N6-(4-Hydroxybenzyl)adenosine - CAS 110505-75-4
Catalog number: 110505-75-4
Category: Inhibitor
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Molecular Formula:
C17H19N5O5
Molecular Weight:
373.36
COA:
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Targets:
P2Y Receptor
Description:
N6-(4-Hydroxybenzyl)adenosine, an imidazopyrimidine derivative, could be effective as an inhibitor of platelet aggregation. IC50: 6.77-141 μM.
Purity:
98%
Appearance:
Powder
Synonyms:
N6-(4-Hydroxybenzyl)-adenosine; 110505-75-4; N6-(4-hydroxybenzyl)adenine riboside; N6-(4-hydroxybenzyl)adenosine; CHEMBL224024; P-Topolin riboside
Solubility:
DMSO:≥ 3.8 mg/mL
Storage:
-20ºC Freeze
MSDS:
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Application:
N6-(4-Hydroxybenzyl)adenosine, an imidazopyrimidine derivative, could be effective as an inhibitor of platelet aggregation.
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Quantity:
Milligrams-Grams
InChIKey:
UGVIXKXYLBAZND-LSCFUAHRSA-N
InChI:
InChI=1S/C17H19N5O5/c23-6-11-13(25)14(26)17(27-11)22-8-21-12-15(19-7-20-16(12)22)18-5-9-1-3-10(24)4-2-9/h1-4,7-8,11,13-14,17,23-26H,5-6H2,(H,18,19,20)/t11-,13-,14-,17-/m1/s1
Canonical SMILES:
C1=CC(=CC=C1CNC2=NC=NC3=C2N=CN3C4C(C(C(O4)CO)O)O)O
1.Design and synthesis of novel dual-action compounds targeting the adenosine A(2A) receptor and adenosine transporter for neuroprotection.
Chen JB;Liu EM;Chern TR;Yang CW;Lin CI;Huang NK;Lin YL;Chern Y;Lin JH;Fang JM ChemMedChem. 2011 Aug 1;6(8):1390-400. doi: 10.1002/cmdc.201100126. Epub 2011 Jun 20.
A novel compound, N⁶-(4-hydroxybenzyl)adenosine, isolated from Gastrodia elata and which has been shown to be a potential therapeutic agent for preventing and treating neurodegenerative disease, was found to target both the adenosine A(2A) receptor (A(2A) R) and the equilibrative nucleoside transporter 1 (ENT1). As A(2A) R and ENT1 are proximal in the synaptic crevice of striatum, where the mutant huntingtin aggregate is located, the dual-action compounds that concomitantly target these two membrane proteins may be beneficial for the therapy of Huntington's disease. To design the desired dual-action compounds, pharmacophore models of the A(2A) R agonists and the ENT1 inhibitors were constructed. Accordingly, potentially active compounds were designed and synthesized by chemical modification of adenosine, particularly at the N⁶ and C⁵' positions, if the predicted activity was within an acceptable range. Indeed, some of the designed compounds exhibit significant dual-action properties toward both A(2A) R and ENT1. Both pharmacophore models exhibit good statistical correlation between predicted and measured activities. In agreement with competitive ligand binding assay results, these compounds also prevent apoptosis in serum-deprived PC12 cells, rendering a crucial function in neuroprotection and potential utility in the treatment of neurodegenerative diseases.
2.[Determination of N6-(4-hydroxybenzyl) adenine riboside in rat plasma by ultra performance liquid chromatography-quadrupole time of flight mass spectrometry].
Tang C;Wang L;Cheng M;Liu X;Xiao H Se Pu. 2015 Jul;33(7):699-703.
An ultra performance liquid chromatography-quadrupole time of flight mass spectrometry (UPLC-QTOF-MS) method was developed and validated for the determination of N6-(4-hydroxybenzyl) adenine riboside and its pharmacokinetics in rat plasma. The chromatographic conditions were optimized. The separation was performed on an Agilent ZORBAX SB-C18 column(150 mm x 3 mm, 1.8 μm) with a gradient elution of 0.2% (v/v) formic acid aqueous solution and acetonitrile as the mobile phases at a flow rate of 0.35 mL/min. The detection was accomplished in positive mode with electrospray ionization (ESI) by UPLC-QTOF-MS, and 6-benzylamino purine was used as the internal standard (IS). The results showed that the linear range of calibration curve was 0.625-160 ng/mL for N6-(4-hydroxybenzyl) adenine riboside in rat plasma with the correlation coefficient more than 0.99. The recoveries were 88.41%-108.26%. The limit of detection was 0.1 ng/mL. The intra-day and inter-day precisions (RSDs) were less than 6%, and intra-day and inter-day accuracies (REs, RE = (measured concentration-spiked concentration)/spiked concentration x 100%) were less than ±15%. The method is rapid, sensitive and accurate for the quantitation of N6-(4-hydroxybenzyl) adenine riboside, which can be used for the study of pharmacokinetics of N6-(4-hydroxybenzyl) adenine riboside.
3.Neuroprotective principles from Gastrodia elata.
Huang NK;Chern Y;Fang JM;Lin CI;Chen WP;Lin YL J Nat Prod. 2007 Apr;70(4):571-4. Epub 2007 Mar 24.
Serum deprivation-induced neuronal-like PC12 cell apoptosis was used as an ischemic/hypoxic model to screen neuroprotective compounds from the rhizomes of Gastrodia elata, a traditional Chinese medicine. Two active compounds, bis(4-hydroxybenzyl)sulfide (1) and N6-(4-hydroxybenzyl)adenine riboside (2), together with 15 known compounds were obtained from the active fraction. Compound 2 was further elucidated by chemical synthesis. Compounds 1 and 2 potently prevented PC12 cell apoptosis in concentration-dependent manners with EC50 values of 7.20 microM and 3.7 x 10-8 M, respectively, and IC50 values of 42.90 microM (Ki 24.10 microM) and 4.660 microM (Ki 2.620 microM), respectively, in an adenosine A2A receptor binding assay.
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