Bimodal system (luminophore and paramagnetic contrastophore) derived from Ln(III) complexes based on a bipyridine-containing macrocyclic ligand

Inorganic Chemistry

Volumn 44, Issue 23, 2005, Pages 8293-8305

  Nasso, Isabelle ^a   Galaup, Chantal ^a   Havas, Fabien ^a   Tisnès, Pierre ^a   Picard, Claude ^a   Laurent, Sophie ^b   Elst, Luce Vander ^b   Muller, Robert N ^b  

^a UPS)   (France)

^b UNIVERSITY OF MONS   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 28344435847     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic0507722     Document Type: Article

References (110)

1. (a) Merbach, A. E.; Toth, E. In The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging; Wiley: London, 2001.
2. (b) Caravan, P.; Ellison, J. J.; McMurry, T. J.; Lauffer, R. B. Chem. Rev. 1999, 99, 2293-2352.
3. (c) Aime, S.; Botta, M.; Fasano, M.; Terreno, E. Chem. Soc. Rev. 1998, 27, 19-29.
4. Weinmann, H.-J.; Ebert, W.; Misselwitz, B.; Schmitt-Willich, H. Eur. J. Radiol. 2003, 46, 33-44.
5. (a) Fatin-Rouge, N.; Toth, E.; Meuli, R.; Bünzli, J.-C. G. J. Alloys Compd. 2004, 374, 298-302.
6. (b) Vander Elst, L.; Port, M.; Raynal, I.; Simonot, C.; Muller, R. N. Eur. J. Inorg. Chem. 2003, 2495-2501.
7. (c) Toth, E.; Helm, L.; Kellar, K. E.; Merbach, A. E. Chem. - Eur. J. 1999, 5, 1202-1211.
8. (d) Muller, R. N.; Radüchel, B.; Laurent, S.; Platzek, J.; Piérart, C.; Mareski, P.; Vander Elst, L. Eur. J. Inorg. Chem. 1999, 1949-1955.
9. (a) Lowe, M. P. Aust. J. Chem. 2002, 55, 551-556.
10. (b) Meade, T. J.; Taylor, A. K.; Bull, S. R. Curr. Opin. Neurobiol. 2003, 13, 597-602.
11. (a) Richardson, F. S. Chem. Rev. 1982, 82, 541-552.
12. (b) Sammes, P. G.; Yahioglu, G. Nat. Prod. Rep. 1996, 13, 1-28.
13. (a) Bünzli, J.-C. G. In Metal Complexes in Tumor Diagnosis and as Anticancer Agents; Sigel, A., Sigel, H., Eds.; Metal Ions in Biological Systems, Vol. 42; Marcel Dekker Inc.: New York, 2004; Chapter 2.
14. (b) Motson, G. R.; Fleming, J. S.; Brooker, S. Adv. Inorg. Chem. 2004, 55, 361-432.
15. (c) Steinkamp, T.; Karst, U. Anal. Bioanal. Chem. 2004, 380, 24-30.
16. (d) Bazin, H.; Trinquet, E.; Mathis, G. Rev. Mol. Biotechnol. 2002, 82, 233-250.
17. (e) Hemmilä, I.; Webb, S. Drug Discovery Today 1997, 2, 373-381.
18. (f) Bioanalytical Applications of Labeling Technologies; Hemmila, I., Stahlberg, T., Mottram, P., Eds.; Wallac Oy: Turku, Finland, 1995.
19. (a) Kolb, A. J.; Burke, J. W.; Mathis, G. In High Throughput Screening: The Discovery of Bioactive Substances; Devlin, J. P., Ed.; Marcel Dekker: New York, 1997; pp 345-360.
20. (b) Frias, J. C.; Bobba, G.; Cann, M. J.; Hutchison, C. J.; Parker, D. Org. Biomol. Chem. 2003, 1, 905-907.
21. (c) Hemmila, I.; Mukkala, V.-M. Crit. Rev. Clin. Lab. Sci. 2001, 38, 441-519.
22. (a) Bornhop, D. J.; Griffin, J. M. M.; Goebel, T. S.; Sudduth, M. R.; Bell, B.; Motamedi, M. Appl. Spectrosc. 2003, 57, 1216-1222.
23. (b) Bornhop, D. J.; Hubbard, D. S.; Houlne, M. P.; Adair, C.; Kiefer, G. E.; Pence, B. C.; Morgan, D. L. Anal. Chem. 1999, 71, 2607-2615.
24. (c) Hubbard, D. S.; Houlne, M. P.; Kiefer, G. E.; McMillan, K.; Bornhop, D. J. Bioimaging 1998, 6, 63-70.
25. (a) Frullano, L.; Rohovec, J.; Peters, J. A.; Geraldes, C. F. G. C. Top. Curr. Chem. 2002, 221, 25-60.
26. (b) Thunus, L.; Lejeune, R. Coord. Chem. Rev. 1999, 184, 125-155.
27. (a) Laurent, S.; Vander Elst, L.; Fu, Y.; Muller, R. N. Bioconjugate Chem. 2004, 15 (1), 99-103.
28. (b) Laurent, S.; Botteman, F.; Vander Elst, L.; Muller, R. N. Eur. J. Inorg. Chem. 2004, 463-468.
29. (c) Laurent, S.; Botteman, F.; Vander Elst, L.; Muller, R. N. Helv. Chim. Acta 2004, 87, 1077-1089.
30. (a) Galaup, C.; Couchet, J.-M.; Bedel, S.; Tisnès, P.; Picard, C. J. Org. Chem. 2005, 70, 2274-2284.
31. (b) Tedeschi, C.; Azéma, J.; Gornitzka, H.; Tisnès, P.; Picard, C. J. Chem. Soc., Dalton Trans. 2003, 1738-1745.
32. (c) Galaup, C.; Azéma, J.; Tisnès, P.; Picard, C.; Ramos, P.; Juanes, O.; Brunet, E.; Rodríguez-Ubis, J. C. Helv. Chim. Acta 2002, 85, 1613-1625.
33. (d) Galaup, C.; Carrié, M.-C.; Tisnès, P.; Picard, C. Eur. J. Org. Chem. 2001, 2165-2175.
34. For a recent example, see: Manning, H. C.; Goebel, T.; Thompson, R. C.; Price, R. R.; Lee, H.; Bornhop, D. J. Bioconjugate Chem. 2004, 15, 1488-1495.
35. Kim, W. D.; Kiefer, G. E.; Maton, F.; McMillan, K.; Muller, R. N.; Sherry, A. D. Inorg. Chem. 1995, 34, 2233-2243.
36. PCTA[12] = 12-membered pyridine containing a triaza macrocycle triacetate ligand, bpyCTA[15] = 15-membered bipyridine containing a triaza macrocycle triacetate ligand, and tpyCTA[18] = 18-membered terpyridine containing a triaza macrocycle triacetate ligand.
37. Aime, S.; Botta, M.; Geninatti Crich, S.; Giovenzana, G. B.; Jommi, G.; Pagliarin, R.; Sisti, M. Inorg. Chem. 1997, 36, 2992-3000.
38. Siaugue, J.-M.; Favre-Réguillon, A.; Dioury, F.; Plancque, G.; Foos, J.; Madic, C.; Moulin, C.; Guy, A. Eur. J. Inorg. Chem. 2003, 2834-2838.
39. Galaup, C.; Couchet, J. M.; Picard, C.; Tisnès, P. Tetrahedron Lett. 2001, 42, 6275-6278.
40. Bünzli, J.-C. G. In Lanthanides, Probes in Life, Chemical and Earth Sciences; Choppin, G. R., Bünzli, J.-C. G., Eds.; Elsevier: Amsterdam, 1989; pp 219-293.
41. (a) Aime, S.; Botta, M.; Frullano, L.; Geninatti Crich, S.; Giovenzana, G. B.; Pagliarin, R.; Palmisano, G.; Sisti, M. Chem. - Eur. J. 1999, 5, 1253-1260.
42. (b) Aime, S.; Benetollo, F.; Bombieri, G.; Colla, S.; Fasano, M.; Paoletti, S. Inorg. Chim. Acta 1997, 254, 63-70.
43. (c) Ibrahim, M. A.; Haughton, V. M.; Hyde, J. S. Am. J. Neuroradiol. 1994, 15, 1907-1910.
44. (d) Mukkala, V.-M.; Kwiatkowski, M.; Kankare, J.; Takalo, H. Helv. Chim. Acta 1993, 76, 893-899.
45. Couchet, J. M.; Galaup, C.; Tisnès, P.; Picard, C. Tetrahedron Lett. 2003, 44, 4869-4872.
46. Atkins, T. J.; Richman, J. E.; Oettle, W. F. Org. Synth. 1978, 58, 86-98.
47. Newkome, G. R.; Pappalardo, S.; Gupta, V. K.; Fronczek, F. R. J. Org. Chem. 1983, 48, 4848-4851.
48. Beeby, A.; Clarkson, I. M.; Dickins, R. S.; Faulkner, S.; Parker, D.; Royle, L.; de Sousa, A. S.; Williams, J. A. G.; Woods, M. J. Chem. Soc., Perkin Trans. 2 1999, 493-503.
49. Supkowski, R. M.; Horrocks Jr., W. D. W. Inorg. Chim. Acta 2002, 340, 44-48.
50. Barthelemy, P. P.; Choppin, G. R. Inorg. Chem. 1989, 28, 3354-3357.
51. Kimura, T.; Kato, Y. J. Alloys Compd. 1998, 275-277, 806-810.
52. Haas, Y.; Stein, G. J. Phys. Chem. 1971, 75, 3668-3677.
53. Nakamaru, K. Bull. Chem. Soc. Jpn. 1982, 55, 2697-2705.
54. Meech, S. R.; Phillips, D. J. Photochem. 1983, 23, 193-217.
55. Laurent, S.; Vander Elst, L.; Copoix, F.; Muller, R. N. Invest. Radiol. 2001, 36, 115-122.
56. Muller, R. N.; Declercq, D.; Vallet, P.; Giberto, F.; Daminet, B.; Fischer, H. W.; Maton, F.; Van Haverbeke, Y. In Proceedings of the ESMRMB, 7th Annual Congress, Strasbourg, France, 1990; European Society for Magnetic Resonance in Medicine and Biology: Vienna, Austria, 1990; p 394
57. Vallet, P. Relaxivity of Nitroxide Stable Free Radicals. Evaluations by Field Cycling Method and Optimisation. Ph.D. Thesis, University of Mons-Hainaut, Belgium, 1992.
58. Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. In Aza-Crown Macrocycles; Wiley: New York, 1993.
59. Richman, J. E.; Atkins, T. J. J. Am. Chem. Soc. 1974, 96, 2268-2270.
60. Bazzicalupi, C.; Bencini, A.; Fusi, V.; Giorgi, C.; Paoletti, P.; Valtancoli, B. J. Chem. Soc., Dalton Trans. 1999, 393-399.
61. (a) Aime, S.; Gianolio, E.; Corpillo, D.; Cavallotti, C.; Palmisano, G.; Sisti, M.; Giovenzana, G. B.; Pagliarin, R. Helv. Chim. Acta 2003, 86, 615-632.
62. (b) Siaugue, J.-M.; Segat-Dioury, F.; Sylvestre, I.; Favre-Reguillon, A.; Foos, J.; Madic, C.; Guy, A. Tetrahedron 2001, 57, 4713-4718.
63. (c) Aime, S.; Botta, M.; Frullano, L.; Geninatti Crich, S.; Giovenzana, G.; Pagliarin, R.; Palmisano, G.; Riccardi Sirtori, F.; Sisti, M. J. Med. Chem. 2000, 43, 4017-4024.
64. (d) Siaugue, J.-M.; Segat-Dioury, F.; Favre-Reguillon, A.; Madic, C.; Foos, J.; Guy, A. Tetrahedron Lett. 2000, 41, 7443-7446.
65. (e) Horiguchi, D.; Katayama, Y.; Sasamoto, K.; Terasawa, H.; Sato, N.; Mochizuki, H.; Ohkura, Y. Chem. Pharm. Bull. 1992, 40, 3334-3337.
66. (a) Nakamoto, K. J. Phys. Chem. 1960, 64, 1420-1425.
67. (b) Howard, S. T. J. Am. Chem. Soc. 1996, 118, 10269-10274.
68. (a) Krumholz, P. J. Am. Chem. Soc. 1951, 73, 3487-3492.
69. (b) Westheimer, F. H.; Benfey, O. T. J. Am. Chem. Soc. 1956, 78, 5309-5311.
70. (c) Linnell, R. H.; Kaczmarczyk, A. J. Phys. Chem. 1961, 65, 1196-1200.
71. Sabbatini, N.; Guardigli, M.; Lehn, J.-M. Coord. Chem. Rev. 1993, 123, 201-228.
72. Stein, G.; Würzberg, E. J. Chem. Phys. 1975, 62, 208-213.
73. (a) Vila-Nova, S. P.; Pereira, G. A. L.; Albuquerque, R. Q.; Mathis, G.; Bazin, H.; Autiero, H.; de Sa, G. F.; Alves, S., Jr. J. Lumin. 2004, 109, 173-179.
74. (b) Weibel, N.; Charbonnière, L. J.; Guardigli, M.; Roda, A.; Ziessel, R. J. Am. Chem. Soc. 2004, 126, 4888-4896.
75. (c) Couchet, J.-M.; Azéma, J.; Tisnès, P.; Picard, C. Inorg. Chem. Commun. 2003, 6, 978-981.
76. (d) Bodar-Houillon, F.; Heck, R.; Bohnenkamp, W.; Marsura, A. J. Lumin. 2002, 99, 335-341.
77. (e) Ulrich, G.; Bedel, S.; Picard, C. Tetrahedron Lett. 2002, 43, 8835-8837.
78. (f) Charbonnière, L.; Ziessel, R.; Guardigli, M.; Roda, A.; Sabbatini, N.; Cesario, M. J. Am. Chem. Soc. 2001, 123, 2436-2437.
79. (g) Ulrich, G.; Ziessel, R.; Manet, I.; Guardigli, M.; Sabbatini, N.; Fraternali, F.; Wipff, G. Chem. - Eur. J. 1997, 3, 1815-1822.
80. (h) Sabbatini, N.; Guardigli, M.; Manet, I.; Ungaro, R.; Casnati, A.; Ziessel, R.; Ulrich, G.; Asfari, Z.; Lehn, J.-M. Pure Appl. Chem. 1995, 67, 135-140.
81. Latva, M.; Takalo, H.; Mukkala, V.-M.; Matachescu, C.; Rodriguez-Ubis, J.-C.; Kankare, J. J. Lumin. 1997, 75, 149-169.
82. (a) Alpha, B.; Ballardini, R.; Balzani, V.; Lehn, J.-M.; Perathoner, S.; Sabbatini, N. Photochem. Photobiol. 1990, 52, 299-306.
83. (b) Bazin, H.; Preaudat, M.; Trinquet, E.; Mathis, G. Spectrochim. Acta A 2001, 57, 2197-2211.
84. Horrocks, W. D. W., Jr.; Sudnick, D. R. J. Am. Chem. Soc. 1979, 101, 334-340.
85. Parker, D.; Williams, J. A. G. J. Chem. Soc., Dalton Trans. 1996, 3613-3628.
86. Morss, L. R. Chem. Rev. 1976, 76, 827-841.
87. Sabbatini, N.; Perathoner, S.; Lattanzi, G.; Dellonte, S.; Balzani, V. J. Phys. Chem. 1987, 91, 6136-6139.
88. (a) Gonçalves e Silva, F. R.; Malta, O. L.; Reinhard, C.; Güdel, H.-U.; Piguet, C.; Moser, J. E.; Bünzli, J.-C. G. J. Phys. Chem. A 2002, 106, 1670-1677.
89. (b) Brunet, E.; Juanes, O.; Sedano, R.; Rodriguez-Ubis, J.-C. Photochem. Photobiol. Sci. 2002, 1, 613-618.
90. (c) Hakala, H.; Liitti, P.; Puukka, K.; Peuralahti, J.; Loman, K.; Karvinen, J.; Ollikka, F.; Ylikoski, A.; Mukkala, V.-M.; Hovinen, J. Inorg. Chem. Commun. 2002, 5, 1059-1062.
91. (d) Zucchi, G.; Ferrand, A.-C.; Scopelliti, R.; Bünzli, J.-C. G. Inorg. Chem. 2002, 41, 2459-2465.
92. (e) Rodriguez-Ubis, J.-C.; Sedano, R.; Barroso, G.; Juanes, O.; Brunet, E. Helv. Chim. Acta 1997, 80, 86-96.
93. (a) Liu, S.; Edwards, D. S. Bioconjugate Chem. 2001, 12, 7-34.
94. (b) Crooks, W. J.; Choppin, G. R.; Rogers, B. E.; Welch, M. J. Nucl. Med. Biol. 1997, 24, 123-125.
95. (c) Parker, D. In Comprehensive Supramolecular Chemistry, Vol 10; Lehn J.-M., Ed.; Pergamon: Oxford, 1996; p 487.
96. (d) Amin, S.; Morrow, J. R.; Lake, C. H.; Churchill, M. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 773-775.
97. Sarka, L.; Burai, L.; Brücher, E. Chem. - Eur. J. 2000, 6, 719-724.
98. Choppin, G. R.; Peterman, D. R. Coord. Chem. Rev. 1998, 174, 283-299.
99. (a) Cross, J. P.; Dadabhoy, A.; Sammes, P. G. J. Lumin. 2004, 110, 113-124.
100. (b) Coates, J.; Gay, E.; Sammes, P. G. Dyes Pigm. 1997, 34, 195-205.
101. Cacheris, W. P.; Nickle, S. K.; Sherry, A. D. Inorg. Chem. 1987, 26, 958-960.
102. Werts, M. H. V.; Verhoeven, J. W.; Hofstraat, J. W. J. Chem. Soc., Perkin Trans. 2 2000, 433-439.
103. Solomon, I. Phys. Rev. 1955, 99, 559-565.
104. Bloembergen, N. J. Chem. Phys. 1957, 27, 572-573.
105. Freed, J. H. J. Chem. Phys. 1978, 68, 4034-4037.
106. Aime, S.; Botta, M.; Fedeli, F.; Gianolio, E.; Terreno, E.; Anelli, P. Chem. - Eur. J. 2001, 7, 5262-5269.
107. Vander Elst, L.; Maton, F.; Laurent, S.; Seghi, F.; Chapelle, F.; Muller, R. N. Magn. Reson. Med. 1997, 38, 604-614.
108. Laurent, S.; Vander Elst, L.; Houzé, S.; Guérit, N.; Muller, R. N. Helv. Chim. Acta 2000, 83, 394-406.
109. Laurent, S.; Botteman, F.; Vander Elst, L.; Muller, R. N. Magn. Reson. Mater. Phys. Biol. Med. 2004, 16, 235-245.
110. Powell, D. H.; Ni Dhubhghaill, O. M.; Pubanz, D.; Helm, L.; Lebedev, Y. S.; Schlaepfer, W.; Merbach, A. E. J. Am. Chem. Soc. 1996, 118, 9333-9346.