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

Journal of Medicinal Chemistry

Volumn 47, Issue 23, 2004, Pages 5674-5682

  Gu, Xianfeng ^a   Yang, Zhenjun ^a   Zhang, Liangren ^a   Kunerth, Svenja ^b   Fliegert, Ralf ^b   Weber, Karin ^b   Guse, Andreas H ^b   Zhang, Lihe ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b UNIVERSITY MEDICAL CENTER HAMBURG EPPENDORF   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC ADENOSINE DIPHOSPHATE RIBOSE; N 1 [(5' ACETOXYETHOXY)METHYL] 2',3' O ISOPROPYLIDENEINOSINE; N 1 [(5' O PHOSPHORYLETHOXY)METHYL] 2',3' O ISOPROPYLIDENE 5' O PHOSPHORYL 8 AZIDOINOSINE 5',5' CYCLICPYROPHOSPHATE; N 1 [(5' O PHOSPHORYLETHOXY)METHYL] 2',3' O ISOPROPYLIDENE 5' O PHOSPHORYL 8 BROMOINOSINE 5',5' CYCLICPYROPHOSPHATE; N 1 [(5' O PHOSPHORYLETHOXY)METHYL] 5' O PHOSPHORYL 8 AMINOINOSINE 5',5' CYCLICPYROPHOSPHATE; N 1 [(5' O PHOSPHORYLETHOXY)METHYL] 5' O PHOSPHORYL 8 AZIDOINOSINE 5',5' CYCLICPYROPHOSPHATE; N 1 [(5' O PHOSPHORYLETHOXY)METHYL] 5' O PHOSPHORYL 8 BROMOINOSINE 5',5' CYCLICPYROPHOSPHATE; N 1 [(5' O PHOSPHORYLETHOXY)METHYL] 5' O PHOSPHORYL 8 CHLOROINOSINE 5',5' CYCLICPYROPHOSPHATE; N 1 [(5' O PHOSPHORYLETHOXY)METHYL] 5' O PHOSPHORYLINOSINE 5',5' CYCLICPYROPHOSPHATE; N 1 [[[5' (PHENYLTHIO)PHOSPHORYL]OXYETHOXY]METHYL] 5' O PHOSPHORYL 2',3' O ISOPROPYLIDENE 8 AZIDOINOSINE; N 1 [[[5' (PHENYLTHIO)PHOSPHORYL]OXYETHOXY]METHYL] 5' O PHOSPHORYL 2',3' O ISOPROPYLIDENE 8 BROMOINOSINE; N 1 [[[BIS 5' (PHENYLTHIO)PHOSPHORYL]OXYETHOXY]METHYL] 5' O (DIANILINOPHOSPHORYL) 2',3' O ISOPROPYLIDENE 8 AZIDOINOSINE; N 1 [[[BIS 5' (PHENYLTHIO)PHOSPHORYL]OXYETHOXY]METHYL] 5' O (DIANILINOPHOSPHORYL) 2',3' O ISOPROPYLIDENE 8 BROMOINOSINE; PURINE NUCLEOSIDE; PYROPHOSPHORIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCIUM CELL LEVEL; CALCIUM SIGNALING; CALCIUM TRANSPORT; CELL MEMBRANE PERMEABILITY; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; HALOGENATION; HUMAN; HUMAN CELL; LEUKEMIA CELL LINE; MOLECULAR MIMICRY; STRUCTURE ACTIVITY RELATION; T LYMPHOCYTE;

ADENOSINE DIPHOSPHATE RIBOSE; CALCIUM SIGNALING; CELL MEMBRANE; HUMANS; INOSINE MONOPHOSPHATE; JURKAT CELLS; MOLECULAR MIMICRY; PERMEABILITY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 7444230429     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm040092t     Document Type: Article

References (39)

1. Ogawa, Y. Role of Ryanodine receptors. Crit. Rev. Biochem. Mol. Biol. 1994, 29, 229-274.
2. Lee, H. C. Mechanism of calcium signaling by cyclic ADP-ribose and NAADP. Physiol. Rev. 1997, 77, 1133-1164.
3. Lee, H. C., Ed. Cyclic ADP-ribose and NAADP. Structures, Metabolism and Functions; Kluwer Academic Publishers: Boston/ Dordrecht/London, 2002.
4. Guse, A. H. Regulation of calcium signaling by the second messenger (cADPR). Curr. Mol. Med. 2004, 4, 239-248.
5. Hellmich, M. R.; Strumwasser, F. Purification and characterization of a molluscan egg-specific NADase, a second-messenger enzyme. Cell Regul. 1991, 2, 193-202.
6. Lee, H. C.; Aarhus, R. The structure of cyclic ADP-ribose. Nature Struct. Biol. 1994, 1, 143-144
7. Okamoto, H. The CD38-cyclic ADP-ribose signaling system in insulin secretion. Mol. Cell Biochem. 1999, 193, 113-118.
8. 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.; Mayr, G. W. Regulation of calcium signaling in T lymphocytes by the second messenger cyclic ADP-ribose. Nature 1999, 398, 70-73.
9. Guse, A. H. Biochemistry, biology, and pharmacology of cyclic adenosine diphosphoribose (cADPR). Curr. Med. Chem. 2004, 11, 847-855.
10. Walseth, T. F.; Aarhus, R.; Karr, J. A.; Lee, C. H. Identification of cyclic ADP-ribose binding proteins by photoaffinity labeling. J. Biol. Chem. 1993, 268, 26686-26691.
11. 2+ release. Biochim. Biophys. Acta 1993, 1178, 235-242.
12. Lee, H. C.; Aarhus, R.; Walseth, T. F. Calcium mobilization by dual receptors during fertilization of sea urchin eggs. Science 1993, 261, 352-355.
13. 2+ release in T lymphocyte cell lines. J. Immunol. 1995, 155, 3353-3359.
14. Rakovic, S.; Galione, A.; Ashamu, G. A.; Potter, B. V. L.; Terrar, D. A. A specific cyclic ADP-ribose antagonist inhibits cardiac excitation- concentration coupling. Curr. Biol. 1996, 6, 989-996.
15. 2+ release. Biochemistry 1997, 36, 9509-9517.
16. Vu, C. Q.; Lu, P. J.; Chen, C. S.; Jacobson, M. K. 2′-Phosphocyclic ADP-ribose, a calcium-mobilizing agent derived from NADP. J. Biol. Chem. 1996, 271, 4747-4754.
17. 2+ release in human T-cell lines. Eur. J. Biochem. 1997, 245, 411-417.
18. 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. 1995, 270, 30327-30333.
19. 2+-mobilizing mimic of cyclic adenosine diphosphate ribose. FEBS Lett. 1996, 370, 227-230
20. Wong, L.; Aarhus, R.; Lee, H. C.; Walseth, T. F. Cyclic 3-deazaadenosine diphosphoribose: a potent and stable analog of cyclic ADP-ribose. Biochim. Biophys. Acta 1999, 1472, 555-564.
21. Zhang, F.-J.; Yamado, S.; Gu, Q.-M. Synthesis and characterization of cyclic ATP-ribose: a potent mediator of calcium release. Bioorg. Med. Chem. Lett. 1996, 6, 1203-1205.
22. Aarhus, R.; Gee, K.; Lee, H. C. Caged cADPR, synthesis and use. J. Biol. Chem. 1995, 270 (13), 7745-7749.
23. 1-pentyl analogue of cyclic inosine diphosphate ribose (cIDPR) as a stable potential mimic of cyclic ADP ribose (cADPR), Eur. J. Org. Chem. 2002, 4234-4238
24. Galeone, A.; Mayol, L.; Oliviero, G.; Piccialli, G.; Varra, M. Synthesis of a novel N-1 carbocyclic, N-9 butyl analogue of cyclic ADP ribose (cADPR). Tetrahedron 2002, 58, 363-368
25. Shuto, S.; Shirato, M.; Sumita, Y.; Ueno, Y.; Matsuda A. Nucleosides and nucleotides 173. Synthesis of cyclic IDP-carbocyclic-ribose, a stable mimic of cyclic ADP-ribose, significant facilitation of the intramolecular condensation reaction of N-1-(carbocyclic-ribosyl) inosine 5′,6′-diphosphate derivatives by an 8-bromo-substitution at the hypoxyanthine moiety. J. Org. Chem. 1998, 63, 1986-1994.
26. 2+-mobilizing second messenger cyclic ADP-ribose. J. Am. Chem. Soc. 2001, 123, 8750-8759.
27. Guse, A. H.; Cakir-Kiefer, 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, 6744-6751.
28. 2+-mobilizing second messenger cyclic ADP-ribose. J. Med. Chem. 2003, 46, 4741-4749.
29. Huang, L. J.; Zhou, Y. Y.; Yuan, L.; Min, J. M.; Zhang, L. H. Chemical synthesis and calcium release activity of N-1-ether strand substituted cADPR mimic. Bioorg. Med. Chem. Lett. 2002, 12, 887-889
30. 1-glycosyl substituted stable mimics of cyclic ADP-ribose. J. Med. Chem. 2002, 45, 5340-5352
31. 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. (Cambridge) 2003, 15, 1944-1945.
32. 2+ entry induced by cyclic ADP-ribose in intact T-lymphocytes. J. Biol. Chem. 1997, 272, 8546-8550.
33. 2+ releasing messengers. EMBO J. 2002, 21, 909-919.
34. 2+ release in sea urchin egg homogenates: modulation by cyclic ADP-ribose. Science 1991, 253, 1143-1146.
35. 2+ pools in Jurkat T-lymphocytes. Biochem. J. 1993, 291, 447-451.
36. 2+ signaling via the T cell receptor/CD3 complex. J. Biol. Chem. 2002, 277, 50636-50642.
37. 2+ entry. J. Biol. Chem. 1998, 273, 133-144.
38. Kunerth, S.; Mayr, G. W.; Koch-Nolte, F.; Guse, A. H. Analysis of subcellular calcium signals in T-lymphocytes. Cell Signal. 2003, 15, 783-792.
39. 2+ signals by cyclic ADP-ribose in 3T3 cells stimulated via purinergic P2Y receptors. J. Cell Biol. 2003, 163, 837-845.