8-Aminoadenine - CAS 28128-33-8
Category: Inhibitor
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Molecular Formula:
C5H6N6
Molecular Weight:
150.14
COA:
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Targets:
Adenosine Receptor
Description:
8-Aminoadenine is an adenine receptor agonist with Ki value of 0.0341 μM in HEK293 cells expressing an adenine binding site. It shows 190-fold increased potency at the human binding site over the rat adenine receptor. It inhibits adenine uptake and isoproterenol-stimulated cAMP accumulation. It may be used in the synthetic preparation of purine derivatives as competitive inhibitors of human erythrocyte membrane phosphatidylinositol 4-kinase. It is important in regulating myocardial oxygen consumption and coronary blood flow. It may take part in inflammation and immune responses.
Purity:
≥98% by HPLC
Synonyms:
9H-Purine-6,8-diamine; 1H-Purine-6,8-diamine (9CI); 6,8-Diamino-purine (8CI); NSC 21698
MSDS:
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InChIKey:
PFUVOLUPRFCPMN-UHFFFAOYSA-N
InChI:
InChI=1S/C5H6N6/c6-3-2-4(9-1-8-3)11-5(7)10-2/h1H,(H5,6,7,8,9,10,11)
Canonical SMILES:
C1=NC2=C(C(=N1)N)NC(=N2)N
1.Theoretical calculations, synthesis and base pairing properties of oligonucleotides containing 8-amino-2'-deoxyadenosine.
García RG;Ferrer E;Macías MJ;Eritja R;Orozco M Nucleic Acids Res. 1999 May 1;27(9):1991-8.
Theoretical calculations on double and triple helices containing 8-amino-2'-deoxyadenosine were made to analyze the possible differences in base pairing properties between 8-aminoadenine and adenine. These calculations indicate a strong preferential stabilization of the triplex over the duplex when adenine is replaced by 8-aminoadenine. In addition, a protected phosphoramidite derivative of 8-amino-2'-deoxyadenosine was prepared for the introduction of 8-aminoadenine into synthetic oligonucleotides using the phosphite-triester approach. DNA triple helical structures are normally observed at acidic pH. However, when oligonucleotides carrying 8-aminoadenine are used, very stable triple helical structures can be observed even at neutral pH. Biological applications of triple helices could benefit from the use of 8-aminoadenine derivatives.
2.Property editing of peptide nucleic acids (PNA): gem-dimethyl, cyanuryl and 8-aminoadenine PNAs.
Ganesh KN;Gourishankar A;Vysabhattar R;Bokil P Nucleic Acids Symp Ser (Oxf). 2007;(51):17-8.
We herein describe the introduction of gem-dimethyl substitution into the aminoethylglycyl backbone of PNA to impart steric constraint and pre-organise PNA for selective recognition of nucleic acids. Introduction of cyanuric acid and 8-aminoadenine as pyrimidine and purine analogs that can form base pairing from either face is also described to overcome the rotameric problems in PNA sidechain orientations and thereby enhance the statistical probability for base pairing. The UV-thermal melting studies of the derived triplexes with complementary DNA provide support for this rationale.
3.Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family.
Borrmann T;Abdelrahman A;Volpini R;Lambertucci C;Alksnis E;Gorzalka S;Knospe M;Schiedel AC;Cristalli G;Müller CE J Med Chem. 2009 Oct 8;52(19):5974-89. doi: 10.1021/jm9006356.
Adenine derivatives bearing substituents in the 2-, N(6)-, 7-, 8-, and/or 9-position and a series of deazapurines were synthesized and investigated in [(3)H]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, K(i) rat: 2.85 microM; K(i) human: 0.515 microM) and 8-aminoadenine (33, K(i) rat: 6.51 microM; K(i) human: 0.
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CAS 28128-33-8 8-Aminoadenine

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