Classification and basic properties of contrast agents for magnetic resonance imaging

Contrast Media and Molecular Imaging

Volumn 4, Issue 1, 2009, Pages 1-23

  Geraldes, Carlos F G C ^a   Laurent, Sophie ^b  

^a UNIVERSITY OF COIMBRA   (Portugal)

^b UNIVERSITY OF MONS   (Belgium)

Author keywords

Contrast agents; Lanthanide complexes; Magnetic resonance imaging

Indexed keywords

ALBUMIN; CHELATE; CONTRAST MEDIUM; ECHOVIST; FERRISELTZ; FERRISTENE; FERUCARBOTRAN; FERUMOXSIL; GADOBENATE DIMEGLUMINE; GADOBUTROL; GADODIAMIDE; GADOFLUORINE 8; GADOFOSVESET; GADOLINIUM CHLORIDE; GADOLINIUM PENTETATE; GADOMELITOL; GADOMER 17; GADOTERATE MEGLUMINE; GADOTERIDOL; GADOVERSETAMIDE; GADOXETIC ACID; IMAGENT GI; LIPOSOME; MANGAFODIPIR; MANGANESE CHLORIDE; PEG FERRON; PERFLEXANE; PERFLUOROOCTYL BROMIDE; PHENANTHROLINE DERIVATIVE; POLYMER; SUPERPARAMAGNETIC IRON OXIDE; ULTRASMALL SUPERPARAMAGNETIC IRON OXIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG; DIAGNOSTIC AGENT;

ALZHEIMER DISEASE; BONE MARROW; BRAIN DISEASE; CLINICAL TRIAL; DIAGNOSTIC ACCURACY; DIAGNOSTIC PROCEDURE; DRUG CLASSIFICATION; DRUG COATING; DRUG DISTRIBUTION; DRUG FORMULATION; DRUG SAFETY; DRUG STRUCTURE; DRUG TARGETING; ENZYME ACTIVITY; HUMAN; IMAGING SYSTEM; LIVER INJURY; LYMPH NODE; MAGNETIC RESONANCE ANGIOGRAPHY; MOLECULAR IMAGING; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; OXIDATION REDUCTION POTENTIAL; PH; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; RELAXATION TIME; REVIEW; TEMPERATURE; ANIMAL; CLASSIFICATION; METHODOLOGY;

ANIMALS; CONTRAST MEDIA; HUMANS; MAGNETIC RESONANCE IMAGING;

EID: 63449107568     PISSN: 15554309     EISSN: 15554317     Source Type: Journal    
DOI: 10.1002/cmmi.265     Document Type: Review

References (164)

1. Mansson S, Bjørnerud A. Physical principles of medical imaging by nuclear magnetic resonance. In The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging, Merbach AE, Tóth E (eds). Wiley: Chichester, 2001; 1-44.
2. Chan KW-Y, Wong W-T. Small molecular gadolinium(III) complexes as MRI contrast agents for diagnostic imaging. Coord. Chem. Rev. 2007; 251: 2428-2451.
3. Caravan P, Ellison JJ, McMurry TJ, Lauffer RB. Gadolinium(III) chelates as MRI contrast agents: structure, dynamics, and applications. Chem. Rev. 1999; 99: 2293-2352.
4. Laurent S, Vander Elst L, Muller RN. Comparative study of the physicochemical properties of six clinical low molecular weight gadolinium contrast agents. Contrast Med. Mol. Imag. 2006; 1(3): 128-137.
5. Toth E, Helm L, Merbach AE. Relaxivity of MRI contrast agents. Top. Curr. Chem. 2002; 221: 61-221.
6. Jacques V, Desreux JF. New classes of MRI contrast agents. Top. Curr. Chem. 2002; 221: 123-164.
7. Aime S, Botta M, Terreno E. Gd(III)-based contrast agents for MRI. Adv. Inorg. Chem. 2005; 57: 173-237.
8. Muller RN, Vander Elst L, Roch A, Peters JA, Csajbók E, Gillis P, Gossuin Y. Relaxation by metal-containing nanosystems. Adv. Inorg. Chem. 2005; 57: 239-292.
9. Aime S, Geninatti Crich S, Gianolio E, Giovenzana GB, Teia L, Terreno E. High sensitivity lanthanide(III) based probes for MR-medical imaging. Coord. Chem. Rev. 2006; 250: 1562-1579.
10. Yablonsky DA, Haacke EM. Theory of NMR signal behavior in magnetically inhomogeneous tissues. The static dephasing regime. Magn. Reson. Med. 1994; 32: 749-763.
11. Koenig SH, Brown RD. Field-cycling relaxometry of protein solutions and tissue: implication for MRI. Prog. Nucl. Magn. Reson. Spectr. 1990; 22: 487-567.
12. Banci L, Bertini I, Luchinat C. Nuclear and Electronic Relaxation. VCH: Weinheim, 1991.
13. Laurent S, Forge D, Port M, Roch A, Robic C, Vander Elst L, Muller RN. Magnetic iron oxide nanoparticles: synthesis, stabilization, vectorization, physico-chemical characterizations and biological applications. Chem. Rev. 2008; 108(6): 2064-2110.
14. Gueron M. Nuclear relaxation in macromolecules by paramagnetic ions: a novel mechanism. J. Magn. Reson. 1975; 19: 58-66.
15. Gillis P, Koenig SH. Transverse relaxation of solvent protons induced by magnetized spheres: application to ferritin, erythrocytes and magnetite. Magn. Reson. Med. 1987; 5: 323-345.
16. Freed JH. Dynamic effects of pair correlation functions on spin relaxation by translational diffusion in liquids. II. Finite jumps and independent T1 processes. J. Chem. Phys. 1978; 68: 4034-4037.
17. 2 NMRD profiles of solutions of magnetic nanoparticles. Magn. Reson. Med. 1995; 34: 227-233.
18. Roch A, Muller RN, Gillis P. Theory of proton relaxation induced by superparamagnetic particles. J. Chem. Phys. 1999; 110: 5403-5411.
19. Vogl TJ, Hammerstingl R, Schwarz W, Mack MG, Muller PK, Pegios W, Keck H, Eibl-Eibesfeldt A, Hoelzl J, Woessmer B, Bergman C, Felix R. Superparamagnetic iron oxide enhanced versus gadolinium-enhanced MR imaging for differential diagnosis of focal liver lesions. Radiology 1996; 198: 881-887.
20. Keller KE, Fujii DK, Gunther WHH, Briely-Sæbø K, Bjørnesud A, Spiller M, Koenig SH. NC100150 injection, a preparation o optimized iron oxide nanoparticles for positive-contrast MR angiography. J. Magn. Reson. Imag. 2000; 11: 488-494.
21. Ahlström KH, Johansson LO, Rodenburg JB, Ragnarsson AS, Åkeson P, Børseth A. Pulmonary MR angiography with ultrasmall superparamagnetic iron oxide particles as a blood pool agent and a navigator echo for respiratory gating: pilot study. Radiology 1999; 211: 865-869.
22. Jung CW, Jacobs P. Physical and chemical properties of super-paramagnetic iron oxide MR contrast agents: ferumoxides, ferumoxtran, ferumoxsil. Magn. Reson. Imag. 1995; 13: 661-674.
23. Bachmann R, Conrad R, Kreft B, Luzar O, Block W, Flacke S, Pauleit D, Träber F, Gieseke J, Saebo K, Schild H. Evaluation of a new ultrasmall superparamagnetic iron oxide contrast agent Clariscan, (NC100150) for MRI of renal perfusion: experimental study in an animal model. J. Magn. Reson. Imag. 2002; 16: 190-195.
24. Groma EV, Josephson L, Lewis JM. US Patent 4827945, 1989.
25. 1-weighted MR imaging. Radiology 1998; 209: 831-836.
26. Bremer C, Alkemper T, Baermig J, Reimer P. Contrast-enhanced 3D-MRA of the upper abdomen with a bolus-injectable SPIO (SH U 555 A). J. Magn. Reson. Imag. 1999; 10: 65-71.
27. Jacobson T, Klaveness J. PCT Int. Appl. WO 00017, 1985.
28. Rinck PA, Smevik O, Nilsen G, Klepp O, Onsrud M, Øksendal A, Borseth A. Oral magnetic particles in MR imaging of the abdomen and pelvis. Radiology 1991; 178: 775-779.
29. Prasad PV, Edelman RR, Epstein FH. Non-invasive evaluation of intra-renal oxygenation using BOLD MRI. Circulation 1996; 94: 3271-3275.
30. Van Wagoner M, Worah D. Gadodiamide injection. First human experience with the nonionic magnetic resonance imaging enhancement agent. Invest. Radiol. 1993; 28: S44-S48.
31. Oskendal A, Hals P. Biodistribution and toxicity of MR imaging contrast media. J. Magn. Reson. Imag. 1993; 3: 157-165.
32. Bellin M-F, Vasile M, Morel-Precetti S. Currently used non-specific extracellular MR contrast media. Eur. Radiol. 2003; 13: 2688-2698.
33. Bellin M-F. MR contrast agents, the old and the new. Eur. J. Radiol. 2006; 60: 314-323.
34. Grobner T. Gadolinium: a specific trigger for the development of nephrogenic fibrosing dermopathy and nephrogenic systemic fibrosis? Nephrol. Dial. Transplant. 2006; 21: 1104-1108.
35. Ersoy H, Rybicki FJ. Biochemical safety profiles of gadolinium-based extracellular contrast agents and nephrogenic systemic fibrosis. J. Magn. Reson. Imag. 2007; 26: 1190-1197.
36. Rofsky NM, Sherry AD, Lenkinsky RE. Nephrogenic systemic fibrosis: a chemical and rational perspective. Radiology 2008; 247: 608-612.
37. Knopp MV, von Tengg-Koblingk H, Floemer F, Schoenberg SO. Contrast agents for MRA: future directions. J. Magn. Reson. Imag. 1999; 10: 314-331.
38. Saeed M, Wendland MF, Higgins CB. Blood pool contrast agents for cardiovascular imaging. J. Magn. Reson. Imag. 2001; 12: 890-898.
39. Daldrup-Link H, Brasch RC. Macromolecular contrast agents for MR mammography: current status. Eur. Radiol. 2003; 13: 354-365.
40. Aime S, Botta M, Fasano M, Crich SG, Terreno E. 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. 1996; 1: 312-319.
41. Lauffer RB, Parmelee DJ, Dunham SU, Ouellet HS, Dolan RP, Witte S, McMurry TJ, Walovitch RC. MS-325: albumin-targeted contrast agent for MR angiography. Radiology 1998; 207: 529-538.
42. Rohrer M, Bauer H, Mintorovitch J, Requardt M, Weinmann H-J. Comparison of magnetic properties of MRI contrast media solutions at different magnetic field strengths. Invest. Radiol. 2005; 40: 715-724.
43. Cavagna FM, Lorusso V, Anelli PL, Maggioni F, de Haën C. Preclinical profile and clinical potential of gadocoletic acid trisodium salt (B22956/1), a new intravascular contrast medium for MRI. Acad. Radiol. 2002; 9: 491-494.
44. Preda A, Novikov V, Möglich M, Turetschek K, Shames DM, Brasch RC, Cavagna FM, Roberts TPL. MRI monitoring of Avastin antiangiogenesis therapy using B22956/1, a new blood pool contrast agent, in an experimental model of human cancer. J. Magn. Reson. Imag. 2004; 20: 865-873.
45. Dong Q, Hurst DR, Weinmann HJ, Chenevert TJ, Londy FJ, Prince MR. Magnetic resonance angiography with Gadomer-17. An animal study original investigation. Invest. Radiol. 1998; 33: 699-708.
46. Misselwitz B, Schmitt-Willich H, Ebert W, Frenzel T, Weinmann HJ. Pharmacokinetics of Gadomer-17, a new dendritic magnetic resonance contrast agent. MAGMA 2001; 12: 128-134.
47. Kobayashi H, Brechbiel MW. Dendrimer-based nanosized MRI contrast agents. Curr. Pharm. Biotechnol. 2004; 5: 539-549.
48. Aime S, Fasano M, Terreno E, Botta M. Protein-bound metal chelates. In The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging, Merbach AE, Tóth E (eds). Wiley: Chichester, 2001; 193-241.
49. Berthezène Y, Vexler V, Price DC, Wisner-Dupon J, Moseley ME, Aicher KP, Brasch RC. Magnetic resonance imaging detection of an experimental pulmonary perfusion deficit using a macromolecular contrast agent. Polylysine-gadolinium-DTPA40. Invest. Radiol, 1992; 27: 346-351.
50. Sieving PF, Watson AD, Rocklage SM. Preparation and characterization of paramagnetic polychelates and their protein conjugates. Bioconjug. Chem. 1990; 1: 65-71.
51. Aime S, Botta M, Crich SG, Giovenzana G, Palmisano G, Sisti M. Novel paramagnetic macromolecular complexes derived from the linkage of a macrocyclic Gd(III) complex to polyamino acids through a squaric acid moiety. Bioconjug. Chem. 1999; 10: 192-199.
52. Curtet C, Maton F, Havet T, Slinkin M, Mishra A, Chatal JF, Muller RN. Polylysine-Gd-DTPA(n) and polylysine-Gd-DOTA(n) coupled to anti-CEA F(ab ')(2) fragments as potential immunocontrast agents-relaxometry, biodistribution, and magnetic resonance imaging in nude mice grafted with human colorectal carcinoma. Invest. Radiol. 1998; 33: 752-761.
53. Wu C, Brechbiel W, Kozak RW, Gansow OA. Metal-chelate-dendrimer-antibody constructs for use in radioimmunotherapy and imaging. Bioorg. Med. Chem. Lett. 1994; 4: 449-454.
54. Lu ZR, Parker DL, Goodrich KC, Wang X, Dalle JG, Buswell HR. Extracellular biodegradable macromolecular gadolinium(III) complexes for MRI. Magn. Reson. Med. 2004; 51: 27-34.
55. Corot C, Violas X, Robert P, Gagneur G, Port M. Comparison of different types of blood pool agents (P792, MS325, USPIO) in a rabbit MR angiography-like protocol. Invest. Radiol. 2003; 38: 311-319.
56. Lokling KE, Fossheim SL, Skurtveit R, Bjornerud A, Klaveness J. pH-sensitive paramagnetic liposomes as MRI contrast agents: in vitro feasibility studies. Magn. Reson. Imag. 2001; 19: 731-738.
57. Weissleder R, Elizondo G, Wittenberg J, Rabito CA, Bengele HH, Josephson L. Ultrasmall superparamagnetic iron oxide: characterization of a new class of contrast agents for MR imaging. Radiology 1990; 175: 489-493.
58. Weinmann HJ, Bauer H, Ebert W, Frenzel T, Radüchel B, Platzek J, Schmitt-Willich H. Comparative studies on the efficacy of MRI contrast agents in MRA. Acad. Radiol. 2002; (Suppl. 1): S135-6.
59. Taupitz M, Schnorr J, Abramjuk C, Wagner S, Pilgrimm H, Hünigen H, Hamm B. New generation of monomer-stabilized very small superparamagnetic iron oxide particles (VSOP) as contrast medium for mr angiography: preclinical results in rats and rabbits. J. Magn. Reson. Imag. 2000; 12: 905-911.
60. Mornet S, Vasseur S, Grasset F, Duguet E. Magnetic nanoparticle design for medical diagnosis and therapy. J. Mater. Chem. 2004; 14: 2164-2175.
61. Mack MG, Balzer JO, Straub R, Eichler K, Vogl TJ. Super-paramagnetic iron oxide-enhanced MR imaging of head and neck lymph nodes. Radiology 2002; 222: 239-244.
62. Schmitt-Willich H, Brehm M, Evers CLJ, Michl G, Muller-Fahrnow A, Petrov O, Platzek J, Raduchel B, Sulzle D. Synthesis and physicochemical characterization of a new gadolinium chelate: the liver-specific magnetic resonance imaging contrast agent Gd-EOB-DTPA. Inorg. Chem. 1999; 38: 1134-1144.
63. Schuhmann-Giampieri G, Schmitt-Willich H, Press WR, Negishi C, Weinmann HJ, Speck U. Preclinical evaluation of Gd-EOB-DTPA as a contrast agent in MR imaging of the hepatobiliary system. Radiology 1992; 183: 59-64.
64. Uggeri F, Aime S, Anelli PL, Botta M, Brocchetta M, Dehaen C, Ermondi G, Grandi M, Paoli P. Novel contrast agents for magnetic resonance imaging. Synthesis and characterization of the ligand BOPTA and its Ln(III) complexes (Ln=Gd, La, Lu). X-ray structure of disodium (TPS-9-145337286-C-S)-[4-Carboxy-5,8,11-tris(carboxymethyl)- 1-phenyl-2-oxa-5,8,11-triaza tridecan-13-oato(5-)]gadolinate(2-) in a mixture with its enantiomer. Inorg. Chem. 1995; 34: 663-642.
65. Henrotte V, Vander Elst L, Laurent S, Muller RN. Comprehensive investigation of the non-covalent binding of MRI contrast agents with human serum albumin. J. Biol. Inorg. Chem. 2007; 12: 929-937.
66. Knopp MV, Schoenberg SO, Rehm C, Floemer F, von Teregg-Kobling KH, Bock M, Hentrich HR. Assessment of gadobenate dimeglumine for magnetic resonance angiography: Phase I studies. Invest. Radiol. 2002; 37: 706-715.
67. Saini S, Nelson RC. Technique for MR imaging of the liver. Radiology 1995; 197: 575-577.
68. Lim KO, Stark DD, Leese PT, Pfefferbaum A, Rocklage SM, Quay SC. Hepatobiliary MR imaging: first human experience with MnDPDP. Radiology 1991; 178: 79-82.
69. Reimer P, Rummeny EJ, Daldrup HE, Balzer T, Tombach B, Berns T, Peters PE. Clinical results with Resovist: a phase 2 clinical trial. Radiology 1995; 195: 489-496.
70. Hamm B, Thoeni RF, Gould RG, Bernardino ME, Luning M, Saini S, Mahfouz AE, Taupitz M, Wolf KJ. Focal liver lesions: characterization with nonenhanced and dynamic contrast material-enhanced MR imaging. Radiology 1994; 190: 417-423.
71. Misselwitz B, Platzek J, Radüchel B, Oellinger JJ, Weinmann H-J. Gadofluorine 8: initial experience with a new contrast medium for interstitial MR lymphography. MAGMA 1999; 8: 1352-8661.
72. Silva AC, Lee JH, Aoki I, Koretsky AP. Manganese-enhanced magnetic resonance imaging (MEMRI): methodological and practical considerations. NMR Biomed. 2004; 17: 532-543.
73. Watanabe T, Tammer R, Boretius S, Frahm J, Michaelis T. Chromium(VI) as a novel MRI contrast agent for cerebral white matter-preliminary results in mouse brain in vivo. Magn. Reson. Med. 2006; 56: 1-6.
74. Poduslo JF, Wengenack TM, Curran GL, Wisniewski T, Sigurdsson EM, Macura SI, Borowski BJ, Jack CR. Molecular targeting of Alzheimer's amyloid plaques for contrast-enhanced magnetic resonance imaging. Neurobiol. Dis. 2002; 11: 315-329.
75. Wadghiri YZ, Sigurdsson EM, Sadowski M, Elliott JI, Li YS, Scholtzova H, Tang CY, Aguinaldo G, Pappolla M, Duff K, Wisniewski T, Turnbull DH. Detection of Alzheimer's amyloid in transgenic mice using magnetic resonance microimaging. Magn. Reson. Med. 2003; 50: 293-302.
76. Takahara T, Saeki M, Nosaka S. Nippon Igaku Hoshasen Gakkai Zasshi. 1995; 55: 697-699.
77. Rubin DL, Falk KL, Sperling MJ, Ross M, Saini S, Rothman B, Shellock F, Zerhouni E, Stark D, Outwater EK, Schmiedl U, Kirby LC, Chezmar J, Coates T, Chang M, Silverman JM, Rofsky N, Burnett K, Engel J, Young SW. A multicenter clinical trial of Gadolite Oral Suspension as a contrast agent for MRI. J. Magn. Reson. Imag. 1997; 7: 865-872.
78. Lonnemark M, Hemmingsson A, Carlsten J, Ericsson A, Holtz E, Klaveness J. Superparamagnetic particles as an MRI contrast agent for the gastrointestinal tract. Acta Radiol. 1988; 29: 599-602.
79. Bogdanov AA, Lewin M, Weissleder R. Approaches and agents for imaging the vascular system. Adv. Drug Deliv. Rev. 1999; 37: 279-293.
80. Nunn AD, Linder KE, Tweedle MF. Can receptors be imaged with MRI agents? Q.J. Nucl. Med. 1997; 41: 155-162.
81. Aime S, Botta M, Garino E, Crich SG, Giovenzana G, Pagliarin R, Palmisano G, Sisti M. Non-covalent conjugates between cationic polyamino acids and GdIII chelates: a route for seeking accumulation of MRI-contrast agents at tumor targeting sites. Chem. Eur. J. 2000; 6: 2609-2617.
82. Frullano L, Rohovec J, Aime S, Maschmeyer T, Prata MIM, de Lima JJP, Geraldes CFGC, Peters JA. Towards targeted MRI: new MRI contrast agents for sialic acid detection. Chem. Eur. J. 2004; 10: 5205-5217.
83. Young SW, Quing F, Harriman A, Sessler JL, Dow WC, Mody TD, Hemmi GW, Hao Y,Miller RA. Gadolinium(III) texaphyrin: A tumor selective radiation sensitizer that is detectable by MRI. Proc. Natl Acad. Sci. USA. 1996; 93: 6610-6615.
84. Ni Y, Pislaru C, Bosmans H, Pislaru S, Miao Y, Bogaert J, Dymarkowski S, Yu J, Semmler W, Van de Werf F, Baert AL, Marchal G. Intracoronary delivery of Gd-DTPA and Gadophrin-2 for determination of myocardial viability with MR imaging. Eur. Radiol. 2001; 11: 876-883.
85. Sipkins DA, Cheresh DA, Kazemi MR, Nevin LM, Bednarski MD, Li KC. Detection of tumor angiogenesis in vivo by alphaVbeta3-targeted magnetic resonance imaging. Nat. Med. 1998; 4: 623-626.
86. 3-targeted nanoparticle and 1.5 Tesla magnetic resonance imaging. Cancer Res. 2003; 63: 5838-5843.
87. Aime S, Cabella C, Colombatto S, Geninatti Crich S, Gianolio E, Maggioni F. Insights into the use of paramagnetic Gd(III) complexes in MR-molecular imaging investigations. J. Magn. Reson. Imag. 2002; 16: 394-406.
88. Crich SG, Biancone L, Cantaluppi V, Duo D, Esposito G, Russo S, Camussi G, Aime S. Improved route for the visualization of stem cells labeled with a Gd-/Eu-chelate as dual (MRI and fluorescence) agent. Magn. Reson. Med. 2004; 51: 938-944.
89. 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. Edn Engl. 2002; 41: 1017-1019.
90. Terreno E, Crich SG, Belfiore S, Biancone L, Cabella C, Esposito G, Manazza AD, Aime S. Effect of the intracellular localization of a Gd-based imaging probe on the relaxation enhancement of water protons. Magn. Reson. Med. 2006; 55: 491-497.
91. Bhorade R, Weissleder R, Nakakoshi T, Moore A, Tung CH. Macrocyclic chelators with paramagnetic cations are internalized into mammalian cells via a HIV-tat derived membrane translocation peptide. Bioconjug. Chem. 2000; 11: 301-305.
92. Heckl S, Pipkorn R, Waldeck W, Spring H, Jenne J, von der Lieth CW, Corban-Wilhelm H, Debus J, Braun K. Intracellular visualization of prostate cancer using magnetic resonance imaging. Cancer Res. 2003; 63: 4766-4772.
93. Kalman FK, Woods M, Caravan P, Jurek P, Spiller M, Tircsó G, Kiraly R, Brücher E, Sherry AD. Potentiometric and relaxometric properties of a gadolinium-based MRI contrast agent for sensing tissue pH. Inorg. Chem. 2007; 46: 5260-5270.
94. Aime S, Crich SG, Gianolio E, Tei L, Terreno E. High sensitivity lanthanide(III) based probes for MR-medical imaging. Coord. Chem. Rev. 2006; 250: 1562-1579.
95. Zhang S, Wu K, Sherry AD. A novel pH-sensitive MRI contrast agent. Angew. Chem. Int. Edn Engl. 1999; 38: 3192-3194.
96. Raghunand N, Howison C, Sherry AD, Zhang S, Gillies R. Renal and systemic pH imaging by contrast-enhanced MRI. Magn. Reson. Med. 2003; 49: 249-257.
97. Garcia-Martin ML, Martinez GV, Raghunand N, Sherry AD, Zhang S, Gillies R. High resolution pHe imaging of rat glioma using pH-dependent relaxivity. Magn. Reson. Med. 2006; 55: 309-315.
98. Mikawa M, Miwa N, Brautigam M, Akaike T, Maruyama A. A pH-sensitive contrast agent for functional magnetic resonance imaging (MRI). Chem. Lett. 1998; 7: 693-694.
99. Aime S, Crich SG, Botta M, Giovenzana G, Palmisano G, Sisti M. A macromolecular Gd(III) complex as pH-responsive relaxometric probe for MRI applications. Chem. Commun. 1999; 1577-1578.
100. Lowe MP, 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.
101. Hovland R, Glogard C, Aasen AJ, Klaveness J. Gadolinium DO3A derivatives mimicking phospholipids; preparation and in vitro evaluation as pH responsive MRI contrast agents. J. Chem. Soc. Perkin Trans. 2 2001; 6: 929-933.
102. Woods M, Zhang S, Ebron VH, Sherry AD. PH-sensitive modulation of the second hydration sphere in Lanthanide(III) tetraamide-DOTA complexes: a novel approach to smart MR contrast media. Chem. Eur. J. 2003; 9: 4634-4640.
103. Aime S, Barge A, Botta M, Howard JAK, Kataly R, Lowe MP, Moloney JM, Parker D, de Sousa AS. Dependence of the relaxivity and luminescence of gadolinium and europium amino-acid complexes on hydrogencarbonate and pH. Chem. Commun. 1999; 1047-1048.
104. Toth E, Bolskar RD, Borel A, Gonzalez G, Helm L, Merbach AE, Sitharaman B, Wilson LJ. Water-soluble gadofullerenes: toward high-relaxivity, pH-responsive MRI contrast agents. J. Am. Chem. Soc. 2005; 127: 799-805.
105. Aime S, Botta M, Fasano M, Terreno E, Kinchesh P, Calabi L, Paleari L. A new ytterbium chelate as contrast agent in chemical shift imaging and temperature sensitive probe for MR spectroscopy. Magn. Reson. Chem. 1996; 35: 648-651.
106. Zuo CS, Mahmood A, Sherry AD. TmDOTA(-): a sensitive probe for MR thermometry in vivo. J. Magn. Reson. 2001; 151: 101-106.
107. Fossheim SL, Il'yasov KA, Hennig J, Bjornerud A. Thermosensitive paramagnetic liposomes for temperature control during MR imaging-guided hyperthermia: in vitro feasibility studies. Acad. Radiol. 2000; 7: 1107-1115.
108. Thulborn KR, Waterton JC, Matthews PM, Radda GK. Oxygenation dependence of the transverse relaxation time of water protons in whole blood at high field. Biochem. Biophys. Acta 1982; 714: 265-270.
109. Ogawa S, Tank DW, Menon R, Ellermann JM, Kim SG, Merkle H, Ugurbil K. Intrinsic signal changes accompanying sensory stimulation: functional brain mapping with magnetic resonance imaging. Proc. Natl Acad. Sci. USA 1992; 89: 5951-5955.
110. Burai L, Scopelliti R, Toth E. Eu-II-cryptate with optimal water exchange and electronic relaxation: a synthon for potential pO(2) responsive macromolecular MRI contrast agents. Chem. Commun. 2002; 20: 2366-2367.
111. Aime S, Botta M, Gianolio E, Terreno E. A p(O-2)-responsive MRI contrast agent based on the redox switch of manganese(II/III)-porphyrin complexes. Angew. Chem. Int. Edn Engl. 2000; 39: 747-750.
112. Louie AY, Huber MM, Ahrens ET, Rothbacher U, Moats R, Jacobs RE, Fraser SE, Meade TJ. In vivo visualization of gene expression using magnetic resonance imaging. Nat. Biotechnol. 2000; 18: 321-325.
113. Himmelreich U, Aime S, Hieronymus T, Justicia C, Uggeri F, Zenke M, Hoehn M. A responsive MRI contrast agent to monitor functional cell status. Neuroimage 2006; 32: 1142-1149.
114. Anelli PL, Bertini I, Fragai M, Lattuada L, Luchinat C, Parigi G. Sulfonamide-functionalized gadolinium DTPA complexes as possible contrast agents for MRI: a relaxometric investigation. Eur. J. Inorg. Chem. 2000; 625-630.
115. 3+ magnetic resonance imaging contrast agents with a prominent receptor-induced magnetization enhancement. Angew. Chem. Int. Edn 2001; 40: 2903-2906.
116. Bogdanov A, Matuszewski L, Bremer C, Petrovsky A, Weissleder R. Oligomerization of paramagnetic substrates result in signal amplification and can be used for MR imaging of molecular targets. Mol. Imag. 2002; 1: 16-23.
117. Duimstra JA, Femia FJ, Meade TM. A gadolinium chelate for detection of beta-glucuronidase: a self-immolative approach. J. Am. Chem. Soc. 2005; 127: 12847-12855.
118. Querol M, Chen JW, Weissleder R, Bogdanov A. DTPA-bisamide-based MR sensor agents for peroxidase imaging. Org. Lett. 2005; 7: 1719-1722.
119. Chen JW, Pham W, Weissleder R, Bogdanov A. Human myeloperoxidase: a potential target for molecular MR imaging in atherosclerosis. Magn. Reson. Med. 2004; 52(5): 1021-1028.
120. Li W-H, Parigi G, Fragai M, Luchinat C, Meade TJ. Mechanistic studies of a calcium-dependent MRI contrast agent. Inorg. Chem. 2002; 41: 4018-4024.
121. Li W-H, Fraser SE, Meade TJ. A calcium-sensitive magnetic resonance imaging contrast agent. J. Am. Chem. Soc. 1999; 121: 1413-1414.
122. 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. 1 2001; 2: 1840-1843.
123. Hanaoka K, Kikuchi K, Urano Y, Narazaki M, Yokawa T, Sakamoto S, Yamaguchi K, Nagano T. Design and synthesis of a novel magnetic resonance imaging contrast agent for selective sensing of zinc ion. Chem. Biol. 2002; 9: 1027-1032.
124. Aime S, Botta M, Fasano M, Terreno E. Gd(III)-Fe(III) heterobimetallic complexes of DTPA-bis-salicylamide. Spectrochim. Acta. 1993; 49A: 1315-1322.
125. Comblin V, Gilsoul D, Hermann M, Humblet V, Jacques V, Mesbahi M, Sauvage C, Desreux JF. Designing new MRI contrast agents: a coordination chemistry challenge. Coord. Chem. Rev. 1999; 185-186: 451-470.
126. Paris J, Gameiro C, Humblet V, Mohapatra PK, Jacques V, Desreux JF. Auto-assembling of ditopic macrocyclic lanthanide chelates with transition-metal ions. Rigid multimetallic high relaxivity contrast agents for magnetic resonance imaging. Inorg. Chem. 2006; 45: 5092-5102.
127. Costa J, Ruloff R, Burai L, Helm L, Merbach AE. Rigid (ML2Gd2III)-L-II (M=Fe, Ru) complexes of a terpyridine-based heteroditopic chelate: A class of candidates for MRI contrast agents. J. Am. Chem. Soc. 2005; 127: 5147-5157.
128. Livramento JB, Weidensteiner C, Prata MIM, Allegrini PR, Geraldes CFGC, Helm L, Kneuer R, Merbach AE, Santos AC, Schmidt P, Tóth E. First in vivo MRI assessment of a self-assembled metallostar compound endowed with a remarkable high field relaxivity. Contrast Med. Mol. Imag. 2006; 1: 30-39.
129. Parac-Vogt TN, Vander Elst L, Kimpe K, Laurent S, Burtéa C, Chen F, Van Deun R, Ni Y, Muller RN, Binnemans K. Pharmacokinetic and in vivo evaluation of a self-assembled gadolinium(III)-iron(II) contrast agent with high relaxivity. Contrast Med. Mol. Imag. 2006; 1: 267-278.
130. Gløgård C, Stensrud G, Aime S. Novel radical-responsive MRI contrast agent based on paramagnetic liposomes. Magn. Reson. Chem. 2003; 41: 585-588.
131. Ward KM, Aletras AH, Balaban RS. A new class of contrast agents for MRI based on proton chemical exchange dependent saturation transfer (CEST). J. Magn. Reson. 2000; 143: 79-87.
132. Zhou J, Wilson DA, Sun PZ, Klaus JA, van Zijl PC. Quantitative description of proton exchange processes between water and endogenous and exogenous agents for WEX, CEST, and APT experiments. Magn. Reson. Med. 2004; 51: 945-952.
133. Guivel-Scharen V, Sinnwell T, Wolff SD, Balaban RS. Detection of proton chemical exchange between metabolites and water in biological tissues. J. Magn. Reson. 1998; 133: 36-45.
134. Zhang S, Winter P, Wu K, Sherry AD. A novel europium(III)-based MRI contrast agent. J. Am. Chem. Soc. 2001; 123: 1517-1518.
135. Zhang S, Merritt M, Woessner DE, Lenkinski RE, Sherry AD. PARACEST agents: modulating MRI contrast via water proton exchange. Acc. Chem. Res. 2003; 36: 783-790.
136. Aime S, Carrera C, Castelli DD, Crich SG, Terreno E. Tunable imaging of cells labeled with MRI-PARACEST agents. Angew. Chem. Int. Edn Engl. 2005; 44: 1813-1815.
137. Aime S, Castelli DD, Terreno E. Novel pH-reporter MRI contrast agents. Angew. Chem. Int. Edn Engl. 2002; 41: 4334-4336.
138. Aime S, Barge A, Castelli DD, Fedeli F, Mortillaro A, Nielsen FU, Terreno E. Paramagnetic lanthanide(III) complexes as pH-sensitive chemical exchange saturation transfer (CEST) contrast agents for MRI applications. Magn. Reson. Chem. 2002; 47: 639-648.
139. Zhang S, Michaudet L, Burgess S, Sherry AD. The amide protons of an ytterbium(III) dota tetraamide complex act as efficient antennae for transfer of magnetization to bulk water. Angew. Chem. Int. Edn Engl. 2002; 41: 1919-1921.
140. Aime S, Castelli DD, Terreno E. A paramagnetic MRI-CEST agent responsive to lactate concentration. J. Am. Chem. Soc. 2002; 124: 9364-9365.
141. Aime S, Castelli DD, Terreno E. Supramolecular adducts between poly- L-arginine and [Tm(III)dotp]: a route to sensitivity-enhanced magnetic resonance imaging-chemical exchange saturation transfer agents. Angew. Chem. Int. Edn Engl. 2003; 42: 4527-4529.
142. Zhang S, Trokowski R, Sherry AD. A paramagnetic CEST agent for imaging glucose by MRI. J.Am. Chem. Soc. 2003; 125: 15288-15289.
143. Trokowski R, Ren J, Kalman FK, Sherry AD. Selective sensing of zinc ions with a PARACEST contrast agent. Angew. Chem. Int. Edn Engl. 2005; 44: 6920-6923.
144. Zhang S, Malloy CR, Sherry AD. MRI thermometry based on PARACEST agents. J. Am. Chem. Soc. 2005; 127: 17572-17573.
145. Yoo B, Pagel MD. A PARACEST MRI contrast agent to detect enzyme activity. J. Am. Chem. Soc. 2006; 128: 14032-14033.
146. Woods M, Woessner DE, Sherry AD. Paramagnetic lanthanide complexes as PARACEST agents for medical imaging. Chem. Soc. Rev. 2006; 35: 500-511.
147. Terreno E, Castelli DD, Cravotto G, Milone L, Aime S. Ln(III)-DOTAMGIY complexes: a versatile series to assess the determinants of the efficacy of paramagnetic chemical exchange saturation transfer agents for magnetic resonance imaging applications. Invest. Radiol. 2004; 39: 235-243.
148. Goffeney N, Bulte JW, Duyn J, Bryant LH, van Zijl PC. Sensitive NMR detection of cationic-polymer-based gene delivery systems using saturation transfer via proton exchange. J. Am. Chem. Soc. 2001; 123: 8628-8629.
149. Snoussi K, Bulte JW, Gueron M, van Zijl PC. 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. 2003; 49: 998-1005.
150. Aime S, Castelli DD, Terreno E. Highly sensitive MRI chemical exchange saturation transfer agents using liposomes. Angew. Chem. Int. Edn Engl. 2005; 44: 5513-5515.
151. Winter PM, Cai K, Chen J, Adair CR, Kiefer GE, Athey PS, Gaffney PJ, Buff CE, Robertson JD, Caruthers SD, Wickline SA, Lanza GM. Targeted PARACEST nanoparticle contrast agent for the detection of fibrin. Magn. Reson. Med. 2006; 56: 1384-1388.
152. Mansson S, Johansson E, Magnusson P, Chai CM, Hansson G, Petersson JS, Stahlberg F, Golman K. C-13 imaging - a new diagnostic platform. Eur. Radiol. 2006; 16: 57-67.
153. Golman K, Ardenkjaer-Larsen JH, Petersson JS, Mansson S, Leunbach I. Molecular imaging with endogenous substances. Proc. Natl Acad. Sci. USA. 2003; 100: 10435-10439.
154. Möller HE, Chen XJ, Saam B, Hagspiel KD, Johnson GA, Altes TA, de Lange EE, Kauczor HU. MRI of the lungs using hyperpolarized noble gases. Magn. Reson. Med. 2002; 47: 1029-1051.
155. van Heeswijk R, Laus S, Morgenthaler F, Gruetter R. Relaxivity of Gd-based contrast agents on X nuclei with long intrinsic relaxation times in aqueous solutions. Magn. Reson. Imag. 2007; 25: 821-825.
156. Bowers CR, Weitekamp DP. Para-Hydrogen and synthesis allow dramatically enhanced nuclear alignment. J. Am. Chem. Soc. 1987; 109: 5541-5542.
157. Abragam A. The Principles of Nuclear Magnetism. Clarendon Press: Oxford, 1961.
158. Johansson E, Olsson LE, Mansson S, Petersson JS, Golman K, Stahlberg F, Wirestam R. Perfusion assessment with bolus differentiation: a technique applicable to hyperpolarized tracers. Magn. Reson. Med. 2004; 52: 1043-1051.
159. Magnusson P, Johansson E, Mansson S, Petersson JS, Chai CM, Hansson G, Axelsson O, Golman K. Passive catheter tracking during interventional MRI using hyperpolarized C-13. Magn. Reson. Med. 2007; 57: 1140-1147.
160. Ardenkjaer-Larsen JH, Fridlund B, Gram A, Hansson G, Hansson L, Lerche MH, Servin R, Thaning M, Golman K. Increase in signal-to-noise ratio of >10,000 times in liquid-state NMR. Proc. Natl Acad. Sci. USA 2003; 100: 10158-10163.
161. Ishii M, Emami K, Kadlecek S, Petersson JS, Golman K, Vahdat V, Yu J, Cadman RV, MacDuffie-Woodburn J, Stephen M, Lipson DA, Rizi RR. Hyperpolarized C-13 MRI of the pulmonary vasculature and parenchyma. Magn. Reson. Med. 2007; 57: 459-463.
162. Olsson LE, Chai CM, Axelsson O, Karlsson M, Golman K, Petersson JS. MR coronary angiography in pigs with intraarterial injections of a hyperpolarized C-13 substance. Magn. Reson. Med. 2006; 55: 731-737.
163. Golman K, Zandt R, Lerche M, Pehrson R, Ardenkjaer-Larsen JH. Metabolic imaging by hyperpolarized C-13 magnetic resonance imaging for in vivo tumor diagnosis. Cancer Res. 2006; 66: 10855-10860.
164. Golman K, Petersson JS, Magnusson P, Johansson E, Åkeson P, Chai C-M, Hansson G, Månsson S. Cardiac metabolism measured noninvasively by hyperpolarized C-13 MRI. Magn. Reson. Med. 2008; 59: 1005-1013.