Cyclic ADP-ribose analogues containing the methylenebisphosphonate linkage: Effect of pyrophosphate modifications on Ca2+ release activity

Journal of Medicinal Chemistry

Volumn 48, Issue 12, 2005, Pages 4177-4181

  Xu, Libo ^a,c   Walseth, Timothy F ^b   Slama, James T ^a  

^a MEDICAL COLLEGE OF OHIO   (United States)

^b UNIVERSITY OF MINNESOTA MEDICAL SCHOOL   (United States)

^c MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE DIPHOSPHATE RIBOSYL CYCLASE; CYCLIC ADENOSINE DIPHOSPHATE RIBOSE; METHYLENEBISPHOSPHONATE CYCLIC 3 DEAZA ADENOSINE DIPHOSPHONATE RIBOSE; METHYLENEBISPHOSPHONATE CYCLIC ADENOSINE DIPHOSPHATE RIBOSE; NICOTINAMIDE ADENINE DINUCLEOTIDE; PHOSPHONIC ACID DERIVATIVE; PYROPHOSPHATE; UNCLASSIFIED DRUG;

APLYSIA; ARTICLE; CALCIUM TRANSPORT; CONCENTRATION RESPONSE; DRUG ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; SEA URCHIN;

ADP-RIBOSYL CYCLASE; ANIMALS; APLYSIA; CALCIUM; CATALYSIS; CYCLIC ADP-RIBOSE; DIPHOSPHONATES; SEA URCHINS;

EID: 20444420114     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049469l     Document Type: Article

References (27)

1. Lee, H. C. Physiological functions of cyclic ADP-ribose and NAADP as calcium messengers. Annu. Rev. Pharmacol. Toxicol. 2001, 41, 317-345.
2. Guse, A. H. Cyclic ADP-ribose. J. Mol. Med. 2000, 78, 26-35.
3. 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 triphosphate. J. Biol. Chem. 1987, 262, 9561-9568.
4. 2+ mobilizing activities of cyclic ADP-ribose and inositol triphosphate. Cell Regul. 1990, 279-290.
5. 2+ release in sea urchin egg homogenates: Modulation by Cyclic ADP-ribose. Science 1991, 253, 1143-1146.
6. Zhang, F. J.; Gu, Q. M.; Sih, C. J. Bioorganic chemistry of cyclic ADP-ribose (cADPR). Bioorg. Med. Chem. 1999, 7, 653-664.
7. Walseth, T. F.; Lee, H. C. Pharmacology of Cyclic ADP-Ribose and NAADP Synthesis and Properties of Analogs. Cyclic ADP-Ribose and NAADP. Structures, Metabolism and Functions; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2002; pp 121-142.
8. Potter, B. V.; Walseth, T. F. Medicinal chemistry and pharmacology of cyclic ADP-ribose. Curr. Mol. Med. 2004, 4, 303-311.
9. Shuto, S.; Matsuda, A. Chemistry of cyclic ADP-ribose and its analogs. Curr. Med. Chem. 2004, 11, 827-845.
10. 2+-mobilizing mimic of cyclic adenosine diphosphate ribose. FEBS Lett. 1996, 379, 227-230.
11. 2+-mobilizing second messenger cyclic ADP-ribose. J. Am. Chem. Soc. 2001, 123, 8750-8759.
12. Zhang, F.; Yamada, S.; Gu, Q. M.; Jing, P.; Sih, C. J. Synthesis and characterization of cyclic ATP-ribose: a potent mediator of calcium release. Bioorg. Med. Chem. Lett. 1996, 6, 1203-1208.
13. Aarhus, R.; Gee, K.; Lee, H. C. Caged cyclic ADP-ribose. Synthesis and use. J. Biol. Chem. 1995, 270, 7745-7749.
14. Meyer, T.; Hilz, H. Production of anti-(ADP-ribose) antibodies with the aid of a dinucleotide-pyrophosphatase-resistant hapten and their application for detection of mono(ADP-ribosyl)ated polypeptides. Eur. J. Biochem. 1986, 155, 157-165.
15. 2-disubstituted pyrophosphates of biological interest. A novel plausible mechamism. J. Am. Chem. Soc. 1997, 119, 3691-3695.
16. Davisson, J. V.; Davis, D. R.; Dixit, V. M.; Poulter, C. D. Synthesis of nucleotide 5′-diphosphates from 5′-O-tosyl nucleosides. J. Org. Chem. 1987, 52, 1794-1801.
17. + containing a methylenebisphosphonate linkage for investigation of ADP-ribosyl cyclase. Chem. Commun. 1996, 2765-2766.
18. Shipitsyn, A. V.; Tarussova, N. B.; Shirokova, E. A.; Krayevsky, A. A. Synthesis of [bis(inosine-5′)]-tetraphosphate and [Bis-(inosine-5′)] -pentaphosphate analogues bearing the residues of methylenediphosphonic acid. Nucleosides, Nucleotides Nucleic Acids 2000, 19, 881-889.
19. Lesiak, K.; Watanabe, K. A.; George, J.; Pankiewicz, K. W. 2-(4-Nitrophenyl)ethyl methylenebis(phosphonate): a versatile re-agent for the synthesis of nucleoside 5′-methylenebis(phosphonates)s. J. Org. Chem. 1998, 63, 1906-1909.
20. Sakami, W. Toluenesulfonylisopropylidene adenosine. Biochem. Prep. 1961, 8, 5-7.
21. Wong, L.; Aarhus, R.; Lee, H. C.; Walseth, T. F. Cyclic 3-deaza-adenosine diphosphate ribose: a potent and stable analog of cyclic ADP-ribose. Biochim. Biophys. Acta 1999, 1472, 555-564.
22. Lee, H. C.; Aarhus, R.; Levitt, D. The crystal structure of cyclic ADP-ribose. Nat. Struct. Biol. 1994, 1, 143-144.
23. 2+ release. Biochim. Biophys. Acta 1993, 1178, 235-242.
24. Guse, A. H.; Cakir-Kiefer, C.; Fukuoka, M.; Shuto, S.; Weber, K.; et al. Novel hydrolysis resistant analogues of cyclic ADP-ribose: Modification of the "northern" ribose and calcium release activity. Biochemistry 2002, 41, 6744-6751.
25. Jarman, M.; Ross, W. C. J. 4-Substituted nicotinic acids and nicotinamides part II. The preparation of 4-methylnicotinamide riboside. J. Chem. Soc. C 1969, 199-203.
26. Mizuno, Y.; Tazawa, S.; Kageura, K. Synthetic studies of potential antimetabolites. XII. Synthesis of 4-substituted 1-(β-D-ribofuranosyl)-1H- imidazo[4,5-c]pyridines. Chem. Pharm. Bull. 1968, 16, 2011-2017.
27. Walseth, T. F.; Aarhus, R.; Gurnack, M. E.; Wong, L.; Breitinger, H. G.; et al. Preparation of cyclic ADP-ribose antagonists and caged cyclic ADP-ribose. Methods Enzymol. 1997, 280, 294-305.