Synthesis of cyclic N¹-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells

• Ahmed Mahal,
• Stefano D’Errico,
• Nicola Borbone,
• Brunella Pinto,
• Agnese Secondo,
• Valeria Costantino,
• Valentina Tedeschi,
• Giorgia Oliviero,
• Vincenzo Piccialli and
• Gennaro Piccialli

Beilstein J. Org. Chem. 2015, 11, 2689–2695, doi:10.3762/bjoc.11.289

• Pietro Castellino 111, 80131 Napoli, Italy 10.3762/bjoc.11.289 Abstract Cyclic N1-pentylinosine monophosphate (cpIMP), a novel simplified inosine derivative of cyclic ADP-ribose (cADPR) in which the N1-pentyl chain and the monophosphate group replace the northern ribose and the pyrophosphate moieties

• neuronal cells. Keywords: calcium mobilization; cIDPR analogues; cyclic ADP-ribose (cADPR); cyclization; Introduction Nucleosides and nucleotides (NNs) are widely used as key intermediates and important core structures in the field of synthetic medicinal chemistry [1][2]. They represent versatile

• ]. Among these NNs there is the cyclic ADP-ribose (cADPR 1, Figure 1), a metabolite strictly involved in the homeostasis of cellular calcium ions. cADPR is a second messenger that activates the ryanodine receptors of the sarcoplasmic reticulum and mobilizes Ca2+ ions in many cell types of protozoa, plants