Responsive Probes

The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging: Second Edition

Volumn , Issue , 2013, Pages 343-385

  Bonnet, Célia S ^a   Tei, Lorenzo ^b   Botta, Mauro ^b   Tóth, Éva ^a  

^a CENTRE DE BIOPHYSIQUE MOLÉCULAIRE   (France)

^b UNIVERSITY OF EASTERN PIEDMONT   (Italy)

Author keywords

Gd3+; Magnetic resonance imaging (MRI) probes; MRI contrast agents; Paramagnetic chemical exchange saturation transfer (PARACEST); Physiological parameters

Indexed keywords

EID: 84887215816     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118503652.ch8     Document Type: Chapter

References (149)

1. de Leon-Rodriguez, L.M., Lubag, A.J.M., Malloy, C.R. et al. (2009) Acc. Chem. Res. 42, 948.
2. Bonnet, C.S. and Tóth, É. (2010) Am. J. Neuroradiol., 31, 401-409.
3. Aime, S., Fedeli, F., Sanino, A., and Terreno, E. (2006) J. Am. Chem. Soc., 128, 11326.
4. Raghunand, N., Howison, C., Sherry, A.D. et al. (2003) Magn. Reson. Med., 49, 249.
5. Terreno, E., Castelli, D.D., Cravotto, G. et al. (2004) Invest. Radiol., 39, 235.
6. Frullano, L., Catana, C., Benner, T. et al. (2010) Angew. Chem. Int. Ed., 49, 2382.
7. Rieke, V. and Pasley, K.B. (2008) J. Mag. Res. Imaging, 27, 376.
8. Ishihara, Y., Calderon, A., Watanabe, H. et al. (1995) Magn. Reson. Med., 34, 814.
9. Berkowitz, B.A., Handa, J.T., and Wilson, C.A. (1992) NMR Biomed., 5, 65.
10. Mason, R.P., Shukla, H., and Antich, P.P. (1993) Magn. Reson. Med., 29, 296.
11. Aime, S., Botta, M., Fasano, M. et al. (1996) Magn. Reson. Med., 35, 648.
12. Hekmatyar, S.K., Hopewell, P., Pakin, S.K. et al. (2005) Magn. Reson. Med., 53, 294.
13. Pakin, S.K., Hekmatyar, S.K., Hopewell, P. et al. (2006) NMR Biomed., 19, 116.
14. Frenzel, T., Roth, K., Kossler, S. et al. (1996) Magn. Reson. Med., 35, 364.
15. Bansal, N., Germann, M.J., Seshan, V. et al. (1993) Biochemistry, 32, 5638.
16. Zuo, C.S., Bowers, J.L., Metz, K.R. et al. (1996) Magn. Reson. Med., 36, 955.
17. Zuo, C.S., Metz, K.R., Sun, Y., and Sherry, A.D. (1998) J. Magn. Reson., 133, 53.
18. Sun, Y., Sugawara, M., Mulkern, R.V. et al. (2000) NMR Biomed., 13, 460.
19. Zuo, C.S., Mahmood, A., and Sherry, A.D. (2001) J. Magn. Reson., 151, 101.
20. Hekmatyar, S.K., Poptani, H., Babsky, A. et al. (2002) Int. J. Hyperthermia, 18, 165.
21. Viswanathan, S., Kovacs, Z., Green, K.N. et al. (2010) Chem. Rev., 110, 2960.
22. Zhang, S.R., Malloy, C.R., and Sherry, A.D. (2005) J. Am. Chem. Soc., 127, 17572.
23. Li, A.X., Wojciechowski, F., Suchy, M. et al. (2008) Magn. Reson. Med., 59, 374.
24. McDannold, N., Fossheim, S.L., Rasmussen, H. et al. (2004) Radiology, 230, 743.
25. Lindner, L.H., Reinl, H.M., Schlemmer, M. et al. (2005) Int. J. Hyperthermia, 21, 575.
26. Fossheim, S.L., Fahlvik, A.K., Klaveness, J., and Muller, R.N. (1999) Magn. Reson. Imaging, 17, 83.
27. Fossheim, S.L., Ilyasov, K.A., Hennig, J., and Bjornerud, A. (2000) Acad. Radiol., 7, 1107.
28. de Smet, M., Langereis, S., van den Bosch, S., and Grüll, H. (2010) J. Control Release, 143, 120.
29. Langereis, S., Keupp, J., van Velthoven, J.N.L.J. et al. (2009) J. Am. Chem. Soc., 131, 1380.
30. Zhang, X., Lin, Y., and Gillies, R.J. (2010) J. Nucl. Med., 51, 1167.
31. Pathak, A.P., Gimi, B., Glunde, K. et al. (2004) Methods Enzymol., 386, 1.
32. Gil, M.S., Zaderenko, P., Cruz, F. et al. (1992) Bioorg. Med. Chem. Lett., 2, 1717.
33. van Sluis, R., Bhujwalla, Z.M., Raghunand, N. et al. (1999) J. Magn. Res. Med., 41, 743.
34. Gallagher, F.A., Kettunen, M.I., Day, S.E. et al. (2008) Nature, 453, 940.
35. Aime, S., Botta, M., Milone, L., and Terreno, E. (1996) Chem Commun., 1265.
36. Kenwright, A.M., Kuprov, I., De Luca, E. et al. (2008) Chem Commun., 2514.
37. Bruce, J.I., Dickins, R.S., Govenlock, L.J. et al. (2000) J. Am. Chem. Soc., 122, 9674.
38. Lowe, M., Parker, D., Reany, O. et al. (2001) J. Am. Chem. Soc., 123, 7601.
39. Woods, M., Kiefer, G.E., Bott, S. et al. (2004) J. Am. Chem. Soc., 126, 9248.
40. Aime, S., Botta, M., Geninatti Crich, S., Giovenana, G., Palmisano, G., Sisti, M. (1999) Chem. Commun., 1577.
41. Gianolio, E., Napolitano, R., Fedeli, F. et al. (2009) Chem. Commun., 6044.
42. Gianolio, E., Maciocco, L., Giovenzana, G.B. et al. (2011) Chem. Commun., 47, 1539.
43. Zhang, S., Wu, K.C., and Sherry, A.D. (1999) Angew. Chem. Int. Ed., 38, 3192.
44. Kálmán, F.K., Woods, M., Caravan, P. et al. (2007) Inorg. Chem., 46, 5260.
45. Ali, M.M., Woods, M., Caravan, P. et al. (2008) Chem. Eur. J., 14, 7250.
46. Garcia-Martin, M.L., Martinez, G.V., Raghunand, N. et al. (2006) Magn. Reson. Med., 55, 309.
47. Woods, M., Zhang, S., Ebron, V.H., and Sherry, A.D. (2003) Chem. Eur. J., 9, 4634.
48. McMahon, M.T., Gilad, A.A., Zhou, J. et al. (2006) Magn. Reson. Med., 55, 836-847.
49. Aime, S., Barge, A., Delli Castelli, D. et al. (2002) Magn. Reson. Med., 47, 639.
50. Aime, S., Delli Castelli, D., and Terreno, E. (2002) Angew. Chem. Int. Ed., 41, 4334.
51. Delli Castelli, D., Terreno, E., and Aime, S. (2011) Angew. Chem. Int. Ed., 50, 1798.
52. Pikkemaat, J.A., Wegh, R.T., Lamerichs, R. et al. (2007) Contrast Media Mol. Imaging, 2, 229.
53. Longo, D.L., Dastrú, W., Digilio, G. et al. (2011) Magn. Reson. Med., 65, 202.
54. Hartman, K.B., Laus, S., Bolskar, R.D. et al. (2008) Nano Lett., 8, 415.
55. Tóth, È, Bolskar, R.D., Borel, A. et al. (2005) J. Am. Chem. Soc., 127, 799.
56. Aime, S., Botta, M., Gianolio, E., and Terreno, E. (2000) Angew. Chem. Int. Ed., 39, 747.
57. Sun, P., Schoening, Z.B., and Jasanoff, A. (2003) Magn. Reson. Med., 49, 609.
58. Aime, S., Ascenzi, P., Comoglio, E. et al. (1995) J. Am. Chem. Soc., 117, 9365.
59. Tóth, E., Burai, L., and Merbach, A.E. (2001) Coord. Chem. Rev., 216-217, 363.
60. Burai, L., Scopelliti, R., and Tóth, É. (2002) Chem. Commun., 2366.
61. Gamaga, N.D.H., Mei, Y., Garcia, J., and Allen, M.J. (2010) Angew. Chem. Int. Ed., 49, 8923.
62. Sahaf, B., Heydari, K., Herzenberg, L.A., and Herzenberg, L.A. (2005) Arch. Biochem. Biophys., 434, 26.
63. Wu, W.S. (2006) Cancer Metastasis Rev., 25, 695.
64. Raghunand, N., Jagadish, B., Trouard, T.P. et al. (2006) Magn. Reson. Med., 55, 1272.
65. Carrera, C., Digilio, G., Baroni, S. et al. (2007) Dalton Trans., 4980.
66. Martinelli, J., Fekete, M., Tei, L., and Botta, M. (2011) Chem. Commun., 47, 3144.
67. Terreno, E., Boffa, C., Menchise, V. et al. (2011) Chem. Commun., 47, 4667.
68. Digilio, G., Catanzaro, V., Fedeli, F. et al. (2009) Chem. Commun., 893.
69. Digilio, G., Menchise, V., Gianolio, E. et al. (2010) J. Med. Chem., 53, 4877-4890.
70. Menchise, V., Digilio, G., Gianolio, E. et al. (2011) Mol. Pharmaceutics. doi: 10.1021/mp2001044
71. Tsien, R.Y. (1980) Biochemistry, 19, 2396.
72. Kikuchi, K., Komatsu, K., and Nagano, T. (2004) Curr. Opin. Chem. Biol., 8, 182.
73. Kerr, J.N.D., Greenberg, D., and Helmchen, F. (2005) Proc. Natl. Acad. Sci. U.S.A., 102, 14063;
74. Ohki, K., Chung, S., Ch'ng, Y.H. et al. (2005) Nature, 433, 597.
75. Angelovski, G. and Mamedov, I. (2011) Curr. Inorg. Chem., 1, 76-90.
76. Bonnet, C.S. and Tóth, É. (2010) Future Med. Chem., 2, 367.
77. Geraldes, C. and Laurent, S. (2009) Contrast. Media Mol. Imaging, 4, 1.
78. Que, E.L., Domaille, D.W., and Chang, C.J. (2008) Chem. Rev., 108, 1517.
79. Yoo, B. and Pagel, M.D. (2008) Front. Biosci., 13, 1733.
80. Forsen, S. and Kordel, J. (1994) in Bioinorganic Chemistry (eds I. Bertini, H.B. Gray, S.J. Lippard, and J.S. Valentine), University Science Books, Mill Valley, CA, p. 107.
81. Li, W., Fraser, S.E., and Meade, T.J. (1999) J. Am. Chem. Soc., 12, 1413.
82. Li, W., Parigi, G., Fragai, M. et al. (2002) Inorg. Chem., 41, 4018.
83. Hammoud, D.A., Hoffman, J.M., and Pomer, M.G. (2007) Radiology, 245, 21.
84. Angelovski, G., Fouskova, P., Mamedov, I. et al. (2008) ChemBioChem, 9, 1729.
85. Atanasijevic, T., Shusteff, M., Fam, P., and Jasanoff, A. (2006) Proc. Natl. Acad. Sci. U.S.A., 103, 14707.
86. Maret, W. and Li, Y. (2009) Chem. Rev., 109, 4682.
87. Zalewski, P., Truong-An, A., Lincoln, S. et al. (2006) BioTechnique, 40, 509.
88. Frederickon, C.J., Koh, J.Y., and Bush, A.I. (2005) Nat. Rev. Neurosci., 6, 449.
89. Hanaoka, K., Kikuchi, K., Urano, Y. et al. (2002) Chem. Biol., 9, 1027.
90. Major, J.L., Boiteau, R.M., and Meade, T.J. (2008) Inorg. Chem., 47, 10788.
91. Major, J.L., Parigi, G., Luchinat, C., and Meade, T.J. (2007) Proc. Natl. Acad. Sci. U.S.A., 104, 13881.
92. Esqueda, A.C., López, J.A., Andreu-de-Riquer, G. et al. (2009) J. Am. Chem. Soc., 131, 11387.
93. Trokowski, R., Ren, J., Kalman, F.K., and Sherry, A.D. (2005) Angew Chem. Int. Ed., 44, 6920.
94. Waggoner, D.J., Bartnikas, T.B., and Gitlin, J.D. (1999) Neurobiol. Dis., 6, 221.
95. Halliwell, B. and Gutteridge, J.M. (1984) Biochem. J., 219, 1.
96. Que, E.L. and Chang, C.J. (2006) J. Am. Chem. Soc., 128, 15942.
97. Que, E.L., Gianolio, E., Baker, S.L. et al. (2009) J. Am. Chem. Soc., 131, 8527.
98. Que, E.L., Gianolio, E., Baker, S.L. et al. (2010) Dalton Trans., 39, 469.
99. Li, W.S., Luo, J., and Chen, Z.N. (2011) Dalton Trans., 40, 484.
100. Drayer, B., Burger, P., Darwin, R. et al. (1986) Am. J. Roentgenol., 147, 103.
101. Zecca, L., Youdim, M.B.H., Riederer, P. et al. (2004) Nat. Rev. Neurosci., 5, 863.
102. Aime, S., Botta, M., Fasano, M., and Terreno, E. (1993) Spectrochim. Acta, 9, 1315-1322.
103. Ruloff, R., van Koten, G., and Merbach, A.E. (2004) Chem. Commun., 842;
104. Costa, J., Ruloff, R., Burai, L. et al. (2005) J. Am. Chem. Soc., 127, 5147.
105. Livramento, J.B., Tóth, E., Sour, A. et al. (2005) Angew. Chem. Int. Ed., 44, 1480;
106. Livramento, J.B., Weidensteiner, C., Prata, M.I.M. et al. (2006) Contrast Med. Mol. Imaging, 1, 30;
107. Livramento, J.B., Sour, A., Borel, A. et al. (2006) Chem. Eur. J., 12, 989.
108. Parac-Vogt, T.N., Vander Elst, L., Kimpe, K. et al. (2006) Contrast Med. Mol. Imaging, 1, 267.
109. Jacques, V. and Desreux, J.F. (2002) Top. Curr. Chem., 221, 125-64.
110. Surman, A.J., Bonnet, C.S., Lowe, M.P. et al. (2011) Chem. Eur. J., 17, 223.
111. Parker, D., Dickins, R.S., Puschmann, H. et al. (2002) Chem. Rev., 102, 1977.
112. Bruce, J.I., Dickins, R.S., Govenlock, L.J. et al. (2000) J. Am. Chem. Soc. 122, 9674;
113. Dickins, R.S., Aime, S., Batsanov, A.S. et al. (2002) J. Am. Chem. Soc., 124, 12697.
114. Dickins, R.S. and Badari, A. (2007) Dalton Trans., 3661.
115. Aime, S., Gianolio, E., Terreno, E. et al. (2000) Chem. Eur. J. Biol. Inorg. Chem., 5, 488.
116. Caravan, P., Amedio, J.C., Dunham, S.U. et al. (2005) Chem. Eur. J., 11, 5866.
117. Botta, M., Aime, S., Barge, A. et al. (2003) Chem. Eur. J., 9, 2102.
118. Aime, S., Botta, M., Bruce, J.I. et al. (2001) Chem. Commun., 115.
119. Pellegatti, L., Zhang, J., Drahos, B. et al. (2008) Chem. Commun., 6591.
120. Huang, C.H. and Morrow, J.R. (2009) J. Am. Chem. Soc., 131, 4206;
121. Huang, C.H., Hammell, J., Ratnakar, J. et al. (2010) Inorg. Chem., 49, 5963;
122. Hammell, J., Buttarazzi, L., Huang, C.H., and Morrow, J.R. (2011) Inorg. Chem., 50, 4857.
123. Moats, R.A., Fraser, S.E., and Meade, T.J. (1997) Angew. Chem., Int. Ed. Engl., 36, 726.
124. Bogdanov, A., Matuszewski, L., Bremer, C. et al. (2002) Mol. Imaging, 1, 1.
125. Chen, J.W., Pham, W., Weissleder, R., and Bogdanov, A. (2004) Magn. Reson. Med., 52, 1021.
126. Querol, M., Chen, J.W., and Bogdanov, A. (2006) Org. Biomol. Chem., 4, 1887.
127. Nahrendorf, M., Sosnovik, D., Chen, J.W. et al. (2008) Circulation, 117, 1153.
128. Breckwoldt, M.O., Chen, J.W., Stangenberg, L. et al. (2008) Proc. Natl. Acad. Sci. U.S.A., 105, 18584.
129. Chen, J.W., Breckwoldt, M.O., Aikawa, E. et al. (2008) Brain, 131, 1123.
130. Rodriguez, E., Nilges, M., Weissleder, R., and Chen, J.W. (2010) J. Am. Chem. Soc., 132, 168.
131. Querol, M., Bennett, D.G., Sotak, C. et al. (2007) ChemBioChem, 8, 1637.
132. Rolla, G.A., Tei, L., Fekete, M. et al. (2011) Bioorg. Med. Chem., 19, 1115.
133. Nahrendorf, M., Aikawa, E., Figueiredo, J.L. et al. (2008) Eur. Heart. J., 29, 445.
134. Tung, C.H., Ho, N.H., Zeng, Q. et al. (2003) ChemBioChem, 4, 897.
135. Mazooz, G., Mehlman, T., Lai, T.S. et al. (2005) Cancer Res., 65, 1369.
136. Tei, L., Mazooz, G., Shellef, Y. et al. (2010) Contrast Media Mol. Imaging, 5, 213.
137. Louie, A.Y., Huber, M.M., Ahrens, E.T. et al. (2000) Nat. Biotech., 18, 321.
138. Lauffer, R.B.; McMurry, T.J., Dunham, S.O. et al. (1997) PCT Int. Appl. WO 9736619.
139. Nivorozhkin, A.L., Kolodziej, A.F., Caravan, P. et al. (2001) Angew. Chem. Int. Ed., 40, 2903.
140. Chang, Y.-T., Cheng, C.-M., Su, Y.-Z. et al. (2007) Bioconjugate Chem., 18, 1716.
141. Himmelreich, U., Aime, S., Hieronymus, T. et al. (2006) Neuroimage, 32, 1142.
142. Lebel, R., Jastrze, B., Therriault, H. et al. (2008) Magn. Res. Med., 60, 1056.
143. Gringeri, C.V., Menchise, V., Rizzitelli, S. et al. (2012) Contrast Media Mol. Imaging 7, 75.
144. Zhao, M., Josephson, L., Tang, Y., and Weissleder, R. (2003) Angew. Chem. Int. Ed., 42, 1375.
145. Mizukami, S., Takikawa, R., Sugihara, F. et al. (2007) J. Am. Chem. Soc., 130, 794.
146. Yoo, B. and Pagel, M.D. (2006) J. Am. Chem. Soc., 128, 14032.
147. Yoo, B., Raam, M.S., Rosenblum, R.M., and Pagel, M.D. (2007) Contrast Media Mol. Imaging, 2, 189.
148. Chauvin, T., Durand, P., Bernier, M. et al. (2008) Angew. Chem. Int. Ed., 47, 4370
149. Chauvin, T., Durand, P., Bernier, M. et al. (2008) Angew. Chem. Int. Ed., 47, 4370