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Mar. Drugs 2018, 16(3), 89; https://doi.org/10.3390/md16030089

Synthesis and Biological Evaluation of a New Structural Simplified Analogue of cADPR, a Calcium-Mobilizing Secondary Messenger Firstly Isolated from Sea Urchin Eggs

1
Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, via Domenico Montesano 49, 80131 Napoli, Italy
2
SYSBIO, Centre of Systems Biology, University of Milano-Bicocca, Piazza della Scienza 2, 20126 Milano, Italy
3
Divisione di Farmacologia, Dipartimento di Neuroscienze, Scienze Riproduttive e Odontostomatologiche, Università degli Studi di Napoli Federico II, Via Sergio Pansini 5, 80131 Napoli, Italy
4
Dipartimento di Biologia Molecolare e Biotecnologie Mediche, Università degli Studi di Napoli Federico II, via Sergio Pansini 5, 80131 Napoli, Italy
*
Author to whom correspondence should be addressed.
Received: 2 January 2018 / Revised: 5 March 2018 / Accepted: 7 March 2018 / Published: 10 March 2018
(This article belongs to the Special Issue Marine Secondary Metabolite II, 2017)
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Abstract

Herein, we reported on the synthesis of cpIPP, which is a new structurally-reduced analogue of cyclic ADP-ribose (cADPR), a potent Ca2+-releasing secondary messenger that was firstly isolated from sea urchin eggs extracts. To obtain cpIPP the “northern” ribose of cADPR was replaced by a pentyl chain and the pyrophosphate moiety by a phophono-phosphate anhydride. The effect of the presence of the new phosphono-phosphate bridge on the intracellular Ca2+ release induced by cpIPP was assessed in PC12 neuronal cells in comparison with the effect of the pyrophosphate bridge of the structurally related cyclic N1-butylinosine diphosphate analogue (cbIDP), which was previously synthesized in our laboratories, and with that of the linear precursor of cpIPP, which, unexpectedly, revealed to be the only one provided with Ca2+ release properties. View Full-Text
Keywords: cADPR; calcium mobilization; PC12 neuronal cells; cyclization; nucleotides; macrocycle conformational sampling cADPR; calcium mobilization; PC12 neuronal cells; cyclization; nucleotides; macrocycle conformational sampling
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D’Errico, S.; Borbone, N.; Catalanotti, B.; Secondo, A.; Petrozziello, T.; Piccialli, I.; Pannaccione, A.; Costantino, V.; Mayol, L.; Piccialli, G.; Oliviero, G. Synthesis and Biological Evaluation of a New Structural Simplified Analogue of cADPR, a Calcium-Mobilizing Secondary Messenger Firstly Isolated from Sea Urchin Eggs. Mar. Drugs 2018, 16, 89.

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