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Molecules (Basel, Switzerland)

Synthesis and calcium mobilization activity of cADPR analogues which integrate nucleobase, northern and southern ribose modifications.


PMID 22491682

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.

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C7344
Cyclic adenosine diphosphate-ribose, ≥90% (HPLC), lyophilized powder
C15H21N5O13P2