Dendrimers in biomedical applications - Reflections on the field

Advanced Drug Delivery Reviews

Volumn 57, Issue 15, 2005, Pages 2106-2129

  Svenson, Sönke ^a   Tomalia, Donald A ^a  

^a Dendritic NanoTechnologies Inc   (United States)

Author keywords

Artificial proteins; Biocompatibility; Cytotoxicity; Dendrimer synthesis; Dendrimers; Drug delivery; Drug release; Encapsulation; Folate receptor; Gene transfection; Imaging agents; MRI; PAMAM; Targeting

Indexed keywords

ADSORPTION; BIOCOMPATIBILITY; BIOMEDICAL ENGINEERING; GENES; MAGNETIC RESONANCE IMAGING; PROTEINS; SYNTHESIS (CHEMICAL); TOXICITY; TUMORS;

CYTOTOXICITY; DENDRIMER SYNTHESIS; DRUG DELIVERY; DRUG RELEASE; IMAGING AGENTS;

DENDRIMERS;

ALPHA CYCLODEXTRIN; ANTIBIOTIC AGENT; ANTIINFECTIVE AGENT; ANTIINFLAMMATORY AGENT; ANTINEOPLASTIC AGENT; BETA CYCLODEXTRIN; CHITOSAN; CISPLATIN; CONTRAST MEDIUM; DENDRIMER; DOXORUBICIN; DRUG CARRIER; FLUOROURACIL; GADOLINIUM PENTETATE; GADOLINIUM PENTETATE DERIVATIVE; GADOTERIC ACID; GAMMA CYCLODEXTRIN; IBUPROFEN; INDOMETACIN; MACROGOL; MACROGOL 2000; MACROGOL 5000; METHOTREXATE; NIFEDIPINE; POLYAMIDOAMINE; POLYLYSINE; POLYMER; SUPERFECT; TIOCONAZOLE; TRIAZINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VIVAGEL;

BIOCOMPATIBILITY; BIOMEDICINE; CANCER THERAPY; CLINICAL TRIAL; CYTOTOXICITY; DIAGNOSTIC IMAGING; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG SYNTHESIS; ENCAPSULATION; GENETIC TRANSFECTION; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; PARTICLE SIZE; PRIORITY JOURNAL; REVIEW; SEXUALLY TRANSMITTED DISEASE;

EID: 28744443398     PISSN: 0169409X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.addr.2005.09.018     Document Type: Note

References (169)

1. S. Svenson Controlling surfactant self-assembly Curr. Opin. Colloid Interface Sci. 9 2004 201 212
2. S. Svenson Self-assembly and self-organization: important processes-but can we predict them? J. Dispers. Sci. Technol. 25 2004 101 118
3. S. Svenson Carrier-based drug delivery ACS Symposium Series vol. 879 2004 American Chemical Society Washington, DC and references therein
4. D.A. Tomalia Birth of a new macromolecular architecture: dendrimers as quantized building blocks for nanoscale synthetic organic chemistry Aldrichimica Acta 37 2004 39 57
5. D.A. Tomalia, H. Baker, J. Dewald, M. Hall, G. Kallos, S. Martin, J. Roeck, J. Ryder, and P. Smith Dendritic macromolecules: synthesis of starburst dendrimers Macromolecules 19 1986 2466 2468
6. D.A. Tomalia Dendrimer molecules Sci. Am. 272 1995 62 66
7. D.A. Tomalia Starburst dendrimers-nanoscopic supermolecules according to dendritic rules and principles Macromol. Symp. 101 1996 243 255
8. C.J. Hawker, and J.M.J. Fréchet Preparation of polymers with controlled molecular architecture. A new convergent approach to dendritic macromolecules J. Am. Chem. Soc. 112 1990 7638 7647
9. A.W. Bosman, H.M. Janssen, and E.W. Meijer About dendrimers: structure, physical properties and applications Chem. Rev. 99 1999 1665 1688
10. D.A. Tomalia, and I. Majoros Dendrimeric supramolecular and supramacromolecular assemblies A. Ciferri Supramolecular Polymers 2000 Marcel Dekker New York 359 435
11. M. Fischer, and F. Vögtle Dendrimers: from design to application-a progress report Angew. Chem., Int. Ed. Engl. 38 1999 884 905
12. Dendrimers Topics Curr. Chem. vol. 197 1998 Springer-Verlag Heidelberg
13. Dendrimers II - Architecture, Nanostructure and Supramolecular Chemistry Topics Curr. Chem. vol. 210 2000 Springer-Verlag Heidelberg
14. Dendrimers III - Design, Dimension, Function Topics Curr. Chem. vol. 212 2001 Springer-Verlag Heidelberg
15. Dendrimers IV - Metal Coordination, Self Assembly, Catalysis Topics Curr. Chem. vol. 217 2001 Springer-Verlag Heidelberg
16. Dendrimers V Topics Curr. Chem. vol. 228 2003 Springer-Verlag Heidelberg
17. J.M.J. Fréchet D.A. Tomalia Dendrimers and Other Dendritic Polymers 2001 Wiley Chichester
18. V. Maraval, A.-M. Caminade, J.-P. Majoral, and J.-C. Blais Dendrimer design: how to circumvent the dilemma of a reduction of steps or an increase of function multiplicity? Angew. Chem., Int. Ed. Engl. 42 2003 1822 1826
19. V. Maraval, J. Pyzowski, A.-M. Caminade, and J.-P. Majoral "Lego" chemistry for the straightforward synthesis of dendrimers J. Org. Chem. 68 2003 6043 6046
20. P. Wu, A.K. Feldman, A.K. Nugent, C.J. Hawker, A. Scheel, B. Voit, J. Pyun, J.M.J. Fréchet, K.B. Sharpless, and V.V. Fokin Efficiency and fidelity in a click-chemistry route to triazole dendrimers by the copper(I)-catalyzed ligation of azides and alkynes Angew. Chem., Int. Ed. Engl. 43 2004 3928 3932
21. D.A. Tomalia, and R. Esfand Dendrons, dendrimers and dendrigrafts Chem. Ind. 11 1997 416 420
22. H.M. Brothers II, L.T. Piehler, and D.A Tomalia Slab-gel and capillary electrophoretic characterization of polyamidoamine dendrimers J. Chromatogr., A 814 1998 233 246
23. J.-P. Majoral, and A.-M. Caminade Dendrimers containing heteroatoms (Si, P, B, Ge or Bi) Chem. Rev. 99 1999 845 880
24. S. Hecht, and J.M.J. Fréchet Dendritic encapsulation of function: applying nature's site isolation principle from biomimetics to materials science Angew. Chem., Int. Ed. Engl. 40 2001 74 91
25. D.L. Jiang, and T. Aida A dendritic iron porphyrin as a novel haemoprotein mimic: effects of the dendrimer cage on dioxygen-binding activity Chem. Commun. 1996 1523 1524
26. P.J. Dandliker, F. Diederich, A. Zingg, J.P. Gisselbrecht, M. Gross, A. Louati, and E. Sanford Dendrimers with porphyrin cores: synthetic models for globular heme proteins Helv. Chim. Acta 80 1997 1773 1801
27. P. Weyermann, J.P. Gisselbrecht, C. Boudon, F. Diederich, and M. Gross Dendritic iron porphyrins with tethered axial ligands: new model compounds for cytochromes Angew. Chem., Int. Ed. Engl. 38 1999 3214 3219
28. H. Arima, F. Kihara, F. Hirayama, and K. Uekama Enhancement of gene expression by polyamidoamine dendrimer conjugates with α-, β-, and γ-cyclodextrins Bioconjug. Chem. 12 2001 476 484
29. T. Hudde, S.A. Rayner, R.M. Comer, M. Weber, J.D. Isaacs, H. Waldmann, D.P.F. Larkin, and A.J.T. George Activated polyamidoamine dendrimers, a nonviral vector for gene-transfer to the cornial endothelium Gene Ther. 6 1999 939 943
30. J.D. Eichman, A.U. Bielinska, J.F. Kukowska-Latallo, and J.R. Baker Jr. The use of PAMAM dendrimers in the efficient transfer of genetic material into cells Pharm. Sci. Technol. Today 3 2000 232 245
31. P. Singh Terminal groups in starburst dendrimers: activation and reactions with proteins Bioconjug. Chem. 9 1998 54 63
32. D.M. Watkins, Y. Sayed-Sweet, J.W. Klimash, N.J. Turro, and D.A. Tomalia Dendrimers with hydrophobic cores and the formation of supramolecular dendrimer-surfactant assemblies Langmuir 13 1997 3136 3141
33. I. Lee, B.D. Athey, A.W. Wetzel, W. Meixner, and J.R. Baker Jr. Structural molecular dynamics studies on polyamidoamine dendrimers for a therapeutic application: effects of pH and generation Macromolecules 35 2002 4510 4520
34. W. Chen, D.A. Tomalia, and J.L. Thomas Unusual pH-dependent polarity changes in PAMAM dendrimers: evidence for pH-responsive conformational changes Macromolecules 33 2000 9169 9172
35. I.B. Rietveld, W.G. Bouwman, M.W.P.L. Baars, and R.K. Heenan Location of the outer shell and influence of pH on carboxylic acid-functionalized poly(propylene imine) dendrimers Macromolecules 34 2001 8380 8383
36. M. Chai, Y. Niu, W.J. Youngs, and P.L. Rinaldi Structure and conformation of DAB dendrimers in solution via multidimensional NMR techniques J. Am. Chem. Soc. 123 2001 4670 4678
37. M. Ballauff, Structure of dendrimers in dilute solution, in [13], 177-194.
38. Y. Sayed-Sweet, D.M. Hedstrand, R. Spinder, and D.A. Tomalia Hydrophobically modified poly(amidoamine) (PAMAM) dendrimers: their properties at the air-water interface and use as nanoscopic container molecules J. Mater. Chem. 7 1997 1199 1205
39. J. Recker, D.J. Tomcik, and J.R. Parquette Folding dendrons: the development of solvent-, temperature-, and generation-dependent chiral conformational order in intramolecularly hydrogen-bonded dendrons J. Am. Chem. Soc. 122 2000 10298 10307
40. U. Boas, A.J. Karlsson, B.F.M. de Waal, and E.W. Meijer Synthesis and properties of new thiourea-functionalized poly(propylene imine) dendrimers and their role as hosts for urea functionalized guests J. Org. Chem. 66 2001 2136 2145
41. D.A. Tomalia, A.M. Naylor, and W.A. Goddard III Starburst dendrimers: molecular level control of size, shape, surface chemistry, topology and flexibility from atoms to macroscopic matter Angew. Chem., Int. Ed. Engl. 29 1990 138 175
42. A.M. Naylor, W.A. Goddard III, G.E. Kiefer, and D.A. Tomalia DA starburst dendrimers: 5. Molecular shape control J. Am. Chem. Soc. 111 1989 2339 2341
43. J.F.G.A. Jansen, E.M.M. Debrabandervandenberg, and E.W. Meijer Encapsulation of guest molecules into a dendritic box Science 266 1994 1226 1229
44. J.F.G.A. Jansen, E.W. Meijer, and E.M.M. Debrabandervandenberg The dendritic box: shape-selective liberation of encapsulated guests J. Am. Chem. Soc. 117 1995 4417 4418
45. R. Esfand, and D.A. Tomalia Poly(amidoamine) (PAMAM) dendrimers: from biomimicry to drug delivery and biomedical applications Drug Discov. Today 6 2001 427 436
46. L.J. Twyman, A.E. Beezer, R. Esfand, M.J. Hardy, and J.C. Mitchell The synthesis of water-soluble dendrimers, and their application as possible drug delivery systems Tetrahedron Lett. 40 1999 1743 1746
47. C.B. Gorman, and J.C. Smith Structure-property relationships in dendritic encapsulation Acc. Chem. Res. 34 2001 60 71
48. T.L. Chasse, J.C. Yohannan, N. Kim, Q. Li, Z. Li, and C.B. Gorman Dendritic encapsulation-roles of cores and branches Tetrahedron 59 2003 3853 3861
49. T.L. Chasse, R. Sachdeva, Q. Li, Z. Li, R.J. Petrie, and C.B. Gorman Structural effects on encapsulation as probed in redox-active core dendrimer isomers J. Am. Chem. Soc. 125 2003 8250 8254
50. P. Wallimann, T. Marti, A. Furer, and F. Diederich Steroids in molecular recognition Chem. Rev. 97 1997 1567 1608
51. P. Wallimann, P. Seiler, and F. Diederich Dendrophanes: novel steroid-recognizing dendritic receptors Helv. Chim. Acta 79 1996 779 788
52. D.K. Smith, A. Zingg, and F. Diederich Dendroclefts: optically active dendritic receptors for the selective recognition and chiroptical sensing of monosaccharide guests Helv. Chim. Acta 82 1999 1225 1241
53. D.K. Smith, and F. Diederich Dendritic hydrogen bonding receptors: enantiomerically pure dendroclefts for the selective recognition of monosaccharides Chem. Commun. 1998 2501 2502
54. S.C. Zimmerman, M.S. Wendland, N.A. Rakow, I. Zharov, and K.S. Suslick Synthetic hosts by monomolecular imprinting inside dendrimers Nature 418 2002 399 403
55. M.A.C. Broeren, J.L.J. van Dongen, M. Pittelkow, J.B. Christensen, M.H.P. van Genderen, and E.W. Meijer Multivalency in the gas phase: the study of dendritic aggregates by mass spectrometry Angew. Chem., Int. Ed. Engl. 43 2004 3557 3562
56. U. Boas, and P.M.H. Heegaard Dendrimers in drug research Chem. Soc. Rev. 33 2004 43 63
57. L.A. Kubasiak, and D.A. Tomalia Cationic dendrimers as gene transfection vectors M.M. Amiji Polymeric Gene Delivery: Principles and Applications 2004 CRC Press Boca Raton, FL 133 157
58. J.M.J. Fréchet Designing dendrimers for drug delivery Pharm. Sci. Technol. Today 2 2000 393 401
59. A.U. Bielinska, C. Chen, J. Johnson, and J.R. Baker Jr. DNA complexing with polyamidoamine dendrimers: implications for transfection Bioconjug. Chem. 10 1999 843 850
60. D.S. Shah, T. Sakthivel, I. Toth, A.T. Florence, and A.F. Wilderspin DNA transfection and transfected cell viability using amphipathic asymmetric dendrimers Int. J. Pharm. 208 2000 41 48
61. J.A. Hughes, A.I. Aronsohn, A.V. Avrutskaya, and R.L. Juliano Evaluation of adjuvants that enhance the effectiveness of antisense oligodeoxynucleotides Pharm. Res. 13 1996 404 410
62. R.L. Juliano, S. Alahari, H. Yoo, R. Kole, and M. Cho Antisense pharmacodynamics: critical issues in the transport and delivery of antisense oligonucleotides Pharm. Res. 16 1999 494 502
63. I. Lebedeva, L. Benimetskaya, C.A. Stein, and M. Vilenchik Cellular delivery of antisense oligonucleotides Eur. J. Pharm. Biopharm. 50 2000 101 119
64. I. Jaaskelainen, S. Peltola, P. Honkakoski, J. Monkkonen, and A. Urtti A lipid carrier with a membrane active component and a small complex size are required for efficient cellular delivery of anti-sense phosphorothioate oligonucleotides Eur. J. Pharm. Sci. 10 2000 187 193
65. C.R. Dass Vehicles for oligonucleotide delivery to tumors J. Pharm. Pharmacol. 54 2002 3 27
66. P.A. Jaffrès, and R.E. Morris Synthesis of highly functionalized dendrimers based on polyhedral silsesquioxane cores J. Chem. Soc., Dalton Trans. 1998 2767 2770
67. S.C.W. Richardson, N.G. Pattrick, Y.K.S. Man, P. Ferruti, and R. Duncan Poly(amidoamine)s as potential nonviral vectors: ability to form interpolyelectrolyte complexes and to mediate transfection in vitro Biomacromolecules 2 2001 1023 1028
68. P. Ferruti, M.A. Marchisio, and R. Duncan Poly(amido-amine)s: biomedical applications Macromol. Rapid Commun. 23 2002 332 355
69. M.X. Tang, and F.C. Szoka The influence of polymer structure on the interactions of cationic polymers with DNA and morphology of the resulting complexes Gene Ther. 4 1997 823 832
70. B.H. Zinselmeyer, S.P. Mackay, A.G. Schatzlein, and I.F. Uchegbu The lower-generation polypropylenimine dendrimers are effective gene-transfer agents Pharm. Res. 19 2002 960 967
71. C.L. Gebhart, and A.V. Kabanov Evaluation of polyplexes as gene transfer agents J. Control. Release 73 2001 401 416
72. D. Joester, M. Losson, R. Pugin, H. Heinzelmann, E. Walter, H.P. Merkle, and F. Diederich Amphiphilic dendrimers: novel self-assembling vectors for efficient gene delivery Angew. Chem., Int. Ed. Engl. 42 2003 1486 1490
73. H. Arima, F. Kihara, F. Hirayama, and K. Uekama Enhancement of gene expression by polyamidoamine dendrimer conjugates with α-, β-, and γ-cyclodextrins Bioconjug. Chem. 12 2001 476 484
74. H. Yoo, and R.L. Juliano Enhanced delivery of antisense oligonucleotides with fluorophore-conjugated PAMAM dendrimers Nucleic Acids Res. 28 2000 4225 4231
75. A.V. Maksimenko, V. Mandrouguine, M.B. Gottikh, J.-R. Bertrand, J.-P. Majoral, and C. Malvy Optimization of dendrimer-mediated gene transfer by anionic oligomers J. Gene Med. 5 2003 61 71
76. H. Sashiwa, H. Yajima, and S. Aiba Synthesis of a chitosan-dendrimer hybrid and its biodegradation Biomacromolecules 4 2003 1244 1249
77. T. Takahashi, K. Kono, T. Itoh, N. Emi, and T. Takagishi Synthesis of novel cationic lipids having polyamidoamine dendrons and their transfection activity Bioconjug. Chem. 14 2003 764 773
78. M. Ohsaki, T. Okuda, A. Wada, T. Hirayama, T. Niidome, and H. Aoyagi In vitro gene transfection using dendritic poly(l-lysine) Bioconjug. Chem. 13 2002 510 517
79. H.-F. Chow, T.-K. Mong, Y.-H. Chan, and C.H.K. Cheng A new class of protein mimics: preparation and electrophoretic properties of polycationic β-alanine-based dendrimers Tetrahedron 59 2003 3815 3820
80. A. Herrmann, G. Mihov, G.W.M. Vandermeulen, H.-A. Klok, and K. Müllen Peptide-functionalized polyphenylene dendrimers Tetrahedron 59 2003 3925 3935
81. J. Kress, A. Rosner, and A. Hirsch Depsipeptide dendrimers J. Chem. Eur. 6 2000 247 257
82. B. Buschhaus, W. Bauer, and A. Hirsch Synthesis and chiroptical properties of a new type of chiral depsipeptide dendrons Tetrahedron 59 2003 3899 3915
83. N. Malik, E.G. Evagorou, and R. Duncan Dendrimer-platinate: a novel approach to cancer chemotherapy Anticancer Drugs 10 1999 767 776
84. L. Balogh, D.R. Swanson, D.A. Tomalia, G.L. Hagnauer, and A.T. McManus Dendrimer-silver complexes and nanocomposites as antimicrobial agents Nano Lett. 1 2001 18 21
85. (a) N. Malik, R. Duncan, Dendritic-platinate drug delivery system, US 6,585,956, 2003;
86. (b) N. Malik, R. Duncan, Method of treating cancerous tumors with a dendritic-platinate drug delivery system, US 6,790,437, 2004.
87. A.E. Beezer, A.S.H. King, I.K. Martin, J.C. Mitchel, L.J. Twyman, and C.F. Wain Dendrimers as potential drug carriers: encapsulation of acidic hydrophobes within water soluble PAMAM derivatives Tetrahedron 59 2003 3873 3880
88. O.L. Padilla De Jesús, H.R. Ihre, L. Gagne, J.M.J. Fréchet, and F.C. Szoka Jr. Polyester dendritic systems for drug delivery applications: in vitro and in vivo evaluation Bioconjug. Chem. 13 2002 453 461
89. C. Kojima, K. Kono, K. Maruyama, and T. Takagishi Synthesis of polyamidoamine dendrimers having poly(ethylene glycol) grafts and their ability to encapsulate anticancer drugs Bioconjug. Chem. 11 2000 910 917
90. D. Bhadra, S. Bhadra, S. Jain, and N.K. Jain A PEGylated dendritic nanoparticulate carrier of fluorouracil Int. J. Pharm. 257 2003 111 124
91. P. Kolhe, E. Misra, R.M. Kannan, S. Kannan, and M. Lieh-Lai Drug complexation, in vitro release and cellular entry of dendrimers and hyperbranched polymers Int. J. Pharm. 259 2003 143 160
92. M. El-Sayed, C.A. Rhodes, M. Ginski, and H. Ghandehari Transport mechanism(s) of poly(amidoamine) dendrimers across Caco-2 cell monolayers Int. J. Pharm. 265 2003 151 157
93. B. Devarakonda, R.A. Hill, and M.M. de Villiers The effect of PAMAM dendrimer generation size and surface functional group on the aqueous solubility of nifedipine Int. J. Pharm. 284 2004 133 140
94. A.S. Chauhan, S. Sridevi, K.B. Chalasani, A.K. Jain, S.K. Jain, N.K. Jain, and P.V. Diwan Dendrimer-mediated transdermal delivery: enhanced bioavailability of indomethacin J. Control. Release 90 2003 335 343
95. W. Tansey, S. Ke, X.-Y. Cao, M.J. Pasuelo, S. Wallace, and C. Li Synthesis and characterization of branched poly(l-glutamic acid) as a biodegradable drug carrier J. Control. Release 94 2004 39 51
96. Q. Cai, Y. Zhao, J. Bei, F. Xi, and S. Wang Synthesis and properties of star-shaped polylactide attached to poly(amidoamine) dendrimer Biomacromolecules 4 2003 828 834
97. E.R. Gillies, and J.M.J. Fréchet Designing macromolecules for therapeutic applications: polyester dendrimer-poly(ethylene oxide) "bow-tie" hybrids with tunable molecular weight and architecture J. Am. Chem. Soc. 124 2002 14137 14146
98. A.J. Khopade, and F. Caruso Stepwise self-assembled poly(amidoamine) dendrimer and poly(styrenesulfonate) microcapsules as sustained delivery vehicles Biomacromolecules 3 2002 1154 1162
99. B.P. Hay, E.J. Werner, and K.N. Raymond Estimating the number of bound waters in Gd(III) complexes revisited. Improved methods for the prediction of q-values Bioconjug. Chem. 15 2004 1496 1502
100. M. Doubrovin, I. Serganova, P. Mayer-Kuckuk, V. Ponomarev, and R.G. Blasberg Multimodality in vivo molecular-genetic imaging Bioconjug. Chem. 15 2004 1376 1388
101. P. Caravan, J.J. Ellison, T.J. McMurry, and R.B. Lauffer Gadolinium (III) chelates as MRI contrast agents: structure, dynamics, and applications Chem. Rev. 99 1999 2293 2352
102. F.N. Franano, W.B. Edwards, M.J. Welch, M.W. Brechbiel, O.A. Gansow, and J.R. Duncan Biodistribution and metabolism of targeted and nontargeted protein-chelate-gadolinium complexes: evidence for gadolinium dissociation in vitro and in vivo Magn. Reson. Imaging 13 1995 201 214
103. H. Kobayashi, N. Sato, S. Kawamoto, T. Saga, A. Hiraga, T. Ishimori, J. Konishi, K. Togashi, and M.W. Brechbiel Novel intravascular macromolecular MRI contrast agent with generation-4 polyamidoamine dendrimer core: accelerated renal excretion with co-injection of lysine Magn. Reson. Med. 46 2001 457 464
104. Z.-R. Lu, X. Wang, D.L. Parker, K.C. Goodrich, and H.R. Buswell Poly(l-glutamic acid) Gd(III)-DOTA conjugate with a degradable spacer for magnetic resonance imaging Bioconjug. Chem. 14 2003 715 719
105. S.M. Deneke Thiol-based antioxidants Curr. Top Cell Regul. 36 2000 151 180
106. http://www.nobel.se/medicine/laureate/2003/press.html, 2003.
107. E.C. Wiener, D.A. Tomalia, and P.C. Lauterbur Relaxivity and stabilities of metal complexes of starburst dendrimers: a new class of MRI contrast agents, in Works in Progress, Society of Magnetic Resonance in Medicine 9th Annual Meeting and Exhibition, New York, New York 1990 1106
108. E.C. Wiener, M.W. Brechbiel, H. Brothers, R.L. Magin, O.A. Gansow, D.A. Tomalia, and P.C. Lauterbur Dendrimer-based metal chelates: a new class of magnetic resonance imaging contrast agents Magn. Reson. Med. 31 1994 1 8
109. H. Kobayashi, and M.W. Brechbiel Dendrimer-based macromolecular MRI contrast agents: characteristics and application Mol. Imaging 2 2003 1 10
110. E.C. Wiener, F.P. Auteri, J.W. Chen, M.W. Brechbiel, O.A. Gansov, D.S. Schneider, R.L. Belford, R.B. Clarkson, and P.C. Lauterbur Molecular dynamics of ion-chelate complexes attached to dendrimers J. Am. Chem. Soc. 118 1996 7774 7782
111. L.H. Bryant Jr., M.W. Brechbiel, C. Wu, J.W.M. Bulte, V. Herynek, and J.A. Frank Synthesis and relaxometry of high-generation (G = 5, 7, 9, and 10) PAMAM dendrimer-DOTA-gadolinium chelates J. Magn. Reson. Imaging 9 1999 348 352
112. L.D. Margerum, B.K. Campion, M. Koo, N. Shargill, J.J. Lai, A. Marumoto, and P.C. Sontum Gadolinium(III) DO3A macrocycles and poly(ethylene glycol) coupled to dendrimers-effect of molecular weight on physical and biological properties of macromolecular magnetic resonance imaging contrast agents J. Alloys Compd. 249 1997 185 190
113. H. Kobayashi, S. Kawamoto, S.-K. Jo, H.L. Bryant Jr., M.W. Brechbiel, and R.A. Star Macromolecular MRI contrast agents with small dendrimers: pharmacokinetic differences between sizes and cores Bioconjug. Chem. 14 2003 388 394
114. 24-Gd-DTPA cascade polymer and Gadomer 17 are both produced by Schering AG, Berlin (Germany).
115. S.-E. Stiriba, H. Frey, and R. Haag Dendritic polymers in biomedical applications: from potential to clinical use in diagnostics and therapy Angew. Chem., Int. Ed. Engl. 41 2002 1329 1334
116. H.C. Roberts, M. Saeed, T.P.L. Roberts, A. Mühler, and R.C. Brasch MRI of acute myocardial ischemia: comparing a new contrast agent, Gd-DTPA-24-cascade-polymer, with Gd-DTPA J. Magn. Reson. Imaging 9 1999 204 208
117. G.M. Nicolle, E. Tóth, H. Schmitt-Willich, B. Radüchel, and A.E. Merbach The impact of rigidity and water exchange on the relaxivity of a dendritic MRI contrast agent Chem. Eur. J. 8 2002 1040 1048
118. S. Langereis, Q.G. de Lussanet, M.H.P. van Genderen, W.H. Backes, and E.W. Meijer Multivalent contrast agents based on gadolinium- diethylenetriaminepentaacetic acid-terminated poly(propylene imine) dendrimersfor magnetic resonance imaging Macromolecules 37 2004 3084 3091
119. M. Takahashi, Y. Hara, K. Aoshima, H. Kurihara, T. Oshikawa, and M. Yamashita Utilization of dendritic framework as a multivalent ligand: a functionalized gadolinium(III) carrier with glycoside cluster periphery Tetrahedron Lett. 41 2000 8485 8488
120. Genisphere; DNA dendrimers and detection kits.
121. C.R. DeMattei, B. Huang, and D.A. Tomalia Designed dendrimer syntheses by self-assembly of single-site, ssDNA functionalized dendrons Nano Lett. 4 2004 771 777
122. J. Gerhart, M. Baytion, S. DeLuca, R. Getts, C. Lopez, R. Niewenhuis, T. Nilsen, S. Olex, H. Weintraub, and M. George-Weinstein DNA dendrimers localize MyoD mRNA in presomitic tissues of the chick embryo J. Cell Biol. 149 2000 825 833
123. R.L. Stears, R.C. Getts, and R.S. Gullans A novel, sensitive detection system for high-density microarrays using dendrimer technology Physiol. Genomics 3 2000 93 99
124. J. Wang, M. Jiang, T.W. Nilsen, and R.C. Getts Dendritic nucleic acid probes for DNA biosensors J. Am. Chem. Soc. 120 1998 8281 8282
125. H. Kobayashi, N. Sato, T. Saga, Y. Nakamoto, T. Ishimori, S. Toyama, K. Togashi, J. Konishi, and M.W. Brechbiel Monoclonal antibody-dendrimer conjugates enable radiolabeling of antibody with markedly high specific activity with minimal loss of immunoreactivity Eur. J. Nucl. Med. 27 2000 1334 1339
126. I.B. Rietveld, E. Kim, and S.A. Vinogradov Dendrimers with tetrabenzoporphyrin cores: near infrared phosphors for in vivo oxygen imaging Tetrahedron 59 2003 3821 3831
127. A.T. Yordanov, A.L. Lodder, E.K. Woller, M.J. Cloninger, N. Patronas, D. Milenic, and M.W. Brechbiel Novel iodinated dendritic nanoparticles for computed tomography (CT) imaging Nano Lett. 2 2002 595 599
128. K. Kono, M. Liu, and J.M.J. Fréchet Design of dendritic macromolecules containing folate or methotrexate residues Bioconjug. Chem. 10 1999 1115 1121
129. A. Quintana, E. Raczka, L. Piehler, I. Lee, A. Myc, I. Majoros, A.K. Patri, T. Thomas, J. Mule, and J.R. Baker Jr. Design and function of a dendrimer-based therapeutic nanodevice targeted to tumor cells through the folate receptor Pharm. Res. 19 2002 1310 1316
130. J.F. Ross, P.K. Chaudhuri, and M. Ratnam Differential regulation of folate receptor isoforms in normal and malignant tissues in vivo and established cell lines. Physiologic and clinical implications Cancer 73 1994 2432 2443
131. S. Shukla, G. Wu, M. Chatterjee, W. Yang, M. Sekido, L.A. Diop, R. Muller, J.J. Sudimack, R.J. Lee, R.F. Barth, and W. Tjarks Synthesis and biological evaluation of folate receptor-targeted boronated PAMAM dendrimers as potential agents for neutron capture therapy Bioconjug. Chem. 14 2003 158 167
132. J.J. Lundquist, and E.J. Toone The cluster glycoside effect Chem. Rev. 102 2002 555 578
133. D. Zanini, and R. Roy Synthesis of new α-thiosialodendrimers and their binding properties to the sialic acid specific lectin from Limax flavus J. Am. Chem. Soc. 119 1997 2088 2095
134. K. Bezouska, M.F. Pospisil, L.F. Vannucci, A.F. Fiserova, K.F. Krausova, O.F. Horvath, V.F. Kren, F.F. Mosca, T.K. Lindhorst, K.F. Sadalapure, and K. Bezouska Design, functional evaluation and biomedical applications of carbohydrate dendrimers (glycodendrimers) Rev. Mol. Biotechnol. 90 2002 269 290
135. R. Roy Syntheses and some applications of chemically defined multivalent glycoconjugates Curr. Opin. Struck. Biol. 6 1996 692 702
136. T.K. Lindhorst Artificial multivalent sugar ligands to understand and manipulate carbohydrate-protein interactions Top. Curr. Chem., Host-Guest Chemistry 218 2002 201 235
137. N. Rockendorf, and T.K. Lindhorst Glycodendrimers Top. Curr. Chem., Dendrimers IV 217 2001 201 238
138. P. Veprek, and J. Jezek Peptide and glycopeptide dendrimers: Part II J. Pept. Sci. 5 1999 203 220
139. S. Andre, R.J. Pieters, I. Vrasidas, H. Kaltner, I. Kuwabara, F.T. Liu, R.M. Liskamp, and H.J. Gabius Wedgelike glycodendrimers as inhibitors of binding of mammalian galectins to glycoproteins, lactose maxiclusters, and cell surface glycoconjugates ChemBiochem 2 2001 822 830
140. R.J. Pieters Interference with lectin binding and bacterial adhesion by multivalent carbohydrates and peptidic carbohydrate mimics Trends Glycosci. Glycotechnol. 16 2004 243 254
141. M.G. Baek, and R. Roy Synthesis and protein binding properties of T-antigen containing GlycoPAMAM dendrimers Bioorg. Med. Chem. 10 2002 11 17
142. R. Roy, M.G. Baek, and K. Rittenhouse-Olson Synthesis of N,N′-bis(acrylamido)acetic acid-based T-antigen glycodendrimers and their mouse monoclonal IgG antibody binding properties J. Am. Chem. Soc. 123 2001 1809 1816
143. R. Roy, and M.G. Baek Glycodendrimers: novel glycotope isosteres unmasking sugar coating. Case study with T-antigen markers from breast cancer MUC1 glycoprotein Rev. Mol. Biotechnol. 90 2002 291 309
144. J.M. Benito, M. Gomez-Garcia, C.O. Mellet, I. Baussanne, J. Defaye, and J.M.G. Fernandez Optimizing saccharide-directed molecular delivery to biological receptors: design, synthesis, and biological evaluation of glycodendrimer- cyclodextrin conjugates J. Am. Chem. Soc. 126 2004 10355 10363
145. H.C. Hansen, S. Haataja, J. Finne, and G. Magnusson Di-, tri-, and tetravalent dendritic galabiosides that inhibit hemagglutination by Streptococcus suis at nanomolar concentration J. Am. Chem. Soc. 119 1997 6974 6979
146. P.M. Rendle, A. Seger, J. Rodrigues, N.J. Oldham, R.R. Bott, J.B. Jones, M.M. Cowan, and B.G. Davies Glycodendriproteins: a synthetic glycoprotein mimic enzyme with branched sugar-display potently inhibits bacterial aggregation J. Am. Chem. Soc. 126 2004 4750 4751
147. S. Shaunak, S. Thomas, E. Gianasi, A. Godwin, E. Jones, I. Teo, K. Mireskandari, P. Luthert, R. Duncan, S. Patterson, P. Khaw, and S. Brocchini Polyvalent dendrimer glucosamine conjugates prevent scar tissue formation Nat. Biotechnol. 22 2004 977 984
148. F. Sanchez-Sancho, E. Perez-Inestrosa, R. Suau, C. Mayorga, M.J. Torres, and M. Blanca Dendrimers as carrier protein mimetics for IgE antibody recognition. Synthesis and characterization of densely penicilloylated dendrimers Bioconjug. Chem. 13 2002 647 653
149. M.-Y. Hong, H.C. Yoon, and H.-S. Kim Protein-ligand interactions at poly(amidoamine) dendrimer monolayers on gold Langmuir 19 2003 416 421
150. N. Nishiyama, H.R. Stapert, G.-D. Zhang, D. Takasu, D.-L. Jiang, T. Nagano, T. Aida, and K. Kataoka Light-harvesting ionic dendrimer porphyrins as new photosensitizers for photodynamic therapy Bioconjug. Chem. 14 2003 58 66
151. G.D. Zhang, A. Harada, N. Nishiyama, D.L. Jiang, H. Koyama, T. Aida, and K. Kataoka Polyion complex micelles entrapping cationic dendrimer porphyrin: effective photosensitizer for photodynamic therapy of cancer J. Control. Release 93 2003 141 150
152. S.H. Battah, C.E. Chee, H. Nakanishi, S. Gerscher, A.J. MacRobert, and C. Edwards Synthesis and biological studies of 5-aminolevulinic acid-containing dendrimers for photodynamic therapy Bioconjug. Chem. 12 2001 980 988
153. A. Paul, S. Hackbarth, A. Molich, C. Luban, S. Oelckers, F. Bohm, and B. Roder Comparative study of the photosensitization of Jurkat cells in vitro by pheophorbide a and a pheophorbide a-diaminobutane poly(propylene imine) dendrimer complex Laser Phys. 13 2003 22 29
154. N. Bourne, L.R. Stanberry, E.R. Kern, G. Holan, B. Matthews, and D.I. Bernstein Dendrimers, a new class of candidate topical microbicides with activity against herpes simplex virus infection Antimicrob. Agents Chemother. 44 2000 2471 2474
155. Product focus: VivaGel™, Starpharma Limited, Melbourne, Australia.
156. Y. Gong, B. Matthews, D. Cheung, T. Tam, I. Gadawski, D. Leung, G. Holan, J. Raff, and S. Sacks Evidence of dual sites of action of dendrimers: SPL-2999 inhibits both virus entry and late stages of herpes simplex virus replication Antivir. Res. 55 2002 319 329
157. M. Witvrouw, V. Fikkert, W. Pluymers, B. Matthews, K. Mardel, D. Schols, J. Raff, Z. Debyser, E. DeClercq, G. Holan, and C. Pannecouque Polyanionic (i.e., polysulfonate) dendrimers can inhibit the replication of human immunodeficiency virus by interfering with both virus adsorption and later steps (Reverse transcriptase/integrase) in the virus replicative cycle Mol. Pharmacol. 58 2000 1100 1108
158. C.Z. Chen, and S.L. Cooper Interactions between dendrimer biocides and bacterial membranes Biomaterials 23 2002 3359 3368
159. C.Z. Chen, N.C. Beck-Tan, P. Dhurjati, T.K. van Dyk, R.A. LaRossa, and S.L. Cooper Quaternary ammonium functionalized poly(propylene imine) dendrimers as effective antimicrobials: structure-activity studies Biomacromolecules 1 2000 473 480
160. N. Nagahori, R.T. Lee, S. Nishimura, D. Page, R. Roy, and Y.C. Lee Inhibition of adhesion of type 1 fimbriated Escherichia coli to highly mannosylated ligands ChemBioChem 3 2002 836 844
161. H. Sashiwa, and S.I. Aiba Chemically modified chitin and chitosan as biomaterials Prog. Polym. Sci. 29 2004 887 908
162. S. Lebreton, N. Newcombe, and M. Bradley Antibacterial single-bead screening Tetrahedron 59 2003 10213 10222
163. R. Jevprasesphant, J. Penny, R. Jalal, D. Attwood, N.B. McKeown, and A. D'Emanuele The influence of surface modification on the cytotoxicity of PAMAM dendrimers Int. J. Pharm. 252 2003 263 266
164. M. El-Sayed, M. Ginski, C. Rhodes, and H. Ghandehari Transepithelial transport of poly(amidoamine) dendrimers across Caco-2 cell monolayers J. Control. Release 81 2002 355 365
165. D. Fischer, Y. Li, B. Ahlemeyer, J. Krieglstein, and T. Kissel In vitro cytotoxicity testing of polycations: influence of polymer structure on cell viability and hemolysis Biomaterials 24 2003 1121 1131
166. N. Malik, R. Wiwattanapatapee, R. Klopsch, K. Lorenz, H. Frey, J.W. Weener, E.W. Meijer, W. Paulus, and R. Duncan Dendrimers: relationship between structure and biocompatibility in vitro, and preliminary studies on the biodistribution of I-125-labelled poly(amidoamine) dendrimers in vivo J. Control. Release 65 2000 133 148
167. L.A. Kubasiak, D.A. Tomalia, in preparation.
168. J.C. Roberts, M.K. Bhalgat, and R.T. Zera Preliminary biological evaluation of poly(amidoamine) (PAMAM) starburst dendrimers J. Biomed. Mater. Res. 30 1996 53 65
169. H. Kobayashi, S. Kawamoto, T. Saga, N. Sato, A. Hiraga, T. Ishimori, J. Konishi, K. Togashi, and M.W. Brechbiel Positive effects of polyethylene glycol conjugation to generation-4 polyamidoamine dendrimers as macromolecular MR contrast agents Magn. Reson. Med. 46 2001 781 788