Paramagnetic CEST MRI Contrast Agents

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

Volumn , Issue , 2013, Pages 387-425

  Terreno, Enzo ^a   Castelli, Daniela Delli ^a   Aime, Silvio ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

Chemical Exchange Saturation Transfer (CEST); Iopamidol; MRI contrast agents; Paramagnetic transition

Indexed keywords

EID: 84887258827     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118503652.ch9     Document Type: Chapter

References (155)

1. Laurent, S., Forge, D., Port, M. et al. (2008) Chem. Rev., 108, 2064.
2. Terreno, E., Delli Castelli, D., Viale, A. and Aime, S. (2010) Chem. Rev., 110, 3019.
3. Lammers, T., Aime, S., Hennink, W.E. et al. (2011) Acc. Chem. Res. doi: 10.1021/ar200019c.
4. Gilad, A.A., Walczak, P., McMahon, M.T. et al. (2008) Magn. Reson. Med., 60 (1).
5. Partlow, K.C., Chen, J., Brant, J.A. et al. (2007) FASEB J., 21, 1647.
6. Viale, A. and Aime, S. (2010) Curr. Opin. Chem. Biol., 14, 90.
7. Ward, K.M., Aletras, A.H. and Balaban, R.S. (2000) J. Magn. Reson., 143, 79.
8. Zhang, S.R., Merritt, M., Woessner, D.E. et al. (2003) Acc. Chem. Res., 36, 783.
9. Zhou, J. and van Zijl Peter, P.C.M. (2006) Prog. Nucl. Magn. Reson. Spectrosc., 48, 109.
10. Woods, M., Donald, E.W.C. and Sherry, A.D. (2006) Chem. Soc. Rev., 35, 500.
11. Sherry, A.D. and Woods, M. (2008) Ann. Rev. Biomed. Eng., 10, 391.
12. Ali, M.M., Liu, G., Shah, T. et al. (2009) Acc. Chem. Res., 42, 915.
13. Wu, Y., Evbuomwan, M., Melendez, M. et al. (2010) Future Med. Chem., 2, 351.
14. Terreno, E., Delli Castelli, D. and Aime, S. (2010) Contrast Media Mol. Imaging, 5, 78.
15. Viswanathan, S., Kovacs, Z., Green, K. et al. (2010) Chem. Rev., 110, 2960.
16. Hancu, I., Dixon, W.T., Woods, M. et al. (2010) Acta Radiol., 51, 910.
17. van Zijl, P.C. and Yadav, N.N. (2011) Magn. Reson. Med., 65, 927.
18. Schroder, L., Lowery, T.J., Hilty, C. et al. (2006) Science, 314, 446.
19. Hilty, C., Lowery, T.J., Wemmer, D.E. and Pines, A. (2006) Angew. Chem. Int. Ed., 45, 70.
20. Schroder, L., Meldrum, T., Smith, M. et al. (2008) Phys. Rev. Lett., 100, 257603.
21. Bloch, F., Hansen, W.W. and Packard, M. (1946) Phys. Rev., 70, 474.
22. Bloch, F. (1946) Phys. Rev., 70, 460.
23. Mc Connell, H.M. and Thompson, D.D.J. (1957) Chem. Phys., 26, 958.
24. Baguet, E. and Roby, C. (1994) J. Magn. Reson., Ser. A, 108, 189.
25. Baguet, E. and Roby, C. (1997) J. Magn. Reson., 128, 149.
26. Kingsley, P.B. and Monahan, W.G. (2000) J. Magn. Reson., 143, 360.
27. Kingsley, P.B. and Monahan, W.G. (2000) Magn. Reson. Med., 43, 810.
28. Forsen, S. and Hoffman, R.A. (1963) Acta Chem. Scand., 17, 1787.
29. Forsen, S. and Hoffman, R.A. (1963) J. Chem. Phys., 39, 2892.
30. Sun, P.Z., Van Zijl, P.C. and Zhou, J. (2005) J. Magn. Reson., 175, 193.
31. Sun, P.Z. and Sorensen, A.G. (2008) Magn. Reson. Med., 60, 390.
32. Woessner, D.E., Zhang, S., Merritt, M. and Sherry, A.D. (2005) Magn. Reson. Med., 53, 790.
33. Li, A.X., Hudson, R.H.E., Barrett, J.W. et al. (2008) Magn. Reson. Med., 60, 1197.
34. Balaban, R.S. and Ceckler, T.L. (1992) Magn. Reson. Q., 8, 116.
35. Sun, P.Z. (2010) J. Magn. Reson., 205, 235.
36. Murase, K. and Tanki, N. (2011) Magn. Reson. Imaging, 29, 126.
37. Shellock, F.G. (2000) J. Magn. Reson. Imaging, 12, 30.
38. Gilad, A.A., van Laarhoven, H.W.M., McMahon, M.T. et al. (2009) Magn. Reson. Med., 61, 970.
39. Aime, S., Nano, R. and Grandi, M. (1888) Invest. Radiol., 23, S267.
40. Aime, S., Botta, M., Barbero, L. et al. (1991) Magn. Reson. Chem., 29, S85.
41. Vander Elst, L., Roch, A., Gillis, P. et al. (2002) Magn. Reson. Med., 47, 1121.
42. Zhou, J., Lal, B., Wilson, D.A. et al. (2003) Nat. Med., 9, 1085.
43. Shah, T., Lu, L., Dell, K.M. et al. (2011) Magn. Reson. Med., 65, 432.
44. Dixon, W.T., Hancu, I., Ratnakar, S.J. et al. (2010) Magn. Reson. Med., 63, 253.
45. Sun, P.Z., Cheung, J.S., Wang, E. et al. (2011) Magn. Reson. Med., 65, 588.
46. Zhu, H., Jones, C.K., van Zijl, P.C.M. et al. (2010) Magn. Reson. Med., 64, 638.
47. Hemkelman, R.M., Stanisz, G.J. and Graham, S.J. (2001) NMR Biomed., 14, 57.
48. Hua, J., Jones, C.K., Blakeley, J. et al. (2007) Magn. Reson. Med., 58, 786.
49. Ramli, N., Rahmat, K., Azmi, K. and Chong, H.T. (2010) J. Clin. Neurosci., 17, 422.
50. Bradley, W.G. (1992) Curr. Opin. Neurol. Neurosurg., 5, 859.
51. Ceckler, T., Maneval, J. and Melkowits, B. (2001) J. Magn. Reson., 151, 9.
52. Yarnykh, V.L. (2002) Magn. Reson. Med., 47, 929.
53. Friedman, J.I., McMahon, M.T., Stivers, J.T. and Van Zijl, P.C.M. (2010) J. Am. Chem. Soc., 132, 1813.
54. Zaiss, M., Schmitt, B. and Bachert, P. (2011) J. Magn. Reson., 211, 149.
55. Zhou, J., Blakeley, J.O., Hua, J. et al. (2008) Magn. Reson. Med., 60, 842.
56. Sun, P.Z., Farrar, C.T. and Sorensen, A.G. (2007) Magn. Reson. Med., 58, 1207.
57. Stancanello, J., Terreno, E., Delli Castelli, D. et al. (2008) Contrast Media Mol. Imaging, 3, 136.
58. Kim, M., Gillen, J., Landman, B.A. et al. (2009) Magn. Reson. Med., 61, 1441.
59. Reeder, S.B., Wen, Z., Yu, H. et al. (2004) Magn. Reson. Med., 51, 35.
60. McMahon, M.T., Gilad, A.A., Zhou, J. et al. (2006) Magn. Reson. Med., 55, 836.
61. Sun, P.Z. (2011) Magn. Reson. Med. doi: 10.1002/mrm.23068.
62. Dixon, W.T., Ren, J., Lubag, A.J.M. et al. (2010) Magn. Reson. Med., 63 (625).
63. Meser Ali, M., Yoo, B. and Pagel, M.D. (2009) Mol. Pharm., 6, 1409.
64. Longo, D.L., Dastru, W., Digilio, G. et al. (2011) Magn. Reson. Med., 65, 202.
65. Keupp, J., Dimitrov, I., Langereis, S. et al. (2011) Proc. Intl. Soc. Magn. Reson. Med., 19, 828.
66. Snoussi, K., Bulte, J.W.M., Gueron, M. and van Zijl, P.C.M. (2003) Magn. Reson. Med., 49, 998.
67. Terreno, E., Delli Castelli, D., Cravotto, G. et al. (2004) Invest. Radiol., 39, 235.
68. Zhang, S., Winter, P., Wu, K. and Sherry, A.D. (2001) J. Am. Chem. Soc., 123, 1517.
69. Aime, S., Barge, A., Delli Castelli, D. et al. (2002) Magn. Reson. Med., 47, 639.
70. Aime, S., Delli Castelli, D. and Terreno, E. (2002) Angew. Chem. Int. Ed., 41, 4334.
71. Aime, S., Carrera, C., Delli Castelli, D. et al. (2005) Angew. Chem. Int. Ed., 44, 1813.
72. Zhou, J., Lal, B., Wilson, D.A. et al. (2003) Magn. Reson. Med., 50, 1120.
73. van Zijl, P.C., Jones, C.K., Ren, J. et al. (2007) Proc. Natl. Acad. Sci. U.S.A., 104, 4359.
74. Ling, W., Regatte, R.R., Navon, G. and Jerschow, A. (2008) Proc. Natl. Acad. Sci. U.S.A., 105, 2266.
75. Haris, M., Cai, K., Singh, A. et al. (2011) Neuroimage, 54, 2079.
76. Jones, C.K., Schlosser, M.J., van Zijl, P.C. et al. (2006) Magn. Reson. Med., 56, 585.
77. Zhou, J., Tryggestad, E., Wen, Z. et al. (2011) Nat. Med., 17, 130.
78. Zhou, J. (2011) Methods Mol. Biol., 711, 227;
79. Schmitt, B., Zbýn, S., Stelzeneder, D. et al. (2011) Radiology, 260, 257.
80. Zhang, S.R. and Sherry, A.D. (2003) J. Solid State Chem., 171, 38.
81. Woods, M., Caravan, P., Geraldes, C.F.G.C. et al. (2008) Invest. Radiol., 43, 861.
82. Zhang, S., Malloy, C.R. and Sherry, A.D. (2005) J. Am. Chem. Soc., 127, 17572.
83. Zhang, S., Trokowski, R. and Sherry, A.D. (2003) J. Am. Chem. Soc., 125, 15288.
84. Trokowski, R., Ren, J., Kalman, F.K. and Sherry, A.D. (2005) Angew. Chem. Int. Ed., 44, 6920.
85. Wu, Y., Soesbe, T.C., Kiefer, G.E. et al. (2010) J. Am. Chem. Soc., 132, 14002.
86. Pubanz, D., Gonzalez, G., Powell, D.H. and Merbach, A.E. (1995) Inorg. Chem., 34, 4447.
87. Zhang, S., Wu, K., Sherry, A.D. (2002) J. Am. Chem. Soc., 124, 4226.
88. Thompson, A.L., Parker, D., Fulton, D.A. et al. (2006) Dalton Trans., 5605.
89. Terreno, E., Boniforte, P., Botta, M. et al. (2003) Eur. J. Inorg. Chem., 3530.
90. Ratnakar, S.J., Woods, M., Lubag, A.J.M. et al. (2008) J. Am. Chem. Soc., 130, 6.
91. Green, K.N., Viswanathan, S., Rojas-Quijano, F.A. et al. (2011) Inorg. Chem., 50, 1648.
92. Aime, S., Barge, A., Batsanov, A.S. et al. (2002) Chem. Commun., 1120.
93. Mani, T., Tircso, G., Togao, O. et al. (2009) Contrast Media Mol. Imaging, 4, 183.
94. Li, A.X., Wojciechowski, F., Suchy, M. et al. (2008) Magn. Reson. Med., 59, 374.
95. Wojciechowski, F., Suchy, M., Li, A.X. et al. (2007) Bioconjugate Chem., 18, 1625.
96. Suchy, M., Li, A.X., Bartha, R. and Hudson, R.H.E. (2008) Bioorg. Med. Chem., 16, 6156.
97. Viswanathan, S., Ratnakar, S.J., Green, K.N. et al. (2009) Angew. Chem. Int. Ed., 48, 9330.
98. Yoo, B. and Pagel, M.D. (2006) J. Am. Chem. Soc., 128, 14032.
99. Yoo, B., Raam, S.M.S., Rosenblum, R.M. and Pagel, M.D. (2007) Contrast Media Mol. Imaging, 2, 189.
100. Yuguo, L., Sheth, V.R., Liu, G. and Pagel, M.D. (2011) Contrast Media Mol. Imaging. doi: 10.1002/cmmi.421.
101. Liu, G., Li, Y. and Pagel, M.D. (2007) Magn. Reson. Med., 58, 1249.
102. Burdinski, D., Lub, J., Pikkemaat, J.A. et al. (2008) Chem. Biodivers., 5, 1505.
103. Woods, M., Woessner, D.E., Zhao, P. et al. (2006) J. Am. Chem. Soc., 128, 10155.
104. Huang, C.H. and Morrow, J.R. (2009) Inorg. Chem., 48, 7237.
105. Huang, C.H. and Morrow, J.R. (2009) J. Am. Chem. Soc., 131, 4206.
106. Hammell, J., Buttarazzi, L., Huang, C.-H. and Morrow, J.R. (2011) Inorg. Chem., 50, 4857.
107. Aime, S., Delli Castelli, D., Fedeli, F. and Terreno, E. (2002) J. Am. Chem. Soc., 124, 9364.
108. Pikkemaat, J.A., Wegh, R.T., Lamerichs, R. et al. (2007) Contrast Media Mol. Imaging, 2, 229.
109. Wu, Y., Zhou, Y., Ouari, O. et al. (2008) J. Am. Chem. Soc., 130, 13854.
110. Wu, Y., Carney, C.E., Denton, M. et al. (2010) Org. Biomol. Chem., 8, 5333.
111. Wu, Y., Zhao, P., Kiefer, G.E. and Sherry, A.D. (2010) Macromolecules, 43, 6616.
112. Winter, P.M., Cai, K., Chen, J. et al. (2006) Magn. Reson. Med., 56, 1384.
113. Vasalatiy, O., Gerard, R.D., Zhao, P. et al. (2008) Bioconjugate Chem., 19, 598.
114. Aime, S., Delli Castelli, D. and Terreno, E. (2003) Angew. Chem. Int. Ed., 42, 4527.
115. Ronen, I. and Kim, S.G. (2001) NMR Biomed., 14, 448.
116. Weidensteiner, C., Horn, M., Fekete, E. et al. (2002) Magn. Reson. Med., 48, 89.
117. van Heeswijk, R.B., Laus, S., Morgenthaler, F.D. and Gruetter, R. (2007) Magn. Reson. Imaging, 25, 821.
118. Gregoriadis, G. (ed.) (2006) Liposome Technology, Informa Healthcare.
119. Terreno, E., Sanino, A., Carrera, C. et al. (2008) J. Inorg. Biochem., 102, 1112.
120. Aime, S., Geninatti Crich, S., Gianolio, E. et al. (2006) Coord. Chem. Rev., 250, 1562.
121. Aime, S., Delli Castelli, D. and Terreno, E. (2005) Angew. Chem. Int. Ed., 44, 5513.
122. Terreno, E., Delli Castelli, D., Violante, E. et al. (2009) Chem. Eur. J., 15, 1440.
123. Zhao, J.M., Har-el, Y., McMahon, M.T. et al. (2008) J. Am. Chem. Soc., 130, 5179.
124. Terreno, E., Cabella, C., Carrera, C. et al. (2007) Angew. Chem. Int. Ed., 46, 966.
125. Chu, S.C.K., Xu, Y., Balschi, J.A. and Springer, C.S. Jr., (1990) Magn. Reson. Med., 13, 239.
126. Kuchel, P.W., Chapman, B.E., Bubb, W.A. et al. (2003) Concepts Magn. Reson. A, 18A, 56.
127. Pencer, J., White, G.F. and Hallett, F.R. (2001) Biophys. J., 81, 2716.
128. Prosser, R.S., Hunt, S.A., DiNatale, J.A. and Vold, R.R. (1996) J. Am. Chem. Soc., 118, 269.
129. Prosser, R.S., Bryant, H., Bryant, R.G. and Vold, R.R. (1999) J. Magn. Reson., 141, 256.
130. Delli Castelli, D., Terreno, E., Carrera, C. et al. (2008) Inorg. Chem., 47, 2928.
131. Aime, S., Delli Castelli, D. and Terreno, E. (2009) Methods Enzymol., 464, 193.
132. Burdinski, D., Pikkemaat, J.A., Emrullahoglu, M. et al. (2010) Angew. Chem. Int. Ed., 49, 2227.
133. Ludden, M.J.W., Reinhoudt, D.N. and Huskens, J. (2006) Chem. Soc. Rev., 35, 1122.
134. Terreno, E., Barge, A., Beltrami, L. et al. (2008) Chem. Commun., 600.
135. Terreno, E., Delli Castelli, D., Milone, L. et al. (2008) Control Med. Mol. Imaging, 3, 38.
136. Terreno, E., Delli Castelli, D., Cabella, C. et al. (2008) Chem. Biodivers., 5, 1901.
137. Aime, S., Delli Castelli, D., Lawson, D. and Terreno, E. (2007) J. Am. Chem. Soc., 129, 2430.
138. Terreno, E., Boffa, C., Menchise, V. et al. (2011) Chem. Commun., 47, 4667.
139. Langereis, S., Keupp, J., van Velthoven, J.L.J. et al. (2009) J. Am. Chem. Soc., 131, 1380.
140. Discher, B.M., Won, Y.Y., Ege, D.S. et al. (1999) Science, 284, 1143.
141. Gruell, H., Langereis, S., Messager, L. et al. (2010) Soft Matter, 6, 4847.
142. Photos, P.J., Bacakova, L., Discher, B. et al. (2003) J. Control. Release, 90, 323.
143. Vinogradov, E., Zhang, S., Lubag, A. et al. (2005) J. Magn. Reson., 176, 54.
144. Vinogradov, E., He, H., Lubag, A. et al. (2007) Magn. Reson. Med., 58, 650.
145. Suchy, M., Ta, R., Li, A.X. et al. (2010) Org. Biomol. Chem., 8, 2560.
146. Li, A.X., Suchy, M., Li, C. et al. (2011) Magn. Reson. Med., 66, 67.
147. Leigh, J.S. (1971) J. Magn. Reson., 4, 308.
148. Granot, J. and Fiat, D. (1974) J. Magn. Reson., 15, 540.
149. Soesbe, T.C., Merritt, M.E., Green, K.N. et al. (2011) Magn. Reson. Med. doi: 10.1002/mrm.22938
150. Swift, T.J. and Connick, R.E. (1962) J. Chem. Phys., 37, 307.
151. Delli Castelli, D., Terreno, E., Cabella, C. et al. (2009) NMR Biomed., 22, 1084.
152. Delli Castelli, D., Dastru, W., Terreno, E. et al. (2010) J. Control. Release, 144, 271.
153. Vinogradov, E., Soesbe, T.C., Balschi, J.A. et al. (2009) Proc. Int. Soc. Magn. Reson. Med., 186.
154. Vinogradov, E. and Lenkinski, R.E. (2010) Contrast Media Mol. Imaging, 5, 333 (Proceedings of the 1st CEST Workshop).
155. Delli Castelli, D., Terreno, E. and Aime, S. (2011) Angew. Chem. Int. Ed., 50, 1798.