Protein-targeted gadolinium-based magnetic resonance imaging (MRI) contrast agents: Design and mechanism of action

Accounts of Chemical Research

Volumn 42, Issue 7, 2009, Pages 851-862

  Caravan, Peter ^a  

^a MASSACHUSETTS GENERAL HOSPITAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHELATING AGENT; CONTRAST MEDIUM; GADOFOSVESET; GADOLINIUM; ORGANOMETALLIC COMPOUND; SERUM ALBUMIN;

ARTICLE; CHEMISTRY; DRUG DESIGN; HUMAN; METABOLISM; NUCLEAR MAGNETIC RESONANCE IMAGING; PROTEIN BINDING;

CHELATING AGENTS; CONTRAST MEDIA; DRUG DESIGN; GADOLINIUM; HUMANS; MAGNETIC RESONANCE IMAGING; ORGANOMETALLIC COMPOUNDS; PROTEIN BINDING; SERUM ALBUMIN;

EID: 67651098771     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar800220p     Document Type: Article

References (45)

1. Werner, E. J.; Avedano, S.; Botta, M.; Hay, B. P.; Moore, E. G.; Aime, S.; Raymond, K. N. Highly soluble tris-hydroxypyridonate Gd(III) complexes with increased hydration number, fast water exchange, slow electronic relaxation, and high relaxivity. J. Am. Chem. Soc. 2007, 129, 1870-1871. (Pubitemid 46318242)
2. Gianolio, E.; Giovenzana, G. B.; Longo, D.; Longo, I.; Menegotto, I.; Aime, S. Relaxometric and modelling studies of the binding of a lipophilic Gd-AAZTA complex to fatted and defatted human serum albumin. Chem.sEur. J. 2007, 13, 5785-5797. (Pubitemid 47117400)
3. Lauffer, R. B.; Parmelee, D. J.; Dunham, S. U.; Ouellet, H. S.; Dolan, R. P.; Witte, S.; McMurry, T. J.; Walovitch, R. C. MS-325: Albumin-targeted contrast agent for MR angiography. Radiology 1998, 207, 529-538. (Pubitemid 28259074)
4. McMurry, T. J.; Parmelee, 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.; Lauffer, R. B. The effect of a phosphodiester linking group on albumin binding, blood half-life, and relaxivity of intravascular diethylenetriaminepentaacetato aquo gadolinium(III) MRI contrast agents. J. Med. Chem. 2002, 45, 3465-3474. (Pubitemid 34824034)
5. 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.; Lauffer, R. B. The interaction of MS-325 with human serum albumin and its effect on proton relaxation rates. J. Am. Chem. Soc. 2002, 124, 3152-3162. (Pubitemid 34249987)
6. Bosch, E.; Kreitner, K. F.; Peirano, M. F.; Thurner, S.; Shamsi, K.; Parsons, E. C. Safety and efficacy of gadofosveset-enhanced MR angiography for evaluation of pedal arterial disease: Multicenter comparative phase 3 study. Am. J. Roentgenol. 2008, 190, 179-186. (Pubitemid 351179949)
7. Idee, J. M.; Port, M.; Medina, C.; Lancelot, E.; Fayoux, E.; Ballet, S.; Corot, C. Possible involvement of gadolinium chelates in the pathophysiology of nephrogenic systemic fibrosis: A critical review. Toxicology 2008, 248, 77-88.
8. Lauffer, R. B. Targeted relaxation enhancement agents for MRI. Magn. Reson. Med. 1991, 22, 339.
9. Andergg, G.; Arnaud-Neu, F.; Delgado, R.; Felcman, J.; Popov, K. Critical evaluation of stability constants of metal complexes of complexones for biomedical and environmental applications. Pure Appl. Chem. 2005, 77, 1445-1495. (Pubitemid 41296278)
10. Caravan, P.; Comuzzi, C.; Crooks, W.; McMurry, T. J.; Choppin, G. R.; Woulfe, S. R. Thermodynamic stability and kinetic inertness of MS-325, a new blood pool agent for magnetic resonance imaging. Inorg. Chem. 2001, 40, 2170-2176. (Pubitemid 32884501)
11. Laurent, S.; Elst, L. V.; Copoix, F.; Muller, R. N. Stability of MRI paramagnetic contrast media: A proton relaxometric protocol for transmetallation assessment. Invest. Radiol. 2001, 36, 115-122. (Pubitemid 32147859)
12. Tyeklar, Z.; Dunham, S. U.; Midelfort, K.; Scott, D. M.; Sajiki, H.; Ong, K.; Lauffer, R. B.; Caravan, P.; McMurry, T. J. Structural, kinetic, and thermodynamic characterization of the interconverting isomers of MS-325, a gadolinium(III)-based magnetic resonance angiography contrast agent. Inorg. Chem. 2007, 46, 6621-6631.
13. Peters, T. J. All About Albumin: Biochemistry, Genetics, and Medical Applications; Academic Press: San Diego, CA, 1996.
14. Caravan, P.; Parigi, G.; Chasse, J. M.; Cloutier, N. J.; Ellison, J. J.; Lauffer, R. B.; Luchinat, C.; McDermid, S. A.; Spiller, M.; McMurry, T. J. Albumin binding, relaxivity, and water exchange kinetics of the diastereoisomers of MS-325, a gadolinium(III)-based magnetic resonance angiography contrast agent. Inorg. Chem. 2007, 46, 6632-6639.
15. Eldredge, H. B.; Spiller, M.; Chasse, J. M.; Greenwood, M. T.; Caravan, P. Species dependence on plasma protein binding and relaxivity of the gadolinium-based MRI contrast agent MS-325. Invest. Radiol. 2006, 41, 229-243. (Pubitemid 44406183)
16. Bloembergen, N.; Morgan, L. O. Proton relaxation times in paramagnetic solutions. Effects of electron spin relaxation. J. Chem. Phys. 1961, 34, 842-850.
17. Solomon, I. Relaxation processes in a system of two spins. Phys. Rev. 1955, 99, 559-565.
18. 3+ complexes in glassy solutions. Appl. Magn. Reson. 2005, 28, 281-295. (Pubitemid 41301754)
19. 3+ complex of a fatty acid analogue of DOTP binds to multiple albumin sites with variable water relaxivities. Inorg. Chem. 2001, 40, 6580-6587. (Pubitemid 33140279)
20. Muller, R. N.; Radü chel, B.; Laurent, S.; Platzek, J.; Pié rart, C.; Mareski, P.; Vander Elst, L. Physicochemical characterization of MS-325, a new gadolinium complex, by multinuclear relaxometry. Eur. J. Inorg. Chem. 1999, 1949-1955.
21. Vander Elst, L.; Maton, F.; Laurent, S.; Seghi, F.; Chapelle, F.; Muller, R. N. A multinuclear MR study of Gd-EOB-DTPA: Comprehensive preclinical characterization of an organ specific MRI contrast agent. Magn. Reson. Med. 1997, 38, 604-614. (Pubitemid 27419225)
22. Caravan, P.; Ellison, J. J.; McMurry, T. J.; Lauffer, R. B. Gadolinium(III) chelates as MRI contrast agents: Structure, dynamics, and applications. Chem. Rev. 1999, 99, 2293-2352. (Pubitemid 30498114)
23. Caravan, P.; Astashkin, A. V.; Raitsimring, A. M. The gadolinium(III)-water hydrogen distance in MRI contrast agents. Inorg. Chem. 2003, 42, 3972-3974. (Pubitemid 37296984)
24. 3+ complexes in orientationally disordered systems. J. Phys. Chem. A 2004, 108, 1900-2001.
25. Zech, S.; Sun, W.-C.; Jacques, V.; Caravan, P.; Astashkin, A. V.; Raitsimring, A. M. Probing the water coordination of protein-targeted MRI contrast agents by pulsed ENDOR spectroscopy. ChemPhysChem 2005, 6, 2570-2577.
26. Raitsimring, A. M.; Astashkin, A. V.; Baute, D.; Goldfarb, D.; Caravan, P. W-band 17O pulsed electron nuclear double resonance study of gadolinium complexes with water. J. Phys. Chem. A 2004, 108, 7318-7323.
27. Cossy, C.; Helm, L.; Powell, D. H.; Merbach, A. E. A change in coordination number from nine to eight along the lanthanide(III) aqua ion series in solution: A neutron diffraction study. New J. Chem. 1995, 19, 27-35.
28. Horrocks, W. D., Jr.; Sudnick, D. R. Lanthanide ion probes of structure in biology. Laser-induced luminescence decay constants provide a direct measure of the number of metal-coordinated water molecules. J. Am. Chem. Soc. 1979, 101, 334-340.
29. 17O ENDOR spectroscopy. ChemPhysChem 2006, 7, 1590-1597.
30. Helm, L.; Merbach, A. E. Water exchange on metal ions: Experiments and simulations. Coord. Chem. Rev. 1999, 187, 151-181.
31. 3+ complexes with slowly exchanging boundwater molecules may offer advantages in the design of responsive MR agents. Invest. Radiol. 2001, 36, 82-86. (Pubitemid 32147854)
32. Caravan, P.; Amedio, J. C.; Dunham, S. U.; Greenfield, M. T.; Cloutier, N. J.; McDermid, S. A.; Spiller, M.; Zech, S. G.; Looby, R. J.; Raitsimring, A. M.; McMurry, T. J.; Lauffer, R. B. When are two waters worse than one? Doubling the hydration number of a Gd-DTPA derivative decreases relaxivity. Chem. Eur. J. 2005, 11, 5866-5874. (Pubitemid 41454685)
33. Livramento, J. B.; Helm, L.; Sour, A.; O'Neil, C.; Merbach, A. E.; Toth, E. A benzene-core trinuclear GdIII complex: Towards the optimization of relaxivity for MRI contrast agent applications at high magnetic field. Dalton Trans. 2008, 1195-1202. (Pubitemid 351264707)
34. Bertini, I.; Kowalewski, J.; Luchinat, C.; Nilsson, T.; Parigi, G. Nuclear spin relaxation in paramagnetic complexes of S ) 1: Electron spin relaxation effects. J. Chem. Phys. 1999, 111, 5795-5807. (Pubitemid 129589851)
35. Dunand, F. A.; Borel, A.; Merbach, A. E. How does internal motion influence the relaxation of the water protons in LnIIIDOTA-like complexes. J. Am. Chem. Soc. 2002, 124, 710-716. (Pubitemid 34101178)
36. Chen, J. W.; Auteri, F. P.; Budil, D. E.; Belford, R. L.; Clarkson, R. B. Use of EPR to investigate rotational dynamics of paramagnetic contrast agents. J. Phys. Chem. 1994, 98, 13452-13459.
37. Zech, S. G.; Eldredge, H. B.; Lowe, M. P.; Caravan, P. Protein binding to lanthanide(III) complexes can reduce the water exchange rate at the lanthanide. Inorg. Chem. 2007, 46, 3576-3584.
38. Caravan, P.; Greenfield, M. T.; Bulte, J. W. Molecular factors that determine Curie spin relaxation in dysprosium complexes. Magn. Reson. Med. 2001, 46, 917-922. (Pubitemid 33019915)
39. Dumas, S.; Troughton, J. S.; Cloutier, N. J.; Chasse, J. M.; McMurry, T. J.; Caravan, P. A high relaxivity magnetic resonance imaging contrast agent targeted to serum albumin. Aust. J. Chem. 2008, 61, 682-686.
40. Baranyai, Z.; Gianolio, E.; Ramalingam, K.; Swenson, R.; Ranganathan, R.; Brucher, E.; Aime, S. The effects of intramolecular H-bond formation on the stability constant and water exchange rate of the Gd(III)-diethylenetriamine- N′-(3-amino-1,1-propylenephosphonic)-N,N,N′,N'-tetraacetate complex. Contrast Media Mol. Imaging 2007, 2, 94-102. (Pubitemid 46863626)
41. Caravan, P.; Das, B.; Dumas, S.; Epstein, F. H.; Helm, P. A.; Jacques, V.; Koerner, S.; Kolodziej, A.; Shen, L.; Sun, W. C.; Zhang, Z. Collagen-targeted MRI contrast agent for molecular imaging of fibrosis. Angew. Chem., Int. Ed. 2007, 46, 8171-8173. (Pubitemid 350096590)
42. Helm, P. A.; Caravan, P.; French, B. A.; Jacques, V.; Shen, L.; Xu, Y.; Beyers, R. J.; Roy, R. J.; Kramer, C. M.; Epstein, F. H. Postinfarction myocardial scarring in mice: Molecular MR imaging with use of a collagen-targeting contrast agent. Radiology 2008, 247, 788-796.
43. Nair, S.; Kolodziej, A. F.; Bhole, G.; Greenfield, M. T.; McMurry, T. J.; Caravan, P. Monovalent and bivalent fibrin-specific MRI contrast agents for detection of thrombus. Angew. Chem., Int. Ed. 2008, 47, 4918-4921.
44. Overoye-Chan, K.; Koerner, S.; Looby, R. J.; Kolodziej, A. F.; Zech, S. G.; Deng, Q.; Chasse, J. M.; McMurry, T. J.; Caravan, P. EP-2104R: A fibrin-specific gadoliniumbased MRI contrast agent for detection of thrombus. J. Am. Chem. Soc. 2008, 130, 6025-6039. (Pubitemid 351620850)
45. Zhang, Z.; Greenfield, M. T.; Spiller, M.; McMurry, T. J.; Lauffer, R. B.; Caravan, P. Multilocus binding increases the relaxivity of protein-bound MRI contrast agents. Angew. Chem., Int. Ed. 2005, 44, 6766-6769. (Pubitemid 41532232)