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.

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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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16 citations in Scopus
15 citations in Web of Science®
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ID Code: 15127
Item Type: Journal Article
Refereed: Yes
Keywords: Adenosine, Antioxidant, A1 adenosine receptor (A1AR) agonist
DOI: 10.1016/j.bmcl.2007.07.035
ISSN: 0960-894X
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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