Gd-based macromolecules and nanoparticles as magnetic resonance contrast agents for molecular imaging

Current Topics in Medicinal Chemistry

Volumn 13, Issue 4, 2013, Pages 411-421

  Huang, Ching Hui ^a   Tsourkas, Andrew ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Contrast agent; Gadolinium; Macromolecule; Magnetic resonance; Molecular imaging; Nanoparticle

Indexed keywords

DENDRIMER; FLUOROCARBON; GADOBENATE DIMEGLUMINE; GADODIAMIDE; GADOFOSVESET; GADOLINIUM; GADOLINIUM PENTETATE MEGLUMINE; GADOTERATE MEGLUMINE; GADOTERIDOL; LIPOSOME; NANOPARTICLE; NUCLEAR MAGNETIC RESONANCE IMAGING AGENT; SILICON DIOXIDE; SINGLE WALLED NANOTUBE;

BIOCOMPATIBILITY; ELECTRON ENERGY LOSS SPECTROSCOPY; HUMAN; IMMUNE RESPONSE; MACROMOLECULE; MOLECULAR IMAGING; NEPHROGENIC SYSTEMIC FIBROSIS; NEPHROTOXICITY; NUCLEAR MAGNETIC RESONANCE IMAGING; REVIEW;

ANIMALS; CONTRAST MEDIA; GADOLINIUM; HUMANS; MACROMOLECULAR SUBSTANCES; MAGNETIC RESONANCE IMAGING; MOLECULAR IMAGING; NANOPARTICLES; ORGANOMETALLIC COMPOUNDS;

EID: 84878790196     PISSN: 15680266     EISSN: 18734294     Source Type: Journal    
DOI: 10.2174/1568026611313040002     Document Type: Review

References (99)

1. Parmelee, D. J., Walovitch, R. C., Ouellet, H. S., Lauffer, R. B., Preclinical Evaluation of the Pharmacokinetics, Biodistribution,and Elimination of MS-325, a Blood Pool Agent for MagneticResonance Imaging. Invest. Radiol. 1997, 32, 741-747.
2. Weissleder, R., Kelly, K., Sun, E. Y., Shtatland, T., Josephson, L., Cell-specific targeting of nanoparticles by multivalent attachmentof small molecules. Nat. Biotechnol. 2005, 23 (11), 1418-1423.
3. Caravan, P., Strategies for increasing the sensitivity of gadoliniumbased MRI contrast agents. Chem. Soc. Rev. 2006, 35 (6), 512-523.
4. Botta, M., Tei, L., Relaxivity Enhancement in Macromolecular and Nanosized GdIII-Based MRI Contrast Agents. Eur. J. Inorg. Chem.2012, (12), 1945-1960
5. Louie, A., Multimodality Imaging Probes: Design and Challenges.Chem. Rev. 2010, 110 (5), 3146-3195.
6. Barrett, T., Kobayashi, H., Brechbiel, M., Choyke, P. L., Macromolecular MRI contrast agents for imaging tumorangiogenesis. Eur. J. Radiol. 2006, 60 (3), 353-366.
7. Bogdanov, A. A., Jr., Weissleder, R., Frank, H. W., Bogdanova, A.V., Nossif, N., Schaffer, B. K., Tsai, E., Papisov, M. I., Brady, T.J., A new macromolecule as a contrast agent for MR angiography:preparation, properties, and animal studies. Radiology 1993, 187(3), 701-706.
8. Brasch, R. C., Rationale and applications for macromolecular Gdbasedcontrast agents. Magn. Reson. Med. 1991, 22 (2), 282-287;discussion 300-283.
9. Bousquet, J. C., Saini, S., Stark, D. D., Hahn, P. F., Nigam, M, Wittenberg, J., Ferrucci, J. T., Gd-DOTA: characterization of anew paramagnetic complex. Radiology 1988, 166 (3), 693-698.
10. Penfield, J. G., Reilly, R. F., Nephrogenic systemic fibrosis risk: isthere a difference between gadolinium-based contrast agents? Semin. Dial. 2008, 21 (2), 129-134.
11. Reilly, R. F., Risk for nephrogenic systemic fibrosis withgadoteridol (ProHance) in patients who are on long-termhemodialysis. Clin. J. Am. Soc. Nephrol. 2008, 3 (3), 747-751.
12. Werner, E. J., Avedano, S., Botta, M., Hay, B. P., Moore, E. G., Aime, S., Raymond, K. N., Highly Soluble Tris-hydroxypyridonateGd(III) Complexes with Increased Hydration Number, Fast WaterExchange, Slow Electronic Relaxation, and High Relaxivity1. J.Am. Chem. Soc. 2007, 129 (7), 1870-1871.
13. Aime, S., Calabi, L., Cavallotti, C., Gianolio, E., Giovenzana, G.B., Losi, P., Maiocchi, A., Palmisano, G., Sisti, M., [Gd-AAZTA]-:A New Structural Entry for an Improved Generation of MRIContrast Agents. Inorg. Chem. 2004, 43 (24), 7588-7590.
14. Xu, J., Franklin, S. J., Whisenhunt, D. W., Raymond, K. N., Gadolinium complex of tris [(3-hydroxy-1-methyl-2-oxo-1,2-didehydropyridine-4-carboxamido)ethyl]-amine: A New Class ofgadolinium magnetic resonance relaxation agents. J. Am. Chem.Soc. 1995, 117 (27), 7245-7246.
15. Avedano, S., Tei, L., Lombardi, A., Giovenzana, G. B., Aime, S., Longo, D., Botta, M., Maximizing the relaxivity of HSA-boundgadolinium complexes by simultaneous optimization of rotationand water exchange. Chem. Commun. 2007, (45), 4726-4728.
16. Aime, S., Barge, A., Borel, A., Botta, M., Chemerisov, S., Merbach, A. E., Muller, U., Pubanz, D., A Multinuclear NMRStudy on the Structure and Dynamics of Lanthanide(III)Complexes of the Poly(amino carboxylate) EGTA4in AqueousSolution. Inorg. Chem. 1997, 36 (22), 5104-5112.
17. Tei, L., Baranyai, Z., Botta, M., Piscopo, L., Aime, S., Giovenzana, G. B., Synthesis and solution thermodynamic study ofrigidified and functionalised EGTA derivatives. Org. Biomol.Chem. 2008, 6 (13), 2361-2368.
18. Tei, L., Botta, M., Lovazzano, C., Barge, A., Milone, L., Aime, S., 1H and 17O NMR relaxometric study in aqueous solution ofGd(III) complexes of EGTA-like derivatives bearingmethylenephosphonic groups. Magn. Reson. Chem. 2008, 46 Suppl 1, S86-93.
19. Senapati, L., Schrier, J., Whaley, K. B., Electronic Transport,Structure, and Energetics of Endohedral Gd@C82Metallofullerenes. Nano Lett. 2004, 4 (11), 2073-2078.
20. Kato, H., Suenaga, K., Mikawa, M., Okumura, M., Miwa, N., Yashiro, A., Fujimura, H., Mizuno, A., Nishida, Y., Kobayashi, K., Shinohara, H., Syntheses and EELS characterization of watersolublemulti-hydroxyl Gd@C82 fullerenols. Chem. Phys. Lett.2000, 324 (4), 255-259.
21. Mikawa, M., Kato, H., Okumura, M., Narazaki, M., Kanazawa, Y., Miwa, N., Shinohara, H., Paramagnetic Water-SolubleMetallofullerenes Having the Highest Relaxivity for MRI ContrastAgents. Bioconjug. Chem. 2001, 12 (4), 510-514.
22. Funasaka, H., Sakurai, K., Oda, Y., Yamamoto, K., Takahashi, T., Magnetic properties of Gd@C82 metallofullerene. Chem. Phys.Lett. 1995, 232 (3), 273-277.
23. Sitharaman, B., Tran, L. A., Pham, Q. P., Bolskar, R. D., Muthupillai, R., Flamm, S. D., Mikos, A. G., Wilson, L. J., Gadofullerenes as nanoscale magnetic labels for cellular MRI. Contrast Media Mol. Imaging 2007, 2 (3), 139-146.
24. Fillmore, H. L., Shultz, M. D., Henderson, S. C., Cooper, P., Broaddus, W. C., Chen, Z. J., Shu, C. Y., Zhang, J., Ge, J., Dorn, H. C., Corwin, F., Hirsch, J. I., Wilson, J., Fatouros, P. P., Conjugation of functionalized gadolinium metallofullerenes withIL-13 peptides for targeting and imaging glial tumors. Nanomedicine (Lond) 2011, 6 (3), 449-458.
25. Baxter, A. B., Lazarus, S. C., Brasch, R. C., In vitro histaminerelease induced by magnetic resonance imaging and iodinatedcontrast media. Invest. Radiol. 1993, 28 (4), 308-312.
26. Bogdanov Jr, A. A., Weissleder, R., Brady, T. J., Long-circulatingblood pool imaging agents. Adv. Drug Delivery Rev. 1995, 16, 335-348.
27. Schuhmann-Giampieri, G., Schmitt-Willich, H., Frenzel, T., Press, W.-R., Weinmann, H.-J., In Vivo and In Vitro Evaluation of Gd-DTPA-Polylysine as a Macromolecular Contrast Agent forMagnetic Resonance Imaging. Invest. Radiol. 1991, 26 (11), 969-974.
28. Vexler, V. S., Clément, O., Schmitt-Willich, H., Brasch, R. C., Effect of varying the molecular weight of the MR contrast agentGd-DTPA-polylysine on blood pharmacokinetics and enhancementpatterns. J. Magn. Reson. Imaging 1994, 4 (3), 381-388.
29. Wen, X., Jackson, E. F., Price, R. E., Kim, E. E., Wu, Q., Wallace, S., Charnsangavej, C., Gelovani, J. G., Li, C., Synthesis andCharacterization of Poly(l-glutamic acid) Gadolinium Chelate:??ANew Biodegradable MRI Contrast Agent. Bioconjug. Chem. 2004,15 (6), 1408-1415.
30. Zhang, G., Zhang, R., Melancon, M. P., Wong, K., You, J., Huang, Q., Bankson, J., Liang, D., Li, C., The degradation and clearance ofPoly(N-hydroxypropyl-L-glutamine)-DTPA-Gd as a blood poolMRI contrast agent. Biomaterials 2012, 33 (21), 5376-5383.
31. Berthezene, Y., Vexler, V., Kuwatsuru, R., Rosenau, W., Muhler, A., Clement, O., Price, D. C., Brasch, R. C., Differentiation ofalveolitis and pulmonary fibrosis with a macromolecular MRimaging contrast agent. Radiology 1992, 185 (1), 97-103.
32. Yuan, Z., Liu, S. Y., Xiao, X. S., Zhong, G. R., Jiang, Q. J., Folatepoly-L-lysine-Gd-DTPA as MR contrast agent for tumor imagingvia folate receptor-targeted delivery. Zhonghua Yi Xue Za Zhi 2007, 87 (10), 673-678.
33. Loubeyre, P., Canet, E., Zhao, S., Benderbous, S., Amiel, M., Revel, D., Carboxymethyl-dextran-gadolinium-DTPA as a bloodpoolcontrast agent for magnetic resonance angiography.Experimental study in rabbits. Invest. Radiol. 1996, 31 (5), 288-293.
34. Sirlin, C. B., Vera, D. R., Corbeil, J. A., Caballero, M. B., Buxton, R. B., Mattrey, R. F., Gadolinium-DTPA-dextran: amacromolecular MR blood pool contrast agent. Acad. Radiol. 2004,11 (12), 1361-1369.
35. Åberg, M., Hedner, U., Bergentz, S.-E., THE ANTITHROMBOTIC EFFECT OF DEXTRAN. Scand. J.Haematol. 1979, 23 (S34), 61-68.
36. Wang, S. C., Wikstrom, M. G., White, D. L., Klaveness, J., Holtz, E., Rongved, P., Moseley, M. E., Brasch, R. C., Evaluation of Gd-DTPA-labeled dextran as an intravascular MR contrast agent:imaging characteristics in normal rat tissues. Radiology 1990, 175(2), 483-488.
37. Bumb, A., Brechbiel, M. W., Choyke, P., Macromolecular anddendrimer-based magnetic resonance contrast agents. Acta Radiol.2010, 7, 751-767.
38. Mehvar, R., Dextrans for targeted and sustained delivery oftherapeutic and imaging agents. J. Control. Rel. 2000, 69 (1), 1-25.
39. Helbich, T. H., Gossman, A., Mareski, P. A., Raduchel, B., Roberts, T. P., Shames, D. M., Muhler, M., Turetschek, K., Brasch, R. C., A new polysaccharide macromolecular contrast agent forMR imaging: biodistribution and imaging characteristics. J. Magn.Reson. Imaging 2000, 11 (6), 694-701.
40. Huang, Y., Zhang, X., Zhang, Q., Dai, X., Wu, J., Evaluation ofdiethylenetriaminepentaacetic acid-manganese(II) complexesmodified by narrow molecular weight distribution of chitosanoligosaccharides as potential magnetic resonance imaging contrastagents. Magn. Reson. Imaging 2011, 29 (4), 554-560.
41. Lebduskova, P., Kotek, J., Hermann, P., Vander Elst, L., Muller, R.N., Lukes, I., Peters, J. A., A gadolinium(III) complex of acarboxylic-phosphorus acid derivative of diethylenetriaminecovalently bound to inulin, a potential macromolecular MRIcontrast agent. Bioconjug. Chem. 2004, 15 (4), 881-889.
42. Schwickert, H. C., Roberts, T. P., Muhler, A., Stiskal, M., Demsar, F., Brasch, R. C., Angiographic properties of Gd-DTPA-24-cascade-polymer--a new macromolecular MR contrast agent. Eur.J. Radiol. 1995, 20 (2), 144-150.
43. Unger, E. C., Shen, D., Wu, G., Stewart, L., Matsunaga, T. O., Trouard, T. P., Gadolinium-containing copolymeric chelates--anew potential MR contrast agent. MAGMA 1999, 8 (3), 154-162.
44. Kaneshiro, T., Ke, T., Jeong, E.-K., Parker, D., Lu, Z.-R., Gd-DTPA L-cystine bisamide copolymers as novel biodegradablemacromolecular contrast agents for MR blood pool imaging. Pharmaceut. Res. 2006, 23 (6), 1285-1294.
45. Mohs, A. M., Wang, X., Goodrich, K. C., Zong, Y., Parker, D. L., Lu, Z.-R., PEG-g-poly(GdDTPA-co-l-cystine): A BiodegradableMacromolecular Blood Pool Contrast Agent for MR Imaging. Bioconjug. Chem. 2004, 15 (6), 1424-1430.
46. Roberts, H. C., Saeed, M., Roberts, T. P. L., Mühler, A., Shames, D. M., Mann, J. S., Stiskal, M., Demsar, F., Brasch, R. C., Comparison of albumin-(Gd-DTPA)30 and Gd-DTPA-24-cascadepolymerfor measurements of normal and abnormal microvascularpermeability. J. Magn. Reson. Imaging 1997, 7 (2), 331-338.
47. Lu, Z.-R., Parker, D. L., Goodrich, K. C., Wang, X., Dalle, J. G., Buswell, H. R., Extracellular biodegradable macromoleculargadolinium(III) complexes for MRI. Magn. Reson. Med. 2004, 51(1), 27-34.
48. Zong, Y., Wang, X., Goodrich, K. C., Mohs, A. M., Parker, D. L., Lu, Z.-R., Contrast-enhanced MRI with new biodegradablemacromolecular Gd(III) complexes in tumor-bearing mice. Magn.Reson. Med. 2005, 53 (4), 835-842.
49. Ke, T., Feng, Y., Guo, J., Parker, D. L., Lu, Z.-R., Biodegradablecystamine spacer facilitates the clearance of Gd(III) chelates inpoly(glutamic acid) Gd-DO3A conjugates for contrast-enhancedMR imaging. Magn. Reson. Imaging 2006, 24 (7), 931-940.
50. Lu, Z.-R., Mohs, A. M., Zong, Y., Feng, Y., Polydisulfide Gd(III)chelates as biodegradable macromolecular magnetic resonanceimaging contrast agents. Intl. J. Nanomed. 2006, 1, 31-40.
51. Mohs, A. M., Nguyen, T., Jeong, E.-K., Feng, Y., Emerson, L., Zong, Y., Parker, D. L., Lu, Z.-R., Modification of Gd-DTPAcystine copolymers with PEG-1000 optimizes pharmacokineticsand tissue retention for magnetic resonance angiography. Magn.Reson. Med. 2007, 58 (1), 110-118.
52. Tomalia, D. A., Naylor, A. M., Goddard, W. A., StarburstDendrimers: Molecular-Level Control of Size, Shape, SurfaceChemistry, Topology, and Flexibility from Atoms to MacroscopicMatter. Angew. Chem. Int. Ed. 1990, 29 (2), 138-175.
53. Bryant, L. H., Jr., Brechbiel, M. W., Wu, C., Bulte, J. W., Herynek, V., Frank, J. A., Synthesis and relaxometry of high-generation (G =5, 7, 9, and 10) PAMAM dendrimer-DOTA-gadolinium chelates. J.Magn. Reson. Imaging 1999, 9 (2), 348-352.
54. Nwe, K., Xu, H., Regino, C. A. S., Bernardo, M., Ileva, L., Riffle, L., Wong, K. J., Brechbiel, M. W., A New Approach in thePreparation of Dendrimer-Based BifunctionalDiethylenetriaminepentaacetic Acid MR Contrast AgentDerivatives. Bioconjug. Chem. 2009, 20 (7), 1412-1418.
55. Nwe, K., Bernardo, M., Regino, C. A. S., Williams, M., Brechbiel, M. W., Comparison of MRI properties between derivatized DTPAand DOTA gadolinium-dendrimer conjugates. Bioorg. Med. Chem.2010, 18 (16), 5925-5931.
56. Konda, S. D., Aref, M., Wang, S., Brechbiel, M., Wiener, E. C., Specific targeting of folate-dendrimer MRI contrast agents to thehigh affinity folate receptor expressed in ovarian tumor xenografts. MAGMA 2001, 12 (2-3), 104-113.
57. Swanson, S. D., Kukowska-Latallo, J. F., Patri, A. K., Chen, C., Ge, S., Cao, Z., Kotlyar, A., East, A. T., Baker, J. R., Targetedgadolinium-loaded dendrimer nanoparticles for tumor-specificmagnetic resonance contrast enhancement. Intl. J. Nanomed. 2008,3 (2), 201-210.
58. Cheng, Z., Thorek, D. L. J., Tsourkas, A., Gadolinium-ConjugatedDendrimer Nanoclusters as a Tumor-Targeted T1 MagneticResonance Imaging Contrast Agent. Angew. Chem. Int. Ed. 2010,49 (2), 346-350.
59. Huang, C.-H., Nwe, K., Al-Zaki, A., Brechbiel, M., Tsourkas, A., Biodegradable polydisulfide dendrimer nanoclusters as MRIcontrast agents. ACS Nano 2012, 6(11), 6416-9424.
60. Tilcock, C., Unger, E., Cullis, P., MacDougall, P., Liposomal Gd-DTPA: preparation and characterization of relaxivity. Radiology 1989, 171 (1), 77-80.
61. Fossheim, S. L., Fahlvik, A. K., Klaveness, J., Muller, R. N., Paramagnetic liposomes as MRI contrast agents: influence ofliposomal physicochemical properties on the in vitro relaxivity. Magn. reson. imaging 1999, 17 (1), 83-89.
62. Tilcock, C., MacDougall, P., Unger, E., Cardenas, D., Fajardo, L., The effect of lipid composition on the relaxivity of Gd-DTPAentrapped in lipid vesicles of defined size. Biochim. Biophys. Acta.1990, 1022 (2), 181-186.
63. Kabalka, G. W., Buonocore, E., Hubner, K., Davis, M., Huang, L., Gadolinium-labeled liposomes containing paramagneticamphipathic agents targeted MRI contrast agents for the liver. Magn. Reson. Med. 1988, 8 (1), 89-95.
64. Mody, V. V., Nounou, M. I., Bikram, M., Novel nanomedicinebasedMRI contrast agents for gynecological malignancies. Adv.Drug Delivery Rev. 2009, 61 (10), 795-807.
65. Discher, B. M., Won, Y. Y., Ege, D. S., Lee, J. C. M., Bates, F. S., Discher, D. E., Hammer, D. A., Polymersomes: Tough vesiclesmade from diblock copolymers. Science 1999, 284 (5417), 1143-1146.
66. Katz, J. S., Zhong, S., Ricart, B. G., Pochan, D. J., Hammer, D. A., Burdick, J. A., Modular Synthesis of Biodegradable DiblockCopolymers for Designing Functional Polymersomes. J. Am.Chem. Soc. 2010, 132 (11), 3654-3655.
67. Cheng, Z., Thorek, D. L. J., Tsourkas, A., Porous Polymersomeswith Encapsulated Gd-Labeled Dendrimers as Highly EfficientMRI Contrast Agents. Adv. Funct. Mater. 2009, 19 (23), 3753-3759.
68. Cheng, Z., Tsourkas, A., Paramagnetic Porous Polymersomes.Langmuir 2008, 24 (15), 8169-8173.
69. Photos, P. J., Bacakova, L., Discher, B., Bates, F. S., Discher, D.E., Polymer vesicles in vivo: correlations with PEG molecularweight. J. Control. Rel. 2003, 90 (3), 323-334.
70. Glogard, C., Hovland, R., Fossheim, S. L., Aasen, A. J., Klaveness, J., Synthesis and physicochemical characterisation of newamphiphilic gadolinium DO3A complexes as contrast agents forMRI. J. Chem. Soc., Perkin Trans. 2 2000, (5), 1047-1052.
71. Torres, S., Martins, J. A., André, J. P., Geraldes, C. F. G. C., Merbach, A. E., Tóth, É., Supramolecular Assembly of anAmphiphilic GdIII Chelate: Tuning the Reorientational CorrelationTime and the Water Exchange Rate. Chem. Eur. J. 2006, 12 (3),940-948.
72. Tei, L., Gugliotta, G., Baranyai, Z., Botta, M., A new bifunctionalGdIII complex of enhanced efficacy for MR-molecular imagingapplications. Dalton Trans. 2009, (44), 9712-9714.
73. Kielar, F., Tei, L., Terreno, E., Botta, M., Large RelaxivityEnhancement of Paramagnetic Lipid Nanoparticles by Restrictingthe Local Motions of the GdIII Chelates. J. Am. Chem. Soc. 2010,132 (23), 7836-7837.
74. Turner, J. L., Pan, D., Plummer, R., Chen, Z., Whittaker, A. K., Wooley, K. L., Synthesis of gadolinium-labeled shell-crosslinkednanoparticles for magnetic resonance imaging applications. Adv.Funct. Mater. 2005, 15, 1248-1254.
75. Flacke, S., Fischer, S., Scott, M. J., Fuhrhop, R. J., Allen, J. S., McLean, M., Winter, P., Sicard, G. A., Gaffney, P. J., Wickline, S.A., Lanza, G. M., Novel MRI Contrast Agent for MolecularImaging of Fibrin. Circulation 2001, 104 (11), 1280-1285.
76. Lanza, G. M., Lorenz, C. H., Fischer, S. E., Scott, M. J., Cacheris, W. P., Kaufmann, R. J., Gaffney, P. J., Wickline, S. A. Enhanceddetection of thrombi with a novel fibrin-targeted magneticresonance imaging agent. Acad. Radiol. 1998, 5, Supplement 1 (0),S173-S176.
77. Winter, P. M., Caruthers, S. D., Yu, X., Song, S.-K., Chen, J., Miller, B., Bulte, J. W. M., Robertson, J. D., Gaffney, P. J., Wickline, S. A., Lanza, G. M., Improved molecular imagingcontrast agent for detection of human thrombus. Magn. Reson.Med. 2003, 50 (2), 411-416.
78. Winter, P., Athey, P., Kiefer, G., Gulyas, G., Frank, K., Fuhrhop, R., Robertson, D., Wickline, S., Lanza, G., Improved paramagneticchelate for molecular imaging with MRI. J. Magn. Magn. Mater.2005, 293 (1), 540-545.
79. [79] Lanza, G., Winter, P., Caruthers, S., Hughes, M., Hu, G., Schmieder, A., Wickline, S., Theragnostics for tumor and plaqueangiogenesis with perfluorocarbon nanoemulsions. Angiogenesis 2010, 13 (2), 189-202.
80. Cyrus, T., Abendschein, D. R., Caruthers, S. D., Harris, T. D., Glattauer, V., Werkmeister, J. A., Ramshaw, J. A., Wickline, S. A., Lanza, G. M., MR three-dimensional molecular imaging ofintramural biomarkers with targeted nanoparticles. J. Cardiovasc.Magn. Reson. 2006, 8 (3), 535-541.
81. Schmieder, A. H., Winter, P. M., Caruthers, S. D., Harris, T. D., Williams, T. A., Allen, J. S., Lacy, E. K., Zhang, H., Scott, M. J., Hu, G., Robertson, J. D., Wickline, S. A., Lanza, G. M., MolecularMR imaging of melanoma angiogenesis with alphanubeta3-targetedparamagnetic nanoparticles. Magn. Reson. Med. 2005, 53 (3), 621-627.
82. Taylor, K. M. L., Kim, J. S., Rieter, W. J., An, H., Lin, W., Lin, W., Mesoporous Silica Nanospheres as Highly Efficient MRIContrast Agents. J. Am. Chem. Soc. 2008, 130 (7), 2154-2155.
83. Kim, J., Kim, H. S., Lee, N., Kim, T., Kim, H., Yu, T., Song, I. C., Moon, W. K., Hyeon, T., Multifunctional Uniform NanoparticlesComposed of a Magnetite Nanocrystal Core and a MesoporousSilica Shell for Magnetic Resonance and Fluorescence Imaging andfor Drug Delivery. Angew. Chem. Int. Ed. 2008, 47 (44), 8438-8441.
84. [84] Carniato, F., Tei, L., Dastru, W., Marchese, L., Botta, M., Relaxivity modulation in Gd-functionalised mesoporous silicas. Chem. Commun. 2009, (10), 1246-1248.
85. McDonald, M. A., Watkin, K. L., Investigations into thePhysicochemical Properties of Dextran Small ParticulateGadolinium Oxide Nanoparticles. Acad. Radiol. 2006, 13 (4), 421-427.
86. Engström, M., Klasson, A., Pedersen, H., Vahlberg, C., Käll, P.-O., Uvdal, K., High proton relaxivity for gadolinium oxidenanoparticles. Magn. Reson. Mater. Phy. 2006, 19 (4), 180-186.
87. Fortin, M.-A.; Jr, R. M. P.; Söderlind, F.; Klasson, A.; Engstr̈m, M.; Veres, T.; Käll, P.-O.; Uvdal, K., Polyethylene glycol-covered ultra-small Gd2O3 nanoparticles for positive contrast at 1.5 T magnetic resonance clinical scanning. Nanotechnology 2007, 18, 395501.
88. Ahren, M., Selegard, L., Klasson, A., Soderlind, F., Abrikossova, N., Skoglund, C., Bengtsson, T., Engstrom, M., Kall, P. O., Uvdal, K., Synthesis and characterization of PEGylated Gd2O3nanoparticles for MRI contrast enhancement. Langmuir 2010, 26(8), 5753-5762.
89. Gu, Z., Peng, H., Hauge, R. H., Smalley, R. E., Margrave, J. L., Cutting Single-Wall Carbon Nanotubes through Fluorination. NanoLett. 2002, 2 (9), 1009-1013.
90. Sitharaman, B., Kissell, K. R., Hartman, K. B., Tran, L. A., Baikalov, A., Rusakova, I., Sun, Y., Khant, H. A., Ludtke, S. J., Chiu, W., Laus, S., Toth, E., Helm, L., Merbach, A. E., Wilson, L.J., Superparamagnetic gadonanotubes are high-performance MRIcontrast agents. Chem. Commun. 2005, (31), 3915-3917.
91. Hartman, K. B., Laus, S., Bolskar, R. D., Muthupillai, R., Helm, L., Toth, E., Merbach, A. E., Wilson, L. J., Gadonanotubes asultrasensitive pH-smart probes for magnetic resonance imaging. Nano Lett. 2008, 8 (2), 415-419.
92. Mackeyev, Y., Hartman, K. B., Ananta, J. S., Lee, A. V., Wilson, L. J., Catalytic Synthesis of Amino Acid and Peptide DerivatizedGadonanotubes. J. Am. Chem. Soc. 2009, 131 (24), 8342-8343.
93. Raja, K. S., Wang, Q., Gonzalez, M. J., Manchester, M., Johnson, J. E., Finn, M. G., Hybrid Virus-Polymer Materials. 1. Synthesisand Properties of PEG-Decorated Cowpea Mosaic Virus. Biomacromolecules 2003, 4 (3), 472-476.
94. [94] Wang, Q., Lin, T., Tang, L., Johnson, J. E., Finn, M. G., Icosahedral Virus Particles as Addressable Nanoscale BuildingBlocks. Angew. Chem. Int. Ed. 2002, 41 (3), 459-462.
95. Liepold, L. O., Abedin, M. J., Buckhouse, E. D., Frank, J. A., Young, M. J., Douglas, T., Supramolecular protein cage compositeMR contrast agents with extremely efficient relaxivity properties. Nano Lett. 2009, 9 (12), 4520-4526.
96. Pokorski, J. K., Breitenkamp, K., Liepold, L. O., Qazi, S., Finn, M.G., Functional virus-based polymer-protein nanoparticles by atomtransfer radical polymerization. J. Am. Chem. Soc. 2011, 133 (24),9242-9245.
97. AE, v. d. V., Reverse cholesterol transport: from classical view tonew insights. World J. Gastroenterol. 2010, 16 (47), 5908-5915.
98. Firestone, R. A., Low-Density Lipoprotein as a Vehicle forTargeting Antitumor Compounds to Cancer Cells. Bioconjug.Chem. 1994, 5 (2), 105-113.
99. Corbin, I. R., Li, H., Chen, J., Lund-Katz, S., Zhou, R., Glickson, J. D., Zheng, G., Low-density lipoprotein nanoparticles asmagnetic resonance imaging contrast agents. Neoplasia 2006, 8 (6),488-498.