MASTER-NAADP: a membrane permeable precursor of the Ca
Journal
Nature communications
ISSN: 2041-1723
Titre abrégé: Nat Commun
Pays: England
ID NLM: 101528555
Informations de publication
Date de publication:
13 Sep 2024
13 Sep 2024
Historique:
received:
17
04
2023
accepted:
20
08
2024
medline:
14
9
2024
pubmed:
14
9
2024
entrez:
13
9
2024
Statut:
epublish
Résumé
Upon stimulation of membrane receptors, nicotinic acid adenine dinucleotide phosphate (NAADP) is formed as second messenger within seconds and evokes Ca
Identifiants
pubmed: 39271671
doi: 10.1038/s41467-024-52024-y
pii: 10.1038/s41467-024-52024-y
doi:
Substances chimiques
NAADP
5502-96-5
NADP
53-59-8
Calcium
SY7Q814VUP
Ryanodine Receptor Calcium Release Channel
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
8008Subventions
Organisme : Deutsche Forschungsgemeinschaft (German Research Foundation)
ID : 335447717; SFB1328
Organisme : Deutsche Forschungsgemeinschaft (German Research Foundation)
ID : 236360313
Organisme : Deutsche Forschungsgemeinschaft (German Research Foundation)
ID : 516286863
Organisme : Deutsche Forschungsgemeinschaft (German Research Foundation)
ID : 236360313
Organisme : Deutsche Forschungsgemeinschaft (German Research Foundation)
ID : 516286863
Organisme : Deutsche Forschungsgemeinschaft (German Research Foundation)
ID : 335447717
Informations de copyright
© 2024. The Author(s).
Références
Lee, H. C. & Aarhus, R. A derivative of NADP mobilizes calcium stores insensitive to inositol trisphosphate and cyclic ADP-ribose. J. Biol. Chem. 270, 2152–2157 (1995).
pubmed: 7836444
doi: 10.1074/jbc.270.5.2152
Patel, S., Gregori, M. & Yuan, Y. Teaming with NAADP. Sci. Signal 14, eabh2798 (2021).
pubmed: 33758059
doi: 10.1126/scisignal.abh2798
Walseth, T. F., Guse, A. H. & NAADP From Discovery to Mechanism. Front. Immunol. 12, 3624 (2021).
doi: 10.3389/fimmu.2021.703326
Marchant, J. S., Gunaratne, G. S., Cai, X., Slama, J. T. & Patel, S. NAADP-binding proteins find their identity. Trends Biochem.Sci. 47, 235–249 (2022).
pubmed: 34810081
doi: 10.1016/j.tibs.2021.10.008
Guse, A. H. NAADP-Evoked Ca
doi: 10.1007/164_2022_623
Yamasaki, M. et al. Role of NAADP and cADPR in the induction and maintenance of agonist-evoked Ca
pubmed: 15886108
doi: 10.1016/j.cub.2005.04.033
Gasser, A., Bruhn, S. & Guse, A. H. Second messenger function of nicotinic acid adenine dinucleotide phosphate revealed by an improved enzymatic cycling assay. J. Biol. Chem. 281, 16906–16913 (2006).
pubmed: 16627475
doi: 10.1074/jbc.M601347200
Rah, S.-Y., Mushtaq, M., Nam, T.-S., Kim, S. H. & Kim, U.-H. Generation of cyclic ADP-ribose and nicotinic acid adenine dinucleotide phosphate by CD38 for Ca
pubmed: 20442403
pmcid: 2898418
doi: 10.1074/jbc.M109.066290
Aarhus, R., Graeff, R. M., Dickey, D. M., Walseth, T. F. & Lee, H. C. ADP-ribosyl cyclase and CD38 catalyze the synthesis of a calcium-mobilizing metabolite from NADP. J. Biol. Chem. 270, 30327–30333 (1995).
pubmed: 8530456
doi: 10.1074/jbc.270.51.30327
Zhao, Z. Y. et al. A Cell-Permeant Mimetic of NMN Activates SARM1 to Produce Cyclic ADP-Ribose and Induce Non-apoptotic Cell Death. iScience 15, 452–466 (2019).
pubmed: 31128467
pmcid: 6531917
doi: 10.1016/j.isci.2019.05.001
Gu, F. et al. Dual NADPH oxidases DUOX1 and DUOX2 synthesize NAADP and are necessary for Ca
pubmed: 34784249
doi: 10.1126/scisignal.abe3800
Angeletti, C. et al. SARM1 is a multi-functional NAD(P)ase with prominent base exchange activity, all regulated bymultiple physiologically relevant NAD metabolites. iScience 25, 103812 (2022).
pubmed: 35198877
pmcid: 8844822
doi: 10.1016/j.isci.2022.103812
Nam, T.-S. et al. Interleukin-8 drives CD38 to form NAADP from NADP+ and NAAD in the endolysosomes to mobilize Ca
pubmed: 32717131
doi: 10.1096/fj.202001249R
Lin-Moshier, Y. et al. Photoaffinity labeling of nicotinic acid adenine dinucleotide phosphate (NAADP) targets in mammalian cells. J. Biol. Chem. 287, 2296–2307 (2012).
pubmed: 22117075
doi: 10.1074/jbc.M111.305813
Walseth, T. F. et al. Nicotinic Acid Adenine Dinucleotide 2’-Phosphate (NAADP) Binding Proteins in T-Lymphocytes. Messenger (Los Angel) 1, 86–94 (2012).
pubmed: 24829846
Guse, A. H. Linking NAADP to ion channel activity: a unifying hypothesis. Sci. Signal 5, pe18 (2012).
pubmed: 22534131
doi: 10.1126/scisignal.2002890
Roggenkamp, H. G. et al. HN1L/JPT2: A signaling protein that connects NAADP generation to Ca
pubmed: 33758062
doi: 10.1126/scisignal.abd5647
Gunaratne, G. S. et al. Essential requirement for JPT2 in NAADP-evoked Ca
pubmed: 33758061
pmcid: 8315109
doi: 10.1126/scisignal.abd5605
Zhang, J., Guan, X., Shah, K. & Yan, J. Lsm12 is an NAADP receptor and a two-pore channel regulatory protein required for calcium mobilization from acidic organelles. Nat. Commun. 12, 4739 (2021).
pubmed: 34362892
pmcid: 8346516
doi: 10.1038/s41467-021-24735-z
Wolf, I. M. A. et al. Frontrunners of T cell activation: Initial, localized Ca
pubmed: 26462735
doi: 10.1126/scisignal.aab0863
Diercks, B.-P. et al. ORAI1, STIM1/2, and RYR1 shape subsecond Ca
pubmed: 30563862
pmcid: 6728084
doi: 10.1126/scisignal.aat0358
Kinnear, N. P. et al. Lysosomes co-localize with ryanodine receptor subtype 3 to form a trigger zone for calcium signalling by NAADP in rat pulmonary arterial smooth muscle. Cell Calcium 44, 190–201 (2008).
pubmed: 18191199
pmcid: 3982125
doi: 10.1016/j.ceca.2007.11.003
Cancela, J. M., Gerasimenko, O. V., Gerasimenko, J. V., Tepikin, A. V. & Petersen, O. H. Two different but converging messenger pathways to intracellular Ca(2+) release: the roles of nicotinic acid adenine dinucleotide phosphate, cyclic ADP-ribose and inositol trisphosphate. EMBO J. 19, 2549–2557 (2000).
pubmed: 10835353
doi: 10.1093/emboj/19.11.2549
Brock, V. J. et al. P2X4 and P2X7 are essential players in basal T cell activity and Ca
Naylor, E. et al. Identification of a chemical probe for NAADP by virtual screening. Nat. Chem. Biol. 5, 220–226 (2009).
pubmed: 19234453
pmcid: 2659327
doi: 10.1038/nchembio.150
Dammermann, W. et al. NAADP-mediated Ca
pubmed: 19541638
pmcid: 2697110
doi: 10.1073/pnas.0809997106
Boittin, F.-X., Galione, A. & Evans, A. M. Nicotinic acid adenine dinucleotide phosphate mediates Ca
pubmed: 12480818
doi: 10.1161/01.RES.0000047507.22487.85
Parkesh, R. et al. Cell-permeant NAADP: a novel chemical tool enabling the study of Ca
pubmed: 17935780
doi: 10.1016/j.ceca.2007.08.006
Galione, A. et al. Synthesis of NAADP-AM as a Membrane-Permeant NAADP Analog. Cold Spring Harb Protoc. 2014, pdb.prot076927 (2014).
Davis, L. C. et al. NAADP activates two-pore channels on T cell cytolytic granules to stimulate exocytosis and killing. Curr. Biol. 22, 2331–2337 (2012).
pubmed: 23177477
pmcid: 3525857
doi: 10.1016/j.cub.2012.10.035
Jessen, H. J., Schulz, T., Balzarini, J. & Meier, C. Bioreversible protection of nucleoside diphosphates. Angew. Chem. Int Ed. Engl. 47, 8719–8722 (2008).
pubmed: 18833560
doi: 10.1002/anie.200803100
Cooperwood, J. S., Boyd, V., Gumina, G. & Chu, C. K. Synthesis of L-3’-hydroxymethylribonucleosides. Nucleosides Nucleotides Nucleic Acids 19, 219–236 (2000).
pubmed: 10772711
doi: 10.1080/15257770008033005
Wang, S. et al. Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers. Angew. Chem. Int Ed. Engl. 57, 2884–2888 (2018).
pubmed: 29356246
doi: 10.1002/anie.201800169
Mikhailopulo, I. A. & Sivets, G. G. A Novel Route for the Synthesis of Deoxy Fluoro Sugars and Nucleosides. Helvetica Chim. Acta 82, 2052–2065 (1999).
doi: 10.1002/(SICI)1522-2675(19991110)82:11<2052::AID-HLCA2052>3.0.CO;2-7
Larsen, C. H., Ridgway, B. H., Shaw, J. T. & Woerpel, K. A. A Stereoelectronic Model To Explain the Highly Stereoselective Reactions of Nucleophiles with Five-Membered-Ring Oxocarbenium Ions. J. Am. Chem. Soc. 121, 12208–12209 (1999).
doi: 10.1021/ja993349z
Vorbrüggen, H., Lagoja, I. M. & Herdewijn, P. Synthesis of ribonucleosides by condensation using trimethylsilyl triflate. Curr Protoc Nucleic Acid Chem Chapter 1, Unit 1.13 (2007).
Huchting, J. et al. Prodrugs of the Phosphoribosylated Forms of Hydroxypyrazinecarboxamide Pseudobase T-705 and Its De-Fluoro Analogue T-1105 as Potent Influenza Virus Inhibitors. J. Med. Chem. 61, 6193–6210 (2018).
pubmed: 29906392
doi: 10.1021/acs.jmedchem.8b00617
Sanghvi, Y. S., Guo, Z., Pfundheller, H. M. & Converso, A. Improved Process for the Preparation of Nucleosidic Phosphoramidites Using a Safer and Cheaper Activator. Org. Process Res. Dev. 4, 175–181 (2000).
doi: 10.1021/op990086k
Yoshikawa, M., Kato, T. & Takenishi, T. A novel method for phosphorylation of nucleosides to 5’-nucleotides. Tetrahedron Lett. 50, 5065–5068 (1967).
pubmed: 6081184
doi: 10.1016/S0040-4039(01)89915-9
Krohn, K., Heins, H. & Wielckens, K. Synthesis and cytotoxic activity of C-glycosidic nicotinamide riboside analogues. J. Med. Chem. 35, 511–517 (1992).
pubmed: 1738143
doi: 10.1021/jm00081a012
Inanaga, J., Hirata, K., Saeki, H., Katsuki, T. & Yamaguchi, M. A Rapid Esterification by Means of Mixed Anhydride and Its Application to Large-ring Lactonization. BCSJ 52, 1989–1993 (1979).
doi: 10.1246/bcsj.52.1989
Mohamady, S. & Jakeman, D. L. An improved method for the synthesis of nucleoside triphosphate analogues. J. Org. Chem. 70, 10588–10591 (2005).
pubmed: 16323879
doi: 10.1021/jo0518598
Knorr, R., Trzeciak, A., Bannwarth, W. & Gillessen, D. New coupling reagents in peptide chemistry. Tetrahedron Lett. 30, 1927–1930 (1989).
doi: 10.1016/S0040-4039(00)99616-3
Markiewicz, W. T. & Wiewiórowski, M. A new type of silyl protecting groups in nucleoside chemistry. Nucleic Acids Res. 5, s185–s190 (1978).
pmcid: 6581304
doi: 10.1093/nar/1.suppl_1.s185
Zhu, X.-F., Williams, H. J. & Scott, A. I. Aqueous trifluoroacetic acid—an efficient reagent for exclusively cleaving the 5′-end of 3′,5′-TIPDS protected ribonucleosides. Tetrahedron Lett. 41, 9541–9545 (2000).
doi: 10.1016/S0040-4039(00)01685-3
Dowden, J. et al. Chemical synthesis of the second messenger nicotinic acid adenine dinucleotide phosphate by total synthesis of nicotinamide adenine dinucleotide phosphate. Angew. Chem. Int Ed. Engl. 43, 4637–4640 (2004).
pubmed: 15352191
doi: 10.1002/anie.200460054
Wender, P. A. et al. The Pinene Path to Taxanes. 6. A Concise Stereocontrolled Synthesis of Taxol. J. Am. Chem. Soc. 119, 2757–2758 (1997).
doi: 10.1021/ja963539z
Shigematsu, M., Kawamura, T. & Kirino, Y. Generation of 2′,3′-Cyclic Phosphate-Containing RNAs as a Hidden Layer of the Transcriptome. Front. Genet. 9, 562 (2018).
pubmed: 30538719
pmcid: 6277466
doi: 10.3389/fgene.2018.00562
Brown, D. M. & Todd, A. R. 13. Nucleotides. Part X. Some observations on the structure and chemical behaviour of the nucleic acids. J. Chem. Soc. 52–58 (1952) https://doi.org/10.1039/JR9520000052 .
Lee, H. C. & Aarhus, R. Structural Determinants of Nicotinic Acid Adenine Dinucleotide Phosphate Important for Its Calcium-mobilizing Activity. J. Biol. Chem. 272, 20378–20383 (1997).
pubmed: 9252343
doi: 10.1074/jbc.272.33.20378
Woelk, L.-M. et al. DARTS: an open-source Python pipeline for Ca
pubmed: 38274810
pmcid: 10809147
doi: 10.3389/fimmu.2023.1299435
Berg, I., Potter, B. V. L., Mayr, G. W. & Guse, A. H. Nicotinic Acid Adenine Dinucleotide Phosphate (Naadp+) Is an Essential Regulator of T-Lymphocyte Ca
pubmed: 10931869
pmcid: 2175191
doi: 10.1083/jcb.150.3.581
Langhorst, M. F., Schwarzmann, N. & Guse, A. H. Ca
pubmed: 15337527
doi: 10.1016/j.cellsig.2004.03.013
Dammermann, W. & Guse, A. H. Functional ryanodine receptor expression is required for NAADP-mediated local Ca
pubmed: 15774471
doi: 10.1074/jbc.M413085200
Brailoiu, G. C. et al. NAADP-mediated channel ‘chatter’ in neurons of the rat medulla oblongata. Biochem J. 419, 91–97, (2009).
pubmed: 19090786
doi: 10.1042/BJ20081138
Brailoiu, G. C. et al. Acidic NAADP-sensitive Calcium Stores in the Endothelium. J. Biol. Chem. 285, 37133–37137 (2010).
pubmed: 20876534
pmcid: 2988319
doi: 10.1074/jbc.C110.169763
Barceló-Torns, M. et al. NAADP mediates ATP-induced Ca
pubmed: 21664355
doi: 10.1016/j.febslet.2011.05.062
Capel, R. A. et al. Two-pore Channels (TPC2s) and Nicotinic Acid Adenine Dinucleotide Phosphate (NAADP) at Lysosomal-Sarcoplasmic Reticular Junctions Contribute to Acute and Chronic β-Adrenoceptor Signaling in the Heart. J. Biol. Chem. 290, 30087–30098 (2015).
pubmed: 26438825
pmcid: 4705968
doi: 10.1074/jbc.M115.684076
Iyer, R. P. et al. Synthesis of acyloxyalkyl acylphosphonates as potential prodrugs of the antiviral, trisodium phosphonoformate (foscarnet sodium). Tetrahedron Lett. 30, 7141–7144 (1989).
doi: 10.1016/S0040-4039(01)93918-8
Srivastva, D. N. & Farquhar, D. Bioreversible phosphate protective groups: Synthesis and stability of model acyloxymethyl phosphates. Bioorg. Chem. 12, 118–129 (1984).
doi: 10.1016/0045-2068(84)90022-1
Singaravelu, K. & Deitmer, J. W. Calcium mobilization by nicotinic acid adenine dinucleotide phosphate (NAADP) in rat astrocytes. Cell Calcium 39, 143–153 (2006).
pubmed: 16289677
doi: 10.1016/j.ceca.2005.10.001
Moreschi, I. et al. NAADP+ is an agonist of the human P2Y11 purinergic receptor. Cell Calcium 43, 344–355 (2008).
pubmed: 17707504
doi: 10.1016/j.ceca.2007.06.006
Gollnest, T. et al. Membrane-permeable Triphosphate Prodrugs of Nucleoside Analogues. Angew. Chem. Int. Ed. 55, 5255–5258 (2016).
doi: 10.1002/anie.201511808
Gollnest, T., de Oliveira, T. D., Schols, D., Balzarini, J. & Meier, C. Lipophilic prodrugs of nucleoside triphosphates as biochemical probes and potential antivirals. Nat. Commun. 6, 8716 (2015).
pubmed: 26503889
doi: 10.1038/ncomms9716
Jain, P., Slama, J. T., Perez-Haddock, L. A. & Walseth, T. F. Nicotinic acid adenine dinucleotide phosphate analogues containing substituted nicotinic acid: effect of modification on Ca(2+) release. J. Med Chem. 53, 7599–7612 (2010).
pubmed: 20942470
pmcid: 3060082
doi: 10.1021/jm1007209
Ali, R. A. et al. 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. Cell Calcium 55, 93–103 (2014).
pubmed: 24439527
doi: 10.1016/j.ceca.2013.12.004
Su, P. et al. Chemo-enzymatic synthesis of adenine substituted nicotinic acid adenine dinucleotide phosphate (NAADP) analogs. Bioorg. Med. Chem. 30, 115901 (2021).
pubmed: 33321420
doi: 10.1016/j.bmc.2020.115901
Martucci, L. L. et al. Endolysosomal TPCs regulate social behavior by controlling oxytocin secretion. Proc. Natl. Acad. Sci. USA 120, e2213682120 (2023).
pubmed: 36745816
pmcid: 9963339
doi: 10.1073/pnas.2213682120
Grynkiewicz, G., Poenie, M. & Tsien, R. Y. A new generation of Ca
pubmed: 3838314
doi: 10.1016/S0021-9258(19)83641-4
Diercks, B.-P., Werner, R., Schetelig, D., Wolf, I. M. A. & Guse, A. H. High-Resolution Calcium Imaging Method for Local Calcium Signaling. in Calcium-Binding Proteins of the EF-Hand Superfamily: From Basics to Medical Applications (ed. Heizmann, C. W.) 27–39 (Springer New York, New York, NY, 2019). https://doi.org/10.1007/978-1-4939-9030-6_3 .
Melville, Z., Kim, K., Clarke, O. B. & Marks, A. R. High-resolution structure of the membrane-embedded skeletal muscle ryanodine receptor. Structure 30, 172–180.e3 (2022).
pubmed: 34469755
doi: 10.1016/j.str.2021.08.001
Hub, T. et al. Streamlined Generation of CRISPR/Cas9-Mediated Single-Cell Knockout Clones in Murine Cell Lines. ACS Pharm. Transl. Sci. 7, 1291–1301 (2024).
doi: 10.1021/acsptsci.3c00338
Conant, D. et al. Inference of CRISPR Edits from Sanger Trace Data. CRISPR J. 5, 123–130 (2022).
pubmed: 35119294
doi: 10.1089/crispr.2021.0113