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

by Borbone, Nicola , Pannaccione, Anna , Oliviero, Giorgia , Petrozziello, Tiziana , Secondo, Agnese , Costantino, Valeria , Piccialli, Ilaria , D’Errico, Stefano , Mayol, Luciano , Piccialli, Gennaro , Catalanotti, Bruno

in Adenosine diphosphate / ADP / Anhydrides / Animals / Bridges / cADPR / Calcium / Calcium (intracellular) / Calcium - metabolism / Calcium ions / calcium mobilization / Cell Line, Tumor / Cyclic ADP-ribose / Cyclic ADP-Ribose - chemistry / Cyclic ADP-Ribose - metabolism / cyclization / Eggs / Evaluation / Invertebrates / macrocycle conformational sampling / Marine invertebrates / Neurons - metabolism / nucleotides / Ovum - metabolism / PC12 Cells / PC12 neuronal cells / Phosphates / Rats / Ribose / Sea Urchins - metabolism / Signal Transduction - physiology / Structure-Activity Relationship / Synthesis

2018

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

2018

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

2018

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Journal Article

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

Borbone, Nicola,

Pannaccione, Anna,

Oliviero, Giorgia,

Petrozziello, Tiziana,

Secondo, Agnese,

Costantino, Valeria,

Piccialli, Ilaria,

D’Errico, Stefano,

Mayol, Luciano,

Piccialli, Gennaro,

Catalanotti, Bruno

2018

Overview

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.

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Publisher

MDPI AG,MDPI

Subject

Adenosine diphosphate

/ ADP

/ Anhydrides

/ Animals

/ Bridges

/ cADPR

/ Calcium