Synthesis and physicochemical characterization of carbon backbone modified [Gd(TTDA)(H2O)]2- derivatives

Inorganic Chemistry

Volumn 50, Issue 4, 2011, Pages 1275-1287

  Chang, Ya Hui ^a   Chen, Chiao Yun ^a,b   Singh, Gyan ^c   Chen, Hsing Yin ^a   Liu, Gin Chung ^a,b   Goan, Yih Gang ^d,e   Aime, Silvio ^f   Wang, Yun Ming ^c  

^a KAOHSIUNG MEDICAL UNIVERSITY HOSPITAL   (Taiwan)

^b KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^c NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

^d KAOHSIUNG VETERANS GENERAL HOSPITAL   (Taiwan)

^e Yuh Ing Junior College of Health Care and Management   (Taiwan)

^f UNIVERSITY OF TURIN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; GADOLINIUM 3,6,10 TRI(CARBOXYMETHYL) 3,6,10 TRIAZADODECANEDIOIC ACID; GADOLINIUM 3,6,10-TRI(CARBOXYMETHYL)-3,6,10-TRIAZADODECANEDIOIC ACID; ORGANOMETALLIC COMPOUND; SERUM ALBUMIN; WATER;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; HUMAN; KINETICS; METABOLISM; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; THERMODYNAMICS;

CARBON; HUMANS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR WEIGHT; ORGANOMETALLIC COMPOUNDS; SERUM ALBUMIN; THERMODYNAMICS; WATER;

EID: 79951586470     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic101799c     Document Type: Article

References (106)

1. Caravan, P. Chem. Soc. Rev. 2006, 35, 512-523
2. Poláşek, M., Şedinová, M., Kotek, J., Vander Elst, L., Muller, R. N., Hermann, P., and Lukeş, I. Inorg. Chem. 2009, 48, 455-465
3. Frangioni, J. V. Nat. Biotechnol. 2006, 24, 909-913
4. Louie, A. Y., Huber, M. M., Ahrens, E. T., Rothbacher, U., Moats, R., Jacobs, R. E., Fraser, S. E., and Meade, T. J. Nat. Biotechnol. 2000, 18, 321-325
5. Costa, J., Tóth, É., Helm, L., and Merbach, A. E. Inorg. Chem. 2005, 44, 4747-4755
6. Solomon, I. Phys. Rev. 1955, 99, 559-565
7. Bloembergen, N. and Morgan, L. O. J. Chem. Phys. 1961, 34, 842-850
8. Fatin-Rouge, N., Tóth, E., Meuli, R., and Bünzli, J. C. G. J. Alloys Compd. 2004, 374, 298-302
9. Vander Elst, Lort, M., Raynal, I., Simonot, C., and Muller, R. N. Eur. J. Inorg. Chem. 2003, 2495-2501
10. Aime, S., Cabella, C., Colombatto, S., Crich, S. G., Gianolio, E., and Maggioni, F. J. Magn. Reson. Imaging 2002, 16, 394-406
11. Weinmann, H. J., Ebert, W., Misselwitz, B., and Schmitt-Willich, H. Eur. J. Radiol. 2003, 46, 33-44
12. Kubíçek, V., Rudovský, J., Kotek, J., Hermann, P., Vander Elst, L., Muller, R. N., Kolar, Z. I., Wolterbeek, H. Teters, J. A., and Lukeş, I. J. Am. Chem. Soc. 2005, 127, 16477-16485
13. Chang, Y. T., Cheng, C. M., Su, Y. Z., Lee, W. T., Hsu, J. S., Liu, G. C., Cheng, T. L., and Wang, Y. M. Bioconjugate Chem. 2007, 18, 1716-1727
14. Duimstra, J. A., Femia, F. J., and Meade, T. J. J. Am. Chem. Soc. 2005, 12847-12855
15. Wang, Y. M., Lee, C. H., Liu, G. C., and Sheu, R. S. Dalton Trans. 1998, 24, 4113-4118
16. Mato-Iglesias, Mlatas-Iglesias, C., Djanashvili, Keters, J. A., Tóth, É., Balogh, E., Muller, R. N., Vander Elst, L., de Blas, A., and Rodríguez-Blas, T. Chem. Commun. 2005, 4729-4731
17. Balogh, E., Mato-Iglesias, Mlatas-Iglesias, C., Tóth, E., Djanashvili, Keters, J. A., de Blas, A., and Rodríguez-Blas, T. Inorg. Chem. 2006, 45, 8719-8728
18. Powell, D. H., Ni Dhubhghaill, O. Mubanz, D., Helm, L., Lebedev, Y. S., Schlaepfer, W., and Merbach, A. E. J. Am. Chem. Soc. 1996, 118, 9333-9346
19. Aime, S., Barge, A., Borel, A., Botta, M., Chemerisov, S., Merbach, A. E., Müller, U., and Pubanz, D. Inorg. Chem. 1997, 36, 5104-5112
20. Ruloff, R., Tóth, É., Scopelliti, R., Tripier, R., Handel, H., and Merbach, A. E. Chem. Commun. 2002, 2630-2631
21. Burai, L., Tóth, E., Sour, A., and Merbach, A. E. Inorg. Chem. 2005, 44, 3561-3568
22. Caravan, P., Cloutier, N. J., Greenfield, M. T., McDermid, S. A., Dunham, S. U., Bulte, J. W., Amedio, J. C., Jr., Looby, R. J., Supkowski, R. M., Horrocks, W. D., Jr., McMurry, T. J., and Lauffer, R. B. J. Am. Chem. Soc. 2002, 124, 3152-3162
23. Lauffer, R. B. and Brady, T. J. Magn. Reson. Imaging 1985, 3, 11-16
24. Lauffer, R. B., Brady, T. J., Brown, R. D., III, Baglin, C., and Koenig, S. H. Magn. Reson. Med. 1986, 3, 541-548
25. Lucas, R. L., Benjamin, M., and Reineke, T. M. Bioconjugate Chem. 2008, 19, 24-27
26. Zhang, G., Zhang, R., Wen, X., Li, L., and Li, C. Biomacromolecules 2008, 9, 36-42
27. Fu, Y., Raatschen, H. J., Nitecki, D. E., Wendland, M. F., Novikov, V., Fournier, L. S., Cyran, C., Rogut, V., Shames, D. M., and Brasch, R. C. Biomacromolecules 2007, 8, 1519-1529
28. Xu, H., Regino, C. A., Koyama, Y., Hama, Y., Gunn, A. J., Bernardo, M., Kobayashi, H., Choyke, P. L., and Brechbiel, M. W. Bioconjugate Chem. 2007, 18, 1474-1482
29. Anderson, E. A., Isaacman, Seabody, D. S., Wang, E. Y., Canary, J. W., and Kirshenbaum, K. Nano Lett. 2006, 6, 1160-1164
30. Yang, J. J., Yang, J., Wei, L., Zurkiya, O., Yang, W., Li, S., Zou, J., Zhou, Y., Maniccia, A. L., Mao, H., Zhao, F., Malchow, R., Zhao, S., Johnson, J., Hu, X., Krogstad, E., and Liu, Z. R. J. Am. Chem. Soc. 2008, 130, 9260-9267
31. Karfeld, L. S., Bull, S. R., Davis, N. E., Meade, T. J., and Barron, A. E. Bioconjugate Chem. 2007, 18, 1697-1700
32. Sirlin, C. B., Vera, D. R., Corbeil, J. A., Caballero, M. B., Buxton, R. B., and Mattrey, R. F. Acad. Radiol. 2004, 11, 1361-1369
33. Cai, J., Shapiro, E. M., and Hamilton, A. D. Bioconjugate Chem. 2009, 20, 205-208
34. Bull, S. R., Guler, M. O., Bras, R. E., Meade, T. J., and Stupp, S. I. Nano Lett. 2005, 5, 1-4
35. Laurent, S., Vander Elst, L., Thirifays, C., and Muller, R. N. Langmuir 2008, 24, 4347-4351
36. Laurent, Vander Elst, L., Thirifays, C., and Muller, R. N. Eur. Biophys. J. 2008, 37, 1007-1014
37. Hermann, P., Kotek, J., Kubíçek, V., and Lukeş, I. Dalton Trans. 2008, 3027-3047
38. Jászberényi, Z., Moriggi, L., Schmidt, P., Weidensteiner, C., Kneuer, R., Merbach, A. E., Helm, L., and Tóth, É. J. Biol. Inorg. Chem. 2007, 12, 406-420
39. Rudovský, J., Botta, M., Hermann, P., Hardcastle, K. I., Lukeş, I., and Aime, S. Bioconjugate Chem. 2006, 17, 975-987
40. Jenkins, B. G., Armstrong, E., and Lauffer, R. B. Magn. Reson. Med. 1991, 17, 164-178
41. Lauffer, R. B. Magn. Reson. Med. 1991, 22, 339-342
42. Lauffer, R. Barmelee, D. J., Dunham, S. U., Ouellet, H. S., Dolan, R. P., Witte, S., McMurry, T. J., and Walovitch, R. C. Radiology 1998, 207, 529-538
43. Parmelee, D. J., Walovitch, R. C., Ouellet, H. S., and Lauffer, R. B. Invest. Radiol. 1997, 32, 741-747
44. Caravan, P., Comuzzi, C., Crooks, W., McMurry, T. J., Choppin, G. R., and Woulfe, S. R. Inorg. Chem. 2001, 40, 2170-2176
45. Artali, R., Botta, M., Cavallotti, C., Giovenzana, G. Balmisano, G., and Sisti, M. Org. Biomol. Chem. 2007, 5, 2441-2447
46. Aime, S., Geninatti Crich, S., Gianolio, E., Giovenzana, G. B., Tei, L., and Terreno, E. Coord. Chem. Rev. 2006, 250, 1562-1579
47. Aime, S., Botta, M., and Terreno, E. Adv. Inorg. Chem. 2005, 57, 173-237
48. Aime, S., Botta, M., Fasano, M., and Terreno, E. Chem. Soc. Rev. 1998, 27, 19-29
49. Sun, Y., Martell, A. E., Reibenspies, J. H., Reichert, D. E., and Welch, M. J. Inorg. Chem. 2000, 39, 1480-1486
50. Wang, Y. M., Li, C. R., Huang, Y. C., Ou, M. H., and Liu, G. C. Inorg. Chem. 2005, 44, 382-392
51. Ou, M. H., Tu, C. H., Tsai, S. C., Lee, W. T., Liu, G. C., and Wang, Y. M. Inorg. Chem. 2006, 45, 244-254
52. Liage, S. U.S. Patent 5905176, 1999.
53. Hsu, J. S., Jaw, T. S., Liu, G. C., Wang, Y. M., Chen, S. H., Kuo, Y. T., Jao, J. C., Li, C. W., and Tsai, K. J. Magn. Reson. Imaging 2004, 20, 632-639
54. Cheng, T. H., Lee, T. M., Ou, M. H., Li, C. R., Liu, G. C., and Wang, Y. M. Helv. Chim. Acta 2002, 85, 1033-1050
55. Cohn, E. J., Strong, L. E., Hughes, W. L., Jr., Mulford, D. J., Ashworth, J. N., Melin, M., and Taylor, H. L. J. Am. Chem. Soc. 1946, 68, 459-475
56. Vollmar, A. and Dunn, M. S. J. Org. Chem. 1960, 25, 387-390
57. Martell, A. E. and Motekaitis, R. J. Determination and Use of Stability Constants, 2 nd ed.; VCH: New York, 1992.
58. McMurry, T. Jarmelee, D. J., Sajiki, H., Scott, D. M., Ouellet, H. S., Walovitch, R. C., Tyeklar, Z., Dumas, S., Bernard, P., Nadler, S., Midelfort, K., Greenfield, M., Troughton, J., and Lauffer, R. B. J. Med. Chem. 2002, 45, 3465-3474
59. Laurent, S., Vander Elst, L., and Muller, R. N. Contrast Media Mol. Imaging 2006, 1, 128-137
60. Laurent, S., Vander Elst, L., Copoix, F., and Muller, R. N. Invest. Radiol. 2001, 36, 115-122
61. Laus, S., Ruloff, R., Tóth, E., and Merbach, A. E. Chem.?- ?Eur. J. 2003, 9, 3555-3566
62. Smith, R. M. and Martell, A. E. Critical Stability Constants; Plenum: New York, 1974.
63. Kumar, K., Tweedle, M. F., Malley, M. F., and Gougoutas, J. Z. Inorg. Chem. 1995, 34, 6472-6480
64. Tei, L., Baranyai, Z., Botta, Miscopo, L., Aime, S., and Giovenzana, G. B. Org. Biomol. Chem. 2008, 6, 2361-2368
65. Rabasso, N., Louaisil, N., and Fadel, A. Tetrahedron. 2006, 62, 7445-7454
66. Kumar, K. and Tweedle, M. F. Inorg. Chem. 1993, 32, 4193-4199
67. Bannochie, C. J. and Martell, A. E. Inorg. Chem. 1991, 30, 1385-1392
68. Tweedle, M. F., Hahan, J. J., Kumar, K., Mantha, S., and Chang, C. A. Magn. Reson. Imaging 1991, 9, 409-415
69. Horrocks, W. D., Jr. and Sudnick, D. R. Acc. Chem. Res. 1981, 14, 384-392
70. Mato-Iglesias, M., Roca-Sabio, Aálinkás, Z., Esteban-Gómez, Dlatas-Iglesias, C., Tóth, E., de Blas, A., and Rodríguez-Blas, T. Inorg. Chem. 2008, 47, 7840-7851
71. Beeby, A., Clarkson, I. M., Dickins, R. S., Faulkner, Sarker, D., Royle, L., Sousa, A. S. d., Williams, J. A. G., and Woods, M. J. Chem. Socerkin Trans. 1999, 2, 493-504
72. Horrocks, W. D. and Sudnick, D. R. J. Am. Chem. Soc. 1979, 101, 334-340
73. Anelli, P. L., Balzani, Vrodi, L., and Uggeri, F. Gazz. Chim. Ital. 1991, 121, 359-364
74. Bryden, C. C. and Reilley, C. N. Anal. Chem. 1982, 54, 610-615
75. Tóth, E., Helm, L., and Merbach, A. E., Eds. The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging; John Wiley and Sons: New York, 2001; pp 45- 119.
76. Swift, T. J. and Connick, R. E. J. Chem. Phys. 1962, 37, 307-320
77. Luz, Z. and Meiboom, S. J. Chem. Phys. 1964, 40, 1058-1066
78. Caravan, Parigi, G., Chasse, J. M., Cloutier, N. J., Ellison, J. J., Lauffer, R. B., Luchinat, C., McDermid, S. A., Spiller, M., and McMurry, T. J. Inorg. Chem. 2007, 46, 6632-6639
79. Aime, S., Botta, M., Fasano, M., and Terreno, E. Acc. Chem. Res. 1999, 32, 941-949
80. Weinmann, H. J., Brasch, R. Cress, W. R., and Wesbey, G. E. Am. J. Roentgenol. 1984, 142, 619-624
81. Koenig, S. H. and Brown, R. D., III. Prog. NMR Spectrosc. 1990, 22, 487-567
82. Gonzalez, Gowell, D. H., Tissiéres, V., and Merbach, A. E. J. Phys. Chem. 1994, 98, 53-59
83. Micskei, K., Helm, L., Brücher, E., and Merbach, A. E. Inorg. Chem. 1993, 32, 3844-3850
84. Micskei, Kowell, D. H., Helm, L., Brücher, E., and Merbach, A. E. Magn. Reson. Chem. 1993, 31, 1011-1020
85. Frey, U., Merbach, A. E., and Powell, D. H. In Solvent Exchange on Metal Ions: A Variable NMR Approach; Delpuech, J.-J., Ed.; John Wiley & Sons: Chichester, U.K., 1995; p 263.
86. Lincoln, S. F. and Merbach, A. E. Adv. Inorg. Chem. 1995, 42, 1-88
87. Tóth, E., Helm, L., Merbach, A. E., Hedinger, R., Hegetschweiler, K., and Janossy, A. Inorg. Chem. 1998, 37, 4104-4113
88. Muller, R. N., Radüchel, B., Laurent, Slatzek, Jiérart, C., Mareski, P., and Vander Elst, L. Eur. J. Inorg. Chem. 1999, 1949-1955
89. Brittain, H. G. and Desreux, J. F. Inorg. Chem. 1984, 23, 4459-4466
90. Abragam, A. The Principles of Nuclear Magnetism; Oxford University Press: London, 1961.
91. Caravan, P., Ellison, J. J., McMurry, T. J., and Lauffer, R. B. Chem. Rev. 1999, 99, 2293-2352
92. Tóth, É., Connac, F., Helm, L., Adzamli, K., and Merbach, A. E. Eur. J. Inorg. Chem. 1998, 2017-2021
93. Klotz, I. M. Ligand Receptor Energetics-A Guide for the Perplexed; John Wiley & Sons: New York, 1987.
94. Hifumi, H., Tanimoto, A., Honda, A., Citterio, D., and Suzuki, K. Anal. Sci. 2007, 23, 1159-1165
95. Jastrzebska, B., Lebel, R., Therriault, H., McIntyre, J. O., Escher, E., Guérin, Baquette, B., Neugebauer, W. A., and Lepage, M. J. Med. Chem. 2009, 52, 1576-1581
96. Sangster, J. Octanol-Water Partition Coefficients, Fundamentals and Physical Chemistry; John Wiley & Sons: Chichester, U.K., 1997.
97. Van de Waterbeemd, H. and Gifford, E. Nat. Rev. Drug Discovery 2003, 2, 192-204
98. Chen, Z. and Weber, S. G. Anal. Chem. 2007, 79, 1043-1049
99. Medić-Sarić, M., Mornar, A., and Jasprica, I. Acta Pharm. 2004, 54, 91-101
100. Molinspiration Cheminformatics Calculation of Molecular Properties and Drug-likeness. http://www.molinspiration.com (accessed 2009).
101. Peters, T. J. All About Albumin: Biochemistry, Genetics, and Medical Applications; Academic Press: San Diego, CA, 1996.
102. Dwek, R. A. Nuclear Magnetic Resonance in Biochemistry, Application to Enzyme System; Clarendon Press: Oxford, 1973.
103. Aime, S., Fasano, M., Terreno, E., and Botta, M., Eds. The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging; John Wiley and Sons: New York, 2001; pp 193- 241.
104. Aime, S., Botta, M., Fasano, M., Geninatti Crich, S., and Terreno, E. J. Biol. Inorg. Chem. 1996, 1, 312-319
105. Aime, S., Chiaussa, M., Digilio, G., Gianolio, E., and Terreno, E. J. Biol. Inorg. Chem. 1999, 4, 766-774
106. Moriggi, L., Cannizzo, Crestinari, C., Berrière, F., and Helm, L. Inorg. Chem. 2008, 47, 8357-8366