8-Bromo-cyclic inosine diphosphoribose: Towards a selective cyclic ADP-ribose agonist

Biochemical Journal

Volumn 422, Issue 1, 2009, Pages 139-149

  Kirchberger, Tanja ^a   Moreau, Christelle ^b   Wagner, Gerd K ^b,d   Fliegert, Ralf ^a   Siebrands, Cornelia C ^a   Nebel, Merle ^a   Schmid, Frederike ^a   Harneit, Angelika ^a   Odoardi, Francesca ^c   Flügel, Alexander ^c   Potter, Barry V L ^b   Guse, Andreas H ^a  

^a UNIVERSITY MEDICAL CENTER HAMBURG EPPENDORF   (Germany)

^b University of Bath   (United Kingdom)

^c UNIVERSITY OF GÖTTINGEN   (Germany)

^d UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

Ca2+ entry; Ca2+ release; Cyclic ADP ribose (cADPR); Cyclic ADP ribose (cADPR) analogue; Member 2 (TRPM2); Subfamily melastatin; T cell activation; Transient receptor potential cation channel

Indexed keywords

CA2+ ENTRY; CA2+ RELEASE; CYCLIC ADP-RIBOSE (CADPR); CYCLIC ADP-RIBOSE (CADPR) ANALOGUE; MEMBER 2 (TRPM2); SUBFAMILY MELASTATIN; T-CELL ACTIVATION; TRANSIENT RECEPTOR POTENTIAL CATION CHANNEL;

ACTIVATION ANALYSIS; BIOLOGICAL RADIATION EFFECTS; CELL CULTURE; CELL MEMBRANES; GADOLINIUM; POSITIVE IONS; RUTHENIUM;

CALCIUM;

1 [2 (4 METHOXYPHENYL) 2 [3 (4 METHOXYPHENYL)PROPOXY]ETHYL] 1H IMIDAZOLE; 8 BROMO CYCLIC INOSINE DIPHOSPHORIBOSE; CALCIUM CHANNEL BLOCKING AGENT; CALCIUM ION; CYCLIC ADENOSINE DIPHOSPHATE RIBOSE; GADOLINIUM; HYDROGEN PEROXIDE; RIBONUCLEOTIDE; RUTHENIUM RED; RYANODINE RECEPTOR; TRANSIENT RECEPTOR POTENTIAL CHANNEL; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ANIMAL CELL; ARTICLE; CALCIUM SIGNALING; CALCIUM TRANSPORT; CELL MEMBRANE PERMEABILITY; CELL STRAIN HEK293; CONTROLLED STUDY; EMBRYO; HUMAN; HUMAN CELL; LEUKEMIA CELL LINE; MEMBRANE TRANSPORT; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; RAT;

ANIMALS; CALCIUM SIGNALING; CELL MEMBRANE PERMEABILITY; CYCLIC ADP-RIBOSE; EXTRACELLULAR SPACE; GADOLINIUM; HUMANS; IMIDAZOLES; INOSINE NUCLEOTIDES; ION CHANNEL GATING; JURKAT CELLS; MICROINJECTIONS; RATS; RUTHENIUM RED; TRPM CATION CHANNELS;

RATTUS;

EID: 68749114125     PISSN: 02646021     EISSN: 14708728     Source Type: Journal    
DOI: 10.1042/BJ20082308     Document Type: Article

References (45)

1. +/ cyclic ADP-ribose system. Ann. N. Y. Acad. Sci. 1028, 176-191
2. Guse, A. H. (2004) Biochemistry, biology, and pharmacology of cyclic adenosine diphosphoribose (cADPR). Curr. Med. Chem. 11, 847-855
3. Guse, A. H. (2005) Second messenger function and the structure-activity relationship of cyclic adenosine diphosphoribose (cADPR). FEBS. J. 272, 4590-4597
4. 2+ stores: a perspective from cyclic ADP-ribose and NAADP. Curr. Mol. Med. 4, 227-237
5. Lee, H. C. (2006) Structure and enzymatic functions of human CD38. Mol. Med. 12, 317-323
6. Clapper, D. L., Walseth, T. F., Dargie, P. J. and Lee, H. C. (1987) Pyridine nucleotide metabolites stimulate calcium release from sea urchin egg microsomes desensitized to inositol trisphosphate. J. Biol. Chem. 262, 9561-9568
7. 2+-mobilizing activity. J. Biol. Chem. 264, 1608-1615
8. 2+ entry induced by cyclic ADP-ribose in intact T-lymphocytes. J. Biol. Chem. 272, 8546-8550
9. Fruman, D. A., Klee, C. B., Bierer, B. E. and Burakoff, S. J. (1992) Calcineurin phosphatase activity in T lymphocytes is inhibited by FK 506 and cyclosporin A. Proc. Natl. Acad. Sci. U.S.A. 89, 3686-3690
10. Crabtree, G. R. and Olson, E. N. (2002) NFAT signaling: choreographing the social lives of cells. Cell 109, S67-S79
11. Liu, J., Koyano-Nakagawa, N., Amasaki, Y., Saito-Ohara, F., Ikeuchi, T., Imai, S., Takano, T., Arai, N., Yokota, T. and Arai, K. (1997) Calcineurin-dependent nuclear translocation of a murine transcription factor NFATx: molecular cloning and functional characterization. Mol. Biol. Cell 8, 157-170
12. Putney, J. W. J. (1986) A model for receptor-regulated calcium entry. Cell Calcium 7, 1-12
13. Putney, J. W. J. (2007) Recent breakthroughs in the molecular mechanism of capacitative calcium entry (with thoughts on how we got here). Cell Calcium 42, 103-110
14. 2+ entry. Science 312, 1220-1223
15. Feske, S., Gwack, Y., Prakriya, M., Srikanth, S., Puppel, S., Tanasa, B., Hogan, P. G., Lewis, R. S., Daly, M. and Rao, A. (2006) A mutation in Orai1 causes immune deficiency by abrogating CRAC channel function. Nature 441, 179-185
16. 2+ store to the plasma membrane. Nature 437, 902-905
17. Guse, A. H., da Silva, C. P., Berg, I., Skapenko, A. L., Weber, K., Heyer, P., Hohenegger, M., Ashamu, G. A., Schulze-Koops, H., Potter, B. V. L. and Mayr, G. W. (1999) Regulation of calcium signalling in T lymphocytes by the second messenger cyclic ADP-ribose. Nature 398, 70-73
18. Kirchberger, T., Wagner, G., Xu, J., Cordiglieri, C., Wang, P., Gasser, A., Fliegert, R., Bruhn, S., Flügel, A., Lund et al. (2006) Cellular effects and metabolic stability of N1-cyclic inosine diphosphoribose and its derivatives. Br. J. Pharmacol. 149, 337-344
19. 2+ pools in Jurkat T-lymphocytes. Biochem. J. 291, 447-451
20. Ben-Nun, A., Wekerle, H. and Cohen, I. R. (1981) The rapid isolation of clonable antigen-specific T lymphocyte lines capable of mediating autoimmune encephalomyelitis. Eur. J. Immunol. 11, 195-199
21. Wagner, G. K., Black, S., Guse, A. H. and Potter, B. V. L. (2003) First enzymatic synthesis of an N1-cyclised cADPR (cyclic-ADP ribose) analogue with a hypoxanthine partial structure: discovery of a membrane permeant cADPR agonist. Chem. Commun. 7, 1944-1945
22. Gasser, A. and Guse, A. H. (2005) Determination of intracellular concentrations of the TRPM2 agonist ADP-ribose by reversed-phase HPLC. J. Chromatogr. B. 821, 181-187
23. Schweitzer, K., Mayr, G. W. and Guse, A. H. (2001) Assay for ADP-ribosyl cyclase by reverse-phase high-performance liquid chromatography. Anal. Biochem. 299, 218-226
24. Kunerth, S., Mayr, G. W., Koch-Nolte, F. and Guse, A. H. (2003) Analysis of subcellular calcium signals in T-lymphocytes. Cell. Signal. 15, 783-792
25. 2+ signals by cyclic ADP-ribose in 3T3 cells stimulated via purinergic P2Y receptors. J. Cell. Biol. 163, 837-845
26. Hamill, O. P., Marty, A., Neher, E., Sakmann, B. and Sigworth, F. J. (1981) Improved patch-clamp techniques for high-resolution current recording from cells and cell-free membrane patches. Pfugers Arch. Eur. J. Physiol. 391, 85-100
27. Fliegert, R., Gasser, A. and Guse, A. H. (2007) Regulation of calcium signalling by adenine-based second messengers. Biochem. Soc. Trans. 35, 109-114
28. Kolisek, M., Beck, A., Fleig, A. and Penner, R. (2005) Cyclic ADP-ribose and hydrogen peroxide synergize with ADP-ribose in the activation of TRPM2 channels. Mol. Cell 18, 61-69
29. Togashi, K., Hara, Y., Tominaga, T., Higashi, T., Konishi, Y., Mori, Y. and Tominaga, M. (2006) TRPM2 activation by cyclic ADP-ribose at body temperature is involved in insulin secretion. EMBO. J. 25, 1804-1815
30. 2+ signaling in T-lymphocytes. Cell. Signal. 16, 1283-1289
31. 2+ channel in Jurkat T lymphocytes. Science 283, 836-839
32. Herscher, C. J. and Rega, A. F. (1996) Pre-steady-state kinetic study of the mechanism of inhibition of the plasma membrane Ca(2+)-ATPase by lanthanum. Biochemistry 35, 14917-14922
33. Zhang, B., Wagner, G. K., Weber, K., Garnham, C., Morgan, A. J., Galione, A., Guse, A. H. and Potter, B. V. L. (2008) 2′-deoxy cyclic adenosine 5′-diphosphate ribose derivatives: importance of the 2′-hydroxyl motif for the antagonistic activity of 8-substituted cADPR derivatives. J. Med. Chem. 51, 1623-1636
34. crac) by ryanodine receptors in inositol 1,4,5-trisphosphate-receptor-deficient DT40 cells. Biochem. J. 360, 17-22
35. Beck, A., Kolisek, M., Bagley, L. A., Fleig, A. and Penner, R. (2006) Nicotinic acid adenine dinucleotide phosphate and cyclic ADP-ribose regulate TRPM2 channels in T lymphocytes. FASEB. J. 20, 962-964
36. Gasser, A., Bruhn, S. and Guse, A. H. (2006) Second messenger function of nicotinic acid adenine dinucleotide phosphate revealed by an improved enzymatic cycling assay. J. Biol. Chem. 281, 16906-16913
37. 2+ trigger. Sci. Signal. 1, re10
38. Guse, A. H., Goldwich, A., Weber, K. and Mayr, G. W. (1995) Non-radioactive, isomer-specific inositol phosphate mass determinations: high-performance liquid chromatography-micro-metal-dye detection strongly improves speed and sensitivity of analyses from cells and micro-enzyme assays. J. Chromatogr. B. Biomed. Appl. 672, 189-198
39. Gu, X., Yang, Z., Zhang, L., Kunerth, S., Fliegert, R., Weber, K., Guse, A. H. and Zhang, L. (2004) Synthesis and biological evaluation of novel membrane-permeant cyclic ADP-ribose mimics: N1-[(5″-O-phosphorylethoxy)methyl]-5′- O-phosphorylinosine 5′,5″-cyclicpyrophosphate (cIDPRE) and 8-substituted derivatives. J. Med. Chem. 47, 5674-5682
40. Guse, A. H., Gu, X., Zhang, L., Weber, K., Kramer, E., Yang, Z., Jin, H., Li, Q., Carrier, L. and Zhang, L. (2005) A minimal structural analogue of cyclic ADP-ribose: synthesis and calcium release activity in mammalian cells. J. Biol. Chem. 280, 15952-15959
41. 2+-mobilizing second messenger. Structure-activity relationship of the N1-ribose moiety. J. Am. Chem. Soc. 127, 8846-8855
42. 2+-mobilizing activity of 8-substituted cyclic inosine 5′-diphosphoribose analogues in T-lymphocytes. J. Med. Chem. 49, 5162-5176
43. Xu, J., Yang, Z., Dammermann, W., Zhang, L., Guse, A. H. and Zhang, L. (2006) Synthesis and agonist activity of cyclic ADP-ribose analogues with substitution of the northern ribose by ether or alkane chains. J. Med. Chem. 49, 5501-5512
44. 2+ signaling via the T cell receptor/CD3 complex. J. Biol. Chem. 277, 50636-50642
45. 3 and dissociation from calcium release. Cell 89, 973-980