PARACEST Agents: Modulating MRI Contrast via Water Proton Exchange

Accounts of Chemical Research

Volumn 36, Issue 10, 2003, Pages 783-790

  Zhang, Shanrong ^a,b   Merritt, Matthew ^b   Woessner, Donald E ^b   Lenkinski, Robert E ^c   Sherry, A Dean ^a,b  

^a UNIVERSITY OF TEXAS AT DALLAS   (United States)

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

^c HARVARD MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONTRAST MEDIUM; GADOLINIUM; LANTHANIDE; PROTON; WATER;

ARTICLE; BINDING AFFINITY; CHEMICAL BINDING; CHEMISTRY; CONTRAST ENHANCEMENT; COORDINATION; ELECTRON SPIN RESONANCE; IMAGE ANALYSIS; NUCLEAR MAGNETIC RESONANCE IMAGING; SIGNAL TRANSDUCTION;

CHELATING AGENTS; CONTRAST MEDIA; GADOLINIUM; HETEROCYCLIC COMPOUNDS, 1-RING; LANTHANOID SERIES ELEMENTS; LANTHANUM; LIGANDS; MAGNETIC RESONANCE IMAGING; MODELS, THEORETICAL; MOLECULAR STRUCTURE; PROTONS; WATER;

EID: 0142213268     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar020228m     Document Type: Article

References (53)

1. Merbach, A. E.; Toth, E. The Chemistry of Contrast Agents in Medical MRI; Wiley: Chichester, 2001.
2. Lauffer, R. B. Paramagnetic metal complexes as water proton relaxation agents for NMR imaging: theory and design. Chem. Rev. 1987, 87, 901-927.
3. Caravan, P.; Ellison, J. J.; McMurray, T. J.; Lauffer, R. B. Gadolinium(III) Chelates as MRI Contrast Agents: Structure, Dynamics, and Applications. Chem. Rev. 1999, 99, 2293-2352.
4. Peters, J. A.; Huskens, J.; Raber, D. J. Lanthanide Induced shifts and relaxation rate enhancements. Prog. NMR Spectrosc. 1996, 28, 283-350.
5. Springer, C. S., Jr. Measurement of metal cation compartmentalization in tissue by high-resolution metal cation NMR. Annu. Rev. Biophys. Biophys. Chem. 1987, 16, 375-399.
6. Bansal, N.; Germann, M. J.; Seshan, V.; Shires, G. T., III; Malloy, C. R.; Sherry, A. D. Thulium 1,4,7,10-tetraazacyclododecane- 1,4,7,10-tetrakis(methylene phosphonate) as a sodium-23 shift reagent for the in vivo rat liver. Biochemistry 1993, 32, 5638-5643.
7. Aime, S.; Barge, A.; Botta, M.; De Sousa, A. S.; Parker, D. 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. Engl. 1998, 37, 2673-2675.
8. Aime, S.; Barge, A.; Bruce, J. I.; Botta, M.; Howard, J. A. K.; Moloney, J. M.; Parker, D.; de Sousa, A. S.; Woods, M. NMR, Relaxometric, and Structural Studies of the Hydration and Exchange Dynamics of Cationic Lanthanide Complexes of Macrocyclic Tetraamide Ligands. J. Am. Chem. Soc. 1999, 121, 5762-5771.
9. Batsanov, A. S.; Beeby, A.; Bruce, J. I.; Howard, J. A. K.; Kenwright, A. M.; Parker, D. Direct NMR and luminescence observation of water exchange at cationic ytterbium and europium centres. Chem. Commun. 1999, 1011-1012.
10. 13+: A Direct Access to Water Exchange and its Role in the Isomerization. J. Am. Chem. Soc. 2000, 122, 1506-1512.
11. 17O NMR Detection of a Lanthanide-Bound Water Molecule at Ambient Temperatures in Pure Water as Solvent. Inorg. Chem. 2001, 40, 4284-4290.
12. 3+ complexes with slowly exchanging bound-water molecules may offer advantages in the design of responsive MR agents. Invest. Radiol. 2001, 36, 82-86.
13. Dunand, F. A.; Dickins, R. S.; Parker, D.; Merbach, A. E. Towards rational design of fast water-exchanging Gd(dota-like) contrast agents? importance of the M/m ratio. Chem. Eur. J. 2001, 7, 5160-5167.
14. Zhang, S.; Wu, K.; Sherry, A. D. Unusually sharp dependence of water exchange rate versus lanthanide ionic radii for a series of tatra-amide complexes. J. Am. Chem. Soc 2002, 124, 4226-4227.
15. Aime, S.; Barge, A.; Batsanov, A. S.; Botta, M.; Castelli, D. D.; Fedeli, F.; Mortillaro, A.; Parker, D.; Puschmann, H. Controlling the variation of axial water exchange rates in macrocyclic lanthanide(III) complexes. Chem. Commun. 2002, 1120-1121.
16. Zhang, S.; Winter, P.; Wu, K.; Sherry, A. D. A Novel Europium(III)-Based MRI Contrast Agent. J. Am. Chem. Soc. 2001, 123, 1517-1518.
17. Wolf, S. D.; Balaban, R. S. Magnetization transfer contrast (MTC) and tissue water proton relaxation in vivo. Magn. Reson. Med. 1989, 10, 135-144.
18. Henkelman, R. M.; Stanisz, G. J.; Graham, S. J. Magnetization transfer in MRI: A review. NMR Biomed. 2001, 14, 57-64.
19. Ward, K. M.; Aletras, A. H.; Balaban, R. S. A New Class of Contrast Agents for MRI Based on Proton Chemical Exchange Dependent Saturation Transfer (CEST). J. Magn. Reson. 2000, 143, 79-87.
20. Sherry, A. D.; Zhang, S.; Wu, K. Paramagnetic metal ion-based macrocyclic magnetization transfer contrast agents and method of use. PCT Int. Appl. WO 0243775, 2002.
21. 2O)]-related to NMR imaging. Inorg. Chem. 1993, 32, 3844-3850.
22. 17O NMR and EPR at several magnetic fields. J. Alloys Compd. 1994, 207-208, 20-4.
23. Cossy, C.; Helm, L.; Merbach, A. E. Water exchange kinetics on lanthanide(III) ions: a variable temperature and pressure oxygen-17 NMR study. Inorg. Chim. Acta 1987, 139, 147-149.
24. Cossy, C.; Helm, L.; Merbach, A. E. Oxygen-17 nuclear magnetic resonance kinetic study of water exchange on the lanthanide(III) aqua ions. Inorg. Chem. 1988, 27, 1973-1979.
25. - in aqueous solution: a variable-pressure, -temperature and -magnetic field oxygen-17 NMR study. Magn. Reson. Chem. 1993, 31, 1011-1020.
26. Aime, S.; Botta, M.; Fasano, M.; Paoletti, S.; Anelli, P. L.; Uggeri, F. ; Virtuani, M. NMR Evidence of a Long Exchange Lifetime for the Coordinated Water in Ln(III)-Bis(methyl amide)-DTPA Complexes (Ln = Gd, Dy). Inorg. Chem. 1994, 33, 4707-4711.
27. 2O)] Complexes along the Lanthanide(III) Series. Inorg. Chem. 1995, 34, 4447-4453.
28. 3+ macrocyclic complex. J. Am. Chem. Soc. 1997, 119, 4767-4768.
29. 1H-NMR Spectroscopy. Inorg. Chem. 1997, 36, 2059-2068.
30. Zhang, S.; Kovacs, Z.; Burgess, S.; Aime, S.; Terreno, E.; Sherry, A. D. {DOTA-bis(amide)} Lanthanide Complexes: NMR Evidence for Differences in Water-molecule Exchange Rates for Coordination Isomers. Chem. Eur. J. 2001, 7, 288-296.
31. Zhang, S.; Sherry, A. D. Paramagnetic CEST Agents: NH versus OH. Int. Soc. Magn. Reson. Med. 2002, 10, 2590.
32. Aime, S.; Botta, M.; Fasano, M.; Terreno, E. Prototropic and Water-Exchange Processes in Aqueous Solutions of Gd(III) Chelates. Acc. Chem. Res. 1999, 32, 941-949.
33. Zhang, S.; Wu, K.; Sherry, A. D. A novel pH-sensitive MRI contrast agent. Angew. Chem., Int. Ed. Engl. 1999, 38, 3192-3194.
34. Raghunand, N.; Howison, C.; Sherry, A. D.; Zhang, S.; Gillies, R. J. Renal and Systemic pH imaging by Contrast-enhanced MRI. Magn. Reson. Med. 2003, 49, 249-257.
35. McConnell, H. M. Reaction Rates by Nuclear Magnetic Resonance. J. Chem. Phys. 1958, 28, 430-431.
36. Woessner, D. E. Nuclear Transfer Effects in Nuclear Magnetic Resonance Pulse Experiments. J. Chem. Phys. 1961, 35, 41-48.
37. Grad, J.; Bryant, R. G. Nuclear magnetic cross-relaxation spectroscopy. J. Magn. Reson. 1990, 90, 1-8.
38. Zhang, S.; Sherry, A. D. Physical characteristics of lanthanide complexes that act as magnetization transfer (MT) contrast agents. J. Solid State Chem. 2003, 171, 38-43.
39. 1 agents. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 8443-8448.
40. Lauffer, R. B.; Betteridge, D. R.; Padmanabhan, S.; Brady, T. J. Albumin binding of paramagnetic hepatobiliary contrast agents: enhancement of outer sphere relaxivity. Nucl. Med. Biol. 1988, 15, 45-46.
41. Toth, E.; Van Uffelen, I.; Helm, L.; Merbach, A. E.; Ladd, D.; Briley-Saebo, K.; Kellar, K. E. Gadolinium-based linear polymer with temperature-independent proton relaxivities: a unique interplay between the water exchange and rotational contributions. Magn. Reson. Chem. 1998, 36, S125-S134.
42. Bogdanov, A.; Matuszewski, L.; Bremer, C.; Petrovsky, A.; Weissleder, R. Oligomerization of Paramagnetic Substrates Results in Signal Amplification and Can Be Used for MR Imaging of Molecular Targets. Mol. Imaging 2001, 1, 1-9.
43. Goffeney, N.; Bulte, J. W. M.; Duyn, J.; Bryant, L. H.; van Zijl, P. C. M. Sensitive NMR detection of cationic-polymer-based gene delivery systems using saturation transfer via proton exchange. J. Am. Chem. Soc. 2001, 123, 8628-8629.
44. Ward, K. M.; Balaban, R. S. Determination of pH using water protons and chemical exchange dependent saturation transfer (CEST). Magn. Reson. Med. 2000, 44, 799-802.
45. Aime, S.; Barge, A.; Castelli, D. D.; Fedeli, F.; Mortrillaro, A.; Nielsen, F. U.; Terreno, E. Paramagnetic Lanthanide(III) complexes as pH-sensitive chemical exchange saturation transfer (CEST) contrast agents for MRI apllication. Magn. Reson. Med. 2002, 47, 639-648.
46. Aime, S.; Castelli, D. D.; Terreno, E. Novel pH-reporter MRI contrast agents. Angew. Chem., Int. Ed. 2002, 41, 4334-4336.
47. Zhang, S.; Michaudet, L.; Burgess, S.; Sherry, A. D. 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. 2002, 41, 1919-1921.
48. Aime, S.; Delli Castelli, D.; Fedeli, F.; Terreno, E. A Paramagnetic MRI-CEST Agent Responsive to Lactate Concentration. J. Am. Chem. Soc. 2002, 124, 9364-9365.
49. Louie, A. Y.; Huber, M. M.; Ahrens, E. T.; Rothbacher, U.; Moats, R.; Jacobs, R. E.; Fraser, S. E.; Meade, T. J. In vivo visualization of gene expression using magnetic resonance imaging. Nat. Biotechnol. 2000, 18, 321-325.
50. Lowe, M. P.; Parker, D.; Reany, O.; Aime, S.; Botta, M.; Castellano, G.; Gianolio, E.; Pagliarin, R. pH-Dependent Modulation of Relaxivity and Luminescence in Macrocyclic Gadolinium and Europium Complexes Based on Reversible Intramolecular Sulfonamide Ligation. J. Am. Chem. Soc. 2001, 123, 7601-7609.
51. Li, W.-h.; Fraser, S. E.; Meade, T. J. A Calcium-Sensitive Magnetic Resonance Imaging Contrast Agent. J. Am. Chem. Soc. 1999, 121, 1413-1414.
52. Hanaoka, K.; Kikuchi, K.; Urano, Y.; Nagano, T. Selective sensing of zinc ions with a novel magnetic resonance imaging contrast agent. J. Chem. Soc., Perkin Trans. 22001, 1840-1843.
53. Peters, J. A.; Frullano, L.; Rohovec, J. Sugar-targeted contrast agents for MRI. J. Inorg. Biochem. 2001, 86, 85-85.