Optimization of gadolinium-based MRI contrast agents for high magnetic-field applications

Future Medicinal Chemistry

Volumn 2, Issue 3, 2010, Pages 385-396

  Helm, Lothar ^a  

^a EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

GADOBENATE DIMEGLUMINE; GADOBUTROL; GADODIAMIDE; GADOFOSVESET; GADOLINIUM; GADOLINIUM PENTETATE; GADOTERATE MEGLUMINE; GADOTERIDOL; GADOVERSETAMIDE; GADOXETIC ACID;

COMPLEX FORMATION; CONTRAST ENHANCEMENT; ELECTRON SPIN RESONANCE; MAGNETIC FIELD; MAGNETIC RESONANCE ANGIOGRAPHY; MATHEMATICAL MODEL; NUCLEAR MAGNETIC RESONANCE IMAGING; PRIORITY JOURNAL; REVIEW; SENSITIVITY ANALYSIS;

ANIMALS; CONTRAST MEDIA; GADOLINIUM; MAGNETIC RESONANCE IMAGING; MAGNETICS; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 77953446479     PISSN: 17568919     EISSN: None     Source Type: Journal    
DOI: 10.4155/fmc.09.174     Document Type: Review

References (67)

1. Ugurbil K, Adriany G, Andersen P et al. Ultrahigh field magnetic resonance imaging and spectroscopy Magn. Reson. Imag.21, 1263-1281 (2003).
2. Schick F. Whole-body MRI at high field: technical limits and clinical potential. Eur. Radiol. 15, 946-959 (2005).
3. Vaughan T, Delabarre L, Snyder C et al. 9.4 T human MRI: preliminary results. Mag. Reson. Med. 56, 1274-1282 (2006).
4. Schild T, Aubert G, Berriaud C et al. The iseult/inumac whole body 11.7 T MRI magnet design. IEEE Trans. Appl. Supercon. 18(2), 904-907 (2008).
5. Trattnig S, Pinker K, Ba-Ssalamah A, Nöbauer-Huhmann I-M. The otimal use of contrast agents at high field MRL Eur. Radiol. 16, 1280-1287(2006).
6. Caravan P. Physicochemical principles of MR contrast agents. In: Molecular and Cellular MR Imaging, Modo MMJ, Bulte JWM (Eds). CRC Press LLC, Boca Raton, FL, USA, 13-26 (2007).
7. Geraldes CFGC, Laurent S. Classification and basic properties of contrast agents for magnetic resonance imaging. Contrast Media Mol. Imaging4(1), 1-23 (2009).
8. Qin J, Laurent S, Jo YS et al. A highperformance magnetic resonance imaging T2 contrast agent. Adv. Mat. 19(14), 1874-1878 (2007).
9. Bellin M-F. MR contrast: agents, the old and the new, Eur. J. Radiol. 60, 314-323 (2006).
10. Airne S, Barge A, Cabella C, Geninatti Crich S, Gianolio E. Targeting cells with mr imaging probes based on paramagnetic Gd(III) chelates Curr. Pharmaceut. Biotech. 5, 509-518 (2004).
11. Wolf M, Hull WE, Miier W et al. Polyamine-substituted Polyamine-substituted gadolinium, chelates: a new class of intracellular contrast agents for magnetic resonance imaging of tumors. J. Med. Chem. 50(1), 139-148 (2007).
12. Mierbach AE, Tóth É (Eds). The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging. John Wiley & Sons Ltd, Chichester, UK (2001).
13. Botta M. Second coordination sphere water molecules and relaxivity of gadolinium(III), Eur. J. Inorg. Chem. 399-407 (2000).
14. 1 contrast agents. Contrast Med. Mol. Imaging4(2), 89-100 (2009).
15. Solomon I. Relaxation processes in a system of two spins. Phys. Rev. 99(2), 559-565 (1955).
16. Bloembergen N. Proton relaxation times in paramagnetic solutions. J. Chem. Phys. 27, 572-573 (1957).
17. Bloembergen N, Morgan LO. Proton relaxation times in paramagnetic solutions. Effects of electron spin relaxation. J. Chem. Phys. 34, 842-850 (1961).
18. Kowalewski J, Nordenskiöld L, Benetis N, Westlund P. Theory of nuclear spin relaxation in paramagnetic systems in solution, Prog. NMR Spectrosc. 17, 141-185 (1985).
19. Kowalewski J. Paramagnetic relaxation in solution. In: Encyclopedia of Nuclear Magnetic Resonance. Grant DM.Harris RK (Eds). John Wiley & Sons, Chichester, UK, 3456-3462 (1996).
20. Kowalewski J, Kruk D, Parigi G. NMR relaxation in solution of paramagnetic complexes: recent theoretical progress for S≥1. In: Advances in Inorganic Chemistry, Van Eldik R, Bertini I (Eds). Elsevier, San Diego, USA, 42-104(2005).
21. Belorizky E, Fries Ph, Helm L et al. Comparison of different methods for calculating the paramagnetic relaxation enhancement of nuclear spins as a function of the magnetic field. J. Chem. Phys. 128(5), 052307 (2008).
22. Fries Ph, Belorizky E. Electronic relaxation of paramagnetic metal ions and. NMR relaxivity in solution: critical analysis of various approaches and application to a Gd(III)-based contrast agent. J. Chem. Phys. 123(12), 124510-124515 (2005).
23. Hermann P, Kotek J, KubicekV, Lukes I. Gadolinium(III) complexes as MRI contrast agents: ligand design arid properties of the complexes. Dalton Trans. 30, 27-47 (2008).
24. Bertini I, Luchinat C, Parigi G. Solution NMR of Paramagnetic Molecules. Elsevier, Amsterdam, The Netherlands, 2, (2001).
25. Hwang LP, Freed JH. Dynamic effects of pair correlation functions on spin relaxation by translational diffusion in liquids. J. Chem. Phys. 63, 4017-4025 (1975).
26. 1 processes, J. Chem. Phys. 69, 4034-4037 (1978).
27. Ayant Y, Belorizky E, Alizon J, Gallice J. Calculation of the spectral densities for relaxation resulting from random translational motion by magnetic dipolar coupling in liquids, J. Physique36, 991-1004 (1975).
28. Port M, Idée JM, Medina C, Robic C, Sabatou M, Corot C. Efficiency, thermodynamic and kinetic stability of marketed, gadolinium, chelates and their possible clinical consequences: a critical review Biometals 21(4), 469-490 (2008).
29. Caravan P, Cloutier NJ, Greenfield MT et al. The interaction of MS-325 with human serum albumin and its effect on proton relaxation rates. J. Am. Chem. Soc. 124(12), 3152-3162 (2002).
30. Brücher E, Sherry AD. Stability and toxicity of contrast agents. In: The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging, Merbach AE, Tóth É (Eds). John Wiley & Sons Ltd, Chichester, UK, 243-279 (2001).
31. Aime S, Calabi L, Cavallotti C. et al. [Gd-AAZTA]: a new structural entry for an improved generation of MRI contrast agents. Inorg. Chem. 43, 7588-7590 (2004).
32. Baranyai Z, Uggeri F, Giovenzana GB, Benyei A, Brucher E, Aime S. Equilibrium and kinetic properties of the lanthanoids (III) and various divalent metal complexes of the heptadentate ligand. AAZTA. Chem. Eur. J 15(7), 1696-1705 (2009).
33. Sengar RS, Nigam A, Geib SJ, Wiener EC. Syntheses and crystal, structures of gadolinium and europium complexes of AAZTA analogues. Polyhedron 28(8), 1525-1531 (2009).
34. Xu J, Franklin SJ, Whisenhunt DW, Raymond KN. Gadolinium complex of tris [ (3 -hydroxy-1 -methyl-2 -oxo-1,2didehydropyridine-4-carboxamido)ethyl] amine: a new class of gadolinium magnetic resonance relaxation agents, J. Am. Chem. Soc. 117,7245-7246(1995).
35. Hajela S, Botta M, Giraudo S, Xu J, Raymond KN, Aime S. A tris-hydroxyrnethylsubstituted derivative of Gd-TREN-MiE-3, 2HOPO: an MRI relaxation agent with improved efficiency. J.Am. Chem. Soc. 122(45), 11228-11229(2000).
36. Pierre VC, Botta M, Aime S, Raymond KN. Tuning the coordination number of hydroxy pyridonate-based gadolinium complexes: implications for MRI contrast agents. J. Am. Chem. Soc. 128(16), 5344-5345 (2006).
37. Matsuura N, Rowlands JA. Towards new functional nanostructures for medical imaging. Med, Phys. 35(10), 4474-4487 (2008).
38. 1 agent is substantially reduced, when targeted to a protein microdomain. Magn. Reson. Imag. 26(5), 608-617 (2008).
39. Helm. L, Merbach AE. Inorganic and. bioinorganic solvent exchange mechanisms. Chem. Rev. 105(6), 1923-1960 (2005).
40. Borel A, Bean JF, Clarkson RB et al. Towards the rational design of mri contrast agents: electron spin relaxation is largely unaffected by the coordination geometry of gadolinium(III)-DOTA-type complexes, Chem. Eur. J. 14(9), 2658-2667 (2008).
41. Benmelouka M, Borel A, Moriggi L, Helm L, Merbach AE. Design of Gd(III)-based magnetic resonance imaging contrast agents: static and transient zero-field splitting contributions to the electronic relaxation and their impact on relaxivity. J. Phys. Chem. B 111(4), 832-840 (2007).
42. 3+ polyamino polypyridine carboxylate complexes: a study of high field effects. J. Phys. Chem. A 111(25), 5399-5407 (2007).
43. Aime S, Terreno E, Botta M, Bruce JI, Parker D, Mainero V. Modulation of the water exchange rates in [Gd-D03A] complex by formation of ternary complexes with carboxylate ligands. Chem. Commun. 1, 115-116 (2001).
44. Terreno E, Botta M, Boniforte P et al. A multinuclear NMR relaxometry study of ternary adducts formed between heptadentate Gd(III) chelates and L-lactate. Chem, Eur. J 11(19), 5531-5537 (2005).
45. 2]-complex. Inorg. Chem, 47(18), 8357-8366 (2008).
46. Pierre VC, Botta M, Aime S, Raymond KN. Substituent effects on Gd(III)-based MRI contrast agents: optimizing the stability and selectivity of the complex and the number of coordinated water molecules. Inorg. Chem. 45(20), 8355-8364 (2006).
47. DattaA, Raymond KN: Gdhydroxypyridinone (HOPO)-based, high-relaxivity magnetic resonance imaging (MRI) contrast agents. Ace. Chem. Res. 938-947 (2009).
48. Thompson MK, Botta M, Nicolle GM et al. A highly stable gadolinium complex with a fast, associative mechanism of water exchange. J. Am. Chem. Soc. 125(47), 14274-14275 (2003).
49. Werner Ej, Avedano S, BottaM et al. Highly soluble tris-hydroxypyridonate Gd(III) complexes with increased hydration number, fast water exchange, slow electronic relaxation, and high relaxivity, J. Am. Chem. Soc. 129(7), 1870-1871 (2007).
50. 1H relaxivity. Dalton Trans. 12(28), 2088-2095 (2009).
51. 3+ ions. Chem. Eur. J 12(4), 989-1003 (2006).
52. Livramento JB, Tóth É, Sour A, Borel A, Merbach AE, Ruloff R. High relaxivity confined to a small molecular space: a metallostar-based, potential. MRI contrast agent. Angew. Chem. Int. Ed. 44, 1480-1481 (2005).
53. Livramento JB, Weideristeiner C, Prata MIM et al. First in vivo MRI assessment of a self-assembled metallostar compound endowed with a remarkable high field relaxivity, Contrast Med. Mol. Imaging 1(1), 30-39 (2006).
54. Livramento JB, Helm L, Sour A, O'Neil C, Merbach AE, Tóth É. A benzene-core trinuclear Gd(III) complex: towards the optimization of relaxivity for MRI contrast agent applications at high magnetic field. Dalton Trans. 1195-1202 (2008).
55. Loureiro DE Sousa P, Livramento JB, Helm L et al. In vivo MRI assessment of a novel Gd(III)-based contrast agent designed for high magnetic field applications. Contrast Med. Mol. Imaging3(2), 78-85 (2008).
56. Lipari G, Szabo A. Model-free approach to the interpretation of nuclear magnetic resonance relaxation in macromolecules. 1. Theory and range of validity. J. Am. Chem. Soc. 104, 4546-4559 (1982).
57. Lipari G, Szabo A. Model-free approach to the interpretation of nuclear magnetic resonance relaxation in macromolecules. 2. Analysis of exerimental results. J. Am. Chem. Soc. 104, 4559-4570 (1982).
58. Caravan P. Strategies for increasing the sensitivity of gadolinium based MRI contrast agents.. Chem. Soc. Rev. 35(6), 512-523 (2006).
59. Debouttiere P-J, Roux S, Vocanson F et al. Design of gold nanoparticles for magnetic resonance imaging. Adv. Funct. Mater. 16(18), 2330-2339 (2006).
60. Alric C, Taleb J, Le Duc G et al. Gadolinium chelate coated, gold, nanoparticles as contrast agents for both x-ray computed tomography and magnetic resonance imaging. J. Am. Chem. Soc. 130(18), 5908-5915 (2008).
61. Park J-A, Reddy Pan, Kim H-K et al. Gold nanoparticles functionalised by Gd-complex of DTPA-bis(amide) conjugate of glutathione as an MRI contrast agent, Bioorg. Med. Chem. Lett. 18, 6135-6137 (2008).
62. Moriggi. L, Cannizzo C., Dumas E, Mayer CR, Ulianov A, Helm L. Gold nanoparticles functionalized with gadolinium chelates as high-relaxivity MRI contrast agents. J. Am. Chem. Soc. 131, 10828-10829 (2009).
63. Aime S, Delli-Castelli D, Crich SG, Gianolio E, Terreno E. Pushing the sensitivity envelope of lanthanide-based magnetic resonance imaging (MRI) contrast agents for molecular imaging applications. Ace. Chem. Res. 42(7), 822-831 (2009).
64. Aime S, Frullano L, Crich SG. Compartmentalization of a gadolinium complex in the apoferritin: cavity: a route to obtain high relaxivity contrast agents for magnetic resonance imaging. Angew. Chem. Int. Ed. 41(6), 1017-1019 (2002).
65. Crich SG, Bussolati B, Tei L et al. Magnetic resonance visualization of tumor angiogenesis by targeting neural cell adhesion molecules with the highly sensitive gadolinium-loaded apoferritin probe. Cancer Res. 66(18), 9196-9201 (2006).
66. Sitharaman B, Kissell KR, Hartman KB et al. Superparamagnetic gadonanotubes are high-performance mri contrast agents. Chem. Commun. 31, 3915-3917 (2005).
67. Sitharaman B, Wilson LJ. Gadonanotubes as new high-performance MRI contrast agents. Int. J. Nanomedicine 1(3), 291-295 (2006).