Chemical exchange saturation transfer contrast agents for magnetic resonance imaging

Annual Review of Biomedical Engineering

Volumn 10, Issue , 2008, Pages 391-411

  Sherry, A Dean ^a,b   Woods, Mark ^a  

^a UNIVERSITY OF TEXAS AT DALLAS   (United States)

^b UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

CEST; MRI contrast agents; PARACEST

Indexed keywords

ATOMS; GADOLINIUM; HEALTH; IMAGING TECHNIQUES; MAGNETIC FIELDS; MAGNETIC RESONANCE; MAGNETIC RESONANCE IMAGING;

CEST; CHEMICAL EXCHANGE SATURATION TRANSFER; CLINICAL MEDICINES; CONTRAST AGENTS; MRI CONTRAST AGENTS; PARACEST;

RESONANCE;

AMIDE; CONTRAST MEDIUM; GADOLINIUM; HYDROXYL GROUP; PROTON;

BIOMECHANICS; CHEMICAL ENVIRONMENT; CHEMICAL EXCHANGE SATURATION TRANSFER; CHEMICAL STRUCTURE; ENDOGENOUS CHEMICAL EXCHANGE SATURATION TRANSFER; NUCLEAR MAGNETIC RESONANCE IMAGING; PARAMAGNETIC CHEMICAL EXCHANGE SATURATION TRANSFER; REVIEW; SPECTRAL SENSITIVITY; TISSUE SPECIFICITY;

CONTRAST MEDIA; IMAGE ENHANCEMENT; IMAGE INTERPRETATION, COMPUTER-ASSISTED; MAGNETIC RESONANCE IMAGING; MOLECULAR PROBE TECHNIQUES;

EID: 50249145152     PISSN: 15239829     EISSN: None     Source Type: Book Series    
DOI: 10.1146/annurev.bioeng.9.060906.151929     Document Type: Review

References (83)

1. Caravan P, Ellison JJ, McMurry TJ, Lauffer RB. 1999. Gadolinium(III) chelates as MRI contrast agents: structure, dynamics, and applications. Chem. Rev. 99:2293-352
2. Toth E, Merbach AE. 2001. Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging. New York: Wiley
3. Kaiman FK, Woods M, Caravan P, Jurek P, Spiller M, et al. 2007. Potentiometric and relaxometric properties of a gadolinium-based MRI contrast agent for sensing tissue pH. Inorg. Chem. 46:5260-70
4. Aime S, Barge A, Botta M, Howard JAK, Kataky R, et al. 1999. Dependence of the relaxivity and luminescence of gadolinium and europium amino-acid complexes on hydrogencarbonate and pH. Chem. Commun. 1999:1047-448
5. Lowe MP, Parker D. 2000. Controllable pH modulation of lanthanide luminescence by intramolecular switching of the hydration state. Chem. Commun. 2000:707-8
6. Aime S, Crich SG, Botta M, Giovenzana G, Palmisano G, Sisti M. 1999. A macromolecular Gd(III) complex as pH-responsive relaxometric probe for MRI applications. Chem. Commun. 1999:1577-78
7. Hovland R, Glogard C, Aasen AJ, Klaveness J. 2001. Gadolinium DO3A derivatives mimicking phospholipids; preparation and in vitro evaluation as pH responsive MRI contrast agents. J. Chem. Soc., Perkin Trans. 2:929-33
8. Glogard C, Hovland R, Fossheim SL, Aasen AJ, Klaveness J. 2000. Synthesis and physicochemical characterisation of new amphiphilic gadolinium DO3A complexes as contrast agents for MRI. J. Chem. Soc., Perkin Trans. 25:1047-52
9. Woods M, Kiefer GE, Bott S, Castillo-Muzquiz A, Eshelbrenner C, et al. 2004. Synthesis, relaxometric and photophysical properties of a new pH-responsive MRI contrast agent: the effect of other ligating groups on dissociation of a p-nitrophenolic pendant arm. J. Am. Chem. Soc. 126:9248-56
10. Hanaoka K, Kikuchi K, Urano Y, Nagano T. 2001. Selective sensing of zinc ions with a novel magnetic resonance imaging contrast agent. J. Chem. Soc., Perkin Trans. 2:1840-43
11. Li W-H, Fraser SE, Meade TJ. 1999. A calcium-sensitive magnetic resonance imaging contrast agent. J. Am. Chem. Soc. 121:1413-14
12. Li W-H, Parigi G, Fragai M, Luchinat C, Meade TJ. 2002. Mechanistic studies of a calcium-dependent MRI contrast agent. Inorg. Chem. 41:4018-24
13. Dickins RS, Gunnlaugsson T, Parker D, Peacock RD. 1998. Reversible anion binding in aqueous solution at a cationic heptacoordinate lanthanide center: selective bicarbonate sensing by time-delayed luminescence. Chem. Commun. 1998:1643-44
14. Dickins RS, Love CS, Puschmann H. 2001. Bidentate lactate binding in aqueous solution in a cationic, heptadentate lanthanide complex: an effective chiral derivatising agent. Chem. Commun. 2001:2308-9
15. Moats RA, Fraser SE, Meade TJ. 1997. A "smart" magnetic resonance imaging agent that reports on specific enzymatic activity. Angew. Chem. Int. Ed. 36:726-28
16. Anelli PL, Bertini I, Fragai M, Lattuada L, Luchinat C, Parigi G. 2000. Sulfonamide-functionalized gadolinium DTPA complexes as possible contrast agents for MRI: a relaxometric investigation. Eur. J. Inorg. Chem. 2000(4):625-30
17. 3+ magnetic resonance imaging contrast agents with a prominent receptor-induced magnetization enhancement. Angew. Chem. Int. Ed. 40:2903-6
18. De Leon-Rodriguez LM, Ortiz A, Weiner AL, Zhang S, Kovacs Z, et al. 2002. Magnetic resonance imaging detects a specific peptide-protein binding event. J. Am. Chem. Soc. 124:3514-15
19. Garcia-Martin ML, Martinez GV, Raghunand N, Sherry AD, Zhang S, Gillies RJ. 2006. High resolution pH imaging of rat glioma using pH-dependent relaxivity. Magn. Reson. Med. 55:309-15
20. Raghunand N, Howison C, Sherry AD, Zhang S, Gillies RJ. 2003. Renal and systemic pH imaging by contrast-enhanced MRI. Magn. Reson. Med. 49:249-57
21. McConnell HM, Thompson DD. 1957. Molecular transfer of nonequilibrium nuclear spin magnetization. J. Chem. Phys. 26:958-59
22. McConnell HM, Thompson DD. 1959. Molecular transfer of nonequilibrium nuclear spin magnetization. J. Chem. Phys. 31:85-88
23. Forsén S, Hoffman RA. 1963. Study of moderately rapid chemical exchange reactions by means of nuclear magnetic resonance double resonance. J. Chem. Phys. 39:2892-901
24. Woods M, Woessner DE, Sherry AD. 2006. Paramagnetic lanthanide complexes as PARACEST agents for medical imaging. Chem. Soc. Rev. 35:500-11
25. Woessner DE, Zhang S, Merritt M, Sherry AD. 2005. Numerical solution of the Bloch equations provides insights into the optimum design of PARACEST agents for MRI. Magn. Reson. Med. 53:790-99
26. Snoussi K, Bulte JWM, Gueron M, van Zijl PCM. 2003. Sensitive CEST agents based on nucleic acid imino proton exchange: detection of poly(rU) and of a dendrimer-poly(rU) model for nucleic acid delivery and pharmacology. Magn. Reson. Med. 49:998-1005
27. Meaney JF. 2003. Magnetic resonance angiography of the peripheral arteries: current status. Eur. Radiol. 13:836-52
28. Eiberg JP, Lundorf E, Thomsen C, Schroeder TV. 2001. Peripheral vascular surgery and magnetic resonance arteriography - a review. Eur. J. Vasc. Endovasc. Surg. 22:396-402
29. Bhakoo K, Chapon C, Jackson J, Jones W. 2006. Application of MRI to cell tracking. In Modern Magnetic Resonance, ed. G Webb, pp. 873-84. New York: Springer
30. Rogers WJ, Meyer CH, Kramer CM. 2006. Technology insight: in vivo cell tracking by use of MRI. Nat. Clin. Pract. Cardiovasc. Med. 3:554-62
31. Arbab AS, Liu W, Frank JA. 2006. Cellular magnetic resonance imaging: current status and future prospects. Expert Rev. Med. Devices 3:427-39
32. Bulte JWM, Kraitchman DL. 2004. Monitoring cell therapy using iron oxide MR contrast agents. Curr. Pharm. Biotechnol. 5:567-84
33. Gilad AA, McMahon MT, Walczak P, Winnard PT Jr, Raman V, et al. 2007. Artificial reporter gene providing MRI contrast based on proton exchange. Nat. Biotech. 25:217-19
34. Goffeney N, Bulte JWM, Duyn J, Bryant LH Jr, van Zijl PCM. 2001. Sensitive NMR detection of cationic-polymer-based gene delivery systems using saturation transfer via proton exchange. J. Am. Chem. Soc. 123:8628-29
35. van Zijl PCM, Jones CK, Ren J, Malloy CR, Sherry AD. 2007. MRI detection of glycogen in vivo by using chemical exchange saturation transfer imaging (glycoCEST). Proc. Natl. Acad. Sci. USA 104:4359-64
36. McMahon MT, Gilad AA, Zhou J, Sun PZ, Bulte JWM, van Zijl PCM. 2006. Quantifying exchange rates in chemical exchange saturation transfer agents using the saturation time and saturation power dependencies of the magnetization transfer effects on the magnetic resonance imaging signal (QUEST and QUESP): pH calibration for poly-L-lysine and a starburst dendrimer. Magn. Reson. Med. 55:836-47
37. Jones CK, Schlosser MJ, van Zijl PCM, Pomper MG, Golay X, Zhou J. 2006. Amide proton transfer imaging of human brain tumors at 3T. Magn. Reson. Med. 56:585-92
38. Zhou J, Payen J-F, Wilson DA, Traystman RJ, van Zijl PCM. 2003. Using the amide proton signals of intracellular proteins and peptides to detect pH effects in MRI. Nat. Med. 9:1085-90
39. Schroeder L, Lowery TJ, Hilty C, Wemmer DE, Pines A. 2006. Molecular imaging using a targeted magnetic resonance hyperpolarized biosensor. Science 314:446-49
40. Oros AM, Shah NJ. 2004. Hyperpolarized xenon in NMR and MRI. Phys. Med. Biol. 49:R105-53
41. 3He gas induced by optical pumping and dipolar exchange. Phys. Rev. Lett. 5:373-75
42. Ward KM, Aletras AH, Balaban RS. 2000. A new class of contrast agents for MRI based on proton chemical exchange dependent saturation transfer (CEST). J. Magn. Reson. 143:79-87
43. Ward KM, Balaban RS. 2000. Determination of pH using water protons and chemical exchange dependent saturation transfer (CEST). Magn. Reson. Med. 44:799-802
44. 3+ complexes of interest in magnetic resonance imaging: an integrated and theoretically self-consistent approach. J. Am. Chem. Soc. 118:9333-46
45. Aime S, Barge A, Botta M, De Sousa AS, Parker D. 1998. Direct NMR spectroscopic observation of a lanthanide-coordinated water molecule whose exchange rate is dependent on the conformation of the complexes. Angew. Chem. Int. Ed. 37:2673-75
46. 3+ macrocyclic complex. J. Am. Chem. Soc. 119:4767-68
47. Aime S, Barge A, Bruce JI, Botta M, Howard JAK, et al. 1999. NMR, relaxometric, and structural studies of the hydration and exchange dynamics of cationic lanthanide complexes of macrocyclic tetraamide ligands. J. Am. Chem. Soc. 121:5762-71
48. Zhang S, Winter P, Wu K, Sherry AD. 2001. A novel europium(III)-based MRI contrast agent. J. Am. Chem. Soc. 123:1517-18
49. 17O NMR detection of a lanthanide-bound water molecule at ambient temperatures in pure water as solvent. Inorg. Chem. 40:4284-90
50. Bleaney B. 1972. Nuclear magnetic resonance shifts in solution due to lanthanide ions. J. Magn. Reson. 8:91-100
51. Bleaney B, Dobson CM, Levine BA, Martin RB, Williams RJP, Xavier AV. 1972. Origin of lanthanide nuclear magnetic resonance shifts and their uses. J. Chem. Soc. Chem. Commun. 1972:791-93
52. Mironov VS, Galyametdinov YG, Ceulemans A, Gorller-Walrand C, Binnemans K. 2002. Room-temperature magnetic anisotropy of lanthanide complexes. A model study for various coordination polyhedraj. Chem. Phys. 116:4673-85
53. Zhang S, Merritt M, Woessner DE, Lenkinski RE, Sherry AD. 2003. PARACEST agents: modu lating MRI contrast via water proton exchange. Acc. Chem. Res. 36:783-90
54. Zhang S, Wu K, Sherry AD. 2002. Unusually sharp dependence of water exchange rate versus lanthanide ionic radii for a series of tetraamide complexes. J. Am. Chem. Soc. 124:4226-27
55. Woods M, Woessner DE, Zhao P, Pasha A, Yang M-Y, et al. 2006. Europium(III) macrocyclic complexes with alcohol pendant groups as chemical exchange saturation transfer agents. J. Am. Chem. Soc. 128:10155-62
56. Zhang S, Michaudet L, Burgess S, Sherry AD. 2002. The amide protons of an ytterbium(III) dota tetraamide complex act as efficient antennae for transfer of magnetization to bulk water. Angew. Chem. Int. Ed. 41:1919-21
57. Terreno E, Castelli DD, Cravotto G, Milone L, Aime S. 2004. Ln(III)-DOTAMGly complexes: a versatile series to assess the determinants of the efficacy of paramagnetic chemical exchange saturation transfer agents for magnetic resonance imaging applications. Investig. Radiol. 39:235-43
58. Aime S, Barge A, Castelli DD, Fedeli F, Mortillaro A, et al. 2002. Paramagnetic Lanthanide(III) complexes as pH-sensitive chemical exchange saturation transfer (CEST) contrast agents for MRI applications. Magn. Reson. Med. 47:639-48
59. Yoo B, Pagel MD. 2007. Peptidyl molecular imaging contrast agents using a new solid-phase peptide synthesis approach. Bioconjug. Chem. 18:903-11
60. Yoo B, Pagel MD. 2006. A PARACEST MRI contrast agent to detect enzyme activity. J. Am. Chem. Soc. 128:14032-33
61. Zhang S, Malloy CR, Sherry AD. 2005. MRI thermometry based on PARACEST agents. J. Am. Chem. Soc. 127:17572-73
62. Wegh RT, Pikkemaat JA, Willard NP. 2006. WO Patent No. 2006-IB51237, 2006114739
63. Willard NP, Wegh RT, Pikkemaat JA, Gruell H. 2006. WO Patent No. 2006-IB51235, 2006114738;
64. Pikkemaat JA, Wegh RT, Lamerichs R, van de Molengraaf RA, Langereis S, et al. 2007. Dendritic PARACEST contrast agents for magnetic resonance imaging. Contrast Media Mol. Imaging 2:229-39
65. 3+ complexes for sensing glucose by MRI. Bioconjug. Chem. 15:1431-40
66. Zhang S, Trokowski R, Sherry AD. 2003. A paramagnetic CEST agent for imaging glucose by MRI. J. Am. Chem. Soc. 125:15288-89
67. Trokowski R, Ren JM, Kaiman FK, Sherry AD. 2005. Selective sensing of zinc ions with a PARACEST contrast agent. Angew. Chem. Int. Ed. 44:6920-23
68. - related to NMR imaging. Inorg. Chem. 32:3844-50
69. Ratnakar J, Woods M, Lubag AJM, Kovacs Z, Sherry AD. 2008. Modulation of water exchange in europium(III) DOTA-tetraamide complexes via electronic substituent effects. J. Am. Chem. Soc. 130:6-7
70. Aime S, Botta M, Fasano M, Crich SG, Terreno E. 1996. Gd(III) complexes as contrast agents for magnetic resonance imaging: a proton relaxation enhancement study of the interaction with human serum albumin. J. Biol. Inorg. Chem. 1:312-19
71. 17O NMR relaxometric investigations on two gadolinium(III) DTPA-like chelates endowed with high binding affinity to human serum albumin. J. Biol. Inorg. Chem. 4:766-74
72. 4; a novel angiographic MRI contrast agent. Org. Biomol. Chem. 1:1707-10
73. Ali M, Woods M, Suh E, Kovacs Z, Tircso G, et al. 2007. Albumin-binding PARACEST agents. J. Biol. Inorg. Chem. 12:855-65
74. Caravan P, Cloutier NJ, Greenfield MT, McDermid SA, Dunham SU, et al. 2002. The interaction of MS-325 with human serum albumin and its effect on proton relaxation rates. J. Am. Chem. Soc. 124:3152-62
75. Zech SG, Eldredge HB, Lowe MP, Caravan P. 2007. Protein binding to lanthanide(III) complexes can reduce the water exchange rate at the lanthanide. Inorg. Chem. 46:3576-84
76. Winter PM, Cai KJ, Chen J, Adair CR, Kiefer GE, et al. 2006. Targeted PARACEST nanoparticle contrast agent for the detection of fibrin. Magn. Reson. Med. 56:1384-88
77. 3-targeted nanoparticle and 1.5 Tesla magnetic resonance imaging. Cancer Res. 63:5838-43
78. Flacke S, Fischer S, Scott MJ, Fuhrhop RJ, Allen JS, et al. 2001. Novel MRI contrast agent for molecular imaging of fibrin implications for detecting vulnerable plaques. Circulation 104:1280-85
79. Adair C, Woods M, Zhao PY, Pasha A, Winters PM, et al. 2007. Spectral properties of a bifunctional PARACEST europium chelate: an intermediate for targeted imaging applications. Contrast Media Mol. Imaging 2:55-58
80. 3-targeted paramagnetic nanoparticles. Magn. Reson. Med. 53:621-27
81. Aime S, Castelli DD, Terreno E. 2005. Highly sensitive MRI chemical exchange saturation transfer agents using liposomes. Angew. Chem. Int. Ed. 44:5513-15
82. 1, susceptibility, and CEST agents, all in one. J. Am. Chem. Soc. 129:2430-31
83. Owing to the relative youth of this field of research, a wide range of background texts are not yet available. For more information, the reader may wish to consult Modo MJM & Bulte JWM. 2007. Molecular and Cellular MR Imaging. Boca Raton, FL: CRC Press