Unexpected Biological Applications of Dendrimers and Specific Multivalency Activities

Dendrimers: Towards Catalytic, Material and Biomedical Uses

Volumn , Issue , 2011, Pages 485-509

  Turrin, Cédric Olivier ^a   Caminade, Anne Marie ^a  

^a LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

Amine terminated PAMAM dendrimers exhibiting antimicrobial activity; Antimicrobial dendrimers compounds, killing or inhibiting pathogenic microorganism development; Evaluating effects of PPH dendrimers on PBMCs; Immunomodulation to regenerative medicine immunomodulation and anti inflammation; Multivalent and dendrimeric effects versatility, for rational design of multiple ligands; Multivalent effects, dendrimer effects overwhelming predicted multivalent effects; Multivalent ligands, in multiple interactions with cell surface receptors; Polycationic dendrimers, microbicidal dendrimers polycationic dendrimers; Unexpected biological applications of dendrimers, and specific multivalency activities; Unexpected gene regulation of human primary macrophages by carbosilane dendrimers and natural killer (NK) cell amplification

Indexed keywords

EID: 84885963000     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781119976530.ch20     Document Type: Chapter

References (132)

1. R. Gras, L. Almonacid, P. Ortega, M. J. Serramia, R. Gomez, F. Javier de la Mata, L. A. Lopez-Fernandez, and M. Angeles Munoz-Fernandez(2009)Changes in gene expression pattern of human primary macrophages induced by carbosilane dendrimer 2G-NN16. Pharm. Res., 26, 577-586.
2. L. Griffe, M. Poupot, P. Marchand, A. Maraval, C. O. Turrin, O. Rolland, P. Métivier, G. Bacquet, J. J. Fournié, A. M. Caminade, R. Poupot, and J. P. Majoral(2007)Multiplication of human natural killer cells by nanosized phosphonate-capped dendrimers. Angew. Chem. Int. Ed., 46, 2523-2526.
3. S. Fruchon, M. Poupot, L. Martinet, C. O. Turrin, J. P. Majoral, J. J. Fournié, A. M. Caminade, and R. Poupot (2009)Anti-inflammatory and immunosuppressive activation of human monocytes by a bioactive dendrimer. J. Leukocyte Biol., 85, 553-562.
4. D. Portevin, M. Poupot, O. Rolland, C.-O. Turrin, J.-J. Fournié, J.-P. Majoral, A.-M. Caminade and R. Poupot(2009)Regulatory activity of azabisphosphonate-capped dendrimers on human CD4+ T cell proliferation for ex-vivo expansion of NK cells from PBMCs and immunotherapy. J. Trans. Med., 7, 82.
5. C. Z. S. Chen and S. L. Cooper(2000)Recent advances in antimicrobial dendrimers. Adv. Mater., 12, 843-846.
6. J. Rojo and R. Delgado(2007)Dendrimers and dendritic polymers as anti-infective agents: new antimicrobial strategies for therapeutic drugs. Anti-Infect. Agents Med. Chem., 6, 151-174.
7. M. Mammen, S. K. Choi, and G. M. Whitesides(1998)Polyvalent interactions in biological systems: implications for design and use of multivalent ligands and inhibitors. Angew. Chem. Int. Ed., 37, 2754-2794.
8. A. Mulder, J. Huskens, and D. N. Reinhoudt(2004)Multivalency in supramolecular chemistry and nanofabrication. Org. Biomolec. Chem., 2, 3409-3424.
9. P. I. Kitov and D. R. Bundle(2003)On the nature of the multivalency effect: a thermodynamic model. J. Am. Chem. Soc., 125, 16271-16284.
10. M. I. Page and W. P. Jencks(1971)Entropic contributions to rate accelerations in enzymic and intramolecular reactions and the chelate effect. Proc. Natl Acad. Sci. USA, 68, 1678-1683.
11. I. Yahara and G. M. Edelman(1973)Modulation of lymphocyte receptor redistribution by concanavalin A, anti-mitotic agents and alterations of pH. Nature, 246, 152-155.
12. G. M. Edelman, I. Yahara, and J. L. Wang(1973)Receptor mobility and receptor-cytoplasmic interactions in lymphocytes. Proc. Natl Acad. Sci. USA, 70, 1442-1446.
13. L. L. Kiessling, J. E. Gestwicki, and L. E. Strong(2000)Synthetic multivalent ligands in the exploration of cell-surface interactions. Curr. Opin. Chem. Biol., 4, 696-703.
14. L. L. Kiessling, L. E. Strong, and J. E. Gestwicki (eds)(2000)Principles for multivalent ligand design, in Annual Reports in Medical Chemistry, vol. 35, Academic Press, chap. 29.
15. L. L. Kiessling, J. E. Gestwicki, and L. E. Strong(2006)Synthetic multivalent ligands as probes of signal transduction. Angew. Chem. Int. Ed., 45, 2348-2368.
16. C. C. Lee, J. A. Mackay, J. M. J. Fréchet, and F. C. Szoka(2005)Designing dendrimers for biological applications. Nature Biotechnol., 23, 1517-1526.
17. H. F. Chow, C. F. Leung, G. X. Wang, and Y. Y. Yang(2003)Dendritic effects in functional dendrimer molecules. C. R. Chim., 6, 735-745.
18. A. Das, Y. X. Zhou, A. A. Ivanov, R. L. Carter, T. K. Harden, and K. A. Jacobson(2009)Enhanced potency of nucleotide-dendrimer conjugates as agonists of the P2Y receptor: multivalent effect in G protein-coupled receptor recognition. Bioconjugate Chem., 20, 1650-1659.
19. J. Folkman(1995)Angiogenesis in cancer, vascular, rheumatoid and other disease. Nat. Med., 1, 27-31.
20. J. Folkman and M. Klagsbrun(1987)Angiogenic factors. Science, 235, 442-447.
21. S. Kasai, H. Nagasawa, M. Shimamura, Y. Uto, and H. Hori(2002)Design and synthesis of antiangiogenic/heparin-binding arginine dendrimer mimicking the surface of endostatin. Bioorg. Med. Chem. Lett., 12, 951-954.
22. 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(2004)Polyvalent dendrimer glucosamine conjugates prevent scar tissue formation. Nat. Biotechnol., 22, 977-984.
23. K. T. Al-Jamal, W. T. Al-Jamal, S. Akerman, J. E. Podesta, A. Yilmazer, J. A. Turton, A. Bianco, N. Vargesson, C. Kanthou, A. T. Florence, G. M. Tozer, and K. Kostarelos(2010)Systemic antiangiogenic activity of cationic poly-L-lysine dendrimer delays tumor growth. Proc. Natl Acad. Sci. USA, 107, 3966-3971.
24. M. J. Cloninger(2008)Glycodendrimers and other macromolecules bearing multiple carbohydrates, in Molecular Recognition and Polymers: Control of Polymer Structure and Self-Assembly (eds V. M. Rotello and S. Thayumanavan), John Wiley & Sons, Inc., Hoboken, New Jersey.
25. P. Niederhafner, M. Reinis, J. Sebestik, and J. Jezek(2008)Glycopeptide dendrimers, Part III-A review: use of glycopeptide dendrimers in immunotherapy and diagnosis of cancer and viral diseases. J. Pept. Sci., 14, 556-587.
26. N. Röckendorf and T. K. Lindhorst(2001)Glycodendrimers, in Dendrimers IV (eds F. Vögtle and C. A. Schalley), vol. 217, Springer.
27. P. Niederhafner, J. Sebestik, and J. Jezek(2008)Glycopeptide dendrimers. Part II. J. Pept. Sci., 14, 44-65.
28. P. Niederhafner, J. Sebestik, and J. Jezek(2008)Glycopeptide dendrimers. Part I. J. Pept. Sci., 14, 2-43.
29. W. B. Turnbull and J. F. Stoddart(2002)Design and synthesis of glycodendrimers. J. Biotechnol., 90, 231-255.
30. K. Bezouska(2002)Design, functional evaluation and biomedical applications of carbohydrate dendrimers (glycodendrimers). J. Biotechnol., 90, 269-290.
31. Y. Li, Y. Cheng, and T. Xu(2007)Design, synthesis and potent pharmaceutical applications of glycodendrimers: a mini review. Curr. Drug Discov. Technol., 4, 246-254.
32. Y. M. Chabre and R. Roy(2008)Recent trends in glycodendrimer syntheses and applications. Curr. Top. Med. Chem., 8, 1237-1285.
33. Y. M. Chabre and R. Roy(2010)Design and creativity in synthesis of multivalent neoglycoconjugates. Adv. Carbohydr. Chem. Biochem., 63, 165-393.
34. D. Zanini and R. Roy(1997)Synthesis of new alpha-thiosialodendrimers and their binding properties to the sialic acid specific lectin from Limax flavus. J. Am. Chem. Soc., 119, 2088-2095.
35. M. Lahmann(2009)Architectures of multivalent glycomimetics for probing carbohydrate-lectin interactions, in Glycoscience and Microbial Adhesion (eds T. K. Lindhorst and S. Oscarson), vol. 288, Springer-Verlag, Berlin.
36. E. M. Munoz, J. Correa, E. Fernandez-Megia, and R. Riguera(2009)Probing the relevance of lectin clustering for the reliable evaluation of multivalent carbohydrate recognition. J. Am. Chem. Soc., 131, 17765-17767.
37. M. L. Wolfenden and M. J. Cloninger(2006)Carbohydrate-functionalized dendrimers to investigate the predictable tunability of multivalent interactions. Bioconjugate Chem., 17, 958-966.
38. A. Rosa Borges and C. L. Schengrund(2005)Dendrimers and antivirals: a review. Curr. Drug Targets Infect. Disord., 5, 247-254.
39. A. Imberty, Y. M. Chabre, and R. Roy(2008)Glycomimetics and glycodendrimers as high affinity microbial anti-adhesins. Chem. Eur. J., 14, 7490-7499.
40. S. André, R. J. Pieters, I. Vrasidas, H. Kaltner, L. Kuwabara, F. T.. Liu, R. M. J. Liskamp, and H. J. Gabius(2001)Wedgelike glycodendrimers as inhibitors of binding of mammalian galectins to glycoproteins, lactose maxiclusters, and cell surface glycoconjugates. ChemBioChem, 2, 822-830.
41. J. L. de Paz, C. Noti, F. Bohm, S. Werner, and P. H. Seeberger(2007)Potentiation of fibroblast growth factor activity by synthetic heparin oligosaccharide glycodendrimers. Chem. Biol., 14, 879-887.
42. L. Vannucci, A. Fiserova, K. Sadalapure, T. K. Lindhorst, M. Kuldova, P. Rossmann, O. Horvath, V. Kren, P. Krist, K. Bezouska, M. Luptovcova, F. Mosca, and M. Pospisil(2003)Effects of N-acetyl-glucosamine-coated glycodendrimers as biological modulators in the B16F10 melanoma model in vivo. Int. J. Oncology, 23, 285-296.
43. M. Vaara(1992)Agents that increase the permeability of the outer membrane. Microbiol. Rev., 56, 395-411.
44. P. Claes, A. Billiau, E. D. Clercq, J. Desmyter, E. Schonne, H. Vanderhaeghe, and P. D. Somer(1970)Polyacetal carboxylic acids: a new group of antiviral polyanions. J. Virol., 5, 313-320.
45. C. Z. S. Chen, N. C. Beck-Tan, P. Dhurjati, T. K. van Dyk, R. A. LaRossa, and S. L. Cooper(2000)Quaternary ammonium functionalized poly(propylene imine) dendrimers as effective antimicrobials: structure-activity studies. B iomacromolecules, 1, 473-480.
46. C. Z. S. Chen and S. L. Cooper(2002)Interactions between dendrimer biocides and bacterial membranes. Biomaterials, 23, 3359-3368.
47. A. A. Alencar de Queiroz, G. A. Abraham, M. A. Pires Camillo, O. Z. Higa, G. S. Silva, M. D. M. Fernandez, and J. San Roman (2006)Physicochemical and antimicrobial properties of boron-complexed polyglycerol-chitosan dendrimers. J. Biomater. Sci., Polym. Ed., 17, 689-707.
48. I. Carlescu, D. Scutaru, M. Popa, and C. V. Uglea(2009)Synthetic sialic-acid-containing polyvalent antiviral inhibitors. Med. Chem. Res., 18, 477-494.
49. C. J. Arnusch, H. Branderhorst, B. De Kruijff, R. M. J. Liskamp, E. Breukink, and R. J. Pieters(2007)Enhanced membrane pore formation by multimeric/oligomeric antimicrobial peptides. Biochemistry, 46, 13437-13442.
50. A. Pini, A. Giuliani, C. Falciani, Y. Runci, C. Ricci, B. Lelli, M. Malossi, P. Neri, G. M. Rossolini, and L. Bracci(2005)Antimicrobial activity of novel dendrimeric peptides obtained by phage display selection and rational modification. Antimicrob. Agents Chemother., 49, 2665-2672.
51. B. Klajnert, J. Janiszewska, Z. Urbanczyk-Lipkowska, M. Bryszewska, D. Shcharbin, and M. Labieniec(2006)Biological properties of low molecular mass peptide dendrimers. Int. J. Pharm., 309, 208-217.
52. S. P. Hong, A. U. Bielinska, A. Mecke, B. Keszler, J. L. Beals, X. Y. Shi, L. Balogh, B. G. Orr, J. R. Baker, and M. M. B. Holl(2004)Interaction of poly(amidoamine) dendrimers with supported lipid bilayers and cells: hole formation and the relation to transport. Bioconjugate Chem., 15, 774-782.
53. S. P. Hong, P. R. Leroueil, E. K. Janus, J. L. Peters, M. M. Kober, M. T. Islam, B. G. Orr, J. R. Baker, and M. M. B. Holl(2006)Interaction of polycationic polymers with supported lipid bilayers and cells: nanoscale hole formation and enhanced membrane permeability. Bioconjugate Chem., 17, 728-734.
54. U. Boas, J. B. Christensen, and P. M. H. Heegaard(2006)Dendrimers in Medicine and Biotechnology, The Royal Society of Chemistry, Cambridge.
55. P. R. Leroueil, S. A. Berry, K. Duthie, G. Han, V. M. Rotello, D. Q. McNerny, J. R. Baker, B. G. Orr, and M. M. B. Holl(2008)Wide varieties of cationic nanoparticles induce defects in supported lipid bilayers. Nano Lett., 8, 420-424.
56. P. R. Leroueil, S. Y. Hong, A. Mecke, J. R. Baker, B. G. Orr, and M. M. B. Holl(2007)Nanoparticle interaction with biological membranes: Does nanotechnology present a Janus face? Acc. Chem. Res., 40, 335-342.
57. J. Chen, J. A. Hessler, K. Putchakayala, B. K. Panama, D. P. Khan, S. Hong, D. G. Mullen, S. C. Dimaggio, A. Som, G. N. Tew, A. N. Lopatin, J. R. Baker, M. M. Holl, and B. G. Orr(2009)Cationic nanoparticles induce nanoscale disruption in living cell plasma membranes. J. Phys. Chem. B, 113, 11179-11185.
58. M. K. Calabretta, A. Kumar, A. M. McDermott, and C. Z. Cai(2007)Antibacterial activities of poly(amidoamine) dendrimers terminated with amino and poly(ethylene glycol) groups. Biomacromolecules, 8, 1807-1811.
59. A. I. Lopez, R. Y. Reins, A. M. McDermott, B. W. Trautner, and C. Cai(2009)Antibacterial activity and cytotoxicity of PEGylated poly(amidoamine) dendrimers. Molec. Bio. Syst., 5, 1148-1156.
60. F. Zhang, Y. Y. Chen, H. Lin, and D. S. Zhang(2008)Performance of cotton fabric treated with an amino-terminated hyperbranched polymer. Fibers and Polymers, 9, 515-520.
61. B. Wang, R. S. Navath, A. R. Menjoge, B. Balakrishnan, R. Bellair, H. Dai, R. Romero, S. Kannan, and R. M. Kannan(2010)Inhibition of bacterial growth and intramniotic infection in a guinea pig model of chorioamnionitis using PAMAM dendrimers. Int. J. Pharm., 395, 298-308.
62. S. Supattapone, H. O. Nguyen, F. E. Cohen, S. B. Prusiner, and M. R. Scott(1999)Elimination of prions by branched polyamines and implications for therapeutics. Proc. Natl Acad. Sci. USA, 96, 14529-14534.
63. S. Supattapone, H. Wille, L. Uyechi, J. Safar, P. Tremblay, F. C. Szoka, F. E. Cohen, S. B. Prusiner, and M. R. Scott(2001)Branched polyamines cure prion-infected neuroblastoma cells. J. Virol., 75, 3453-3461.
64. J. Solassol, C. Crozet, V. Perrier, J. Leclaire, F. Beranger, A. M. Caminade, B. Meunier, D. Dormont, J. P. Majoral, and S. Lehmann(2004)Cationic phosphorus-containing dendrimers reduce prion replication both in cell culture and in mice infected with scrapie. J. Gen. Virol., 85, 1791-1799.
65. P. M. H. Heegaard, H. G. Pedersen, J. Flink, and U. Boas(2004)Amyloid aggregates of the prion peptide PrP106-126 are destabilised by oxidation and by the action of dendrimers. FEBS Lett., 577, 127-133.
66. L. Giehm, C. Christensen, U. Boas, P. M. H. Heegaard, and D. E. Otzen(2008)Dendrimers destabilize proteins in a generation-dependent manner involving electrostatic interactions. Biopolymers, 89, 522-529.
67. H. Cordes, U. Boas, P. Olsen, and P. M. H. Heegaard(2007)Guanidino-and urea-modified dendrimers as potent solubilizers of misfolded prion protein aggregates under non-cytotoxic conditions. Dependence on dendrimer generation and surface charge. Biomacromolecules, 8, 3578-3583.
68. B. Klajnert, M. Cortijo-Arellano, J. Cladera, J. P. Majoral, A. M. Caminade, and M. Bryszewska(2007)Influence of phosphorus dendrimers on the aggregation of the prion peptide PrP 185-208. Biochem. Biophys. Res. Commun., 364, 20-25.
69. B. Klajnert, J. Cladera, and M. Bryszewska(2006)Molecular interactions of dendrimers with amyloid peptides: pH dependence. Biomacromolecules, 7, 2186-2191.
70. B. Klajnert, M. Cortijo-Arellano, J. Cladera, and M. Bryszewska(2006)Influence of dendrimer's structure on its activity against amyloid fibril formation. Biochem. Biophys. Res. Commun., 345, 21-28.
71. B. Klajnert, M. Cangiotti, S. Calici, J. P. Majoral, A. M. Carninade, J. Cladera, M. Bryszewska, and M. F. Ottaviani(2007)EPR study of the interactions between dendrimers and peptides involved in Alzheimer's and prion diseases. Macromol. Biosci., 7, 1065-1074.
72. B. Klajnert, M. Cortijo-Arellano, M. Bryszewska, and J. Cladera(2006)Influence of heparin and dendrimers on the aggregation of two amyloid peptides related to Alzheimer's and prion diseases. Biochem. Biophys. Res. Commun., 339, 577-582.
73. B. Klajnert, M. Cangiotti, S. Calici, M. Ionov, J. P. Majoral, A. M. Caminade, J. Cladera, M. Bryszewska, and M. F. Ottaviani (2009)Interactions between dendrimers and heparin and their implications for the anti-prion activity of dendrimers. New J. Chem., 33, 1087-1093.
74. P. M. H. Heegaard, U. Boas, and D. E. Otzen(2007)Dendrimer effects on peptide and protein fibrillation. Macromol. Biosci., 7, 1047-1059.
75. B. Klajnert, D. Appelhans, H. Komber, N. Morgner, S. Schwarz, S. Richter, B. Brutschy, M. Ionov, A. K. Tonkikh, M. Bryszewska, and B. Voit (2008)The influence of densely organized maltose shells on the biological properties of poly(propylene imine) dendrimers: new effects dependent on hydrogen bonding. Chem. Eur. J., 14, 7030-7041.
76. M. Fischer, D. Appelhans, S. Schwarz, B. Klajnert, M. Bryszewska, B. Voit, and M. Rogers(2010)Influence of surface functionality of poly(propylene imine) dendrimers on protease resistance and propagation of the scrapie prion protein. Biomacromolecules, 11, 1314-1325.
77. P. De Somer, E. De Clercq, A. Billiau, E. Schonne, and M. Claesen(1968)Antiviral activity of polyacrylic and polymethacrylic acids. II. Mode of action in vivo. J. Virol., 2, 886-893.
78. P. De Somer, E. De Clercq, A. Billiau, E. Schonne, and M. Claesen(1968)Antiviral activity of polyacrylic and polymethacrylic acids. I. Mode of action in vitro. J. Virol., 2, 878-885.
79. J. Balzarini and L. Van Damme(2007)Microbicide drug candidates to prevent HIV infection. Lancet, 369, 787-797.
80. D. Schols, R. Pauwels, J. Desmyter, and E. De Clercq(1990)Dextran sulfate and other polyanionic anti-HIV compounds specifically interact with the viral gp120 glycoprotein expressed by T-cells persistently infected with HIV-1. Virology, 175, 556-561.
81. R. M. Grant, D. Hamer, T. Hope, R. Johnston, J. Lange, M. M. Lederman, J. Lieberman, C. J. Miller, J. P. Moore, D. E. Mosier, D. D. Richman, R. T. Schooley, M. S. Springer, R. S. Veazey, and M. A. Wainberg(2008)Whither or wither microbicides? Science, 321, 532-534.
82. G. C. Morris and C. J. Lacey(2010)Microbicides and HIV prevention: lessons from the past, looking to the future. Curr. Opin. Infect. Dis., 23, 57-63.
83. D. Tyssen, S. A. Henderson, A. Johnson, J. Sterjovski, K. Moore, J. La, M. Zanin, S. Sonza, P. Karellas, M. P. Giannis, G. Krippner, S. Wesselingh, T. McCarthy, P. R. Gorry, P. A. Ramsland, R. Cone, J. R. Paull, G. R. Lewis, and G. Tachedjian(2010)Structure activity relationship of dendrimer microbicides with dual action antiviral activity. PLoS One, 5.
84. M. Witvrouw, V. Fikkert, W. Pluymers, B. Matthews, K. Mardel, D. Schols, J. Raff, Z. Debyser, E. De Clercq, G. Holan and C. Pannecouque(2000)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. Molec. Pharmacol., 58, 1100-1108.
85. S. R. Meyers, F. S. Juhn, A. P. Griset, N. R. Luman, and M. W. Grinstaff(2008)Anionic amphiphilic dendrimers as antibacterial agents. J. Am. Chem. Soc., 130, 14444.
86. "Starpharma commences phase 2 bacterial vaginosis study of VivaGel®" [online]. Accessed 16/08/2010, http://www.starpharma.com/data/100816_StarpharmaAnnouncesPhase2BVstudyofVivaGel.pdf.
87. M. Moulard, H. Lortat-Jacob, I. Mondor, G. Roca, R. Wyatt, J. Sodroski, L. Zhao, W. Olson, P. D. Kwong, and Q. J. Sattentau(2000)Selective interactions of polyanions with basic surfaces on human immunodeficiency virus type 1 gp120. J. Virol., 74, 1948-1960.
88. N. Bourne, L. R. Stanberry, E. R. Kern, G. Holan, B. Matthews, and D. I. Bernstein(2000)Dendrimers, a new class of candidate topical microbicides with activity against herpes simplex virus infection. Antimicrob. Agents Chemother., 44, 2471-2474.
89. C. S. Dezzutti, V. N. James, A. Ramos, S. T. Sullivan, A. Siddig, T. J. Bush, L. A. Grohskopf, L. Paxton, S. Subbarao, and C. E. Hart(2004)In vitro comparison of topical microbicides for prevention of human immunodeficiency virus type 1 transmission. Antimicrob. Agents Chemother., 48, 3834-3844.
90. E. Gong, B. Matthews, T. McCarthy, J. H. Chu, G. Holan, J. Raff, and S. Sacks(2005)Evaluation of dendrimer SPL7013, a lead microbicide candidate against herpes simplex viruses. Antiviral Res., 68, 139-146.
91. Y. H. Gong, B. Matthews, D. Cheung, T. Tam, I. Gadawski, D. Leung, G. Holan, J. Raff, and S. Sacks(2002)Evidence of dual sites of action of dendrimers: SPL-2999 inhibits both virus entry and late stages of herpes simplex virus replication. Antiviral Res., 55, 319-329.
92. D. I. Bernstein, L. R. Stanberry, S. Sacks, N. K. Ayisi, Y. H. Gong, J. Ireland, R. J. Mumper, G. Holan, B. Matthews, T. McCarthy, and N. Bournel(2003)Evaluations of unformulated and formulated dendrimer-based microbicide candidates in mouse and guinea pig models of genital herpes. Antimicrob. Agents Chemother., 47, 3784-3788.
93. T. McCarthy, P. Karellas, S. Henderson, M. Giannis, D. O'Keefe, B. Matthews, B. Braggs, J. Paull, G. Heery, G. Krippner, and G. Holan(2004)Design and preclinical development of dendrimer based topical microbicides for HIV and STI prevention. Antiviral Res., 62, A44-A44.
94. D. L. Patton, Y. T. C. Sweeney, T. D. McCarthy, and S. L. Hillier(2006)Preclinical safety and efficacy assessments of dendrimer-based (SPL microbicide gel formulations in a nonhuman primate model. Antimicrob. Agents Chemother., 50, 1696-1700.
95. R. Rupp, S. L. Rosenthal, and L. R. Stanberry(2007)VivaGel (TM) (SPL7013 Gel): a candidate dendrimer microbicide for the prevention of HIV and HSV infection. Int. J. Nanomed., 2, 561-566.
96. T. D. McCarthy, P. Karellas, S. A. Henderson, M. Giannis, D. F. O'Keefe, G. Heery, J. R. A. Paull, B. R. Matthews, and G. Holan(2005)Dendrimers as drugs: discovery and preclinical and clinical development of dendrimer-based microbicides for HIV and STI prevention. Molec. Pharm., 2, 312-318.
97. R. D. Kensinger, B. J. Catalone, F. C. Krebs, B. Wigdahl, and C. L. Schengrund(2004)Novel polysulfated galactose-derivatized dendrimers as binding antagonists of human immunodefi-ciency virus type 1 infection. Antimicrob. Agents Chemother., 48, 1614-1623.
98. A. Pérez-Anes, G. Spataro, Y. Coppel, C. Moog, M. Blanzat, C. O. Turrin, A. M. Caminade, I. Rico-Lattes, and J. P. Majoral(2009)Phosphonate terminated PPH dendrimers: influence of pendant alkyl chains on the in vitro anti-HIV-1 properties. Org. Biomolec. Chem., 7, 3491-3498.
99. O. Rolland, C. O. Turrin, A. M. Caminade, and J. P. Majoral(2009)Dendrimers and nanomedicine: multivalency in action. New J. Chem., 33, 1809-1824.
100. M. Poupot, L. Griffe, P. Marchand, A. Maraval, O. Rolland, L. Martinet, F. E. L'Faqihi-Olive, C. O. Turrin, A. M. Caminade, J. J. Fournie, J. P. Majoral, and R. Poupot(2006)Design of phosphorylated dendritic architectures to promote human monocyte activation. FASEB J., 20, 2339-2351.
101. O. Rolland, L. Griffe, M. Poupot, A. Maraval, A. Ouali, Y. Coppel, J. J. Fournié, G. Bacquet, C. O. Turrin, A. M. Caminade, J. P. Majoral, and R. Poupot(2008)Tailored control and optimisation of the number of phosphonic acid termini on phosphorus-containing dendrimers for the ex-vivo activation of human monocytes. Chem. Eur. J., 14, 4836-4850.
102. O. Rolland, C. O. Turrin, G. Bacquet, R. Poupot, M. Poupot, A. M. Caminade, and J. P. Majoral(2009)Efficient synthesis of phosphorus-containing dendrimers capped with isosteric functions of amino-bismethylene phosphonic acids. Tetrahedron Lett., 50, 2078-2082.
103. P. Marchand, L. Griffe, M. Poupot, C. O. Turrin, G. Bacquet, J. J. Fournié, J. P. Majoral, R. Poupot, and A. M. Caminade(2009)Dendrimers ended by non-symmetrical azadiphosphonate groups: synthesis and immunological properties. Bioorg. Med. Chem. Lett., 19, 3963-3966.
104. M. Poupot, R. Poupot, J. J. Fournié, D. Portevin, S. Fruchon, J. L. Davignon, C. O. Turrin, A. M. Caminade, J. P. Majoral, and O. Rolland(2010)Phosphorylated dendrimers as antiinflammatory drugs, Patent WO2010013086, February 4, 2010.
105. M. Poupot, V. Maraval, A. Ouali, O. Rolland, L. Griffe, P. Marchand, G. Spataro, J. P. Majoral, J. J. Fournié, C. O. Turrin, R. Poupot and A. M. Caminade, Interior versus exterior, which is the most important?, unpublished results.
106. A. S. Chauhan, P. V. Diwan, N. K. Jain, and D. A. Tomalia(2009)Unexpected in vivo anti-inflammatory activity observed for simple, surface functionalized poly(amidoamine) dendrimers. Biomacromolecules, 10, 1195-1202.
107. M. W. Grinstaff(2002)Biodendrimers: new polymeric biomaterials for tissues engineering. Chem. Eur. J., 8, 2838-2846.
108. J. M. Oliveira, A. J. Salgado, N. Sousa, J. F. Mano, and R. L. Reis(2010)Dendrimers and derivatives as potential therapeutic tool in regenerative medicine strategies-a review. Prog. Polym. Sci., 35, 1163-1194.
109. N. Joshi and M. Grinstaff(2008)Applications of dendrimers in tissue engineering. Curr. Top. Med. Chem., 8, 1225-1236.
110. M. Goldberg, R. Langer, and X. Q. Jia(2007)Nanostructured materials for applications in drug delivery and tissue engineering. J. Biomater. Sci.-Polym. Ed., 18, 241-268.
111. M. Kawase, N. Kurikawa, S. Higashiyama, N. Miura, T. Shiomi, C. Ozawa, T. Mizoguchi, and K. Yagi(1999)Effectiveness of polyamidoamine dendrimers modified with tripeptide growth factor, glycyl-L-histidyl-L-lysine, for enhancement of function of hepatoma cells. J. Biosci. Bioengng, 88, 433-437.
112. M. Kawase, N. Kurikawa, N. Miura, T. Shiomi, C. Ozawa, S. Higashiyama, T. Mizoguchi, and K. Yagi(2000)Immobilization of ligand-modified polyamidoamine dendrimer for cultivation of hepatoma cells. Artificial Organs, 24, 18-22.
113. M. Kawase, T. Shiomi, H. Matsui, Y. Ouji, S. Higashiyama, T. Tsutsui, and K. Yagi(2001)Suppression of apoptosis in hepatocytes by fructose-modified dendrimers. J. Biomed. Mater. Res., 54, 519-524.
114. M. H. Kim, M. Kino-Oka, M. Kawase, K. Yagi, and M. Taya(2007)Response of human epithelial cells to culture surfaces with varied roughnesses prepared by immobilizing dendrimers with/without D-glucose display. J. Biosci. Bioengng, 103, 192-199.
115. S. R. Benhabbour, H. Sheardown, and A. Adronov(2008)Cell adhesion and proliferation on hydrophilic dendritically modified surfaces. Biomaterials, 29, 4177-4186.
116. G. Decher(1997)Fuzzy nanoassemblies: toward layered polymeric multicomposites. Science, 277, 1232-1237.
117. J. L. Hernandez-Lopez, H. L. Khor, A. M. Caminade, J. P. Majoral, S. Mittler, W. Knoll, and D. H. Kim(2008)Bioactive multilayer thin films of charged N, N-disubstituted hydrazine phosphorus dendrimers fabricated by layer-by-layer self-assembly. Thin Solid Films, 516, 1256-1264.
118. S. H. M. Sontjens, D. L. Nettles, M. A. Carnahan, L. A. Setton, and M. W. Grinstaff(2006)Biodendrimer-based hydrogel scaffolds for cartilage tissue repair. Biomacromolecules, 7, 310-316.
119. M. W. Grinstaff(2007)Designing hydrogel adhesives for corneal wound repair. Biomaterials, 28, 5205-5214.
120. M. C. Wathier, M. A. Carnahan, P. J. Jung, T. Kim, and M. W. Grinstaff(2005)Dendrimer hydrogels as new alternative for the repair of clear corneal incisions. Investigative Ophthalmology and Visual Science, 46, abstract 4993.
121. M. A. Carnahan, C. Middleton, J. Kim, T. Kim, and M. W. Grinstaff(2002)Hybrid dendritic-linear polyester-ethers for in situ photopolymerization. J. Am. Chem. Soc., 124, 5291-5293.
122. L. Degoricija, C. S. Johnson, M. Wathier, T. Kim, and M. W. Grinstaff(2007)Photo cross-linkable biodendrimers as ophthalmic adhesives for central lacerations and penetrating keratoplasties. Investigative Ophthalmology and Visual Science, 48, 2037-2042.
123. L. Degoricija, P. N. Bansal, S. H. M. Sontjens, N. S. Joshi, M. Takahashi, B. Snyder, and M. W. Grinstaff(2008)Hydrogels for osteochondral repair based on photocrosslinkable carbamate dendrimers. Biomacromolecules, 9, 2863-2872.
124. M. Wathier, P. J. Jung, M. A. Camahan, T. Kim, and M. W. Grinstaff(2004)Dendritic macromers as in situ polymerizing biomaterials for securing cataract incisions. J. Am. Chem. Soc., 126, 12744-12745.
125. M. Wathier, C. S. Johnson, T. Kim, and M. W. Grinstaff(2006)Hydrogels formed by multiple peptide ligation reactions to fasten corneal transplants. Bioconjugate Chem., 17, 873-876.
126. M. Wathier, M. S. Johnson, M. A. Carnahan, C. Baer, B. W. McCuen, T. Kim, and M. W. Grinstaff(2006)In situ polymerized hydrogels for repairing scleral incisions used in pars plana vitrectomy procedures. ChemMedChem, 1, 821-825.
127. X. Duan and H. Sheardown(2006)Dendrimer crosslinked collagen as a corneal tissue engineering scaffold: mechanical properties and corneal epithelial cell interactions. Biomaterials, 27, 4608-4617.
128. X. D. Duan, C. McLaughlin, M. Griffith, and H. Sheardown(2007)Biofunctionalization of collagen for improved biological response: scaffolds for corneal tissue engineering. Biomaterials, 28, 78-88.
129. D. Q. Zhao, S. M. Ong, Z. L. Yue, Z. Y. Jiang, Y. C. Toh, M. Khan, J. H. Shi, C. H. Tan, J. P. Chen, and H. R. Yu(2008)Dendrimer hydrazides as multivalent transient inter-cellular linkers. Biomaterials, 29, 3693-3702.
130. X. Mo, Q. Li, L. W. Yi Lui, B. Zheng, C. H. Kang, B. Nugraha, Z. Yue, R. R. Jia, H. X. Fu, D. Choudhury, T. Arooz, J. Yan, C. T. Lim, S. Shen, C. Hong Tan, and H. Yu(2010)Rapid construction of mechanically-confined multi-cellular structures using dendrimeric intercellular linker. Biomaterials, 31, 7455-7467.
131. A. Moretta, C. Bottino, M. Vitale, D. Pende, C. Cantoni, M. C. Mingari, R. Biassoni and L. Moretta(2001)Activating receptors and coreceptors involved in human natural killer cell-mediated cytolysis. Ann. Rev. Immunol., 19, 197-223.
132. M. Hayder, M. Poupot, M. Baron, D. Nigon, C. O. Turrin, A. M. Caminade, J. P. Majoral, R. A. Eisenberg, J. J. Fournié, A. Cantagrel, R. Poupot, and J. L. Davignon(2001)A phosphorus-based dendrimer targets inflammation and osteoclastogenesis in experimental arthritis. Science Trans. Med., 3, 81 ra 35.