Synthesis, structural and biological evaluation of GlyAla based lanthanide macrocyclic conjugates as supramolecular ribonuclease mimics

Polyhedron

Volumn 22, Issue 5, 2003, Pages 711-724

  Gunnlaugsson, Thorfinnur ^a   Davies, R Jeremy H ^b   Nieuwenhuyzen, Mark ^b   O'Brien, John E ^a   Stevenson, Clarke S ^b   Mulready, Sinéad ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

^b QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

2 Hydroxypropyl p nitrophenyl phosphate; Benzyl alanine esters; Glycine alanine; Lanthanide complexes

Indexed keywords

AMIDES; AMINO ACIDS; COORDINATION REACTIONS; HYDROLYSIS; HYDROPHOBICITY; MOLECULES; PH; RARE EARTH ELEMENTS; SYNTHESIS (CHEMICAL); TERBIUM COMPOUNDS; X RAY CRYSTALLOGRAPHY;

2-HYDROXYPROPYL P-NITROPHENYL PHOSPHATE; BENZYL ALANINE ESTER; BIOLOGICAL EVALUATION; CONJUGATED LIGANDS; GLYCINE-ALANINE; LANTHANIDES COMPLEXES; MACROCYCLICS; P-NITROPHENYL PHOSPHATE; STRUCTURAL EVALUATION; SYNTHESIS EVALUATION;

ESTERS;

2 HYDROXYPROPYL 4 NITROPHENYLPHOSPHATE; ALANINE; CARBONYL DERIVATIVE; ESTER DERIVATIVE; GLYCINE; LANTHANIDE; MESSENGER RNA; METAL COMPLEX; OXYGEN; PHOSPHORUS DERIVATIVE; RIBONUCLEASE; TERBIUM; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATE; GENE; GEOMETRY; HYDROLYSIS; HYDROPHOBICITY; MOLECULAR MIMICRY; PH; PRISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0037339763     PISSN: 02775387     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0277-5387(02)01402-X     Document Type: Article

References (90)

1. (a) E. Kimura, Acc. Chem. Res. 34 (2001) 171;
2. (b) N.V. Kaminskaia, B. Spingler, S.J. Lippard, J. Am. Chem. Soc. 123 (2001) 6555;
3. (c) N.V. Kaminskaia, C. He, S.J. Lippard, Inorg. Chem. 93 (2000) 3365;
4. (d) A.J. Kirby, Angew. Chem., Int. Ed. 35 (1996) 707;
5. (e) E. Kimura, Prog. Inorg. Chem. 41 (1994) 443;
6. (f) A.J. Kirby, Angew. Chem., Int. Ed. 33 (1994) 551.
7. (a) T. Habicher, F. Diederich, V. Cramlich, Helv. Chem. Acta 82 (1999) 1066;
8. (b) S.J. Franklin, Curr. Opin. Chem. Biol. 5 (2001) 201;
9. (c) R. Kramer, Coord. Chem. Rev. 182 (1999) 243;
10. (d) M.C. Feiters, A.E.R.J. Rowan Nolte, Chem. Soc. Rev. 29 (2000) 375;
11. (e) R. Häner, J. Hall, A. Pfützer, D. Hüsker, Pure Appl. Chem. 70 (1998) 111;
12. (f) A. Blaskó, T.C. Bruice, Acc. Chem. Res. 32 (1999) 475.
13. (a) M. Komiyama, J. Sumaoka, Curr. Opin. Chem. Biol. 2 (1998) 751;
14. (b) W.N. Lipscomb, N. Stäter, Chem. Rev. 96 (1996) 2375.
15. (a) B.N. Trawick, A.T. Daniher, J.K. Bashkin, Chem. Rev. 98 (1998) 939;
16. (b) R. Häner, Chimia 55 (2001) 286;
17. (c) C.J. Leumann, Chimia 55 (2001) 295;
18. (d) W.C. Putnam, A.T. Daniher, B.N. Trwick, J.K. Bashkin, Nucleic Acid Res. 29 (2001) 2199;
19. (e) B.F. Baker, S.S. Lot, J. Kringel, S. Cheng-Flournoy, P. Villiet, H.M. Sasmor, A.M. Siwkowski, L.L. Chappell, J.R. Morrow, Nucleic Acid Res. 27 (1999) 1547.
20. (a) J.A. Cowan, Chem. Rev. 98 (1998) 1067;
21. (b) D.M. Perreault, E.V. Anslyn, Angew. Chem., Int. Ed. 36 (1997) 432;
22. (c) P. Molenveld, J.F.J. Engbersen, D.M. Reinhoudt, Chem. Soc. Rev. 29 (2000) 75;
23. (d) M. Komiyama, N. Takeda, H. Shigekawa, Chem. Commun. (1999) 14443;
24. (e) N.H. Williams, B. Takasaki, M. Wall, J. Chin, Acc. Chem. Res. 32 (1999) 485;
25. (f) J. Chin, Acc. Chem. Res. 24 (1991) 145;
26. (g) R. Breslow, D.-L. Huang, E. Anslyn, Proc. Natl. Acad. Sci. USA 86 (1989) 1746;
27. (h) E. Anslyn, R. Breslow, J. Am. Chem. Soc. 111 (1989) 4473.
28. D.E. Wilcox, Chem. Rev. 96 (1996) 2435 (and references therein).
29. (a) P. Molenveld, J.F.J. Engbersen, D.M. Reinhoudt, Angew. Chem., Int. Ed. 38 (1999) 3189;
30. (b) C. Sissi, P. Rossi, F. Fulluga, F. Formaggio, M. Palumbo, P. Tecilla, C. Toniolo, P. Scrimin, J. Am. Chem. Soc. 123 (2001) 3169;
31. (c) S. Liu, Z. Lou, A.D. Hamilton, Angew. Chem., Int. Ed. 36 (1997) 2678;
32. (d) W.H. Chapman, Jr., R. Breslow, J. Am. Chem. Soc. 117 (1995) 5462;
33. (e) M. Wall, R.C. Hynes, J. Chin, Angew. Chem., Int. Ed. 32 (1993) 1633;
34. (f) E.U. Chung, Akkaya, T.K. Venkatachalam, A.W. Czarnik, Tetrhedron Lett. 38 (1990) 5413.
35. (a) P. Gómez-Tagle, A.K. Yatsimirsky, Inorg. Chem. 40 (2001) 3786;
36. (b) T.A. Osiek, J.K. Bashkin, New J. Chem. 25 (2001) 541;
37. (c) U. Baykal, M.S. Akkaya, E.U. Akkaya, J. Mol. Cat. A. Chem. 145 (1999) 309;
38. (d) A. Kuzuya, M. Akai, M. Komiyama, Chem. Lett. (1999) 1035;
39. (e) M. Kalesse, A. Loos, Bioorg. Med. Chem. Lett. (1996) 2063;
40. (f) K.G. Ragunathan, H.-J. Schneider, Angew. Chem., Int. Ed. 35 (1996) 1219;
41. (g) P. Hurst, B.K. Takasaki, J. Chin, J. Am. Chem. Soc. 118 (1996) 9982;
42. (h) M. Yashiro, A. Ishikubo, T. Takarada, M. Komiyama, Chem. Lett. (1995) 655;
43. (i) K.O.A. Chin, J.R. Morrow, Inorg. Chem. 33 (1994) 5036;
44. (j) N. Hayashi, N. Takeda, T. Shiiba, M. Yashiro, K. Watanabe, M. Komiyama, Inorg. Chem. 32 (1993) 5899;
45. (k) H.-J. Schneider, J. Rammo, R. Hettich, Angew. Chem., Int. Ed. 32 (1993) 1716;
46. (l) J.R. Morrow, L.A. Buttrey, V.M. Shelton, K.A. Berack, J. Am. Chem. Soc. 114 (1992) 1903.
47. (a) A. Roigh, H.-J. Schneider, Eur. J. Org. Chem. (2001) 205;
48. (b) D.K. Chand, P.K. Bharadwaj, H.-J. Schneider, Tetrahedron 57 (2001) 6727;
49. (c) P. Molenveld, W.M.G. Stikvoort, H. Kooijman, A.L. Spek, J.F.J. Engbersen, D.N. Reinhoudt, J. Org. Chem. 64 (1999) 3896;
50. (d) S. Liu, A.D. Hamilton, Tetrahedron Lett. 38 (1997) 1107;
51. (e) V. Jubian, A. Veronese, R.P. Dixon, A.D. Hamilton, Angew. Chem., Int. Ed. Engl. 34 (1995) 1237;
52. (f) P. Rossi, F. Felluga, P. Tecilla, F. Formaggio, M. Crisma, C. Tonilo, P. Scrimin, Biopolymers 55 (2000) 496;
53. (g) F. Chu, J. Smith, V.M. Lynch, E.V. Anslyn, Inorg. Chem. 34 (1995) 5689.
54. (a) T. Gunnlaugsson, A.J. Harte, J.P. Leonard, M. Nieuwenhuyzen, Chem. Commun. 1 (2002) 2134;
55. (b) T. Gunnlaugsson, Tetrahedron Lett. 42 (2001) 8901;
56. (c) T. Gunnlaugsson, D.A. Mac Dónaill, D. Parker, J. Am. Chem. Soc. 123 (2001) 12866;
57. (d) T. Gunnlaugsson, D.A. Mac Dónaill, D. Parker, Chem. Commun. (2000) 93.
58. T. Gunnlaugsson, R.J.H. Davies, M. Nieuwenhuyzen, C.S. Stevenson, R. Viguier, S. Mulready, Chem. Commun. 1 (2002) 2136.
59. (a) Handbook of Chemistry and Physics, 78th ed., CRC Press, Boca Raton, FL, 1997.;
60. (b) C.M. Frrey, J. Stuehr, Metal Ions Biol. Sys. 1 (1974) 51.
61. P. Caravan, J.J. Ellison, T.J. McMurry, R.B. Lauffer, Chem. Rev. 99 (1999) 2293.
62. (a) O. Reany, T. Gunnlaugsson, D. Parker, Chem. Commun. (2000) 473;
63. (b) O. Reany, T. Gunnlaugsson, D. Parker, J. Chem. Soc. Perkin Tans. 2 (2000) 1819;
64. (c) M.P. Lowe, D. Parker, Chem. Commun. (2000) 707;
65. (d) R.S. Dickins, T. Gunnlaugsson, D. Parker, R.D. Peacock, Chem. Commun. (1998) 1643;
66. (e) A. Beeby, D. Parker, J.A.G.J. Williams, Chem. Soc. Perkin Tans. 2 (1996) 1565.
67. (a) W.C. Putnam, J.K. Bashkin, Chem. Commun. (2000) 767;
68. (b) J.K. Bashkin, E.I. Frolova, U.-S. Sampath, J. Am. Chem. Soc. 116 (1994) 5981.
69. B.D. White, J. Mallen, K.A. Arnold, F.R. Fronczek, R.D. Gandour, L.M.B. Gehrig, G.W. Gokel, J. Org. Chem. 54 (1989) 937.
70. (a) D. Parker, R.S. Dickins, H. Puschmann, C. Crossland, J.A.K. Howard, Chem. Rev. 102 (2002) 1977;
71. (b) J.A.K. Howard, A.M. Kenwright, J.M. Moloney, D. Parker, M. Prot, M. Naet, O. Rousseau, M. Woods, Chem. Commun. (1998) 1381.
72. (a) AINT-NT, Brüker AXS Madison, WI, 1998.;
73. (b) G.M. Sheldrick, University of Göttingen, Göttingen, Germany, 1998.
74. (a) M. Woods, S. Amie, M. Botta, J.A.K. Howard, J.M. Moloney, M. Vavet, D. Parker, M. Port, O. Rousseaux, J. Am. Chem. Soc. 122 (2000) 9781;
75. (b) S. Aime, A. Barge, J.I. Bruce, M. Botta, J.A.K. Howard, J.M. Moloney, D. Parker, A.S. de Sausa, M. Woods, J. Am. Chem. Soc. 121 (1999) 5762;
76. (c) R.S. Dickens, J.A.K. Howard, C.L. Maupin, J.M. Moloney, D. Parker, P.D. Peacock, J.P. Riehl, G. Siligardi, New J. Chem. (1998) 891.
77. R. Breslow, D.-L. Huang, Proc. Natl. Acad. Sci. USA 88 (1991) 4080.
78. S. Amin, J.R. Morrow, C.H. Lake, M.R. Churchill, Angew. Chem., Int. Ed. 33 (1994) 773.
79. U. Baykal, E.U. Akkaya, Tetrahedron Lett. 39 (1998) 5861.
80. M. Oivanen, S. Kuusela, H. Lönnberg, Chem. Rev. 98 (1998) 961 (and reference therein).
81. J.P. Collman, R.R. Gagne, C.A. Reed, T.R. Halbert, G. Lang, W.T. Robinson, J. Am. Chem. Soc. 97 (1975) 1427.
82. C.J. Boxwell, P.H. Walton, Chem. Commun. (1999) 1647.
83. (a) E.L. Hegg, J.N. Bursyn, Coord. Chem. Rev. 173 (1998) 133;
84. (b) K.A. Deal, J.N. Burstyn, Inorg. Chem. 35 (1996) 2792;
85. (c) J. Chin, X. Zou, J. Am. Chem. Soc. 110 (1988) 223;
86. (d) J. Chin, M. Banaszczyk, V. Jubian, X. Zou, J. Am. Chem. Soc. 111 (1989) 186;
87. (e) P. Hendry, A.M. Sargeson, J. Am. Chem. Soc. 111 (1989) 2521.
88. S. Aime, A.S. Batsanov, M. Botta, R.S. Dickins, S. Faulkner, C.E. Foster, A. Harrison, J.A.K. Howard, J.M. Moloney, T.J. Norman, D. Parker, L. Royle, J.A.G. Williams, J. Chem. Soc., Dalton Trans. (1997) 3623.
89. J.H. Coates, G.J. Gentle, S.F. Lincoln, Nature 249 (1974) 773.
90. P. Molenveld, J.F.J. Engbersen, D.M. Reinhoudt, J. Am. Chem. Soc. 119 (1999) 2949.