Dual acting antioxidant A1 adenosine receptor agonists
Gregg, Alison D., Bottle, Steven E., Devine, Shane M., Figler, Heidi, Linden, Joel, White, Paul, Pouton, Colin W., Urmaliya, Vijay, & Scammells, Peter J. (2007) Dual acting antioxidant A1 adenosine receptor agonists. Bioorganic & Medicinal Chemistry Letters, 17(9), pp. 5437-5441.
Herein we report the synthesis and biological evaluation of some potent and selective A1 adenosine receptor agonists, which incorporate a functionalised linker attached to an antioxidant moiety. N6-(2,2,5,5-Tetramethylpyrrolidin-1-yloxyl-3-ylmethyl)adenosine (VCP28, 2e) proved to be an agonist with high affinity (Ki = 50 nM) and good selectivity (A3/A1 400) for the A1 adenosine receptor. N6-[4-[2-[1,1,3,3-Tetramethylisoindolin-2-yloxyl-5-amido]ethyl]phenyl]adenosine (VCP102, 5a) has higher binding affinity (Ki = 7 nM), but lower selectivity (A3/A1 = 3). All compounds bind weakly (Ki > 1 μM) to A2A and A2B receptors. The combination of A1 agonist activity and antioxidant activity has the potential to produce cardioprotective effects.
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|Item Type:||Journal Article|
|Keywords:||Adenosine, Antioxidant, A1 adenosine receptor (A1AR) agonist|
|Subjects:||Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > MEDICINAL AND BIOMOLECULAR CHEMISTRY (030400) > Medicinal and Biomolecular Chemistry not elsewhere classified (030499)|
|Divisions:||Past > QUT Faculties & Divisions > Faculty of Science and Technology|
|Copyright Owner:||Copyright 2007 Elsevier|
|Copyright Statement:||Reproduced in accordance with the copyright policy of the publisher.|
|Deposited On:||13 Oct 2008 00:00|
|Last Modified:||29 Feb 2012 13:37|
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