Dendrimers as carriers for contrast agents in magnetic resonance imaging

Chinese Science Bulletin

Volumn 55, Issue 27-28, 2010, Pages 3085-3093

  Yan, Guo Ping ^a   Ai, Chao Wu ^a   Li, Liang ^a   Zong, Rong Feng ^a   Liu, Fan ^a  

^a WUHAN INSTITUTE OF TECHNOLOGY   (China)

Author keywords

contrast agents; dendrimers; magnetic resonance imaging (MRI); paramagnetic metal chelates; tissue or organ targeting

Indexed keywords

EID: 77958472095     PISSN: 10016538     EISSN: 18619541     Source Type: Journal    
DOI: 10.1007/s11434-010-3267-4     Document Type: Review

References (101)

1. Lauterbur P C. Image formation by induced local interactions: Examples employing nuclear magnetic resonance. Nature, 1973, 242: 190-191.
2. Gallez B, Swartz H M. In vivo EPR: When, how and why? NMR Biomed, 2004, 17: 223-225.
3. Lauffer R B. Paramagnetic metal complexes as water proton relaxation agents for NMR imaging: Theory and design. Chem Rev, 1987, 87: 901-927.
4. Sener R N. Diffusion MRI findings in phenylketonuria. Eur Radiol, 2003, 13: L226-L229.
5. Caravan P, Ellison J J, Mcmurry T J, et al. Gadolinium (III) chelates as MRI contrast agents: Structure, dynamics, and applications. Chem Rev, 1999, 99: 2293-2352.
6. Yan G P, Zhuo R X. Research progress of magnetic resonance imaging contrast agents. Chinese Sci Bull, 2001, 46: 1233-1237.
7. Yan G P, Robinsonand L, Hogg P. Magnetic resonance imaging contrast agents: Overview and perspectives. Radiography, 2007, 13: e5-e19.
8. Yan G P, Peng L, Jian S Q, et al. Spin probes for electron paramagnetic resonance imaging. Chinese Sci Bull, 2008, 53: 3777-3789.
9. Yan G P, Bischa D, Bottle S E. Synthesis and properties of novel porphyrin spin probes containing isoindoline nitroxides. Free Radic Biol Med, 2007, 43: 111-116.
10. Platas-Iglesias C, Mato-Iglesias M, Djanashvili K, et al. Lanthanide chelates containing pyridine units with potential application as contrast agents in magnetic resonance imaging. Chem Eur J, 2004, 10: 3579-3590.
11. Weinmann H J, Brash R C, Press W R, et al. Characteristic of gadolinium-DTPA complex: A potential NMR contrast agent. Am J Radiology, 1984, 142: 619-624.
12. Comblin V, Gilsoul D, Hermann M, et al. Designing new MRI contrast agents: A coordination chemistry challenge. Coord Chem Rev, 1999, 185: 451-470.
13. Wedeking P, Sotak C H, Telser J, et al. Quantitative dependence of MR signal intensity on tissue concentration of Gd(HP-DO3A) in the nephrectomized rat. Magn Reson Imaging, 1992, 10: 97-108.
14. 2- related to NMR imaging. Inorg Chem, 1993, 32: 3844-3850.
15. Zhuo R X, Lu Z R, Wei J F, et al. The methods of synthesis of polyaminocarboxylates metal complexes. Chinese Patent, 1995, 95-1 19302. 3.
16. Lowe M P. MRI contrast agents: The next generation. Aust J Chem, 2002, 55: 551-556.
17. Waters E A, Wickline S A. Contrast agents for MRI. Basic Res Cardiol, 2008, 103: 114-121.
18. Yan G P, Zhang J Y, Zhou J X, et al. Targeted contrast agents for molecular imaging in magnetic resonance imaging (MRI). In: Chen X Y, ed. Recent Advances of Bioconjugate Chemistry in Molecular Imaging. Kerala, India: Research Signpost, 2008. 371-398.
19. Wallace R A, Haar J P, Miller D B, et al. Synthesis and preliminary evaluation of MP-2269: A novel, nonaromatic small-molecule blood-pool MR contrast agent. Magn Reson Med, 1998, 40: 733-739.
20. Duarte M G, Gil M H, Peters J A, et al. Synthesis, characterization, and relaxivity of two linear Gd(DTPA)-polymer conjugates. Bioconjugate Chem, 2001, 12: 170-177.
21. Tóth E, Uffelen I V, Helm L, 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.
22. Mohs A M, Wang X H, Goodrich K C, et al. PEG-g-poly (DTPA-co-L-cystine): A biodegradable macromolecular blood pool contrast agent for MR imaging. Bioconjugate Chem, 2004, 15: 1424-1430.
23. Lu Z R, Parker D L, Goodrich K C, et al. Extracellular biodegradable macromolecular gadolinium(III) complexes for MRI. Magn Reson Med, 2004, 51: 27-34.
24. Ouyang M, Zhuo R X, Fu G C. Study on synthesis and relaxivity of paramagnetic polyester metal complexes for MRI. Ion Exchange Adsorpt, 1996, 12: 324-327.
25. Bai Z W, Zhuo R X. The synthesis and relaxivity of polyester-amide MRI contrast agent. Ion Exchange Adsorpt, 1996, 12: 332-335.
26. Yan G P, Zhuo R X, Zhang X, et al. Hepatic targeting macromolecular MRI contrast agents. Polym Int, 2002, 51: 892-898.
27. Brasch R C. Rationable and applications for macromolecular Gd-based contrast agents. Magn Reson Med, 1991, 22: 282-287.
28. 3+-complex. J Biol Inorg Chem, 1997, 2: 470-479.
29. Schuhmann-Giampieri G, Schmitt-Willich H, Frenzel T, et al. 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.
30. Roberts H C, Saeed M, Roberts T P L, et al. 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.
31. Judd R M, Reeder S B, May-Newman K. Effects of water exchange on the measurement of myocardial perfusion using paramagnetic contrast agents. Magn Reson Med, 1999, 41: 334-342.
32. Wen X X, Jackson E F, Price R E, et al. Synthesis and characterization of poly(L-glutamic acid) gadolinium chelate: A new biodegradable MRI contrast agent. Bioconjugate Chem, 2004, 15: 1408-1415.
33. Lu Z R, Wang X H, Parker D L, et al. Poly(L-glutamic acid) Gd(III)-DOTA conjugate with a degradable spacer for magnetic resonance imaging. Bioconjugate Chem, 2003, 14: 715-719.
34. Uzgiris E E, Cline H, Moasser B, et al. Conformation and structure of polymeric contrast agents for medical imaging. Biomacromolecules, 2004, 5: 54-61.
35. Yan G P, Wang X Y, Wang X L, et al. Synthesis and in vitro property study of polyaspartamides. Chin J Chem, 2007, 25: 1748-1753.
36. Yan G P, Zhuo R X, Xu M Y, et al. Liver-targeting Macromolecular MRI Contrast Agents. Sci China Ser B-Chem, 2001, 44: 344-352.
37. Waeckerle-Mena Y, Groettrupa M. PLGA microspheres for improved antigen delivery to dendritic cells as cellular vaccines. Adv Drug Deliv Rev, 2005, 57: 475-482.
38. Tansey W, Ke S, Cao X Y, et al. Synthesis and characterization of branched poly(L-glutamic acid) as a biodegradable drug carrier. J Control Release, 2004, 94: 39-51.
39. Patri A K, Majoros I J, Baker J R. Dendritic polymer macromolecular carriers for drug delivery. Curr Opin Chem Biol, 2002, 6: 466-471.
40. Bezouska K. Design, functional evaluation and biomedical applications of carbohydrate dendrimers glycodendrimers. Rev Mol Biotechnol, 2002, 90: 269-290.
41. Choia J S, Namb K, Parkb J Y, et al. Enhanced transfection efficiency of PAMAM dendrimer by surface modification with L-arginine. J Control Release, 2004, 99: 445-456.
42. Namazi H, Adeli M. Dendrimers of citric acid and poly (ethylene glycol) as the new drug-delivery agents. Biomaterials, 2005, 26: 1175-1183.
43. Devarakonda B, Hill R A, de Villiers M M. The effect of PAMAM dendrimer generation size and surface functional group on the aqueous solubility of nifedipine. Int J Pharm, 2004, 284: 133-140.
44. Metullio L, Ferrone M, Coslanich A, et al. Polyamidoamine (yet not PAMAM) dendrimers as bioinspired materials for drug delivery: Structure-activity relationships by molecular simulations. Biomacromolecules, 2004, 5: 1371-1378.
45. Zhou J H, Wu J Y, Hafdi N, et al. PAMAM dendrimers for efficient siRNA delivery and potent gene silencing. Chem Commun, 2006: 2362-2364.
46. Sanchez-Sancho F, Perez-Inestrosa E, Suau R, et al. Dendrimers as carrier protein mimetics for IgE antibody recognition: Synthesis and characterization of densely penicilloylated dendrimers. Bioconjugate Chem, 2002, 13: 647-653.
47. Allen M J, Raines R T, Kiessling L L. Contrast agents for mgnetic resonance imaging synthesized with ring-opening metathesis polymerization. J Am Chem Soc, 2006, 128: 6534-6535.
48. Neerman M F, Zhang W, Parrish A R, et al. In vitro and in vivo evaluation of a melamine dendrimer as a vehicle for drug delivery. Int J Pharm, 2004, 281: 129-132.
49. Beezer A E, King A S H, Martin K, et al. Dendrimers as potential drug carriers; encapsulation of acidic hydrophobes within water soluble PAMAM derivatives. Tetrahedron, 2003, 59: 3873-3880.
50. Vandamme T F, Brobeck L. Poly(amidoamine) dendrimers as ophthalmic vehicles for ocular delivery of pilocarpine nitrate and tropicamide. J Control Release, 2005, 102: 23-38.
51. Schatzleina A G, Zinselmeyera B H, Dufesa A C, et al. Preferential liver gene expression with polypropylenimine dendrimers. J Control Release, 2005, 101: 247-258.
52. Balogh L, de Leuze-Jallouli A, Dvornic P, et al. Architectural copolymers of PAMAM dendrimers and ionic polyacetylenes. Macromolecules, 1999, 32: 1036-1042.
53. Hudson S D, Jung H T, Percec V, et al. Direct visualization of individual cylindrical and spherical supramolecular dendrimers. Science, 1997, 278: 449-452.
54. Kleinman M H, Flory J H, Tomalia D A, et al. Effect of protonation and PAMAM dendrimer size on the complexation and dynamic mobility of 2-naphthol. J Phys Chem B, 2000, 104: 11472-11479.
55. Nicolle G M, Toth E, Schmitt-Willich H, et al. The impact of rigidity and water exchange on the relaxivity of a dendritic MRI contrast agent. Chem Eur J, 2002, 8: 1040-1048.
56. Stiriba S E, Frey H, Haag R. Dendritic polymers in biomedical applications: From potential to clinical use in diagnostics and therapy. Angew Chem Int Ed, 2002, 41: 1329-1334.
57. Esfand R, Tomalia D A. Poly(amidoamine) (PAMAM) dendrimers: From biomimicry to drug delivery and biomedical applications. Drug Discov Today, 2001, 6: 427-436.
58. Kobayshi H, Kawamoto S, Jo S K, et al. Macromolecular MRI contrast agents with small dendrimers: Pharmacokinetic differences between sizes and cores. Bioconjugate Chem, 2003, 14: 388-394.
59. Margerum L D, Campion B K, Koo M, et al. Gadolinium (III) DO3A macrocycles and polyethylene glycol coupled to dendriers effect of molecular weight on physical and biological properties of macromolecular magnetic resonance imaging contrast agents. J Alloy Comp, 1997, 249: 185-190.
60. Fischer M, Vögtle F. Dendrimers: From design to application-A progress report. Angew Chem Int Ed, 1999, 38: 884-905.
61. Wiener E C, Brechbiel M W, Brothers H, et al. Dendrimer-based metal chelates: A new class of magnetic resonance imaging contrast agents. Magn Reson Med, 1994, 31: 1-8.
62. Kobayashi H, Jo S K, Kawamoto S, 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.
63. Kobayashi H, Kawamoto S, Saga T, et al. Positive effects of polyethylene glycol conjugation to generation-4 polyamidoamine dendrimers as macromolecular MR contrast agents. Magn Reson Med, 2001, 46: 781-788.
64. Wiener E C, Auteri F P, Chen J W, et al. Molecular dynamics of Ion-chelate complexes attached to dendrimers. J Am Chem Soc, 1996, 118: 7774-7782.
65. Bryant L H, Brechbiel M W, Wu C C, et al. 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.
66. Langereis S, de Lussanet Q G, van Genderen M H P, et al. Evaluation of Gd(III)DTPA-terminated poly(propylene imine) dendrimers as contrast agents for MR imaging. NMR Biomed, 2006, 19: 133-141.
67. Canetta E, Maino G. Molecular dynamic analysis of the structure of dendrimers. Nucl Instrum Meth Phys Res B, 2004, 213: 71-74.
68. Kobayashi H, Brechbiel M W. Nano-sized MRI contrast agents with dendrimer cores. Adv Drug Deliv Rev, 2005, 57: 2271-2286.
69. Kobayashi H, Kawamoto S, Star R A, et al. Micro-magnetic resonance lymphangiography in mice using a novel dendrimer-based magnetic resonance imaging contrast agent. Cancer Res, 2003, 63: 271-276.
70. Kobayashi H, Kawamoto S, Choyke P L, et al. Comparison of dendrimer-based macromolecular contrast agents for dynamic micro-magnetic resonance lymphangiography. Magn Reson Med, 2003, 50: 758-766.
71. Francese G, Dunand F A, Loosli C, et al. Functionalization of PAMAM dendrimers with nitronyl nitroxide radicals as models for the outer-sphere relaxation in dentritic potential MRI contrast agents. Magn Reson Chem, 2003, 41: 81-83.
72. Winalski C S, Shortkroff S, Mulkern R V, et al. Magnetic resonance relaxivity of dendrimer-linked nitroxides. Magn Reson Med, 2002, 48: 965-972.
73. Strable E, Bulte J W M, Moskowitz B, et al. Synthesis and characterization of soluble iron oxide-dendrimer composites. Chem Mater, 2001, 13: 2201-2209.
74. Yan G P, Liu M L, Li L Y. Studies on polyaspartamide gadolinium complexes containing sulfadiazine groups as MRI contrast agents. Bioconjugate Chem, 2005, 16: 967-971.
75. Yan G P, Liu M L, Li L Y. Studies on polyaspartamide gadolinium complexes as potential magnetic resonance imaging contrast agents. Radiography, 2005, 11: 117-122.
76. Yan G P, Zheng C Y, Cao W, et al. Synthesis and preliminary evaluation of gadolinium complexes containing sulfonamide groups as potential MRI contrast agents. Radiography, 2003, 9: 35-41.
77. Yan G P, Zhuo R X, Yang Y H, et al. Tumor-selective macromolecular MRI contrast agents. J Bioact Compat Polym, 2002, 17: 139-151.
78. Sega E I, Low P S. Tumor detection using folate receptor-targeted imaging agents. Cancer Metastasis Rev, 2008, 27: 655-664.
79. Wiener E C, Konda S, Shadron A, et al. Targeting dendrimer-chelates to tumours and tumour cells expressing the high-affinity folate receptor. Invest Radiol, 1997, 32: 748-754.
80. Konda S D, Aai]ref M, Wang S, et al. Specific targeting of folate-dendrimer MRI contrast agents to the high affinity folate receptor expressed in ovarian tumor xenografts. Magnetic Resonance Materials in Physics. Biol Med, 2001, 12: 104-113.
81. Sun C, Sze R, Zhang M Q. Folic acid-PEG conjugated superparamagnetic nanoparticles for targeted cellular uptake and detection by MRI. J Biomed Mater Res A, 2006, 78A: 550-557.
82. Kobayashi H, Kawamoto S, Saga T, et al. Avidin-dendrimer-(1B4M-Gd)254: A tumor-targeting therapeutic agent for gadolinium neutron capture therapy of intraperitoneal disseminated tumor which can be monitored by MRI. Bioconjugate Chem, 2001, 12: 587-593.
83. Yan G P, Hu B, Liu M L, et al. Synthesis and evaluation of gadolinium complexes based on PAMAM as MRI contrast agents. J Pharm Pharmacol, 2005, 57: 351-357.
84. Du B, Zhou R J, Zhou R X. Synthesis of cyclic core dendritic polymer and its usage as a vector for transferring foreign DNA into human cells. Chin Chem Lett, 1998, 9: 635-638.
85. Yan G P, Bottle S E, Zhuo R X, et al. Evaluation on dendritic gadolinium complexes as MRI contrast agents. J Bioact Compatible Polym, 2004, 19: 453-465.
86. Langereis S, Dirksen A, Hackeng T M, et al. Dendrimers and magnetic resonance imaging. New J Chem, 2007, 31: 1152-1160.
87. Lu Z R, Ye F R, Vaidya A. Polymer platforms for drug delivery and biomedical imaging. J Control Release, 2007, 122: 269-277.
88. Kim J H, Park K, Nam H Y, et al. Polymers for bioimaging. Prog Polym Sci, 2007, 32: 1031-1053.
89. Lee L J, Park K, Lee S, et al. New generation of multifunctional nanoparticles for cancer imaging and therapy. Adv Funct Mater, 2009, 19: 1553-1566.
90. Mulder A, Huskens J, Reinhoudt D N. Multivalency in supramolecular chemistry and nanofabrication. Org Biomol Chem, 2004, 2: 3409-3424.
91. Badjic J D, Nelson A, Cantrill S J, et al. Multivalency and cooperativity in supramolecular chemistry. Ace Chem Res, 2005, 38: 723-732.
92. Koyama Y, Talanov V S, Bernardo M, et al. A dendrimer-based nanosized contrast agent dual-labeled for magnetic resonance and optical fluorescence imaging to localize the sentinel lymph node in mice. J Magn Reson Imaging, 2007, 25: 866-871.
93. Dirksen A, Langereis S, de Waal B F M, et al. A supramolecular approach to multivalent target-specific MRI contrast agents for angiogenesis. Chem Commun, 2005: 2811-2813.
94. Liu J Y, Zheng Y F. Development of magnetic resonance imaging contrast agents with PAMAM dendrimer cores. Mater Rev, 2007, 5: 69-72.
95. Talanov V S, Regin O C A, Kobayashi H, et al. Dendrimer-based nanoprobe for dual modality magnetic resonance and fluorescence imaging. Nano Lett, 2006, 6: 1459-1463.
96. Wu P, Malkoch M, Hunt J N, et al. Multivalent, bifunctional dendrimers prepared by click chemistry. Chem Commun, 2005: 5775-5777.
97. Lee C C, MacKay J A, Frechet J M, et al. Designing dendrimers for biological applications. Nat Biotechnol, 2005, 23: 1517-1526.
98. Bai J F, Gu W, Ye L. The potential application of dendrimers in medicine. Chemistry, 2001, 64: W119.
99. Sadler K, Tam J P. Peptide dendrimers: Applications and synthesis. Rev Mol Biotechnol, 2002, 90: 157-354.
100. Turnbull W B, Stoddart J F. Design and synthesis of glycodendrimers. Rev Mol Biotechnol, 2002, 90: 231-255.
101. Dirksen A, Meijer E W, Adriaens W, et al. Strategy for the synthesis of multivalent peptide-based nonsymmetric dendrimers by native chemical ligation. Chem Commun, 2006, 1667-1669.