Cyclen based lanthanide ion ribonuclease mimics: The effect of pyridine cofactors upon phosphodiester HPNP hydrolysis

Tetrahedron Letters

Volumn 46, Issue 21, 2005, Pages 3761-3766

  Gunnlaugsson, Thorfinnur ^a   Davies, R Jeremy H ^b   Kruger, Paul E ^a   Jensen, Paul ^a   McCabe, Thomas ^a   Mulready, Sinead ^a   O'Brien, John E ^a   Stevenson, Clarke S ^b   Fanning, Ann Marie ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

^b QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

Cyclen; Eu(III); HPNP; Hydrolysis; La(III); Lanthanides; Ribonuclease mimics

Indexed keywords

4 NITROPHENYLPHOSPHATASE; ESTER DERIVATIVE; EUROPIUM; LANTHANIDE; PYRIDINE DERIVATIVE; RIBONUCLEASE;

ARTICLE; DRUG HALF LIFE; DRUG SYNTHESIS; HYDROLYSIS; ISOMER; LUMINESCENCE; PH; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 17844399827     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.150     Document Type: Article

References (59)

1. C. Liu, M. Wang, T. Zhang, and H. Sun Coord. Chem. Rev. 248 2004 147 168
2. J.R. Morrow, and O. Iranzo Curr. Opin. Chem. Biol. 8 2004 192 200
3. S.J. Franklin Curr. Opin. Chem. Biol. 5 2001 201 208
4. P. Molenveld, F.J. Engbersen, and D.M. Reinhoudt Chem. Soc. Rev. 29 2000 75 86
5. A. Blaskó, and T.C. Bruice Acc. Chem. Res. 32 1999 475 484
6. J.K. Baskin Curr. Opin. Chem. Biol. 3 1999 752 758
7. J.A. Cowan Curr. Opin. Chem. Biol. 5 2001 634 642
8. N. Trawick, A.T. Daniher, and J.K. Bashkin Chem. Rev. 98 1998 939 960
9. H.-J. Schneider, and A.K. Yatsimirsky H. Sigle The Lanthanides and their Interrelations with Biosystems 2003 Marcel Dekker Inc. New York 463 475
10. M. Komiyama, and J. Sumaoka Curr. Opin. Chem. Biol. 2 1998 751 757
11. M. Ovianen, S. Kuusela, and H. Lönnberg Chem. Rev. 98 1998 961 990
12. D.M. Perreault, and E.V. Anslyn Angew. Chem., Int. Ed. 36 1997 432 450
13. A.J. Kirby Angew. Chem., Int. Ed. 35 1996 707 724
14. D.E. Wilcox Chem. Rev. 96 1996 2435 2458
15. J. Chin Acc. Chem. Res. 24 1991 145 152
16. J.A. Cowan Chem. Rev. 98 1998 1067 1088
17. W. Lipcomb, and N. Sträter Chem. Rev. 96 1996 2375 2433
18. T. Gunnlaugsson, R.J.H. Davies, M. Nieuwenhuyzen, C.S. Stevenson, J.E. O'Brein, and S. Mulready Polyhedron 22 2003 711 724
19. T. Gunnlaugsson, R.J.H. Davies, M. Nieuwenhuyzen, C.S. Stevenson, R. Viguier, and S. Mulready Chem. Commun. 2002 2136 2137
20. T. Gunnlaugsson, J.E. O'Brien, and S. Mulready Tetrahedron Lett. 43 2002 8493 8497
21. O. Iranzo, T. Elmer, J.P. Richard, and J.R. Morrow Inorg. Chem. 42 2003 7737 7746
22. R.T. Kovacic, J.T. Welch, and S.J. Franklin J. Am. Chem. Soc. 125 2003 6656 6662
23. K. Worm, F. Chu, K. Matsumoto, J. Sumaoka, S. Tobey, V.M. Lynch, and E.V. Anslyn Chem. Eur. J. 9 2003 741 747
24. F. Medrano, A. Calderon, and A.K.Y. Yatsimirsky Chem. Commun. 2003 1968 1969
25. L. Zhu, O. dos Santos, C.W. Koo, M. Rybstein, L. Papa, and J.W. Canary Inorg. Chem. 42 2003 7912 7920
26. T. Gunnlaugsson, M. Nieuwenhuyzen, and C. Nolan Polyhedron 22 2003 3231 3242
27. Y. Kim, and S.J. Franklin Inorg. Chem. Acta 341 2002 107 112
28. Wang, S. Choudhary, C.B. Vink, E.A. Secord, and J.R. Morrow Chem. Commun. 2000 2509 2510
29. A. Roigh, and H.-J. Schneider Eur. J. Org. Chem. 2001 205 209
30. M.E. Branum, A.K. Tipton, S. Zhu, and L.J. Que J. Am. Chem. Soc. 123 2001 1898 1904
31. D.K. Chand, P.K. Bharadwaj, and H.-J. Schneider Tetrahedron 57 2001 6727 6732
32. I.O. Fritsky, R. Ott, H. Pritzkow, and R. Krämer Chem. Eur. J. 7 2001 1221 1231
33. A. Bencini, E. Berni, A. Binachi, V. Fedi, C. Giorgi, P. Paoletti, and B. Valtancoli Inorg. Chem. 38 1999 6323 6325
34. S. Liu, Z. Lou, and A.D. Hamilton Angew. Chem., Int. Ed. 36 1997 2678 2680
35. U. Baykal, and E.U. Akkaya Tetrahedron Lett. 39 1998 5861 5865
36. J.R. Morrow, L.A. Buttrey, V. Shelton, and K.A. Berback J. Am. Chem. Soc. 114 1992 1903 1905
37. L. Canaple, D. Hüsken, J. Hall, and R. Häner Bioconjugate Chem. 13 2002 945 951
38. S. Sakamoto, T. Tamura, T. Fukukawa, Y. Komatsu, E. Ohtsuka, M. Kitamura, and H. Inoue Nucleic Acids Res. 31 2003 1416 1425
39. D. Parker, R.S. Dickins, H. Puschmann, C. Cossland, and J.A.K. Howard Chem. Rev. 102 2002 1977 2020
40. We have previously developed lanthanide cyclen complexes as luminescent sensors and switches: T. Gunnlaugsson, J.P. Leonard, K. Sénéchal, and A.J. Harte Chem. Commun. 2004 782 783
41. T. Gunnlaugsson, and J.P. Leonard Chem. Commun. 2003 2424 2425
42. T. Gunnlaugsson, J.P. Leonard, K. Sénéchal, and A.J. Harte J. Am. Chem. Soc. 125 2003 12062 12063
43. T. Gunnlaugsson, A.J. Harte, J.P. Leonard, and M. Nieuwenhuyzen Supramol. Chem. 15 2003 505 519
44. T. Gunnlaugsson, A. Harte, J.P. Leonard, and M. Nieuwenhuyzen Chem. Commun. 2002 2134 2135
45. T. Gunnlaugsson, D.A. MacDónaill, and D. Parker J. Am. Chem. Soc. 123 2001 12866 12876
46. D. Parker Coord. Chem. Rev. 205 2000 109 131
47. P. Caravan, J.J. Ellison, T.J. McMurry, and R.B. Lauffer Chem. Rev. 99 1999 2292 2300
48. P.S. Amin, J.R. Morrow, C.H. Lake, and M.R. Churchill Angew. Chem., Int. Ed. Engl. 33 1994 773 775
49. A. Beeby, I.M. Clarkson, R.S. Dickins, S. Faulkner, D. Parker, L. Royle, A.S. de Sousa, J.A.G. Williams, and M. Woods J. Chem. Soc., Perkin Trans. 2 1999 493 504
50. R.S. Dickins, D. Parker, A.S. de Sousa, and J.A.G. Williams Chem. Commun. 1996 697 698
51. a's of the corresponding 2-, 3- and 4-acetamidopyridines have been determined as 4.09, 4.46 and 5.87, respectively: R.A. Jones, and A.R. Katritzky J. Chem. Soc. 1959 1317 1963
52. A similar mechanism has been proposed: J.S.W. Tsang, A.A. Neverov, and R.S. Brown J. Am. Chem. Soc. 125 2003 1559 1560
53. E.L. Hegg, and J.N. Bursyn Coord. Chem. Rev. 173 1998 133 165
54. K.A. Deal, and J.N. Burstyn Inorg. Chem. 35 1996 2792 2798
55. J. Chin, M. Banaszczyk, V. Jubian, and X. Zou J. Am. Chem. Soc. 111 1989 186 190
56. P. Hendry, and A.M. Sargeson J. Am. Chem. Soc. 111 1989 2521 2527
57. SAINT-NT, Brüker AXS Madison, Wisconsin, 1998
58. Sheldrick, G.M.; University of Göttingen, Göttingen, Germany, 1998
59. R. Breslow, and D.-L Huang Proc. Natl. Acad. Sci. USA 88 1991 4080 4083