Radiography
Volume 13 , Pages e5-e19 , December 2007

Magnetic resonance imaging contrast agents: Overview and perspectives

  • Guo-Ping Yan

      Affiliations

    • School of Material Science and Engineering, Wuhan Institute of Technology, Wuhan 430073, PR China
    • School of Physical and Chemical Sciences, Queensland University of Technology, GPO Box 2434, Brisbane, Q4001, Australia
    • Corresponding Author InformationCorresponding author. Wuhan Institute of Technology, School of Material Science and Engineering, 693 Xiongchu Road, Wuhan 430073, Wuhan, Hubei Province 430073, PR China. Tel.: +86 27 63186388; fax: +86 27 87195661.
    • ,
  • Leslie Robinson

      Affiliations

    • School of Health Care Professions, University of Salford, Salford, Greater Manchester, M6 6PU, UK
    • ,
  • Peter Hogg

      Affiliations

    • School of Health Care Professions, University of Salford, Salford, Greater Manchester, M6 6PU, UK

Received 21 September 2005 ,Accepted 31 July 2006.

References 

  1. Lauterbur PC. Image formation by induced local interactions: examples employing nuclear magnetic resonance. Nature. 1973;242:190–191
  2. Gallez B, Swartz HM. In vivo EPR: when, how and why?. NMR Biomed. 2004;17:223–225
  3. Lauffer RB. Paramagnetic metal complexes as water proton relaxation agents for NMR imaging: theory and design. Chem Rev. 1987;87:901–927
  4. 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
  5. Yan GP, Zhuo RX. Research progress of magnetic resonance imaging contrast agents. Chin Sci Bull. 2001;46(15):1233–1237
  6. Nelson KL, Runge VM. Principles of MR contrast. In:  Runge VM editors. Contrast-enhanced clinical magnetic resonance imaging. USA: The University Press of Kentucky; 1996;p. 1–14
  7. Lauffer RB. MRI contrast agents: basic principles. In:  Edelman RR,  Hesselink JR,  Zlatkin MB editor. Clinical magnetic resonance imaging. 2nd ed.. Pennsylvania: WB Saunders Company; 1996;p. 176–191
  8. Månsson S, Bjørnerud A. Physical principles of medical imaging by nuclear magnetic resonance. In:  Merbach AE,  Tóth É editor. The chemistry of contrast agents in medical magnetic resonance imaging. Chichester: John Wiley; 2001;p. 1–44
  9. Kim DK, Mikhaylova M, Wang FH, Kehr J, Bjelke B, Zhang Y, et al. Starch-coated superparamagnetic nanoparticles as MR contrast agents. Chem Mater. 2003;15:4343–4351
  10. Mornet S, Vasseur S, Grasset F, Duguet E. Magnetic nanoparticle design for medical diagnosis and therapy. J Mater Chem. 2004;14:2161–2175
  11. Jensen JH, Helpern JA, Iron-fortified MRI. effects and applications of iron-induced NMR relaxation in biological tissues. NMR Biomed. 2004;17:425–426
  12. Wu EX, Tang HY, Jensen JH. Applications of ultrasmall superparamagnetic iron oxide contrast agents in the MR study of animal models. NMR Biomed. 2004;17:478–483
  13. Kehagias DT, Gouliamos AD, Smyrniotis V, Vlahos LJ. Diagnostic efficacy and safety of MRI of the liver with superparamagnetic iron oxide particles (SHU 555 A). J Magn Reson Imaging. 2001;14:595–601
  14. Morimoto N, Ebara M, Kato H, Obata T, Fujita J, Kondo F, et al. Early detection of radiation-induced liver injury in rat by superparamagnetic iron oxide-enhanced MR imaging. J Magn Reson Imaging. 1999;9:573–578
  15. Bulte JW, Brooks RA, Moskowitz BM, Bryant LH, Frank JA. Relaxometry and magnetometry of the MR contrast agent MION-46L. Magn Reson Med. 1999;42:379–384
  16. Jung CW, Jacobs P. Physical and chemical properties of superparamagnetic iron oxide MR contrast agents: ferumoxides, ferumoxtran, ferumoxsil. Magn Reson Imaging. 1995;13:661–674
  17. Bogdanov AA, Martin C, Weissleder R, Brady TJ. Trapping of dextran-coated colloids in liposomes by transient binding to aminophospholipid: preparation of ferrosomes. Biochim Biophys Acta. 1994;1193:212–218
  18. Bulte JW, de Cuyper M, Despres D, Frank JA. Preparation, relaxometry, and biokinetics of PEGylated magnetoliposomes as MR contrast agent. J Magn Reson Mater. 1999;194:204–209
  19. Bulte JW, Brooks RA. Scientific and clinical applications of magnetic carriers. In:  Hafeli U,  Schutt W,  Tellar J,  Zborowski M editor. New York: Plenum Press; 1997;p. 527
  20. Bachmann R, Conrad R, Kreft B, Luzar O, Block W, Flacke S, et al. 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 Imaging. 2000;16:190–195
  21. Vlahos L, Gouliamos A, Athanasopoulou A, Kotoulas G, Claus W, Hatziioannou A, et al. A comparative study between Gd-DTPA and oral magnetic particles (OMP) as gastrointestinal (GI) contrast agents for MRI of the abdomen. Magn Reson Imaging. 1994;12:719–726
  22. Hahn PF, Stark DD, Lewis JM, Saini S, Elizondo G, Weissleder R, et al. First clinical trial of a new superparamagnetic iron oxide for use as an oral gastrointestinal (GI) MR contrast agent. Radiology. 1990;175:695–700
  23. Taupitz M, Schnorr J, Abramjuk C, Wagner S, Pilgrimm H, Hünigen H, et al. New generation of monomer-stabilized very small superparamagnetic iron oxide partials (VSOP) as contrast medium for MR angiography: preclinical results in rats and rabbits. J Magn Reson Imaging. 2000;12:905–911
  24. Strable E, Bulte JWM, Moskowitz B, Vivekanandan K, Allen M, Douglas T. Synthesis and characterization of soluble iron oxide-dendrimer composites. Chem Mater. 2001;13:2201–2209
  25. Artemov D, Mori N, Okollie B, Bhujwalla ZM. MR molecular imaging of the Her-2/neu receptor in breast cancer cells using targeted iron oxide nanoparticles. Magn Reson Med. 2003;49:403–408
  26. Schaffer BK, Linker C, Papisov M, Tsai E, Nossiff N, Shibata T, et al. MINO-ASF: biokinetics of a MR receptor agent. Magn Reson Imaging. 1993;11:411–417
  27. Shen TT, Bogdanov A, Poss K, Brady TJ, Weissleder R. Magnetically labeled secretin retains receptor affinity to pancreas acinar cells. Bioconjugate Chem. 1996;7:311–316
  28. Reimer O, Weissleder R, Shen TT, Knoefel WT, Brady TJ. Pancreatic receptors: initial feasibility studies with a targeted contrast agent for MR imaging. Radiology. 1994;193:527–531
  29. Platas-Iglesias C, Mato-Iglesias M, Djanashvili K, Muller RN, Elst LV, Peters JA, et al. Lanthanide chelates containing pyridine units with potential application as contrast agents in magnetic resonance imaging. Chem Eur J. 2004;10:3579–3590
  30. Weinmann HJ, Brash RC, Press WR, Wesbey GE. Characteristic of gadolinium-DTPA complex: a potential NMR contrast agent. Am J Radiol. 1984;142:619–624
  31. Comblin V, Gilsoul D, Hermann M, Humblet V, Jacques V, Mesbahi M, et al. Designing new MRI contrast agents: a coordination chemistry challenge. Coord Chem Rev. 1999;185–6:451–470
  32. Wedeking P, Sotak CH, Telser J, Kumar K, Chang CA, Tweedle MF. Quantitative dependence of MR signal intensity on tissue concentration of Gd(HP-DO3A) in the nephrectomized rat. Magn Reson Imaging. 1992;10:97–108
  33. Mikei K, Helm L, Brucher E, Merbach A. 17O NMR study of water exchange on Gd(DTPA)(H2O)2- and Gd(DOTA)(H2O)2- related to NMR imaging. Inorg Chem. 1993;32:3844–3850
  34. Zhuo RX, Lu ZR, Wei JF, Yan GP. The methods of synthesis of polyaminocarboxylates metal complexes. Chinese Patent 95 1 19302.3 1995:1–20.
  35. Lowe MP. MRI contrast agents: the next generation. Aust J Chem. 2002;55:551–556
  36. Aime S, Dastrù W, Crich SG, Gianolio E, Mainero V. Innovative magnetic resonance imaging diagnostic agents based on paramagnetic Gd(III) complexes. Biopolymers (Pept Sci). 2002;66:419–428
  37. Botta M. Second coordination sphere water molecules and relaxivity of gadolinium(III) complexes: implication for MRI contrast agents. Eur J Inorg Chem. 2000;399–407
  38. Laurent S, Elst LV, Houzé S, Guérit N, Muller RN. Synthesis and characterization of various benzyl diethylenetriaminepentaacetic acids (dtpa) and their paramagnetic complexes, potential contrast agents for magnetic resonance imaging. Helv Chim Acta. 2000;83:394–406
  39. Safavy A, Smith DC, Bazooband A, Buchsbaum DJ. Synthesis of the first diethylenetriaminepentahydroxamic acid (DTPH) bifunctional chelating agent. Bioconjugate Chem. 2002;13:327–332
  40. Laurent S, Botteman F, Elst LV, Muller RN. New bifunctional contrast agents: bis-amide derivatives of C-substituted Gd-DTPA. Eur J Inorg Chem. 2004;463–468
  41. Zhuo RX, Wen J, Wang L. Synthesis and evaluation of aromatic DTPA-bis(amide) gadolinium complexes as magnetic resonance imaging contrast agents. Chem Res Chin Univ. 1997;13(2):150–155
  42. Wang YM, Cheng TH, Liu GC, Shen RS. Synthesis of some N,N′- bis(amide) derivatives of diethylenetriaminepentaacetic acid and the stabilities of their complexes with Gd3+, Ca2+, Cu2+, and Zn2+. J Chem Soc Dalton Trans. 1997;5:833–838
  43. Bligh SWA, Chowdhury AHMS, Kennedy D, Luchinat C, Parigi G. Non-ionic bulky Gd(III) DTPA-bisamide complexes as potential contrast agents for magnetic resonance imaging. Magn Reson Med. 1999;41:767–773
  44. Zhuo RX, Lu ZR, Wen J. Syntheses and characterization of metal complexes of L-lysine-N,N,N′,N′-tetraacetic acid and L-lysine-N,N,N′,N′-tetramethylene phosphonic acid. Chem Res Chin Univ. 1995;11(2):276–280
  45. Luo Y, Zhuo RX, Fan CL. Studies on the magnetic resonance imaging contrast agents: synthesis and spin-lattice relaxivity of amino acids and oligopeptidyl derivatives of Gd-DTPA. Chin Chem Lett. 1995;6(5):377–381
  46. Bai ZW, Zhuo RX. Synthesis and relaxivity of DTPA diester Gd3+ complexes. Chin J Magn Reson. 1997;14(4):347–351
  47. Weinmann HJ, Ebert W, Misselwitz B, Schmitt-Willich H. Tissue-specific MR contrast agents. Eur J Radiol. 2003;46:33–44
  48. Artemov D. Molecular magnetic resonance imaging with targeted contrast agents. J Cell Biochem. 2003;90:518–524
  49. Enochs WS, Weissleder R. Organ- and tissue-directed MRI contrast agents. In:  Edelman RR,  Hesselink JR,  Zlatkin MB editor. Clinical magnetic resonance imaging. 2nd ed.. Pennsylvania: WB Saunders Company; 1996;p. 192–219
  50. Van Beers BE, Gallez B, Pringot J. Contrast-enhanced MR imaging of the liver. Radiology. 1997;203:297–306
  51. Wen J, Zhuo RX, Wang L. Aromatic DTPA-bis(amide) gadolinium complexes as hepatobiliary contrast agents for magnetic resonance imaging. Chin J Magn Reson. 1998;15(3):217–222
  52. Petre C, Ni Y, Marchal G, Yu J, Wevers M, Lauffer RB, et al. Detection and characterization of primary liver cancer in rats by MS-264-enhanced MRI. Magn Reson Med. 1996;35(4):532–539
  53. Lorusso V, Arbughi T, Tirone P, de Haen C. Pharmacokinetics and tissue distribution in animals of gadobenate ion, the magnetic resonance imaging contrast enhancing component of gadobenate dimeglumine 0.5M solution for injection (MultiHance). J Comput Assist Tomogr. 1999;1(23):S181–S194
  54. Cavagna F, Dapri M, Maggioni F, de Hahn C, Felder E. Gd-BOPTA/Dimeg: experimental disease imaging. Magn Reson Med. 1991;22:329–333
  55. Schuhmann-Giampieri G, Schmitt-Willich H, Press WR, Negishi C, Weinmann HJ, Speak U. Preclinical evaluation of Gd-EOB-DTPA as a contrast agent in MR imaging of the hepatobiliary system. Radiology. 1993;183(1):59–64
  56. Cynthia R, Rogers J, Arias IM. Use of an asialoglycoprotein receptor-targeted magnetic resonance contrast agent to study changes in receptor biology during liver regeneration endoloxemia in rats. Hepatology. 1996;23(6):1631–1638
  57. Fu YJ, Zhuo RX. Studies on D-galactose-containing DTPA bisamide gadolinium complexes as liver-targeting MRI contrast agents. Chem J Chin Univ. 1997;18(7):1072–1075
  58. Moats RA, Fraser SE, Meade TJ. A “smart” magnetic resonance contrast agent that reports on specific enzymatic activity. Angew Chem Int Ed Engl. 1997;36(7):726–728
  59. Leveille-Webster C, Rogers J, Arias IM. Use of an asialoglycoprotein receptor-targeted magnetic resonance agent to study changes in receptor biology during liver regeneration and endotoxemia in rats. Hepatology. 1996;23:1631–1641
  60. Zhuo RX, Fu YJ, Liao J. Synthesis, relaxivity and biodistribution of novel magnetic resonance imaging (MRI) contrast agents: polylysine (Gd-DTPA/DOTA) with pendent galactose moieties as hepatocyte-targeting groups. Chin Chem Lett. 1997;8(2):157–160
  61. Rocklage SM, Cacheris WP, Quay SC, Hahn FE, Raymond KN. Manganese(II) N,N′-dipyridoxyl ethylenediamine-N,N′-diactate-5, 5′-bis(phosphate): synthesis and characterization of a paramagnetic chelate for magnetic resonance imaging enhancement. Inorg Chem. 1989;28:477–485
  62. Rummeny E, Ehrenheim C, Gehl HB, Hamm B, Laniado M, Lodemann KP, et al. Manganese-DPDP as a hepatobiliary contrast agent in the magnetic resonance imaging of liver tumors: results of clinical phase II trials in Germany including 141 patients. Invest Radiol. 1991;26:S142–S145
  63. Mitchell DG, Alam F. Mangafodipir trisodium: effects on T2- and T1-weighted MR cholangiography. J Magn Reson Imaging. 1999;9:366–368
  64. Wei JF, Zhuo RX. Studies on the novel liver-targeting MRI contrast agents containing vitamin B6. Chin Sci Bull. 1997;42(14):1519–1523
  65. Yan GP, Zhuo RX, Xu MY, Li LY, Tang YF. Liver-targeting macromolecular MRI contrast agents. Sci China Ser B. 2001;44(4):344–352
  66. Yan GP, Zhuo RX, Xu MY, Zhang X, Li LY, Liu ML, et al. Hepatic targeting macromolecular MRI contrast agents. Polym Int. 2002;51:892–898
  67. Yan GP, Hu B, Liu ML, Li LY. Synthesis and evaluation of gadolinium complexes based on PAMAM as MRI contrast agents. J Pharm Pharmacol. 2005;57:1–7
  68. Yan GP, Bottle SE, Zhuo RX, Wei L, Liu ML, Li LY. Evaluation on dendritic gadolinium complexes as MRI contrast agents. J Bioact Compatible Polym. 2004;19(6):453–465
  69. Yan GP, Liu ML, Li LY. Studies on polyaspartamide gadolinium complexes as potential magnetic resonance imaging contrast agents. Radiography. 2005;11:117–122
  70. Aime S, Frullano L, Geninatti-Crich S. 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. 2002;41:1017–1022
  71. Anelli PL, Lattuada L, Lorusso V, Lux G, Morisetti A, Morosini P, et al. Conjugates of gadolinium complexes to bile acids as hepatocyte-directed contrast agents for magnetic resonance imaging. J Med Chem. 2004;47:3629–3641
  72. Anelli PL, Calabi L, de Haen C, Fedeli F, Losi P, Murru M, et al. A new approach to hepatospecific MRI contrast agents: gadolinium complexes conjugated to iodinated synthons. Gazz Chim Ital. 1996;126:89–97
  73. Kimpe K, Para-Vogt TN, Laurent S, Piérart C, Elat LV, Muller RN, et al. Potential MRI contrast agents based on micellar incorporation of amphiphilic bis(alkylamide) derivatives of [(Gd-DTPA)(H2O)]2−. Eur J Inorg Chem. 2003;3021–3027
  74. Para-Vogt TN, Kimpe K, Laurent S, Piérart C, Elat LV, Muller RN, et al. Gadolinium DTPA-monoamide complexes incorporated into mixed micelles as possible MRI contrast agents. Eur J Inorg Chem. 2004;3538–3543
  75. Sipkins DA, Cheresh DA, Kazemi MR, Levin LM, Bednarski MD, Li KC. Detection of tumour angiogenesis in vivo by alphaVbeta3-targeted magnetic resonance imaging. Nat Med. 1998;4:623–626
  76. Nelson JA, Schmiedl U. Porphyrins as contrast media. Magn Reson Med. 1991;22:366–371
  77. Luo Y, Mei EW, Zhuo RX. Studies on water-soluble metalloporphyrins as tumor targeting magnetic resonance imaging contrast agents. Chem J Chin Univ. 1995;16(10):1629–1636
  78. Chen C, Cohen JS, Myers CE, Sohn M. Paramagnetic metalloporphyrins as potential contrast agents in NMR imaging. FEBS Lett. 1984;168:70–74
  79. Shahbazi-Gahrouei D, Williams M, Rizvi S, Allen BJ. In vivo studies of Gd-DTPA-monoclonal antibody and Gd-porphyrins: potential magnetic resonance imaging contrast agents for melanoma. J Magn Reson Imaging. 2001;14:169–174
  80. Chandrashekar TK, Venkatraman S. Core-modified expanded porphyrins: new generation organic materials. Acc Chem Res. 2003;36:676–691
  81. Ni Y, Marchal G, Herijgers P, Flameng W, Petre C, Ebert W, et al. Paramagnetic metalloporphyrins: from enhancers of malignant tumors to markers of myocardial infarcts. Acad Radiol. 1996;3(2):S395–S397
  82. Sessler JL, Murai T, Lynch V, Cyr M. An “expanded porphyrin”: the synthesis and structure of a new aromatic pentadentate ligand. J Am Chem Soc. 1988;110:5586–5588
  83. Young SW, Sidhu MK, Qing F, Muller HH, Neuder M, Zanassi G, et al. Preclinical evaluation of gadolinium (III) texaphyrin complex: a new paramagnetic contrast agent for magnetic resonance imaging. Invest Radiol. 1994;29:330–338
  84. Hofmann B, Bogdanov A, Marecos E, Ebert W, Semmler W, Weissleder R. Mechanism of Gadophrin-2 accumulation in tumor necrosis. J Magn Reson Imaging. 1999;9:336–341
  85. Matthews SE, Pouton CW, Threadgill MD. Synthesis of porphyrin α,ω-bis(methylamino)peptide constructs. New J Chem. 1999;23:1087–1096
  86. Konda SD, Aref M, Wang S, Brechbiel M, Wiener EC. Specific targeting of folate-dendrimer MRI contrast agents to the high affinity folate receptor expressed in ovarian tumor xenografts. Magn Reson Mater Phys Biol Med. 2001;12:104–113
  87. Wiener EC, Konda S, Shadron A, Brechbiel M, Gansow O. Targeting dendrimer-chelates to tumours and tumour cells expressing the high-affinity folate receptor. Invest Radiol. 1997;32:748–754
  88. Schmalbrock P, Hines JV, Lee SM, Ammar GM, Kwok WCE. T1 measurements in cell cultures: a new tool for characterizing contrast agents at 1.5T. J Magn Reson Imaging. 2001;14:636–648
  89. Mangiapia G, Accardo A, Cocelso F, Tesauro D, Morelli G, Radulescu A, et al. Mixed micelles composed of peptides and gadolinium complexes as tumor-specific contrast agents in MRI: a SANS study. J Phys Chem B. 2004;18:17611–17617
  90. Frullano L, Rohovec J, Aime S, Maschmeyer T, Prata MI, de Lima JJP, et al. Towards targeted MRI: new MRI contrast agents for sialic acid detection. Chem Eur J. 2004;10:5205–5217
  91. Huang JL, Wang HY, Zhou CL. Ring-opening polymerization of ethylene oxide by anion initiation using sulfadiazine as parent compound. J Appl Polym Sci. 1995;58:11–18
  92. Yan GP, Zheng CY, Cao W, Li W, Li LY, Liu ML, et al. Synthesis and preliminary evaluation of gadolinium complexes containing sulfonamide groups as potential MRI contrast agents. Radiography. 2003;9:35–41
  93. Wallace RA, Haar JP, Miller DB, Woulfe SR, Polta JA, Galen KP, et al. Synthesis and preliminary evaluation of MP-2269: a novel, nonaromatic small-molecule blood-pool MR contrast agent. Magn Reson Med. 1998;40(5):733–739
  94. Caravan P, Cloutier NJ, Greenfield MT, McDermid SA, Dunham SU, Bulte JWM, et al. The interaction of MS-325 with human serum albumin and its effect on proton relaxation rates. J Am Chem Soc. 2002;124(12):3152–3162
  95. Adzamli K, Yablonskiy DA, Chicoine MR, Won EK, Galen KP, Zahner MC, et al. Albumin-binding MR blood pool agents as MRI contrast agents in an intracranial mouse glioma model. Magn Reson Med. 2003;49:586–590
  96. Corot C, Port M, Raynal I, Dencausse A, Schaefer M, Rousseaux O, et al. Physical, chemical, and biological evaluations of P760: a new gadolinium complex characterized by a low rate of interstitial diffusion. J Magn Reson Imaging. 2000;11:182–191
  97. Fonchy E, Lahrech H, François-Joubert A, Dupeyre R, Benderbous S, Corot C, et al. A new gadolinium-based contrast agent for magnetic resonance imaging of brain tumors: kinetic study on a C6 rat glioma model. J Magn Reson Imaging. 2001;14:97–105
  98. Zheng J, Carr J, Harris K, Saker MB, Cavagna FM, Maggioni F, et al. Three-dimensional MR pulmonary perfusion imaging and angiography with an injection of a new blood pool contrast agent B-22956/1. J Magn Reson Imaging. 2001;14:425–432
  99. André JP, Fischer H, Toth É, Seelig A, Mäcke HR, Merbach AE. High relaxivity for monomeric Gd(DOTA)-based MRI contrast agents, thanks to micellar self-organization. Chem Eur J. 1999;5(10):2977–2983
  100. Duarte MG, Gil MH, Peters JA, Colet JM, Elst LV, Muller RN, et al. Synthesis, characterization, and relaxivity of two linear Gd(DTPA)-polymer conjugates. Bioconjugate Chem. 2001;12:170–177
  101. Tóth E, Uffelen IV, Helm L, Merbach AE, Ladd D, Briley-Sæbø K, et al. 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
  102. Mohs AM, Wang XH, Goodrich KC, Zong YD, Parker DL, Lu ZR. PEG-g-poly(DTPA-co-L-cystine): a biodegradable macromolecular blood pool contrast agent for MR imaging. Bioconjugate Chem. 2004;15:1424–1430
  103. Lu ZR, Parker DL, Goodrich KC, Wang XH, Dalle JG, Buswell HR. Extracellular biodegradable macromolecular gadolinium(III) complexes for MRI. Magn Reson Med. 2004;51:27–34
  104. Ouyang M, Zhuo RX, Fu GC. Study on synthesis and relaxivity of paramagnetic polyester metal complexes for MRI. Ion Exchange Adsorption. 1996;12(4):324–327
  105. Bai ZW, Zhuo RX. The synthesis and relaxivity of polyester-amide MRI contrast agent. Ion Exchange Adsorption. 1996;12(4):332–335
  106. Brasch RC. Rationable and applications for macromolecular Gd-based contrast agents. Magn Reson Med. 1991;22:282–287
  107. Aime S, Botta M, Crich SG, Giovenzana GB, Pagliarin R, Piccinini M, et al. Towards MRI contrast agent of improved efficacy NMR relaxometric investigations of the binding interaction HSA of a novel heptadentate macrocyclic triphosphonate Gd3+-complex. J Biol Inorg Chem. 1997;2(4):470–479
  108. Schuhmann-Giampieri G, Schmitt-Willich H, Frenzel T, Press WR, Weinmann HJ. In vivo and in vitro evaluation of Gd-DTPA-polylysine as a macromolecular contrast agent for magnetic resonance imaging. Invest Radiol. 1991;26:969–974
  109. Roberts HC, Saeed M, Roberts TPL, Mühler A, Brasch RC. MRI of acute myocardial ischemia: comparing a new contrast agent, Gd-DTPA-24-cascade-polymer, with Gd-DTPA. J Magn Reson Imaging. 1999;9:204–208
  110. Judd RM, Reeder SB, May-Newman K. Effects of water exchange on the measurement of myocardial perfusion using paramagnetic contrast agents. Magn Reson Med. 1999;41:334–342
  111. Wen XX, Jackson EF, Price RE, Kim EE, Wu QP, Wallace S, et al. Synthesis and characterization of poly(L-glutamic acid) gadolinium chelate: a new biodegradable MRI contrast agent. Bioconjugate Chem. 2004;15:1408–1415
  112. Lu ZR, Wang XH, Parker DL, Goodrich KC, Buswell HR. Poly(L-glutamic acid) Gd(III)-DOTA conjugate with a degradable spacer for magnetic resonance imaging. Bioconjugate Chem. 2003;14:715–719
  113. Uzgiris EE, Cline H, Moasser B, Grimmond B, Amaratunga M, Smith JF, et al. Conformation and structure of polymeric contrast agents for medical imaging. Biomacromolecules. 2004;5:54–61
  114. Esfand R, Tomalia DA. Poly(amidoamine) (PAMAM) dendrimers: from biomimicry to drug delivery and biomedical applications. Drug Discovery Today. 2001;6(8):427–436
  115. Kobayshi H, Kawamoto S, Jo SK, Bryant HL, Brechbiel MW, Star RA. Macromolecular MRI contrast agents with small dendrimers: pharmacokinetic differences between sizes and cores. Bioconjugate Chem. 2003;14:388–394
  116. Margerum LD, Campion BK, Koo M, Shargill N, Lai JJ, Marumoto A, et al. Gadolinium(III) DO3A macrocycles and polyethylene glycol coupled to dendrimers effect of molecular weight on physical and biological properties of macromolecular magnetic resonance imaging contrast agents. J Alloys Compd. 1997;249:185–190
  117. Patri AK, Majoros IJ, Baker JR. Dendritic polymer macromolecular carriers for drug delivery. Curr Opin Chem Biol. 2002;6:466–471
  118. Fischer M, Vögtle F. Dendrimers: from design to application—a progress report. Angew Chem Int Ed. 1999;38:884–905
  119. Wiener EC, Brechbiel MW, Brothers H, Magin RL, Gansow OA, Tomalia DA, et al. Dendrimer-based metal chelates: a new class of magnetic resonance imaging contrast agents. Magn Reson Med. 1994;31:1–8
  120. Stiriba SE, Frey H, Haag R. Dendritic polymers in biomedical applications: from potential to clinical use in diagnostics and therapy. Angew Chem Int Ed. 2002;41(8):1329–1334
  121. Neerman MF, Zhang W, Parrish AR, Simanek EE. In vitro and in vivo evaluation of a melamine dendrimer as a vehicles for drug delivery. Int J Pharmacol. 2004;281:129–132
  122. Wiener EC, Auteri FP, Chen JW, Brechbiel MW, Gansow OA, Schneider DS, et al. Molecular dynamics of ion-chelate complexes attached to dendrimers. J Am Chem Soc. 1996;118:7774–7782
  123. Nicolle GM, Toth E, Schmitt-Willich H, Raduchel B, Merbach AE. The impact of rigidity and water exchange on the relaxivity of a dendritic MRI contrast agent. Chem Eur J. 2002;8(5):1040–1048
  124. Bryant LH, Brechbiel MW, Wu CC, Bulte JWM, Herynek V, Frank JA. Synthesis and relaxometry of high-generation (G=5, 7, 9, and 10) PAMAM dendrimer-DOTA-gadolinium chelates. J Magn Reson Imaging. 1999;9:348–352
  125. Stiriba SE, Frey H, Haag R. Dendritic polymers in biomedical applications: from potential to clinical in diagnostics and therapy. Angew Chem Int Ed. 2002;41(8):1329–1334
  126. Kobayashi H, Jo SK, Kawamoto S, Yasuda H, Hu XZ, Knopp MV, et al. Polyamine dendrimer-based MRI contrast agents for functional kidney imaging to diagnose acute renal failure. J Magn Reson Imaging. 2004;20:512–518
  127. Aime S, Botta M, Fedeli F, Gianolio E, Terreno E, Anelli P. High-relaxivity contrast agents for magnetic resonance imaging based on multisite interactions between a β-cyclodextrin oligomer and suitably functionalized Gd(III) chelates. Chem Eur J. 2001;7(24):5261–5269
  128. Aime S, Gianolio E, Terreno E, Menegotto I, Bracco C, Milone L, et al. β-Cyclodextrin adducts of Gd(III) chelates: useful models for investigating the structural and dynamic determinants of the relaxivity of gadolinium-based systems. Magn Reson Chem. 2003;41:800–805
  129. Stevens CV, Meriggi A, Booten K. Chemical modification of inulin, a valuable renewable resource, and its industrial application. Biomacromolecules. 2001;2(1):1–16
  130. Crosi DM, Elst LV, Muller RN, van Bekkum H, Peters JA. Inulin as a carrier for contrast agents in magnetic resonance imaging. Chem Eur J. 2001;7(1):64–71
  131. Mikawa M, Kato H, Okumura M, Narazaki M, Kanazawa Y, Miwa N, et al. Paramagnetic water-soluble metallofullerenes having the highest relaxivity for MRI contrast agents. Bioconjugate Chem. 2001;12:510–514
  132. Fu YJ, Laurent S, Muller RN. Synthesis of a sialyl LewisX mimetic conjugated with DTPA, potential ligand of new contrast agents for medical imaging. Eur J Org Chem. 2002;3966–3973
  133. Barber PA, Foniok T, Kirk D, Buchan AM, Laurent S, Boutry SB, et al. MR molecular imaging of early endothelial activation in focal ischemia. Ann Neurol. 2004;56:116–120
  134. Weisslerder R, Lee AS, Fischman AJ, Reimer P, Shen T, Wilkinson R, et al. Polyclonal human immunoglobulin G labeled with polymeric iron oxide: antibody MR imaging. Radiology. 1991;181:245–249
  135. Harisinghani MG, Barentsz J, Hahn PF, Deserno WM, Tabatabaei S, van de Kaa CH, et al. Noninvasive detection of clinically occult lymph-node metastases in prostate cancer. N Engl J Med. 2003;348:2491–2499
  136. Hudgins PA, Anzai Y, Morris MR, Lucas MA. Ferumoxtran-10, a superparamagnetic iron oxide as a magnetic resonance enhancement agent for imaging lymph nodes: a phase 2 dose study. Am J Neuroradiol. 2002;23(4):649–656
  137. Poduslo JF, Curran GL, Peterson JA, McCormick DJ, Fauq AH, Khan MA, et al. Design and chemical synthesis of a magnetic resonance contrast agent with enhanced in vitro binding, high blood-brain barrier permeability, and in vivo targeting to Alzheimer's disease amyloid plaques. Biochemistry. 2004;43:6064–6075
  138. Bligh SWA, Harding CT, McEwen AB, Sadler PJ, Kelly JD, Marriott JA. Synthesis, characterization and comparative study of aminophosphonate chelates of gadolinium (III) ions as magnetic resonance imaging contrast agents. Polyhedron. 1994;13:1937–1943
  139. Aime S, Botta M, Terreno E, Anelli PL, Uggeri F. Gd(DOTP)5-outer-sphere relaxation enhancement promoted by nitrogen bases. Magn Reson Med. 1993;30(5):583–591
  140. Manning HC, Goebel T, Thompson RC, Price RR, Lee H, Bornhop DJ. Targeted molecular imaging agents for cellular-scale biomodal imaging. Bioconjugate Chem. 2004;15:1488–1495
  141. Josephson L, Tung CH, Moore A, Weissleder R. High-efficiency intracellular magnetic labeling with novel superparamagnetic-Tat peptide conjugates. Bioconjugate Chem. 1999;10:186–191
  142. 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. Bioconjugate Chem. 2000;11:301–305
  143. Schwarz R, Schuurmans M, Seelig J, Künnecke B. 19F-MRI of perfluorononane as a novel contrast modality for gastrointestinal imaging. Magn Reson Med. 1999;41:80–86
  144. Lowe MP, Parker D, Reany O, Aime S, Botta M, Castellano G, et al. 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
  145. Woods M, Kiefer GE, Bott S, Castillo-Muzquiz A, Eshelbrenner C, Michaudet L, et al. 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. 2004;126:9248–9256
  146. Løkling KE, Skurtveit R, Bjørnerud A, Fossheim SL. Novel pH-sensitive paramagnetic liposomes with improved MR properties. Magn Reson Med. 2004;51:688–696
  147. Aime S, Botta M, Gianolio E, Terreno E. A p(O2)-responsive MRI contrast agent based on the redox switch of manganese (II/III)-porphyrin complexes. Angew Chem. 2000;112(4):763–766
  148. Rudin M, Beckmann N, Porszasz R, Reese T, Bochelen D, Sauter A. In vivo magnetic resonance methods in pharmaceutical research: current status and perspectives. NMR Biomed. 1999;12:69–97
  149. Hayes C, Padhani AR, Leach MO. Assessing changes in tumour vascular function using dynamic contrast-enhanced magnetic resonance imaging. NMR Biomed. 2002;15:154–163
  150. Ohtomo K. MR imaging next step-where is a new frontier?. Eur J Radiol. 2003;46:1–2

PII: S1078-8174(06)00088-5

doi: 10.1016/j.radi.2006.07.005

Radiography
Volume 13 , Pages e5-e19 , December 2007

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