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

被引：15

作者：

Lee, Hyuk Woo ^{[1
]}

Kim, Hea Ok ^{[2
]}

Choi, Won Jun ^{[1
,3
]}

Choi, Sun ^{[2
]}

Lee, Jin Hee ^{[2
]}

Park, Seul-gi ^{[2
]}

Yoo, Lena ^{[4
]}

Jacobson, Kenneth A. ^{[4
]}

Jeong, Lak Shin ^{[1
,2
]}

机构：

[1] Ewha Womans Univ, Dept Bioinspired Sci, Coll Pharm, Seoul 120750, South Korea

[2] Ewha Womans Univ, Coll Pharm, Med Chem Lab, Seoul 120750, South Korea

[3] Dongguk Univ, Coll Pharm, Kyonggi Do 410774, South Korea

[4] Natl Inst Diabet Digest Dis & Kidney Dis, Mol Recognit Sect, Bioorgan Chem Lab, NIH, Bethesda, MD 20892 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2010年 / 18卷 / 19期

关键词：

Homologation; A(3) adenosine receptor; Binding affinity; Truncated 4 '-thioadenosine; STRUCTURAL DETERMINANTS; SELECTIVE AGONISTS; HIGHLY POTENT; LIGANDS; D-4'-THIOADENOSINE; ANTAGONISTS; EFFICACY;

D O I：

10.1016/j.bmc.2010.08.018

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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 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. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：7015 / 7021

页数：7

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