Click
here to close Hello! We notice that
you are using Internet Explorer, which is not supported by Echinobase
and may cause the site to display incorrectly. We suggest using a
current version of Chrome,
FireFox,
or Safari.
Mar Drugs
2019 Aug 17;178:. doi: 10.3390/md17080476.
Show Gene links
Show Anatomy links
New Linear Precursors of cIDPR Derivatives as Stable Analogs of cADPR: A Potent Second Messenger with Ca2+-Modulating Activity Isolated from Sea Urchin Eggs.
D'Errico S
,
Basso E
,
Falanga AP
,
Marzano M
,
Pozzan T
,
Piccialli V
,
Piccialli G
,
Oliviero G
,
Borbone N
.
???displayArticle.abstract???
Herein, we report on the synthesis of a small set of linear precursors of an inosine analogue of cyclic ADP-ribose (cADPR), a second messenger involved in Ca2+ mobilization from ryanodine receptor stores firstly isolated from sea urchin eggs extracts. The synthesized compounds were obtained starting from inosine and are characterized by an N1-alkyl chain replacing the "northern" ribose and a phosphate group attached at the end of the N1-alkyl chain and/or 5''-sugar positions. Preliminary Ca2+ mobilization assays, performed on differentiated C2C12 cells, are reported as well.
Figure 1. The structures of cyclic adenosine diphosphate ribose (cADRP; 1) and some of its analogues (2–5).
Scheme 1. Reagents and conditions. (i) 7a–c, N,N-dimethylformamide (DMF), 50 °C, 16 h; (ii) tetrabutylammonium fluoride (TBAF), tetrahydrofuran (THF), r.t., 1 h; (iii) (a) di-tert-butyl N,N-diisopropylphosphoramidite ((tBuO)2PN(iPr)2), 1-H-tetrazole, THF, r.t., 6 h, (b) tert-butyl hydroperoxide (tBuOOH), THF, r.t., 1 h; (iv) 50% trifluoroacetic acid (TFA) in H2O, r.t., 4 h.
Scheme 2. Reagents and conditions. (i) 50% TFA in H2O, r.t., 4 h.
Figure 2. Effect of compounds 11a–c (left), 14a–c, 16, and 18 (right) on cytosolic [Ca2+]. Representative traces of normalized Fura-2 fluorescence ratio for differentiated C2C12 cells. 1 µM of each compound was added, then 10 mM caffeine was added 5 min after the addition of each compound as a control for Ca2+ release from ryanodine receptors. The inset in the left panel shows 10 mM caffeine addition to untreated cells.
Airey,
Ryanodine receptor protein is expressed during differentiation in the muscle cell lines BC3H1 and C2C12.
1991, Pubmed
Airey,
Ryanodine receptor protein is expressed during differentiation in the muscle cell lines BC3H1 and C2C12.
1991,
Pubmed
Barbado,
Gene regulation by voltage-dependent calcium channels.
2009,
Pubmed
Baszczyňski,
Synthesis of Terminal Ribose Analogues of Adenosine 5'-Diphosphate Ribose as Probes for the Transient Receptor Potential Cation Channel TRPM2.
2019,
Pubmed
Cho,
A focus on extracellular Ca2+ entry into skeletal muscle.
2017,
Pubmed
Clapham,
Calcium signaling.
2007,
Pubmed
Clapper,
Pyridine nucleotide metabolites stimulate calcium release from sea urchin egg microsomes desensitized to inositol trisphosphate.
1987,
Pubmed
,
Echinobase
D'Errico,
A facile synthesis of 5'-fluoro-5'-deoxyacadesine (5'-F-AICAR): a novel non-phosphorylable AICAR analogue.
2012,
Pubmed
D'Errico,
Synthesis of new acadesine (AICA-riboside) analogues having acyclic D-ribityl or 4-hydroxybutyl chains in place of the ribose.
2013,
Pubmed
D'Errico,
Synthesis of 5-Aminoimidazole-4-Carboxamide Riboside (AICAR) and Its Derivatives Using Inosine as Starting Material.
2015,
Pubmed
D'Errico,
Synthesis and Biological Evaluation of a New Structural Simplified Analogue of cADPR, a Calcium-Mobilizing Secondary Messenger Firstly Isolated from Sea Urchin Eggs.
2018,
Pubmed
,
Echinobase
D'Errico,
Solid-phase synthesis of a new diphosphate 5-aminoimidazole-4-carboxamide riboside (AICAR) derivative and studies toward cyclic AICAR diphosphate ribose.
2011,
Pubmed
Dutka,
Effects of carnosine on contractile apparatus Ca²⁺ sensitivity and sarcoplasmic reticulum Ca²⁺ release in human skeletal muscle fibers.
2012,
Pubmed
Fliegert,
Regulation of calcium signalling by adenine-based second messengers.
2007,
Pubmed
Galione,
Cyclic ADP-ribose and the regulation of calcium-induced calcium release in eggs and cardiac myocytes.
1998,
Pubmed
,
Echinobase
Gul,
Nicotinic Acid Adenine Dinucleotide Phosphate (NAADP) and Cyclic ADP-Ribose (cADPR) Mediate Ca2+ Signaling in Cardiac Hypertrophy Induced by β-Adrenergic Stimulation.
2016,
Pubmed
Guse,
Regulation of calcium signalling in T lymphocytes by the second messenger cyclic ADP-ribose.
1999,
Pubmed
Guse,
Novel hydrolysis-resistant analogues of cyclic ADP-ribose: modification of the "northern" ribose and calcium release activity.
2002,
Pubmed
Guse,
Biochemistry, biology, and pharmacology of cyclic adenosine diphosphoribose (cADPR).
2004,
Pubmed
Guse,
Second messenger function and the structure-activity relationship of cyclic adenosine diphosphoribose (cADPR).
2005,
Pubmed
Higashida,
Cyclic ADP-ribose as a potential second messenger for neuronal Ca2+ signaling.
2001,
Pubmed
Kolisek,
Cyclic ADP-ribose and hydrogen peroxide synergize with ADP-ribose in the activation of TRPM2 channels.
2005,
Pubmed
Mahal,
Synthesis of cyclic N (1)-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells.
2015,
Pubmed
Mangoni,
The new carotenoid pigment moraxanthin is associated with toxic microalgae.
2011,
Pubmed
Moreau,
CD38 Structure-Based Inhibitor Design Using the N1-Cyclic Inosine 5'-Diphosphate Ribose Template.
2013,
Pubmed
Neher,
Multiple roles of calcium ions in the regulation of neurotransmitter release.
2008,
Pubmed
Oliviero,
Synthesis of a new N-9 ribityl analogue of cyclic inosine diphosphate ribose (cIDPR) as a mimic of cyclic ADP ribose (cADPR).
2005,
Pubmed
Oliviero,
Synthesis of a new ribose modified analogue of cyclic inosine diphosphate ribose.
2007,
Pubmed
Oliviero,
Synthesis of N-1-alkyl analogues of cyclic inosine diphosphate ribose (cIDPR) by a new solid phase approach.
2008,
Pubmed
Pinto,
Calcium signaling and cell proliferation.
2015,
Pubmed
Potter,
Medicinal chemistry and pharmacology of cyclic ADP-ribose.
2004,
Pubmed
Qi,
A novel membrane-permeant cADPR antagonist modified in the pyrophosphate bridge.
2011,
Pubmed
Rosen,
Synthesis and use of cell-permeant cyclic ADP-ribose.
2012,
Pubmed
,
Echinobase
Ríos,
Calcium-induced release of calcium in muscle: 50 years of work and the emerging consensus.
2018,
Pubmed
Shuto,
Chemistry of cyclic ADP-ribose and its analogs.
2004,
Pubmed
Swarbrick,
Total synthesis of a cyclic adenosine 5'-diphosphate ribose receptor agonist.
2012,
Pubmed
Swarbrick,
'Click cyclic ADP-ribose': a neutral second messenger mimic.
2014,
Pubmed
,
Echinobase
Swarbrick,
Cyclic adenosine 5'-diphosphate ribose analogs without a "southern" ribose inhibit ADP-ribosyl cyclase-hydrolase CD38.
2014,
Pubmed
Swarbrick,
Designer small molecules to target calcium signalling.
2015,
Pubmed
Takasawa,
Pancreatic beta-cell death, regeneration and insulin secretion: roles of poly(ADP-ribose) polymerase and cyclic ADP-ribose.
2002,
Pubmed
Wagner,
Rapid synthetic route toward structurally modified derivatives of cyclic adenosine 5'-diphosphate ribose.
2005,
Pubmed
Wang,
Calcium-Mobilizing Behaviors of Neutral Cyclic ADP-Ribose Mimics that Integrate Modifications to the Nucleobase, Northern Ribose and Pyrophosphate.
2018,
Pubmed
Wei,
Roles and mechanisms of the CD38/cyclic adenosine diphosphate ribose/Ca(2+) signaling pathway.
2014,
Pubmed
Wissing,
A novel Ca2+-induced Ca2+ release mechanism mediated by neither inositol trisphosphate nor ryanodine receptors.
2002,
Pubmed
Xu,
Synthesis and agonist activity of cyclic ADP-ribose analogues with substitution of the northern ribose by ether or alkane chains.
2006,
Pubmed
Yu,
Direct Gating of the TRPM2 Channel by cADPR via Specific Interactions with the ADPR Binding Pocket.
2019,
Pubmed
Zhang,
Cyclic adenosine 5'-diphosphoribose (cADPR) mimics used as molecular probes in cell signaling.
2015,
Pubmed
