Abstract
We synthesized homologated truncated 4′-thioadenosine analogues 3 in which a methylene (CH2) group was inserted in place of the glycosidic bond of a potent and selective A3 adenosine receptor antagonist 2. The analogues were designed to induce maximum binding interaction in the binding site of the A3 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.
Original language | English |
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Pages (from-to) | 7015-7021 |
Number of pages | 7 |
Journal | Bioorganic and Medicinal Chemistry |
Volume | 18 |
Issue number | 19 |
DOIs | |
State | Published - 1 Oct 2010 |
Bibliographical note
Funding Information:This work was supported by the grant from the Korea Research Foundation ( NRF-2008-314-E00304 ) and the NIDDK Intramural Research Program . H.W.L. acknowledges the research professor fellowship from the Ewha Womans University (2009).
Keywords
- A adenosine receptor
- Binding affinity
- Homologation
- Truncated 4′-thioadenosine