A novel fluorescent cell membrane-permeable caged cyclic ADP-ribose analogue

Journal of Biological Chemistry

Volumn 287, Issue 29, 2012, Pages 24774-24783

  Yu, Pei Lin ^a,b   Zhang, Zhe Hao ^b   Hao, Bai Xia ^b   Zhao, Yong Juan ^b   Zhang, Li He ^a   Lee, Hon Cheung ^b   Zhang, Liangren ^a   Yue, Jianbo ^b  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ADP-RIBOSE; CELLULAR PROCESS; CYCLIC ADENOSINE; ENDOPLASMIC RETICULUM; FLUORESCENT CELLS; HEK293 CELLS; INOSINE; JURKAT CELL; MEMBRANE-PERMEABLE; RYANODINE RECEPTORS; SPATIAL CONTROL; T-LYMPHOCYTES; WILD-TYPE CELLS;

CALCIUM; CELL MEMBRANES; ETHERS; PHOSPHATES;

CYTOLOGY;

CALCIUM ION; COUMARIN CAGED ISOPROPYLIDENE PROTECTED CYCLIC INOSINE DIPHOSPHORIBOSE ETHER; CYCLIC ADENOSINE DIPHOSPHATE RIBOSE; RYANODINE RECEPTOR 2; RYANODINE RECEPTOR 3; SHORT HAIRPIN RNA; STROMAL INTERACTION MOLECULE 1; TRANSIENT RECEPTOR POTENTIAL CHANNEL M2; UNCLASSIFIED DRUG;

ARTICLE; CALCIUM TRANSPORT; CELL MEMBRANE PERMEABILITY; CELL STRAIN HEK293; CONTROLLED STUDY; ENDOPLASMIC RETICULUM; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; LEUKEMIA CELL LINE; PRIORITY JOURNAL; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; SYNTHESIS; ULTRAVIOLET RADIATION; WESTERN BLOTTING; WILD TYPE;

ALKENES; BLOTTING, WESTERN; CALCIUM; CELL LINE; CELL MEMBRANE; COUMARINS; CYCLIC ADP-RIBOSE; FLUORESCENCE; HEK293 CELLS; HUMANS; JURKAT CELLS; MEMBRANE PROTEINS; NEOPLASM PROTEINS; REAL-TIME POLYMERASE CHAIN REACTION; RYANODINE RECEPTOR CALCIUM RELEASE CHANNEL; TRPM CATION CHANNELS;

EID: 84863798406     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M111.329854     Document Type: Article

References (41)

1. Lee, H. C. (2001) Physiological functions of cyclic ADP-ribose and NAADP as calcium messengers. Annu. Rev. Pharmacol. Toxicol. 41, 317-345
2. Guse, A. H. (2004) Biochemistry, biology, and pharmacology of cyclic adenosine diphosphoribose (cADPR). Curr. Med. Chem. 11, 847-855
3. Galione, A., and Churchill, G. C. (2000) Cyclic ADP-ribose as a calcium-mobilizing messenger. Sci. STKE 2000, PE1
4. 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
5. Thomas, J. M., Masgrau, R., Churchill, G. C., and Galione, A. (2001) Pharmacological characterization of the putative cADP-ribose receptor. Biochem. J. 359, 451-457 (Pubitemid 32999792)
6. Walseth, T. F., Aarhus, R., Kerr, J. A., and Lee, H. C. (1993) Identification of cyclic ADP-ribose-binding proteins by photoaffinity labeling. J. Biol. Chem. 268, 26686-26691 (Pubitemid 23361754)
7. 2+ from islet microsomes. J. Biol. Chem. 272, 3133-3136
8. Zhang, X., Tallini, Y. N., Chen, Z., Gan, L., Wei, B., Doran, R., Miao, L., Xin, H. B., Kotlikoff, M. I., and Ji, G. (2009) Dissociation of FKBP12.6 from ryanodine receptor type 2 is regulated by cyclic ADP-ribose but not β-adrenergic stimulation in mouse cardiomyocytes. Cardiovasc. Res. 84, 253-262
9. Thomas, J. M., Summerhill, R. J., Fruen, B. R., Churchill, G. C., and Galione, A. (2002) Calmodulin dissociation mediates desensitization of the cADPR-induced Ca2+ release mechanism. Curr. Biol. 12, 2018-2022 (Pubitemid 35474116)
10. Shirato, M., Shuto, S., Ueno, Y., and Matsuda, A. (1995) Synthetic study on carbocyclic analogues of cyclic ADP-ribose. Nucleic Acids Symp. Ser. (Oxf.) 165-166
11. Shuto, S., and Matsuda, A. (2004) Chemistry of cyclic ADP-ribose and its analogues. Curr. Med. Chem. 11, 827-845 (Pubitemid 38425918)
12. 2+-mobilizing second messenger. Nucleic Acids Symp. Ser. (Oxf.) 109-110
13. Morgan, A. J., and Galione, A. (2008) Investigating cADPR and NAADP in intact and broken cell preparations. Methods 46, 194-203
14. Fukuoka, M., Shuto, S., Minakawa, N., Ueno, Y., and Matsuda, A. (2000) An efficient synthesis of cyclic IDP- and cyclic 8-bromo-IDP-carbocyclicriboses using a modified Hata condensation method to form an intramolecular pyrophosphate linkage as a key step: an entry to a general method for the chemical synthesis of cyclic ADP-ribose analogues J. Org. Chem. 65, 5238-5248 (Pubitemid 30666435)
15. Zhang, B., Bailey, V. C., and Potter, B. V. (2008) Chemoenzymatic synthesis of 7-deaza cyclic adenosine 5′-diphosphate ribose analogues, membrane-permeant modulators of intracellular calcium release. J. Org. Chem. 73, 1693-1703 (Pubitemid 351438884)
16. Zhang, B., Wagner, G. K., Weber, K., Garnham, C., Morgan, A. J., Galione, A., Guse, A. H., and Potter, B. V. (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 (Pubitemid 351438846)
17. Kirchberger, T., Wagner, G., Xu, J., Cordiglieri, C., Wang, P., Gasser, A., Fliegert, R., Bruhn, S., Flügel, A., Lund, F. E., Zhang, L. H., Potter, B. V., and Guse, A. H. (2006) Cellular effects and metabolic stability of N1-cyclic inosine diphosphoribose and its derivatives. Br. J. Pharmacol. 149, 337-344 (Pubitemid 44582240)
18. 1-[(5″-O- phosphorylethoxy)methyl]-5′-O-phosphorylinosine 5′,5″- cyclicpyrophosphate (cIDPRE) and 8-substituted derivatives. J. Med. Chem. 47, 5674-5682
19. Guse, A. H., Gu, X., Zhang, L., Weber, K., Krämer, E., Yang, Z., Jin, H., Li, Q., and Carrier, L. (2005) A minimal structural analogue of cyclic ADPribose: synthesis and calcium release activity in mammalian cells. J. Biol. Chem. 280, 15952-15959 (Pubitemid 40616718)
20. Xu, J., Yang, Z., Dammermann, W., Zhang, L., Guse, A. H., and Zhang, L. H. (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 (Pubitemid 44376318)
21. 1-[(5″-O-phosphorylethoxy) methyl]-5′-O-phosphorylinosine-5′,5″-cyclic pyrophosphate (8-CF(3)-cIDPRE) and its calcium release activity in T cells. Org. Biomol. Chem. 8, 4705-4715
22. 2+-mobilizing activity in T-lymphocytes. Org. Biomol. Chem. 8, 1843-1848
23. Qi, N., Jung, K., Wang, M., Na, L. X., Yang, Z. J., Zhang, L. R., Guse, A. H., and Zhang, L. H. (2011) A novel membrane-permeant cADPR antagonist modified in the pyrophosphate bridge Chem. Commun. 47, 9462-9464
24. Li, L. J., Lin, B. C., Yang, Z. J., Zhang, L. R., and Zhang, L. H. (2008) A concise route for the preparation of nucleobase-simplified cADPR mimics by click chemistry. Tetrahedron Lett. 49, 4491-4493
25. Wu, H., Yang, Z., Zhang, L., and Zhang, L. (2010) Concise synthesis of novel acyclic analogues of cADPR with an ether chain as the northern moiety. New J. Chem. 34, 956-966
26. Lagisetti, C., Urbansky, M., and Coates, R. M. (2007) The dioxanone approach to (2S,3R)-2-C-methylerythritol 4-phosphate and 2,4-cyclodiphosphate, and various MEP analogues. J. Org. Chem. 72, 9886-9895
27. Yue, J., and Ferrell, J. E., Jr. (2006) Mechanistic studies of the mitotic activation of Mos. Mol. Cell. Biol. 26, 5300-5309 (Pubitemid 44036200)
28. 2+ pathway promotes cell proliferation and delays nerve growth factor-induced differentiation in PC12 cells. J. Biol. Chem. 284, 29335-29342
29. 2+-ATPase (SERCA). PLoS One 7, e31905
30. Wong, L., Aarhus, R., Lee, H. C., and Walseth, T. F. (1999) Cyclic 3-deaza-adenosine diphosphoribose: a potent and stable analogue of cyclic ADPribose. Biochim. Biophys. Acta 1472, 555-564 (Pubitemid 29516644)
31. Furuta, T., Momotake, A., Sugimoto, M., Hatayama, M., Torigai, H., and Iwamura, M. (1996) Acyloxycoumarinylmethyl-caged cAMP, the photolabile and membrane-permeable derivative of cAMP that effectively stimulates pigment-dispersion response of melanophores. Biochem. Biophys. Res. Commun. 228, 193-198 (Pubitemid 26390652)
32. Higashida, H., Salmina, A. B., Olovyannikova, R. Y., Hashii, M., Yokoyama, S., Koizumi, K., Jin, D., Liu, H. X., Lopatina, O., Amina, S., Islam, M. S., Huang, J. J., and Noda, M. (2007) Cyclic ADP-ribose as a universal calcium signal molecule in the nervous system. Neurochem. Int. 51, 192-199 (Pubitemid 47176716)
33. Lee, H. C., Aarhus, R., Graeff, R., Gurnack, M. E., and Walseth, T. F. (1994) Cyclic ADP-ribose activation of the ryanodine receptor is mediated by calmodulin. Nature 370, 307-309 (Pubitemid 24250128)
34. 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 (Pubitemid 40444648)
35. Aarhus, R., Gee, K., and Lee, H. C. (1995) Caged cyclic ADP-ribose: synthesis and use. J. Biol. Chem. 270, 7745-7749
36. 2+ influx. Curr. Biol. 15, 1235-1241
37. 2+ channel activity. Proc. Natl. Acad. Sci. U.S.A. 103, 9357-9362
38. Roos, J., DiGregorio, P. J., Yeromin, A. V., Ohlsen, K., Lioudyno, M., Zhang, S., Safrina, O., Kozak, J. A., Wagner, S. L., Cahalan, M. D., Veliçelebi, G., and Stauderman, K. A. (2005) STIM1, an essential and conserved component of store-operated Ca2+ channel function. J. Cell Biol. 169, 435-445 (Pubitemid 40686694)
39. Starkus, J. G., Fleig, A., and Penner, R. (2010) The calcium-permeable nonselective cation channel TRPM2 is modulated by cellular acidification. J. Physiol. 588, 1227-1240
40. Sumoza-Toledo, A., and Penner, R. (2011) TRPM2: a multifunctional ion channel for calcium signaling. J. Physiol. 589, 1515-1525
41. Kirchberger, T., Moreau, C., Wagner, G. K., Fliegert, R., Siebrands, C. C., Nebel, M., Schmid, F., Harneit, A., Odoardi, F., Flügel, A., Potter, B. V., and Guse, A. H. (2009) 8-Bromo-cyclic inosine diphosphoribose: toward a selective cyclic ADP-ribose agonist. Biochem. J. 422, 139-149