Rigid MIIL2Gd2III (M = Fe, Ru) complexes of a terpyridine-based heteroditopic chelate: A class of candidates for MRI contrast agents

Journal of the American Chemical Society

Volumn 127, Issue 14, 2005, Pages 5147-5157

  Costa, Jérôme ^a   Ruloff, Robert ^a   Burai, László ^a   Helm, Lothar ^a   Merbach, André E ^a  

^a EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; MAGNETIC RESONANCE IMAGING; MOLECULAR WEIGHT; NITROGEN COMPOUNDS; RATE CONSTANTS; RUTHENIUM; SELF ASSEMBLY; THERMODYNAMIC STABILITY; TITRATION;

CHELATES; HIGH-MOLECULAR WEGHT; POTENTIOMETRY; PROTONATION;

IRON;

CHELATE; CONTRAST MEDIUM; GADOLINIUM CHELATE; IRON COMPLEX; POLYAMINOCARBOXYLATE DIETHYLENETRIAMINE N,N,N',N' TETRAACETATE; PYRIDINE DERIVATIVE; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG; WATER;

ABSORPTION SPECTROSCOPY; AQUEOUS SOLUTION; ARTICLE; COMPLEX FORMATION; CONTRAST ENHANCEMENT; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; MOLECULAR MODEL; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE IMAGING; POTENTIOMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; THERMODYNAMICS;

EID: 17144386184     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0424169     Document Type: Article

References (80)

1. Tóth, É.; Helm, L.; Merbach, A. E. Relaxivity of Gadolinium(III) Complexes: Theory and Mechanism. In The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging; Tóth, É., Merbach, A. E., Eds.; Wiley: Chichester, 2001.
2. Ruloff, R.; Tóth, É.; Scopelliti, R.; Tripier, R.; Handel, H.; Merbach, A. E. Chem. Commun. 2002, 2630.
3. Laus, S.; Ruloff, R.; Tóth, É.; Merbach, A. E. Chem. Eur. J. 2003, 9, 3555.
4. Ruloff, R.; van Koten, G.; Merbach, A. E. Chem. Commun. 2004, 842.
5. Desreux, J. F.; Jacques, V.; Humblet, V.; Hermann, M.; Comblin-Tholet, V.; Tweedle, M. F. U.S. Patent 6,056,939, 2000; filed: 1998.
6. Comblin, V.; Gilsoul, D.; Hermann, M.; Humblet, V.; Jacques, V.; Mesbahi, M.; Sauvage, C.; Desreux, J. F. Coord. Chem. Rev. 1999, 185-186, 451.
7. Bernhard, P.; Biner, M.; Ludi, A. Polyhedron 1990, 9, 1095.
8. Irving, H. M.; Miles, M. G.; Pettit, L. D. Anal. Chim. Acta 1967, 38, 475.
9. Ammann, C.; Meier, P.; Merbach, A. E. J. Magn. Reson. 1982, 46, 319.
10. Hugi, A. D.; Helm, L.; Merbach, A. E. Helv. Chim. Acta 1985, 68, 508.
11. Cusanelli, A.; Nicula-Dadci, L.; Frey, U.; Merbach, A. E. Inorg. Chem. 1997, 36, 2211.
12. Vold, R. L.; Waugh, J. S.; Klein, M. P.; Phelps, D. E. J. Chem. Phys. 1968, 48, 3831.
13. Meiboom, S.; Gill, D. Rev. Sci. Instrum. 1958, 29, 688.
14. Schmalbein, D.; Maresch, G. G.; Kamlowski, A.; Hofer, P. Appl. Magn. Reson. 1999, 16, 185.
15. Smith, G. M.; Lesurf, J. C. G.; Mitchell, R. H.; Riedi, P. C. Rev. Sci. Instrum. 1998, 69, 3924.
16. Fujitsu. CAChe WorkSystem Pro 6.1; 2000-2003.
17. Yerly, F. VISUALISEUR 2.3.4; Université de Lausanne: Lausanne, Switzerland, 1999.
18. Yerly, F. OPTIMISEUR 2.3.4; Université de Lausanne: Lausanne, Switzerland, 1999.
19. Zekany, L.; Nagypal, I. Computational Methods for Determination of Formation Constants; Plenum Press: New York, 1985.
20. Puigdomenech, I. MEDUSA 25; Royal Institute of Technology: Stockholm, Sweden, 1998.
21. Binstead, R. A.; Zuberbühler, A. D.; Jung, B. SPECFIT 3.06; 1993-2004.
22. Helm, L.; Borel, A.; Yerly, F. NMRICMA 3.0.4; EPFL: Lausanne, Switzerland, 2004.
23. Aebischer, N.; Sidorenkova, E.; Ravera, M.; Laurenczy, G.; Osella, D.; Weber, J.; Merbach, A. E. Inorg. Chem. 1997, 36, 6009.
24. Ruloff, R.; Gelbrich, T.; Sieler, J.; Hoyer, E.; Beyer, L. Z. Naturforsch., B: Chem. Sci. 1997, 52, 805.
25. Ruloff, R.; Muller, R. N.; Pubanz, D.; Merbach, A. E. Inorg. Chim. Acta 1998, 275-276, 15.
26. Stone, M. L.; Crosby, G. A. Chem. Phys. Lett. 1981, 79, 169.
27. Creutz, C.; Chou, M.; Netzel, T. L.; Okamura, M.; Suttin, N. J. Am. Chem. Soc. 1980, 102, 1309.
28. Lin, C.-T.; Böttcher, W.; Chou, M.; Creutz, C.; Sutin, N. J. Am. Chem. Soc. 1976, 98, 6536.
29. Young, R. C.; Nagle, J. K.; Meyer, T. J.; Whitten, D. G. J. Am. Chem. Soc. 1978, 100, 4773.
30. Kirchhoff, J. R.; McMillin, D. R.; Marnot, P. A.; Sauvage, J.-P. J. Am. Chem. Soc. 1985, 107, 1138.
31. Hacker, C. R.; Gushurst, A. K. I.; McMillin, D. R. Inorg. Chem. 1991, 30, 538.
32. Ruloff, R.; Arnold, K.; Beyer, L.; Dietze, F.; Gründer, W.; Wagsner, M.; Hoyer, E. Z. Anorg. Allg. Chem. 1995, 621, 807.
33. IUPAC Stability Constants 1.05; Academic Software and K. J. Powell: Yorks, 1999.
34. Letkeman, P.; Martell, A. E. Inorg. Chem. 1979, 18, 1284.
35. Nazeeruddin, M. K.; Zakeeruddin, S. M.; Humphry-Baker, R.; Kaden, T. A.; Grätzel, M. Inorg. Chem. 2000, 39, 4542.
36. Kim, K. Y.; Nancollas, G. H. J. Phys. Chem. 1977, 10, 948.
37. Brandt, W. W.; Wright, J. P. J. Am. Chem. Soc. 1954, 76, 3082.
38. Martin, R. B.; Lissfelt, J. A. J. Am. Chem. Soc. 1956, 78, 938.
39. Holyer, R. H.; Hubbard, C. D.; Kettle, S. F. A.; Wilkins, R. G. Inorg. Chem. 1966, 5, 622.
40. Bullock, J. I.; Simpson, P. W. G. J. Chem. Soc., Perkin Trans. 1 1981, 77, 1991.
41. Schilt, A. A.; Wong, S.-W. J. Coord. Chem. 1984, 13, 331.
42. Elsbernd, H.; Beattie, J. K. J. Inorg. Nucl. Chem. 1972, 14, 771.
43. Mikkelsen, K.; Nielsen, S. O. J. Phys. Chem. 1960, 64, 632.
44. Castellano, S.; Gunther, H.; Ebersole, S. J. Phys. Chem. 1965, 69, 4166.
45. Sherry, A. D.; Cacheris, W. P.; Kuan, K. T. Magn. Reson. Med. 1988, 8, 180.
46. Wang, Y.-M.; Lee, C.-H.; Liu, G.-C.; Sheu, R.-S. J. Chem. Soc., Dalton Trans. 1998, 4113.
47. Baxendale, J. H.; George, P. Trans. Faraday Soc. 1950, 55.
48. Martell, A. E.; Motekaitis, R. J.; Clarke, E. T.; Delgado, R.; Sun, Y.; Ma, R. Supramol. Chem. 1996, 6, 353.
49. Vasil'eva, V. F.; Lavrova, O. Y.; Dyatlova, N. M.; Yashunskii, V. G. Zh. Obshch. Khim. 1966, 36, 1724.
50. Paul-Roth, C.; Raymond, K. N. Inorg. Chem. 1995, 34, 1408.
51. Tse, P.-K.; Powell, J. E. Inorg. Chem. 1985, 24, 2727.
52. Micskei, K.; Helm, L.; Brücher, E.; Merbach, A. E. Inorg. Chem. 1993, 32, 3844.
53. González, G.; Powell, D. H.; Tissières, V.; Merbach, A. E. J. Phys. Chem. 1994, 98, 53.
54. McLachlan, A. D. Proc. R. Soc. London 1964, A280, 271.
55. Powell, D. H.; Merbach, A. E.; González, G.; Brücher, E.; Micskei, K.; Ottaviani, M. F.; Köhler, K.; von Zelewsky, A.; Grinberg, O. Y.; Lebedev, Y. S. Helv. Chim. Acta 1993, 76, 1.
56. Rast, S.; Fries, P. H.; Belorizky, E. J. Chem. Phys. 2000, 113, 8724.
57. Powell, D. H.; Dhubhghaill, O. M. N.; Pubanz, D.; Helm, L.; Lebedev, Y. S.; Schlaepfer, W.; Merbach, A. E. J. Am. Chem. Soc. 1996, 118, 9333.
58. Rast, S.; Borel, A.; Helm, L.; Belorizky, E.; Fries, P. H.; Merbach, A. E. J. Am. Chem. Soc. 2001, 123, 2637.
59. Rast, S.; Fries, P. H.; Belorizky, E.; Borel, A.; Helm, L.; Merbach, A. E. J. Chem. Phys. 2001, 115, 7554.
60. Dunand, F. A.; Borel, A.; Helm, L. Inorg. Chem. Commun. 2002, 5, 811.
61. Bertini, I.; Galas, O.; Luchinat, C.; Parigi, G. J. Magn. Reson. 1995, 113A, 151.
62. Lincoln, S. F.; Merbach, A. E. Adv. Inorg. Chem. 1995, 42, 1.
63. Micskei, K.; Powell, D. H.; Helm, L.; Brücher, E.; Merbach, A. E. Magn. Reson. Chem. 1993, 31, 1011.
64. Frey, U.; Merbach, A. E.; Powell, D. H. Solvent Exchange on Metal Ions: A Variable Pressure Approach. In Dynamics of Solutions and Fluid Mixtures by NMR; Delpuech, J.-J., Ed.; John Wiley & Sons: New York, 1995.
65. Cossy, C.; Helm, L.; Merbach, A. E. Inorg. Chem. 1989, 28, 2699.
66. Spirlet, M.-R.; Rebizant, J.; Desreux, J. F.; Loncin, M.-F. Inorg. Chem. 1984, 23, 359.
67. Stezowski, J. J.; Hoard, J. L. Isr. J. Chem. 1984, 24, 323.
68. Chang, C. A.; Francesconi, L. C.; Malley, M. F.; Kumar, K.; Gougoutas, J. Z.; Tweedle, M. F.; Lee, D. W.; Wilson, L. J. Inorg. Chem. 1993, 32, 3501.
69. Raitsimring, A. M.; Astashkin, A. V.; Baute, D.; Goldfarb, D.; Caravan, P. J. Phys. Chem. A 2004, 108, 7318.
70. Astashkin, A. V.; Raitsimring, A. M.; Caravan, P. J. Phys. Chem. A 2004, 108, 1990.
71. Tóth, É.; Helm, L.; Kellar, K. E.; Merbach, A. E. Chem. Eur. J. 1999, 5, 1202.
72. Tóth, É.; Burai, L.; Brücher, E.; Merbach, A. E. J. Chem. Soc., Dalton Trans. 1997, 1587.
73. Aime, S.; Geninatti Crich, S.; Gianolio, E.; Terreno, E.; Beltrami, A.; Uggieri, F. Eur. J. Inorg. Chem. 1998, 1283.
74. Tóth, É.; Connac, F.; Helm, L.; Adzamli, K.; Merbach, A. E. Eur. J. Inorg. Chem. 1998, 2017.
75. André, J. P.; Maecke, H. R.; Tóth, É.; Merbach, A. E. J. Biol. Inorg. Chem. 1999, 4, 341.
76. Nicolle, G. M.; Yerly, F.; Imbert, D.; Böttger, U.; Bünzli, J.-C.; Merbach, A. E. Chem. Eur. J. 2003, 9, 5453.
77. Schumann, H.; Boettger, U.; Weisshoff, H.; Ziemer, B.; Zschunke, A. Eur. J. Inorg. Chem. 1999, 1735.
78. Ranganathan, R. S.; Fernandez, M. E.; Kang, S. I.; Nunn, A. D.; Ratsep, P. C.; Pillai, K. M. R.; Zhang, X.; Tweedle, M. F. Invest. Radiol. 1998, 33, 779.
79. Dunand, F. A.; Borel, A.; Merbach, A. E. J. Am. Chem. Soc. 2002, 124, 710.
80. Yerly, F.; Hardcastle, K. I.; Helm, L.; Aime, S.; Botta, M.; Merbach, A. E. Chem. Eur. J. 2002, 8, 1031.