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Bioorg Med Chem. 2010 Oct 1;18(19):7015-21. doi: 10.1016/j.bmc.2010.08.018. Epub 2010 Aug 14.

Design, synthesis, and binding of homologated truncated 4'-thioadenosine derivatives at the human A3 adenosine receptors.

Author information

1
Department of Bioinspired Science, College of Pharmacy, Ewha Womans University, Seoul 120-750, Republic of Korea.

Abstract

We synthesized homologated truncated 4'-thioadenosine analogues 3 in which a methylene (CH(2)) group was inserted in place of the glycosidic bond of a potent and selective A(3) adenosine receptor antagonist 2. The analogues were designed to induce maximum binding interaction in the binding site of the A(3) adenosine receptor. However, all homologated nucleosides were devoid of binding affinity at all subtypes of adenosine receptors, indicating that free rotation through the single bond allowed the compound to adopt an indefinite number of conformations, disrupting the favorable binding interaction essential for receptor recognition.

PMID:
20826090
PMCID:
PMC3724522
DOI:
10.1016/j.bmc.2010.08.018
[Indexed for MEDLINE]
Free PMC Article

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