Synthesis and agonist activity of cyclic ADP-ribose analogues with substitution of the northern ribose by ether or alkane chains

Journal of Medicinal Chemistry

Volumn 49, Issue 18, 2006, Pages 5501-5512

  Xu, Jianfeng ^a   Yang, Zhenjun ^a   Dammermann, Werner ^b   Zhang, Liangren ^a   Guse, Andreas H ^b   Zhang, Li He ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b UNIVERSITY MEDICAL CENTER HAMBURG EPPENDORF   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE; ALKANE DERIVATIVE; BRIDGED COMPOUND; CALCIUM ION; CYCLIC ADENOSINE DIPHOSPHATE RIBOSE; ETHER DERIVATIVE; IMIDAZOLE DERIVATIVE; N1 [(4'' O PHOSPHORYL)BUTYL] 5' O PHOSPHORYLADENOSINE 5',5'' CYCLIC PYROPHOSPHATE; N1 [(5'' O PHOSPHORYL)ETHOXYETHYL] 5' O PHOSPHORYLADENOSINE 5',5'' CYCLIC PYROPHOSPHATE; N1 [(5'' O PHOSPHORYL)PENTYL] 5' O PHOSPHORYLADENOSINE 5',5'' CYCLIC PYROPHOSPHATE; N1 [(6'' O PHOSPHORYL)HEXYL] 5' O PHOSPHORYLADENOSINE 5',5'' CYCLIC PYROPHOSPHATE; OKT 3; RYANODINE RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; CALCIUM MOBILIZATION; CALCIUM SIGNALING; CELL MEMBRANE PERMEABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYCLIZATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ADENINE; ALKANES; CALCIUM; CELL MEMBRANE PERMEABILITY; CYCLIC ADP-RIBOSE; ETHERS; HUMANS; JURKAT CELLS; RECEPTORS, CELL SURFACE; RYANODINE RECEPTOR CALCIUM RELEASE CHANNEL; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33748618971     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060320e     Document Type: Article

References (28)

1. Clapper, D. L.; Walseth, T. F.; Dargie, P. J.; Lee, H. C. Pyridine nucleotide metabolites stimulate calcium release from sea urchin egg microsomes desensitized to inositol trisphosphate. J. Biol. Chem. 1987, 262, 9561-9568.
2. 2+-mobilizing activity. J. Biol. Chem. 1989, 264, 11725-11731.
3. 2+ stores: A perspective from cyclic ADP-ribose and NAADP. Curr. Mol. Med. 2004, 4, 227-237.
4. Guse, A. H. Regulation of calcium signaling by the second messenger cyclic adenosine diphosphoribose (cADPR). Curr. Mol. Med. 2004, 4, 239-248.
5. 2+ release. Biochim. Biophys. Acta 1993, 1178 (3), 235-242.
6. Vu, C. Q.; Lu, P. J.; Chen, C. S.; Jacobson, M. K. 2′-Phospho- cyclic ADP-ribose, a calcium-mobilizing agent derived from NADP. J. Biol. Chem. 1996, 271, 4747-4754.
7. 2+ release in human T-cell lines. Eur. J. Biochem. 1997, 245 (2), 411-417.
8. 2+ release. Biochemistry 1997, 36, 9509-9517.
9. Guse, A. H.; CakirKiefer, C.; Fukuoka, M.; Shuto, S.; Weber, K.; Bailey, V. C.; Matsuda, A.; Mayr, G. W.; Oppenheimer, N.; Schuber, F.; Potter, B. V. L. Novel hydrolysis-resistant analogues of cyclic ADP-ribose: modification of the "northern" ribose and calcium release activity. Biochemistry 2002, 41 (21), 6744-6751.
10. Zhang, F. J.; Yamada, S.; Gu, Q. M. Synthesis and characterization of cyclic ATP-ribose: A potent mediator of calcium release. Bioorg. Med. Chem. Lett. 1996, 6 (11), 1203-1208.
11. 2+-mobilizing mimic of cyclic adenosine diphosphate ribose. FEBS Lett. 1996, 379, 227-230.
12. 2+-mobilizing second messenger cyclic ADP-ribose. J. Am. Chem. Soc. 2001, 123 (36), 8750-8759.
13. 2+-mobilizing second messenger. Structure-activity relationship of the N1-ribose moiety. J. Am. Chem. Soc. 2005, 127 (24), 8846-8855
14. Huang, L. J.; Zhao, Y. Y.; Yuan, L.; Min, J. M.; Zhang, L. H. Syntheses and calcium mobilizing evaluations of N1-glycosyl substituted stable mimics of Cyclic ADP-ribose. J. Med. Chem. 2002, 45, 5340-5352.
15. Gu, X. F.; Yang, Z. J.; Zhang, L. R.; Zhang, L. H. Synthesis and biological evaluation of novel membrane-permeant cyclic ADP-ribose mimics: N1-[(5″-O-phosphoryl-ethoxy)-methyl]-5′-O-phosphorylinosine 5′,5″-cyclicpyrophosphate (cIDPRE) and 8-substituted derivatives. J. Med. Chem. 2004, 47, 5674-5682.
16. Wagner, G. K.; Guse, A. H.; Potter, B. V. L. Rapid synthetic route toward structurally modified derivatives of cyclic adenosine 5′-diphosphate ribose. J. Org. Chem. 2005, 70 (12), 4810-4819.
17. Graeff, R. M.; Walseth, T. F.; Hill, H. K.; Lee, H. C. Fluorescent analogs of cyclic ADP-ribose: Synthesis, spectral characterization, and use. Biochemistry 1996, 35, (2), 379-386.
18. Guse, A. H.; Gu, X. F.; Zhang, L. R.; Weber, K.; Zhang, L. H. A minimal structural analogue of cyclic ADP-ribose. J. Biol. Chem. 2005, 280, 15952-15959.
19. Hutchinson, E. J.; Taylor, B. F.; Blackburn, G. M. Stereospecific synthesis of 1,9-bis(beta-D-glycosyl)adenines: a chemical route to stable analogues of cyclic-ADP ribose (cADPR). J. Chem. Soc., Chem. Commun. 1997, 1859-1860.
20. 2+-mobilizing second messenger cyclic ADP-ribose. J. Med. Chem. 2003, 46, 4741-4749.
21. Yoshikawa, M.; Kato, T.; Takenishi, T. Study of phosphorylation. III. Selective phosphorylation of unprotected nucleotides. Bull. Chem. Soc. Jpn. 1969, 42, 3505-3508.
22. Hata, T.; Kamimura, T. A new method for the synthesis of oligodeoxyribonucleotides bearing a 5′-terminal phosphate group. Chem. Lett. 1987, 117-120.
23. 2+ signaling in T-lymphocytes. Crit. Rev. Immunol. 1998, 18, 419-448.
24. Guse, A. H. Biochemistry, biology, and pharmacology of cyclic adenosine diphosphoribose (cADPR). Curr. Med. Chem. 2004, 11, 847-855.
25. Kunerth, S.; Mayr, G. W.; Koch-Nolte, F.; Guse, A. H. Analysis of subcellular calcium signals in T-lymphocytes. Cell. Signalling 2003, 15, 783-792.
26. 2+ signals by cyclic ADP-ribose and the type 3 ryanodine receptor in T cells. J. Cell Sci. 2004, 117, 2141-2149.
27. Wagner, G. K.; Black, S.; Guse, A. H.; Potter, B. V. L. 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. 2003, 15, 1944-1945.
28. Kirchberger, T.; Wagner, G.; Xu, J. F.; Cordiglieri, C.; Wang, P.; Gasser, A.; Fliegert, R.; Bruhn, S.; Flügel, A.; Lund, F. E. Zhang, L. H.; Potter, B. V. L.; Guse, A. H. Cellular effects and metabolic stability of N1-cyclic inosine diphosphoribose and its devivatives. Br. J. Pharmacol., in press.