Fluorescent N2,N3-ε-adenine nucleoside and nucleotide probes: Synthesis, spectroscopic properties, and biochemical evaluation

ChemBioChem

Volumn 7, Issue 9, 2006, Pages 1361-1374

  Sharon, Einat ^a   Lévesque, Sébastien A ^b   Munkonda, Mercedes N ^b   Sévigny, Jean ^b   Ecke, Denise ^c   Reiser, Georg ^c   Fischer, Bilha ^a  

^a BAR ILAN UNIVERSITY   (Israel)

^b LAVAL UNIVERSITY   (Canada)

^c OTTO VON GUERICKE UNIVERSITY   (Germany)

Author keywords

Fluorescent probes; NTPDase; Nucleosides; Nucleotides; P2Y1 receptor

Indexed keywords

2' DEOXY 6 N METHYLADENOSINE 3',5' BISPHOSPHATE; ADENINE DERIVATIVE; ADENOSINE TRIPHOSPHATE; FLUORESCENT DYE; N2,N3 EPSILON ADENINE NUCLEOSIDE; N2,N3 EPSILON ADENINE NUCLEOTIDE; N2,N3 ETHENOGUANOSINE 3; PURINE P2Y RECEPTOR; UNCLASSIFIED DRUG; ADENINE; ADENOSINE; ADENOSINE PHOSPHATE; ADENOSINE TRIPHOSPHATASE; APYRASE; CALCIUM; CD39 ANTIGEN; DRUG DERIVATIVE; ECTOATPASE; ENZYME INHIBITOR; LEUKOCYTE ANTIGEN; PURINE P2 RECEPTOR; PURINE P2Y1 RECEPTOR;

ABSORPTION; ANIMAL CELL; ARTICLE; CELL STRAIN COS7; CELL STRAIN HEK293; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; FLAME PHOTOMETRY; FLUORESCENCE POLARIZATION; HUMAN; HUMAN CELL; HYDROGEN BOND; MOLECULAR PROBE; MOLECULAR RECOGNITION; NONHUMAN; PH; PRIORITY JOURNAL; PROTEIN BINDING; SPECTROSCOPY; SYNTHESIS; ANIMAL; CELL LINE; CHEMISTRY; DRUG ANTAGONISM; DRUG POTENTIATION; METABOLISM; RAT; SPECTROFLUOROMETRY; ULTRAVIOLET SPECTROPHOTOMETRY;

ADENINE; ADENOSINE; ADENOSINE MONOPHOSPHATE; ADENOSINE TRIPHOSPHATASES; ADENOSINE TRIPHOSPHATE; ANIMALS; ANTIGENS, CD; APYRASE; CALCIUM; CELL LINE; CYCLIZATION; ENZYME INHIBITORS; FLUORESCENT DYES; HUMANS; MOLECULAR STRUCTURE; RATS; RECEPTORS, PURINERGIC P2; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 33748570154     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200600070     Document Type: Article

References (55)

1. P. R. Callis, Annu. Rev. Phys. Chem. 1983, 34, 329.
2. R. W. Thomas, N. J. Leonard, Heterocycles 1976, 5, 839.
3. J. A. Secrist III, J. R. Barrio, N.J. Leonard, G. Weber, Biochemistry 1972, 11, 3499.
4. N.J. Leonard, CRC Crit. Rev. Biochem. 1984, 15, 125.
5. N. J. Leonard, Chemtracts: Biochem. Mol. Biol. 1992, 3, 273.
6. J. A. Secrist III, J. R. Barrio, N. J. Leonard, Science 1972, 175, 646.
7. H. Nakayama, T. Yamaga, Biophys. Chem. 1998, 75, 1.
8. C. H. Lee, J. G. Wetmur, Biochem. Biophys. Res. Commun. 1973, 50, 879.
9. R. B. Meyer, Jr., D. A. Shuman, R. K. Robins, J. P. Miller, L. N. Simon, J. Med. Chem. 1973, 16, 1319.
10. G. L. Tolman, J. R. Barrio, N. J. Leonard, Biochemistry 1974, 73, 4869.
11. J. Gualix, M. Abal, J. Pintor, M. T. Miras-Portugal, FEBS Lett. 1996, 391, 195.
12. S. C. Harvey, H. C. Cheung, Biochem. Biophys. Res. Commun. 1976, 73, 865.
13. R. A. Worthington, M. A. Hansen, M. R. Bennett, J. A. Barden, V. J. Balcar, Biochem. Biophys. Res. Commun. 1998, 249, 166.
14. V. R. Caiolfa, D. Gill, A. H. Parola, Biophys. Chem. 1998, 70, 45.
15. K. H. Schram, L. B. Townsend, Tetrahedron Lett. 1974, 15, 1345.
16. J. Zhou, J. G. Gao, B. Fischer, Youji Huaxue 2004, 24, 498.
17. R. Eritja, B. E. Kaplan, D. Mhaskar, L. C. Sowers, J. Petruska, M. F. Goodman, Nucleic Acids Res. 1986, 14, 5869.
18. N. K. Kochetkov, V. W. Shibaev, A. A. Kost, Tetrahedron Lett. 1971, 12, 1993.
19. P. D. Sattsangi, N. J. Leonard, C. R. Frihart, J. Org. Chem. 1977, 42, 3292.
20. J. T. Kusmierek, D. E. Jensen, S. J. Spengler, R. Stolarski, B. Singer, J. Org. Chem. 1987, 52, 2374.
21. J. T. Kusmierek, B. Singer, Chem. Res. Toxicol. 1992, 5, 634.
22. J. Boryski, Nucleosides Nucleotides 1990, 9, 803.
23. J. T. Kusmierek, D. E. Jensen, S. J. Spengler, R. Stolarski, B. Singer, Tetrahedron Lett. 2000, 41, 1695.
24. K. Kikugawa, T. Kawashima, Chem. Pharm. Bull. 1971, 19, 2629.
25. K. Arun, P. Mandel, A. Shrotri, D. Ghogare, Synth. Commun. 1986, 16, 221
26. J. Campbell, E. Greene, D. Lavagnino, D. Gardner, A. Pike, J. Snoddy, J. Heterocycl. Chem. 1986, 23, 669.
27. C. Nguyen, B. Emile, Synth. Commun. 1984, 14, 765.
28. R. Simon, K. Vinod, Tetrahedron 1988, 44, 6367.
29. G. Guillermo, B. Angeles, R. Nuria, G. Teresa, G. Rosario, Heterocycles 2002, 56, 501.
30. J. Michael, M. Jean, Helv. Chim. Acta 1998, 81, 1921.
31. A. John, S. Anita, B. Lee, A. John, Nucleosides Nucleotides 1994, 13, 1017.
32. J. W. Jack, H. Alexander, L. Iris, J. Am. Chem. Soc. 1958, 80, 1669.
33. J. T. Kusmierek, W. Folkman, B. Singer, Chem. Res. Toxicol. 1989, 2, 230.
34. L. L. Lebruska, I. I. Kuzmine, M. J. Fedor, Chem. Biol. 2002, 9, 465.
35. D. T. Major, A. Laxer, B. Fischer, J. Org. Chem. 2002, 67, 790.
36. S. M. Hand, W. W. Paudler, Tetrahedron 1982, 38, 49.
37. F. A. Beland, N. F. Fullerton, R. H. Heflich, J. Chromatogr. 1984, 308, 121.
38. J. R. Barrio, J. A. Secrist III, Y.-h. Chien, P. J. Taylor, J. L. Robinson, N. J. Leonard, FEBS Lett. 1973, 29, 215.
39. P. B. Conibear, D. S. Jeffreys, C. K. Seehra, R. J. Eaton, C. R. Bagshaw, Biochemistry 1996, 35, 2299.
40. S. S. Rosenfeld, E. W. Taylor, J. Biol. Chem. 1984, 259, 11 920.
41. C. Vöhringer, R. Schäfer, G. Reiser, Biochem. Pharmacol. 2000, 59, 791.
42. G. Zündorf, R. Schäfer, C. Vöhringer, E. Halbfinger, B. Fischer, G. Reiser, Biochem. Pharmacol. 2001, 61, 1259.
43. E. Sharon, G. Zündorf, S. A. Levesque, A. R. Beaudoin, G. Reiser, B. Fischer, Bioorg. Med. Chem. 2004, 12, 6119.
44. K. A. Jacobson, S. Moro, C. Hoffmann, Y. C. Kim, H. S. Kim, R. G. Ravi, T. K. Harden, J. L. Boyer, Farmaco 2001, 56, 71.
45. E. R. Lazarowski, W. C. Watt, M. J. Stutts, R. C. Boucher, T. K. Harden, Br. J. Pharmacol. 1995, 176, 1619.
46. F.-P. Gendron, J. T. Neary, P. M. Theiss, G. Y. Sun, F. A. Gonzalez, G. A. Weisman, Am. J. Physiol. Cell Physiol. 2003, 284, C571.
47. F. Kukulski, S. A. Levesque, E. G. Lavoie, J. Lecka, F. Bigonnesse, A. F. Knowles, S. C. Robson, T. L. Kirley, J. Sevigny, Purinergic Signalling 2005, 7, 193.
48. R. Khazanchi, P. L. Yu, F. Johnson, J. Org. Chem. 1993, 58, 2552.
49. B. Fischer, J. L. Boyer, C. H. V. Hoyle, A. U. Ziganshim, A. L. Brizzolara, G. E. Knight, J. Zimmet, G. Burnstock, T. K. Harden, K. A. Jacobson, J. Med. Chem. 1993, 36, 3937.
50. A. T. C. Tsin, H. A. Pedrozo-Fernandez, J. M. Callas, J. P. Chambers, Life Sci. 1988, 43, 1379.
51. J. J. Ubl, G. Reiser, Glia 1997, 21, 361.
52. J. J. Ubl, M. Sergeeva, G. Reiser, J. Physiol. 2000, 525, 319.
53. M. E. Tulapurkar, W. Laubinger, V. Nahum, B. Fischer, G. Reiser, Br. J. Pharmacol. 2004, 142, 869.
54. A. A. Baykov, O. A. Evtushenko, S. M. Avaeva Anal. Biochem. 1988, 171, 266.
55. M. M. Bradford, Anal. Biochem. 1976, 72, 248.