Synthesis of cyclic N1-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells
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...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2015-12-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.11.289 |
| _version_ | 1818932915656982528 |
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| author | Ahmed Mahal Stefano D’Errico Nicola Borbone Brunella Pinto Agnese Secondo Valeria Costantino Valentina Tedeschi Giorgia Oliviero Vincenzo Piccialli Gennaro Piccialli |
| author_facet | Ahmed Mahal Stefano D’Errico Nicola Borbone Brunella Pinto Agnese Secondo Valeria Costantino Valentina Tedeschi Giorgia Oliviero Vincenzo Piccialli Gennaro Piccialli |
| author_sort | Ahmed Mahal |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-20T04:40:04Z |
| format | Article |
| id | doaj.art-c0a144f868cf4151ae35c3660c809dc9 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-20T04:40:04Z |
| publishDate | 2015-12-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-c0a144f868cf4151ae35c3660c809dc92022-12-21T19:53:10ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-12-011112689269510.3762/bjoc.11.2891860-5397-11-289Synthesis of cyclic N1-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cellsAhmed Mahal0Stefano D’Errico1Nicola Borbone2Brunella Pinto3Agnese Secondo4Valeria Costantino5Valentina Tedeschi6Giorgia Oliviero7Vincenzo Piccialli8Gennaro Piccialli9Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via D. Montesano 49, 80131, Napoli, ItalyDipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via D. Montesano 49, 80131, Napoli, ItalyDipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via D. Montesano 49, 80131, Napoli, ItalyDipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via D. Montesano 49, 80131, Napoli, ItalyDipartimento di Neuroscienze e Scienze Riproduttive ed Odontostomatologiche, Università degli Studi di Napoli Federico II, Via Pansini 5, 80131 Napoli, ItalyDipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via D. Montesano 49, 80131, Napoli, ItalyDipartimento di Neuroscienze e Scienze Riproduttive ed Odontostomatologiche, Università degli Studi di Napoli Federico II, Via Pansini 5, 80131 Napoli, ItalyDipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via D. Montesano 49, 80131, Napoli, ItalyDipartimento di Scienze Chimiche, Università degli Studi di Napoli Federico II, Napoli, ItalyDipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via D. Montesano 49, 80131, Napoli, ItalyCyclic 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.https://doi.org/10.3762/bjoc.11.289calcium mobilizationcIDPR analoguescyclic ADP-ribose (cADPR)cyclization |
| spellingShingle | Ahmed Mahal Stefano D’Errico Nicola Borbone Brunella Pinto Agnese Secondo Valeria Costantino Valentina Tedeschi Giorgia Oliviero Vincenzo Piccialli Gennaro Piccialli Synthesis of cyclic N1-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells Beilstein Journal of Organic Chemistry calcium mobilization cIDPR analogues cyclic ADP-ribose (cADPR) cyclization |
| title | Synthesis of cyclic N1-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells |
| title_full | Synthesis of cyclic N1-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells |
| title_fullStr | Synthesis of cyclic N1-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells |
| title_full_unstemmed | Synthesis of cyclic N1-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells |
| title_short | Synthesis of cyclic N1-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells |
| title_sort | synthesis of cyclic n1 pentylinosine phosphate a new structurally reduced cadpr analogue with calcium mobilizing activity on pc12 cells |
| topic | calcium mobilization cIDPR analogues cyclic ADP-ribose (cADPR) cyclization |
| url | https://doi.org/10.3762/bjoc.11.289 |
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