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Cell Calcium
2019 Nov 01;83:102060. doi: 10.1016/j.ceca.2019.102060.
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The synthesis and characterization of a clickable-photoactive NAADP analog active in human cells.
Asfaha TY
,
Gunaratne GS
,
Johns ME
,
Marchant JS
,
Walseth TF
,
Slama JT
.
???displayArticle.abstract??? Nicotinic acid adenine dinucleotide phosphate (NAADP) is a potent Ca2+ mobilizing second messenger which triggers Ca2+ release in both sea urchin egg homogenates and in mammalian cells. The NAADP binding protein has not been identified and the regulation of NAADP mediated Ca2+ release remains controversial. To address this issue, we have synthesized an NAADP analog in which 3-azido-5-azidomethylbenzoic acid is attached to the amino group of 5-(3-aminopropyl)-NAADP to produce an NAADP analog which is both a photoaffinity label and clickable. This ''all-in-one-clickable'' NAADP (AIOC-NAADP) elicited Ca2+ release when microinjected into cultured human SKBR3 cells at low concentrations. In contrast, it displayed little activity in sea urchin egg homogenates where very high concentrations were required to elicit Ca2+ release. In mammalian cell homogenates, incubation with low concentrations of [32P]AIOC-NAADP followed by irradiation with UV light resulted in labeling 23 kDa protein(s). Competition between [32P]AIOC-NAADP and increasing concentrations of NAADP demonstrated that the labeling was selective. We show that this label recognizes and selectively photodervatizes the 23 kDa NAADP binding protein(s) in cultured human cells identified in previous studies using [32P]5-N3-NAADP.
Aarhus,
ADP-ribosyl cyclase and CD38 catalyze the synthesis of a calcium-mobilizing metabolite from NADP.
1995, Pubmed
Aarhus,
ADP-ribosyl cyclase and CD38 catalyze the synthesis of a calcium-mobilizing metabolite from NADP.
1995,
Pubmed
Aarhus,
Activation and inactivation of Ca2+ release by NAADP+.
1996,
Pubmed
,
Echinobase
Albrieux,
Calcium signaling by cyclic ADP-ribose, NAADP, and inositol trisphosphate are involved in distinct functions in ascidian oocytes.
1998,
Pubmed
Aley,
A functional role for nicotinic acid adenine dinucleotide phosphate in oxytocin-mediated contraction of uterine smooth muscle from rat.
2010,
Pubmed
Ali,
Activity of nicotinic acid substituted nicotinic acid adenine dinucleotide phosphate (NAADP) analogs in a human cell line: difference in specificity between human and sea urchin NAADP receptors.
2014,
Pubmed
,
Echinobase
Ali,
Nicotinic Acid Adenine Dinucleotide Phosphate Plays a Critical Role in Naive and Effector Murine T Cells but Not Natural Regulatory T Cells.
2016,
Pubmed
Arredouani,
An emerging role for NAADP-mediated Ca2+ signaling in the pancreatic β-cell.
2010,
Pubmed
Arredouani,
Nicotinic Acid Adenine Dinucleotide Phosphate (NAADP) and Endolysosomal Two-pore Channels Modulate Membrane Excitability and Stimulus-Secretion Coupling in Mouse Pancreatic β Cells.
2015,
Pubmed
Berg,
Nicotinic acid adenine dinucleotide phosphate (NAADP(+)) is an essential regulator of T-lymphocyte Ca(2+)-signaling.
2000,
Pubmed
Bernofsky,
Nicotinic acid adenine dinucleotide phosphate (NAADP+).
1980,
Pubmed
Berridge,
Calcium signalling remodelling and disease.
2012,
Pubmed
Berridge,
The versatility and universality of calcium signalling.
2000,
Pubmed
Billington,
Role of the nicotinic acid group in NAADP receptor selectivity.
2005,
Pubmed
,
Echinobase
Brailoiu,
Nicotinic acid adenine dinucleotide phosphate potentiates neurite outgrowth.
2005,
Pubmed
Brailoiu,
Intracellular cannabinoid type 1 (CB1) receptors are activated by anandamide.
2011,
Pubmed
Brailoiu,
Essential requirement for two-pore channel 1 in NAADP-mediated calcium signaling.
2009,
Pubmed
Calcraft,
NAADP mobilizes calcium from acidic organelles through two-pore channels.
2009,
Pubmed
Cancela,
Coordination of agonist-induced Ca2+-signalling patterns by NAADP in pancreatic acinar cells.
1999,
Pubmed
,
Echinobase
Chen,
Ultrasensitive fluorescent proteins for imaging neuronal activity.
2013,
Pubmed
Churchill,
NAADP mobilizes Ca(2+) from reserve granules, lysosome-related organelles, in sea urchin eggs.
2002,
Pubmed
,
Echinobase
Churchill,
Sperm deliver a new second messenger: NAADP.
2003,
Pubmed
,
Echinobase
Cordiglieri,
Nicotinic acid adenine dinucleotide phosphate-mediated calcium signalling in effector T cells regulates autoimmunity of the central nervous system.
2010,
Pubmed
Dammermann,
NAADP-mediated Ca2+ signaling via type 1 ryanodine receptor in T cells revealed by a synthetic NAADP antagonist.
2009,
Pubmed
Dammermann,
Functional ryanodine receptor expression is required for NAADP-mediated local Ca2+ signaling in T-lymphocytes.
2005,
Pubmed
Galione,
A primer of NAADP-mediated Ca(2+) signalling: From sea urchin eggs to mammalian cells.
2015,
Pubmed
,
Echinobase
Gasser,
Second messenger function of nicotinic acid adenine dinucleotide phosphate revealed by an improved enzymatic cycling assay.
2006,
Pubmed
Genazzani,
Unique inactivation properties of NAADP-sensitive Ca2+ release.
1996,
Pubmed
,
Echinobase
Graeff,
Acidic residues at the active sites of CD38 and ADP-ribosyl cyclase determine nicotinic acid adenine dinucleotide phosphate (NAADP) synthesis and hydrolysis activities.
2006,
Pubmed
Gunaratne,
5-Azido-8-ethynyl-NAADP: A bifunctional, clickable photoaffinity probe for the identification of NAADP receptors.
2019,
Pubmed
,
Echinobase
Guse,
Second messenger signaling: multiple receptors for NAADP.
2009,
Pubmed
Hohenegger,
Nicotinic acid-adenine dinucleotide phosphate activates the skeletal muscle ryanodine receptor.
2002,
Pubmed
Hong,
Analysis and optimization of copper-catalyzed azide-alkyne cycloaddition for bioconjugation.
2009,
Pubmed
Hosoya,
Design of dantrolene-derived probes for radioisotope-free photoaffinity labeling of proteins involved in the physiological Ca2+ release from sarcoplasmic reticulum of skeletal muscle.
2005,
Pubmed
Hosoya,
Novel bifunctional probe for radioisotope-free photoaffinity labeling: compact structure comprised of photospecific ligand ligation and detectable tag anchoring units.
2004,
Pubmed
Jain,
Nicotinic acid adenine dinucleotide phosphate analogues containing substituted nicotinic acid: effect of modification on Ca(2+) release.
2010,
Pubmed
,
Echinobase
Jaiswal,
Calcium - how and why?
2001,
Pubmed
Lam,
Improving FRET dynamic range with bright green and red fluorescent proteins.
2012,
Pubmed
Lee,
Structural determinants of nicotinic acid adenine dinucleotide phosphate important for its calcium-mobilizing activity.
1997,
Pubmed
,
Echinobase
Lee,
Functional visualization of the separate but interacting calcium stores sensitive to NAADP and cyclic ADP-ribose.
2000,
Pubmed
,
Echinobase
Lee,
A derivative of NADP mobilizes calcium stores insensitive to inositol trisphosphate and cyclic ADP-ribose.
1995,
Pubmed
,
Echinobase
Lee,
Cyclic ADP-ribose and nicotinic acid adenine dinucleotide phosphate (NAADP) as messengers for calcium mobilization.
2012,
Pubmed
Lee,
Nicotinic acid adenine dinucleotide phosphate (NAADP)-mediated calcium signaling.
2005,
Pubmed
,
Echinobase
Lin-Moshier,
Photoaffinity labeling of nicotinic acid adenine dinucleotide phosphate (NAADP) targets in mammalian cells.
2012,
Pubmed
,
Echinobase
Lin-Moshier,
The Two-pore channel (TPC) interactome unmasks isoform-specific roles for TPCs in endolysosomal morphology and cell pigmentation.
2014,
Pubmed
Mattson,
Calcium orchestrates apoptosis.
2003,
Pubmed
Meldal,
Cu-catalyzed azide-alkyne cycloaddition.
2008,
Pubmed
Morgan,
Investigating cADPR and NAADP in intact and broken cell preparations.
2008,
Pubmed
,
Echinobase
Morgan,
Preparation and use of sea urchin egg homogenates.
2014,
Pubmed
,
Echinobase
Munshi,
High-level expression of recombinant Aplysia ADP-ribosyl cyclase in offhia pastoris by fermentation.
1997,
Pubmed
Munshi,
Characterization of the active site of ADP-ribosyl cyclase.
1999,
Pubmed
Neelarapu,
Design, synthesis, docking, and biological evaluation of novel diazide-containing isoxazole- and pyrazole-based histone deacetylase probes.
2011,
Pubmed
Presolski,
Copper-Catalyzed Azide-Alkyne Click Chemistry for Bioconjugation.
2011,
Pubmed
Raffaello,
Calcium at the Center of Cell Signaling: Interplay between Endoplasmic Reticulum, Mitochondria, and Lysosomes.
2016,
Pubmed
Schomer,
Redox changes during fertilization and maturation of marine invertebrate eggs.
1998,
Pubmed
,
Echinobase
Speers,
Profiling enzyme activities in vivo using click chemistry methods.
2004,
Pubmed
Trabbic,
Nicotinic Acid Adenine Dinucleotide Phosphate Analogues Substituted on the Nicotinic Acid and Adenine Ribosides. Effects on ReceptorMediated Ca²⁺ Release.
2015,
Pubmed
,
Echinobase
Walseth,
Nicotinic Acid Adenine Dinucleotide 2'-Phosphate (NAADP) Binding Proteins in T-Lymphocytes.
2012,
Pubmed
Walseth,
Photoaffinity labeling of high affinity nicotinic acid adenine dinucleotide phosphate (NAADP)-binding proteins in sea urchin egg.
2012,
Pubmed
,
Echinobase
Wolf,
Frontrunners of T cell activation: Initial, localized Ca2+ signals mediated by NAADP and the type 1 ryanodine receptor.
2015,
Pubmed
Zhang,
Reconstitution and characterization of a nicotinic acid adenine dinucleotide phosphate (NAADP)-sensitive Ca2+ release channel from liver lysosomes of rats.
2007,
Pubmed
van Geel,
Preventing thiol-yne addition improves the specificity of strain-promoted azide-alkyne cycloaddition.
2012,
Pubmed