28128-33-8

Usage

Biological Activity

8-aminoadenine is an agonist of adenine receptor with ki value of 0.0341 μm [1].adenine receptor is a g protein-coupled receptor activated by the nucleoside adenosine. there are four types of adenosine receptors: a1, a2a, a2b and a3. a1 and a2a receptors play an important role in the heart, regulating coronary blood flow and myocardial oxygen consumption. a2b and a3 receptors are involved in inflammation and immune responses.8-aminoadenine is an adenine receptor agonist with ki values of 0.0341 and 6.51 μm for human and rat, respectively. in hek293 cell membrane, 8-aminoadenine was more potent than adenine (ki = 0.0471 μm) and exhibited 190-fold more potent than the rat binding site. in 1321n1 astrocytoma cells expressing the rade1r, 8-aminoadenine (500 μm) inhibited isoproterenol-stimulated camp accumulation, which suggested that 8-aminoadenine inhibited adenine uptake [1].

references

[1]. borrmann t, abdelrahman a, volpini r, et al. structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family. j med chem, 2009, 52(19): 5974-5989.

InChI:InChI=1/C5H6N6/c6-3-2-4(9-1-8-3)11-5(7)10-2/h1-2H,(H4,6,7,8,9,10,11)

Upstream product

• 6974-78-3 8-bromoadenine 
• 79270-98-7 8-Azidoadenine 
• 127820-06-8 8-Benzylaminoadenine 
• 127133-10-2 8-Amino-2',3'-dideoxyadenosine 
• 13231-00-0 diceto-6,8 purine 
• 19916-15-5 6,8-dichloro-7(9)H-purine 

Downstream Products

• 13389-09-8 8-amino-2'-deoxyadenosine 

Relevant academic research and scientific papers

Synthesis of 8-amino and 8-substituted amino derivatives of acyclic purine nucleoside and nucleotide analogs. Alkylation of 8-substituted purine bases

Two synthetic approaches were used for preparation of 8-amino-, 8-methylamino-, and 8-dimethylaminoadenine and -guanine analogs of PME and HPMP series: (a) direct modification of 8-bromopurine acyclic nucleotide analogs at the 8-position of the base, (b) alkylation of 8-modified purine bases with alkylation agents.

Synthesis of 8-amino-and N-substituted 8-aminoadenine derivatives of acyclic nucleoside and nucleotide analogs

8-Aminoadenine derivatives 2 were obtained from 8-bromoadenines 1 in one-pot reaction via 8-azidoadenines. Reaction of 8-bromoadenines 1 with methylamine or dimethylamine in ethanol afforded the corresponding N9-substituted 8-(methylamino)adeni

Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family

Adenine derivatives bearing substituents in the 2-, N6-, 7-, 8-, and/or 9-position and a series of deazapurines were synthesized and investigated in [3H]adenine binding studies at the adenine receptor in rat brain cortical membrane preparations (rAde1R). Steep structure-activity relationships were observed. Substitution in the 8-position (amino, dimethylamino, piperidinyl, piperazinyl) or in the 9-position (2-morpholinoethyl) with basic residues or introduction of polar substituents at the 6-amino function (hydroxy, amino, acetyl) represented the best modifications. Functional evaluation of selected adenine derivatives in adenylate cyclase assays at 1321N1 astrocytoma cells stably expressing the rAde1R showed that all compounds investigated were agonists or partial agonists. A subset of compounds was additionally investigated in binding studies at human embryonic kidney (HEK293) cells, which also express a high-affinity adenine binding site. Structure-affinity relationships at the human cell line were similar to those at the rAde1R, but not identical. In particular, N 6-acetyladenine (25, Ki rat: 2.85 μM; Ki human: 0.515 μM) and 8-aminoadenine (33, Ki rat: 6.51 μM; Ki human: 0.0341 μM) were much more potent at the human as compared to the rat binding site. The new AdeR ligands may serve as lead structures and contribute to the elucidation of the functions of the adenine receptor family. 2009 American Chemical Society.

Kinetics for the Acid-catalysed Hydrolysis of O-, S- and N-Bridged 5',8-Cyclonucleosides Related to Adenosine

Kinetics of the acid-catalysed hydrolysis of O5',8-cycloadenosine, S5',8-cyclo-5'-thioadenosine and N5',8-cyclo-5'-amino-5'-deoxyadenosine have been studied.The S- and N-bridged cyclonucleosides are hydrolysed exclusively by the rupture of the N-glycosidic bond, while the O-bridged compound undergoes concurrent cleavage of the N-glycosidic and 5',8-cyclo linkages, the proportion of the former reaction being markedly increased with increasing temperature.The conformations of the same cyclonucleosides have been elucidated by molecular modelling (SYBYL) and 1H NMR spectroscopy.The effect of the sugar ring puckering on the hydrolytic stability is discussed.

Purine Derivatives as Competitive Inhibitors of Human Erythrocyte Membrane Phosphatidylinositol 4-Kinase

The possibility of deriving a potent, cell-penetrating inhibitor of human erythrocyte PI 4-kinase, competitive with respect to ATP, has been investigated in a series of purine derivatives and analogues.The purine nucleus is not essential for binding to th