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Molecules 2012, 17(4), 4343-4356; doi:10.3390/molecules17044343

Synthesis and Calcium Mobilization Activity of cADPR Analogues Which Integrate Nucleobase, Northern and Southern Ribose Modifications

1
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China
2
Department of Physiology, University of Hong Kong, Hong Kong, China
*
Author to whom correspondence should be addressed.
Received: 24 February 2012 / Revised: 31 March 2012 / Accepted: 5 April 2012 / Published: 10 April 2012
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Abstract

Novel cADPR mimics, which integrate nucleobase, northern and southern ribose modifications were synthesized. The key steps of the synthesis were a Cu(I)-catalyzed Hüisgen [3+2] cycloaddition and a microwave-assisted intramolecular pyrophosphorylation. Preliminary biological investigations showed that these cADPR mimics are membrane-permeating agonists of the calcium signaling pathway. The introduction of chlorine or fluorine at the 2'-position of the southern riboses led to a decrease of activity. The existence of a hydrophobic group on the 3'-OH of the southern riboses does not obviously alter the agonistic activity.
Keywords: cADPR analogue; nucleotide; synthesis; calcium mobilization cADPR analogue; nucleotide; synthesis; calcium mobilization
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Zhou, Y.; Yu, P.; Jin, H.; Yang, Z.; Yue, J.; Zhang, L.; Zhang, L. Synthesis and Calcium Mobilization Activity of cADPR Analogues Which Integrate Nucleobase, Northern and Southern Ribose Modifications. Molecules 2012, 17, 4343-4356.

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