Design and synthesis of 4″,6″-unsaturated cyclic ADP-carbocyclic-ribose, a Ca2+-mobilizing agent selectively active in T cells

Tetrahedron

Volumn 64, Issue 41, 2008, Pages 9754-9765

  Kudoh, Takashi ^a   Murayama, Takashi ^b   Hashii, Minako ^c   Higashida, Haruhiro ^c   Sakurai, Takashi ^b   Maechling, Clarisse ^d   Spiess, Bernard ^d   Weber, Karin ^e   Guse, Andreas H ^e   Potter, Barry V L ^f   Arisawa, Mitsuhiro ^a   Matsuda, Akira ^a   Shuto, Satoshi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b JUNTENDO UNIVERSITY SCHOOL OF MEDICINE   (Japan)

^c KANAZAWA UNIVERSITY GRADUATE SCHOOL OF MEDICAL SCIENCE   (Japan)

^d Laboratoire de Pharmacochimie   (France)

^e UNIVERSITY MEDICAL CENTER HAMBURG EPPENDORF   (Germany)

^f University of Bath   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4'',6'' DIDEHYDRO CYCLIC ADENOSINE DIPHOSPHATE CARBOCYCLIC RIBOSE; 4'',6'' DIDEHYDRO CYCLIC INOSINE DIPHOSPHATE CARBOCYCLIC RIBOSE; ADENOSINE DERIVATIVE; ARISTEROMYCIN; CYCLIC ADENOSINE DIPHOSPHATE RIBOSE; CYCLIC ADENOSINE DIPHOSPHATE RIBOSE DERIVATIVE; NEPLANOCIN A; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CALCIUM MOBILIZATION; CALCIUM TRANSPORT; CELL MEMBRANE DEPOLARIZATION; CONFORMATION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG EFFECT; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA CELL LINE; MOLECULAR DYNAMICS; NERVE CELL; NONHUMAN; POLYMERIZATION; PRIORITY JOURNAL; SEA URCHIN; SECOND MESSENGER; STRUCTURE ACTIVITY RELATION; T LYMPHOCYTE;

ECHINOIDEA;

EID: 49849083261     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.07.068     Document Type: Article

References (65)

1. Clapper D.L., Walseth T.F., Dargie P.J., and Lee H.C. J. Biol. Chem. 262 (1987) 9561-9568
2. Galione A. Science 259 (1993) 325-326
3. Guse A.H. Cell. Signalling 11 (1999) 309-316
4. In: Lee H.C. (Ed). Cyclic ADP-ribose and NAADP: Structures, Metabolism and Functions (2002), Kluwer Academic, Dordrecht
5. Jin D., Liu H.-X., Hirai H., Torashima T., Nagao T., Lopatina O., Shnayder N.A., Yamada K., Noda M., Seika T., Fujita K., Takasawa S., Yokoyama S., Koizumi K., Shiraishi Y., Tanaka S., Hashii M., Yoshihara T., Higashida K., Islam M.S., Yamada N., Hayashi K., Noguchi N., Kato I., Okamoto H., Matsushima A., Salmina A., Munesue T., Shimizu N., Mochida S., Asana M., and Higashida H. Nature 446 (2007) 41-45
6. Zhang F.-J., Gu Q.-M., and Sih C.J. Bioorg. Med. Chem. 7 (1999) 653-664
7. Shuto S., and Matsuda A. Curr. Med. Chem. 11 (2004) 827-845
8. Guse A.H. Curr. Med. Chem. 11 (2004) 847-855
9. Potter B.V.L., and Walseth T.F. Curr. Mol. Med. 4 (2004) 303-311
10. For example:
11. Walseth T.F., and Lee H.C. Biochem. Biophys. Acta 1178 (1993) 235-242
12. Lee H.C., Aarhus R., and Walseth T.F. Science 261 (1993) 352-355
13. Zhang F.-J., and Sih C.J. Bioorg. Med. Chem. Lett. 5 (1995) 1701-1706
14. Ashamu G.A., Galione A., and Potter B.V.L. J. Chem. Soc., Chem. Commun. (1995) 1359-1360
15. Wagner G.K., Black S., Guse A.H., and Potter B.V.L. Chem. Commun. (2003) 1944-1945
16. Mort C.J.W., Migaud M.E., Galione A., and Potter B.V.L. Bioorg. Med. Chem. 12 (2004) 475-488
17. Wagner G.K., Guse A.H., and Potter B.V.L. J. Org. Chem. 70 (2005) 4810-4819
18. Bailey V.C., Fortt S.M., Summerhill R.J., Galione A., and Potter B.V.L. FEBS Lett. 379 (1996) 227-230
19. Shuto S., Shirato M., Sumita Y., Ueno Y., and Matsuda A. J. Org. Chem. 63 (1998) 1986-1994
20. Shuto S., Shirato M., Sumita Y., Ueno Y., and Matsuda A. Tetrahedron Lett. 39 (1998) 7341-7344
21. Fukuoka M., Shuto S., Minakawa N., Ueno Y., and Matsuda A. J. Org. Chem. 65 (2000) 5238-5248
22. Shuto S., Fukuoka M., Manikowsky M., Ueno Y., Nakano T., Kuroda R., Kuroda H., and Matsuda A. J. Am. Chem. Soc. 123 (2001) 8750-8759
23. Guse A.H., Cakir-Kiefer C., Fukuoka M., Shuto S., Weber K., Matsuda A., Mayer G.W., Oppenheimer N., Schuber F., and Potter B.V.L. Biochemistry 41 (2002) 6744-6751
24. Shuto S., Fukuoka M., Kudoh T., Garnham C., Galione A., Potter B.V.L., and Matsuda A. J. Med. Chem. 46 (2003) 4741-4749
25. Hashii M., Shuto S., Fukuoka M., Kudoh T., Matsuda A., and Higashida H. J. Neurochem. 94 (2005) 316-323
26. Kudoh T., Fukuoka M., Ichikawa S., Murayama T., Ogawa Y., Hashii M., Higashida H., Kunerth S., Weber K., Guse A.H., Potter B.V.L., Matsuda A., and Shuto S. J. Am. Chem. Soc. 127 (2005) 8846-8855
27. Kudoh T., Murayama T., Ogawa Y., Matsuda A., and Shuto S. Nucleosides Nucleotides Nucleic Acids 25 (2006) 583-599
28. Kudoh T., Murayama T., Matsuda A., and Shuto S. Bioorg. Med. Chem. 15 (2007) 3032-3040
29. For example:
30. Galeone A., Mayol L., Oliviero G., Piccialli G., and Varra M. Tetrahedron 58 (2002) 363-368
31. Huang L.-J., Zhao Y.-Y., Yuan L., Min J.-M., and Zhang L.-H. J. Med. Chem. 45 (2002) 5340-5352
32. Gu X., Yang Z., Zhang L., Kunerth S., Fliegert R., Weber K., Guse A.H., and Zhang L. J. Med. Chem. 47 (2004) 5674-5682
33. Xu J., Yang Z., Dammermann W., Zhang L., Guse A.H., and Zhang L.-H. J. Med. Chem. 49 (2006) 5501-5512
34. Moreau C., Wagner G.K., Weber K., Guse A.H., and Potter B.V.L. J. Med. Chem. 49 (2006) 5162-5176
35. Lee H.C., and Aarhus R. Biochim. Biophys. Acta 1164 (1993) 68-74
36. A preliminary account of this study:. Kudoh T., Weber K., Guse A.H., Potter B.V.L., Hashii M., Higashida H., Arisawa M., Matsuda A., and Shuto S. Tetrahedron Lett. 49 (2008) 3976-3979
37. Agrofoglio L.A., and Challand S.R. Acyclic, Carbocyclic and l-Nucleosides (1998), Kluwer Academic, Dordrecht
38. Wolfe M.S., and Borchardt R.T. J. Med. Chem. 34 (1991) 1521-1530
39. Kusaka T., Yamamoto H., Shibata M., Muroi M., and Kishi T. J. Antibiot. 21 (1968) 255-263
40. Yaginuma S., Muto N., Tsujino M., Sudate Y., Hayashi M., and Otani M. J. Antibiot. 34 (1981) 359-366
41. Shuto S., Minakawa N., Niizuma S., Kim S.-H., Wataya Y., and Matsuda A. J. Med. Chem. 45 (2002) 748-751 and references therein
42. Norstrom A., Bryman I., Lindblom B., and Christensen N.J. Prostaglandins 29 (1985) 337-346
43. Andreotti D., Biondi S., and Modugno E.D. In: Abraham D.J. (Ed). Burger's Medicinal Chemistry and Drug Discovery. 6th ed. Vol. 5 (2003), John Wiley & Sons, New York, NY pp 607-735
44. Saenger W. Principles of Nucleic Acid Structure (1983), Springer, New York, NY
45. Hutchinson E.J., Taylor B.F., and Blackburn G.M. Chem. Commun. (1997) 1859-1860
46. De Napoli L., Messere A., Montesarchio D., Piccialli G., and Varra M.J. J. Chem. Soc., Perkin Trans. 1 (1997) 2079-2082
47. Choi W.J., Moon H.R., Kim H.O., Too B.N., Lee J.A., Shin D.H., and Jeong L.S. J. Org. Chem. 69 (2004) 2634-2636
48. A similar transformation of a chiral cyclopentenone to the corresponding cyclopentenylamine has been previously reported:. Marquez V.E., Lim M.-I., Tseng C.K.-H., Markovac A., Priest M.A., Khan M.S., and Kaskar B. J. Org. Chem. 53 (1988) 5709-5714
49. Sekine M., Nishiyama S., Kamimura T., Osaki Y., and Hata T. Bull. Chem. Soc. Jpn. 58 (1985) 850-860
50. Sekine M., and Hata T. Curr. Org. Chem. 3 (1993) 25-66
51. Yoshikawa M., Kato T., and Takenishi T. Bull. Chem. Soc. Jpn. 42 (1969) 3505-3508
52. Hata T., Kamimura T., Urakami K., Kohno K., Sekine M., Kumagai I., Shinozaki K., and Miura K. Chem. Lett. (1987) 117-120
53. 3: see Ref. 20.
54. Shiwa S., Murayama T., and Ogawa Y. Am. J. Physiol. Regul. Integr. Comp. Physiol. 282 (2002) R727-R737
55. Frassineti C., Ghelli S., Gans P., Sabatini A., Moruzzi M.S., and Vacca A. Anal. Biochem. 231 (1995) 374-382
56. Kim H., Jacobson E.L., and Jacobson M.K. Biochem. Biophys. Res. Commun. 194 (1993) 1143-1147
57. Martin R.B. Acc. Chem. Res. 18 (1985) 32-38
58. Blindauer C.A., Holy A., Dvorakova H., and Sigel H. J. Chem. Soc., Perkin Trans. 2 (1997) 2353-2363
59. Felemez M., Bernard P., Schlewer G., and Spiess B. J. Am. Chem. Soc. 122 (2000) 3156-3165
60. Blum H.C., Bernard P., and Spiess B. J. Am. Chem. Soc. 123 (2001) 3399-3400
61. Rudiger V., and Schneider H.J. Chem.-Eur. J. 6 (2000) 3771-3776
62. Rudiger V., and Schneider H.J. Magn. Reson. Chem. 38 (2000) 85-89
63. Mernissi-Arifi K., Schmitt L., Schlewer G., and Spiess B. Anal. Chem. 67 (1995) 2567-2574
64. Togashi K., Hara Y., Tominaga T., Higashi T., Konishi Y., Mori Y., and Tominaga M. EMBO J. 25 (2006) 1804-1815
65. Kolisek M., Beck A., Fleig A., and Penner R. Mol. Cell 18 (2005) 61-69