Enterovirus 71 infected in human RD cells assessed as cell viability after 3 days by MTS assay	[PMID: 26854380]

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 K_m =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].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

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.

Molecular Weight

357.36

Formula

C₁₇H₁₉N₅O₄

CAS No.

4294-16-0

Appearance

Solid

Color

White to off-white

SMILES

O[C@H]1[C@@H](O)[C@H](N2C(N=CN=C3NCC4=CC=CC=C4)=C3N=C2)O[C@@H]1CO

Structure Classification

Others

Initial Source

Plants

Umbelliferae

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

4°C, protect from light

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Solvent & Solubility

In Vitro:

DMSO : 125 mg/mL (349.79 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	2.7983 mL	13.9915 mL	27.9830 mL
5 mM	0.5597 mL	2.7983 mL	5.5966 mL
10 mM	0.2798 mL	1.3991 mL	2.7983 mL

View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

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In Vivo Dissolution Calculator

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Purity & Documentation

Purity: 99.43%

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Data Sheet (278 KB) SDS (393 KB)

COA (253 KB) HNMR (255 KB) LCMS (271 KB)

Handling Instructions (2659 KB)

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. [Content Brief]

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

[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. [Content Brief]

[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. [Content Brief]

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg

DMSO	1 mM	2.7983 mL	13.9915 mL	27.9830 mL	69.9575 mL
	5 mM	0.5597 mL	2.7983 mL	5.5966 mL	13.9915 mL
	10 mM	0.2798 mL	1.3991 mL	2.7983 mL	6.9957 mL
	15 mM	0.1866 mL	0.9328 mL	1.8655 mL	4.6638 mL
	20 mM	0.1399 mL	0.6996 mL	1.3991 mL	3.4979 mL
	25 mM	0.1119 mL	0.5597 mL	1.1193 mL	2.7983 mL
	30 mM	0.0933 mL	0.4664 mL	0.9328 mL	2.3319 mL
	40 mM	0.0700 mL	0.3498 mL	0.6996 mL	1.7489 mL
	50 mM	0.0560 mL	0.2798 mL	0.5597 mL	1.3991 mL
	60 mM	0.0466 mL	0.2332 mL	0.4664 mL	1.1660 mL
	80 mM	0.0350 mL	0.1749 mL	0.3498 mL	0.8745 mL
	100 mM	0.0280 mL	0.1399 mL	0.2798 mL	0.6996 mL

N6-Benzyladenosine Related Classifications

Reference Standards

Natural Product Standards

Others

Inflammation/Immunology Cancer

Cancer Targeted Therapy Cancer Metabolism and Metastasis

Apoptosis GPCR/G Protein

Apoptosis Adenosine Receptor

Help & FAQs

Do most proteins show cross-species activity?
Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

N6-Benzyladenosine4294-16-0BenzyladenosineApoptosisAdenosine ReceptorP1 receptorFPPSFarnesyl pyrophosphate synthasemass spectrometryanti-tumorneoplastic cellscaspase-3/9anti-toxoplasmaadenosine kinaseTgAKS3gliomabenzyladenosine hydroxylatedcytokinin activityInhibitorinhibitorinhibit

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N6-Benzyladenosine (Synonyms: Benzyladenosine)

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