'Click cyclic ADP-ribose': a neutral second messenger mimic

Analogues of the potent Ca(2+) releasing second messenger cyclic ADP-ribose (cADPR) with a 1,2,3-triazole pyrophosphate bioisostere were synthesised by click-mediated macrocyclisation. The ability to activate Ca(2+) release was surprisingly retained, and hydrolysis of cADPR by CD38 could also be inh...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2014-01, Vol.50 (19), p.2458-2461
Main Authors: Swarbrick, Joanna M, Graeff, Richard, Garnham, Clive, Thomas, Mark P, Galione, Antony, Potter, Barry V L
Format: Article
Language:English
Subjects:
Animals
Calcium - metabolism
Click Chemistry
Cyclic ADP-Ribose - chemistry
Cyclic ADP-Ribose - pharmacology
Diphosphates - chemistry
Female
Hydrolysis
Inhibition
Modulators
Ovum
Pathways
Releasing
Sea Urchins
Second Messenger Systems
Signalling
Synthesis
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Summary:Analogues of the potent Ca(2+) releasing second messenger cyclic ADP-ribose (cADPR) with a 1,2,3-triazole pyrophosphate bioisostere were synthesised by click-mediated macrocyclisation. The ability to activate Ca(2+) release was surprisingly retained, and hydrolysis of cADPR by CD38 could also be inhibited, illustrating the potential of this approach to design drug-like signalling pathway modulators.
ISSN:1359-7345
1364-548X
DOI:10.1039/c3cc49249d