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, respectively, was synthesized. The role played by the position of the phosphate group in the key cyclization step, which consists in the formation of a phosphodiester bond, was thoroughly investigated. We have also examined the influence of the phosphate bridge on the ability of cpIMP to mobilize Ca2+ in PC12 neuronal cells in comparison with the pyrophosphate bridge present in the cyclic N1-pentylinosine diphosphate analogue (cpIDP) previously synthesized in our laboratories. The preliminary biological tests indicated that cpIMP and cpIDP induce a rapid increase of intracellular Ca2+ concentration in PC12 neuronal cells.

Synthesis of cyclic N1-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells / Mahal, Ahmed; D'Errico, Stefano; Borbone, Nicola; Pinto, Brunella; Secondo, Agnese; Costantino, Valeria; Tedeschi, Valentina; Oliviero, Giorgia; Piccialli, Vincenzo; Piccialli, Gennaro. - In: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1860-5397. - 11:(2015), pp. 2689-2695. [10.3762/bjoc.11.289]

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

D'ERRICO, STEFANO;BORBONE, NICOLA;PINTO, BRUNELLA;SECONDO, AGNESE;COSTANTINO, VALERIA;TEDESCHI, VALENTINA;OLIVIERO, GIORGIA;PICCIALLI, VINCENZO;PICCIALLI, GENNARO
2015

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, respectively, was synthesized. The role played by the position of the phosphate group in the key cyclization step, which consists in the formation of a phosphodiester bond, was thoroughly investigated. We have also examined the influence of the phosphate bridge on the ability of cpIMP to mobilize Ca2+ in PC12 neuronal cells in comparison with the pyrophosphate bridge present in the cyclic N1-pentylinosine diphosphate analogue (cpIDP) previously synthesized in our laboratories. The preliminary biological tests indicated that cpIMP and cpIDP induce a rapid increase of intracellular Ca2+ concentration in PC12 neuronal cells.
2015
Synthesis of cyclic N1-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells / Mahal, Ahmed; D'Errico, Stefano; Borbone, Nicola; Pinto, Brunella; Secondo, Agnese; Costantino, Valeria; Tedeschi, Valentina; Oliviero, Giorgia; Piccialli, Vincenzo; Piccialli, Gennaro. - In: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1860-5397. - 11:(2015), pp. 2689-2695. [10.3762/bjoc.11.289]
File in questo prodotto:
File Dimensione Formato  
1860-5397-11-289-2.pdf

accesso aperto

Descrizione: Articolo principale
Tipologia: Altro materiale allegato
Licenza: Creative commons
Dimensione 445.6 kB
Formato Adobe PDF
445.6 kB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/635109
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 20
  • ???jsp.display-item.citation.isi??? 19
social impact