Glycosylated carriers for cell-selective and nuclear delivery of nucleic acids

Frontiers in Bioscience

Volumn 16, Issue 7, 2011, Pages 2970-2987

  Wijagkanalan, Wassana ^a,b,c   Kawakami, Shigeru ^a   Hashida, Mitsuru ^a,c  

^a KYOTO UNIVERSITY   (Japan)

^b JAPAN SOCIETY FOR THE PROMOTION OF SCIENCE   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

Carbohydrate; Gene delivery; Glycosylated carrier; Glycotargeting; Lectin; Nuclear import; Nucleic acids; Review

Indexed keywords

DRUG CARRIER; NUCLEIC ACID;

ANIMAL; BIOLOGICAL MODEL; CELL NUCLEUS; CHEMISTRY; CYTOLOGY; DENDRITIC CELL; DRUG EFFECT; ENDOSOME; GENE THERAPY; GENE TRANSFER; GENETICS; GLYCOSYLATION; HUMAN; LIVER CELL; LUNG; MACROPHAGE; METABOLISM; METHODOLOGY; NEOPLASM; REVIEW; STELLATE CELL; TARGETED GENE REPAIR;

ANIMALS; CELL NUCLEUS; DENDRITIC CELLS; DRUG CARRIERS; ENDOSOMES; GENE THERAPY; GENE TRANSFER TECHNIQUES; GLYCOSYLATION; HEPATIC STELLATE CELLS; HEPATOCYTES; HUMANS; LUNG; MACROPHAGES; MODELS, BIOLOGICAL; NEOPLASMS; NUCLEIC ACIDS; TARGETED GENE REPAIR;

EID: 79959545208     PISSN: 27686701     EISSN: 27686698     Source Type: Journal    
DOI: 10.2741/3892     Document Type: Article

References (150)

1. I. Goldstein, R. Hugues, M. Monsigny, T. Osawa and N. Sharon: What should be called a lectin? Nature 285, 66 (1980)
2. D. Kilpatrick: Animal lectins: a historical introduction and overview. Biochim Biophys Acta 1572, 187-197 (2002) (Pubitemid 35246344)
3. J. Hubert, A. Sève, P. Facy and M. Monsigny: Are nuclear lectins and nuclear glycoproteins involved in the modulation of nuclear functions? Cell Differ Dev 27, 69-81 (1989) (Pubitemid 19195256)
4. N. Sharon and H. Lis: Lectins: cell-agglutinating and sugarspecific proteins. Science 177, 949-959 (1972)
5. M. Monsigny, A. Roche and P. Midoux: Endogenous lectins and drug targeting. Ann N Y Acad Sci 551, 399-413 (1988)
6. M. Brownlee and A. Cerami: A glucose-controlled insulindelivery system: semisynthetic insulin bound to lectin. Science 206, 1190-1191 (1979) (Pubitemid 10159659)
7. G. Wu and C. Wu: Receptor-mediated in vitro gene transformation by a soluble DNA carrier system. J Biol Chem 262, 4429-4432 (1987) (Pubitemid 17102799)
8. P. Midoux, C. Mendes, A. Legrand, J. Raimond, R. Mayer, M. Monsigny and A. Roche: Specific gene transfer mediated by lactosylated poly-L-lysine into hepatoma cells. Nucleic Acids Res 21, 871-878 (1993) (Pubitemid 23152994)
9. R. Mahato, S. Takemura, K. Akamatsu, M. Nishikawa, Y. Takakura and M. Hashida: Physicochemical and disposition characteristics of antisense oligonucleotides complexed with glycosylated poly(L-lysine). Biochem Pharmacol 53, 887-895 (1997) (Pubitemid 27145791)
10. M. Wadhwa and K. Rice: Receptor mediated glycotargeting. J Drug Target 3, 111-127 (1995)
11. M. Monsigny, P. Midoux, R. Mayer and A. Roche: Glycotargeting: influence of the sugar moiety on both the uptake and the intracellular trafficking of nucleic acid carried by glycosylated polymers. Biosci Rep 19, 125-132 (1999) (Pubitemid 29334205)
12. S. Kawakami, J. Wong, A. Sato, Y. Hattori, F. Yamashita and M. Hashida: Biodistribution characteristics of mannosylated, fucosylated, and galactosylated liposomes in mice. Biochim Biophys Acta 1524, 258-265 (2000)
13. H. Yan and K. Tram: Glycotargeting to improve cellular delivery efficiency of nucleic acids. Glycoconj J 24, 107-123 (2007) (Pubitemid 46352522)
14. S. Kawakami, F. Yamashita, M. Nishikawa, Y. Takakura and M. Hashida: Asialoglycoprotein receptormediated gene transfer using novel galactosylated cationic liposomes. Biochem Biophys Res Commun 252, 78-83 (1998) (Pubitemid 28534630)
15. A. Sato, M. Takagi, A. Shimamoto, S. Kawakami and M. Hashida: Small interfering RNA delivery to the liver by intravenous administration of galactosylated cationic liposomes in mice. Biomaterials 28, 1434-1442 (2007) (Pubitemid 44959042)
16. M. Monsigny, C. Rondanino, E. Duverger, I. Fajac and A. Roche: Glyco-dependent nuclear import of glycoproteins, glycoplexes and glycosylated plasmids. Biochim Biophys Acta 1673, 94-103 (2004) (Pubitemid 38844797)
17. K. Kawabata, Y. Takakura and M. Hashida: The fate of plasmid DNA after intravenous injection in mice: involvement of scavenger receptors in its hepatic uptake. Pharm Res 12, 825-830 (1995)
18. R. Mahato, K. Kawabata, Y. Takakura and M. Hashida: In vivo disposition characteristics of plasmid DNA complexed with cationic liposomes. J Drug Target 3, 149-157 (1995)
19. Y. Oh, J. Kim, H. Yoon, J. Kim, J. Yang and C. Kim: Prolonged organ retention and safety of plasmid DNA administered in polyethylenimine complexes. Gene Ther 8, 1587-1592 (2001) (Pubitemid 33061898)
20. W. Yeeprae, S. Kawakami, S. Suzuki, F. Yamashita and M. Hashida: Physicochemical and pharmacokinetic characteristics of cationic liposomes. Pharmazie 61, 102-105 (2006) (Pubitemid 43293890)
21. K. Wagstaff and D. Jans: Nucleocytoplasmic transport of DNA: enhancing non-viral gene transfer. Biochem J 406, 185-202 (2007) (Pubitemid 47310949)
22. W. Weis, M. Taylor and K. Drickamer: The C-type lectin superfamily in the immune system. Immunol Rev 163, 19-34 (1998) (Pubitemid 28327859)
23. G. Ashwell and J. Harford: Carbohydrate-specific receptors of the liver. Annu Rev Biochem 51, 531-554 (1982)
24. P. Stahl, J. Rodman, M. Miller and P. Schlesinger: Evidence for receptor-mediated binding of glycoproteins, glycoconjugates, and lysosomal glycosidases by alveolar macrophages. Proc Natl Acad Sci U S A 75, 1399-1403 (1978) (Pubitemid 8301644)
25. R. Haltiwanger, M. Lehrman, A. Eckhardt and R. Hill: The distribution and localization of the fucose-binding lectin in rat tissues and the identification of a high affinity form of the mannose/N-acetylglucosamine-binding lectin in rat liver. J Biol Chem 261, 7433-7439 (1986) (Pubitemid 17224748)
26. P. Crocker and S. Gordon: Mouse macrophage hemagglutinin (sheep erythrocyte receptor) with specificity for sialylated glycoconjugates characterized by a monoclonal antibody. J Exp Med 169, 1333-1346 (1989) (Pubitemid 19104966)
27. K. Drickamer: Clearing up glycoprotein hormones. Cell, 67, 1029-1032 (1991) (Pubitemid 121001516)
28. W. Yeeprae, S. Kawakami, Y. Higuchi, F. Yamashita and M. Hashida: Biodistribution characteristics of mannosylated and fucosylated O/W emulsions in mice. J Drug Target 13, 479-487 (2005) (Pubitemid 43347845)
29. W. Yeeprae, S. Kawakami, F. Yamashita and M. Hashida: Effect of mannose density on mannose receptor-mediated cellular uptake of mannosylated O/W emulsions by macrophages. J Control Release 114, 193-201 (2006) (Pubitemid 44291840)
30. W. Wijagkanalan, S. Kawakami, M. Takenaga, R. Igarashi, F. Yamashita and M. Hashida: Efficient targeting to alveolar macrophages by intratracheal administration of mannosylated liposomes in rats. J Control Release 125, 121-130 (2008) (Pubitemid 350299608)
31. W. Wijagkanalan, Y. Higuchi, S. Kawakami, M. Teshima, H. Sasaki and M. Hashida: Enhanced anti-inflammation of inhaled dexamethasone palmitate using mannosylated liposomes in an endotoxin-induced lung inflammation model. Mol Pharmacol 74, 1183-1192 (2008)
32. T. Kim, H. Jin, H. Kim, M. Cho and C. Cho: Mannosylated chitosan nanoparticle-based cytokine gene therapy suppressed cancer growth in BALB/c mice bearing CT-26 carcinoma cells. Mol Cancer Ther 5, 1723-1732 (2006) (Pubitemid 44323240)
33. M. Hashimoto, M. Morimoto, H. Saimoto, Y. Shigemasa, H. Yanagie, M. Eriguchi and T. Sato: Gene transfer by DNA/mannosylated chitosan complexes into mouse peritoneal macrophages. Biotechnol Lett, 28(11), 815-21 (2006) doi:10.1007/s10529-006-9006-x (Pubitemid 43926904)
34. S. Diebold, M. Kursa, E. Wagner, M. Cotten and M. Zenke: Mannose polyethylenimine conjugates for targeted DNA delivery into dendritic cells. J Biol Chem 274, 19087-19094 (1999)
35. Y. Lee, R. Townsend, M. Hardy, J. Lönngren, J. Arnarp, M. Haraldsson and H. Lönn: Binding of synthetic oligosaccharides to the hepatic Gal/GalNAc lectin. Dependence on fine structural features. J Biol Chem 258, 199-202 (1983)
36. E. Biessen, D. Beuting, H. Roelen, G. van de Marel, J. van Boom and T. van Berkel: Synthesis of cluster galactosides with high affinity for the hepatic asialoglycoprotein receptor. J Med Chem 38, 1538-1546 (1995)
37. J. Kuiper, H. Bakkeren, E. Biessen and T. Van Berkel: Characterization of the interaction of galactose-exposing particles with rat Kupffer cells. Biochem J 299, 285-290 (1994) (Pubitemid 24106320)
38. A. Fadden, O. Holt and K. Drickamer: Molecular characterization of the rat Kupffer cell glycoprotein receptor. Glycobiology 13, 529-537 (2003) (Pubitemid 36850126)
39. M. Monsigny, C. Kieda and A. Roche: Membrane glycoproteins, glycolipids and membrane lectins as recognition signals in normal and malignant cells. Biol Cell 47, 95-110 (1983) (Pubitemid 13087967)
40. P. Facy, A. Seve, M. Hubert, M. Monsigny and J. Hubert: Analysis of nuclear sugar-binding components in undifferentiated and in vitro differentiated human promyelocytic leukemia cells (HL60). Exp Cell Res 190, 151-160 (1990)
41. E. Duverger, C. Pellerin-Mendes, R. Mayer, A. Roche and M. Monsigny: Nuclear import of glycoconjugates is distinct from the classical NLS pathway. J Cell Sci 108, 1325-1332 (1995)
42. C. Rondanino, M. Bousser, M. Monsigny and A. Roche: Sugar-dependent nuclear import of glycosylated proteins in living cells. Glycobiology 13, 509-519 (2003) (Pubitemid 36850124)
43. T. Hara, Y. Aramaki, S. Takada, K. Koike and S. Tsuchiya: Receptor-mediated transfer of pSV2CAT DNA to mouse liver cells using asialofetuin-labeled liposomes. Gene Ther 2), 784-788 (1995) (Pubitemid 26043291)
44. J. Remy, A. Kichler, V. Mordvinov, F. Schuber and J. Behr: Targeted gene transfer into hepatoma cells with lipopolyamine-condensed DNA particles presenting galactose ligands: a stage toward artificial viruses. Proc Natl Acad Sci U S A 92, 1744-1748 (1995)
45. M. Nishikawa, S. Takemura, Y. Takakura and M. Hashida: Targeted delivery of plasmid DNA to hepatocytes in vivo: optimization of the pharmacokinetics of plasmid DNA/galactosylated poly(L-lysine) complexes by controlling their physicochemical properties. J Pharmacol Exp Ther 287, 408-415 (1998) (Pubitemid 29140227)
46. J. Han and Y. Il Yeom: Specific gene transfer mediated by galactosylated poly-L-lysine into hepatoma cells. Int J Pharm 202, 151-160 (2000) (Pubitemid 30466241)
47. M. Zanta, O. Boussif, A. Adib and J. Behr: In vitro gene delivery to hepatocytes with galactosylated polyethylenimine. Bioconjug Chem 8, 839-844 (1997) (Pubitemid 27526411)
48. K. Morimoto, M. Nishikawa, S. Kawakami, T. Nakano, Y. Hattori, S. Fumoto, F. Yamashita and M. Hashida: Molecular weight-dependent gene transfection activity of unmodified and galactosylated polyethyleneimine on hepatoma cells and mouse liver. Mol Ther 7, 254-261 (2003) (Pubitemid 36395361)
49. S. Kawakami, S. Fumoto, M. Nishikawa, F. Yamashita and M. Hashida: In vivo gene delivery to the liver using novel galactosylated cationic liposomes. Pharm Res 17, 306-313 (2000) (Pubitemid 30225134)
50. I. Park, T. Kim, Y. Park, B. Shin, E. Choi, E. Chowdhury, T. Akaike and C. Cho: Galactosylated chitosan-graft-poly(ethylene glycol) as hepatocytetargeting DNA carrier. J Control Release 76, 349-362 (2001) (Pubitemid 32913442)
51. S. Gao, J. Chen, X. Xu, Z. Ding, Y. Yang, Z. Hua and J. Zhang: Galactosylated low molecular weight chitosan as DNA carrier for hepatocyte-targeting. Int J Pharm 255, 57-68 (2003) (Pubitemid 36369591)
52. M. Morille, C. Passirani, E. Letrou-Bonneval, J. Benoit and B. Pitard: Galactosylated DNA lipid nanocapsules for efficient hepatocyte targeting. Int J Pharm 379, 293-300 (2009)
53. H. Jiang, J. Kwon, Y. Kim, E. Kim, R. Arote, H. Jeong, J. Nah, Y. Choi, T. Akaike, M. Cho and C. Cho: Galactosylated chitosan-graft-polyethylenimine as a gene carrier for hepatocyte targeting. Gene Ther 14, 1389-1398 (2007) (Pubitemid 47423738)
54. K. Wada, H. Arima, T. Tsutsumi, F. Hirayama and K. Uekama: Enhancing effects of galactosylated dendrimer/alpha-cyclodextrin conjugates on gene transfer efficiency. Biol Pharm Bull 28, 500-505 (2005) (Pubitemid 40879976)
55. H. Arima, S. Yamashita, Y. Mori, Y. Hayashi, K. Motoyama, K. Hattori, T. Takeuchi, H. Jono, Y. Ando, F. Hirayama and K. Uekama: In vitro and in vivo gene delivery mediated by Lactosylated dendrimer/alphacyclodextrin conjugates (G2) into hepatocytes. J Control Release 146, 106-117 (2010)
56. P. Erbacher, M. Bousser, J. Raimond, M. Monsigny, P. Midoux and A. Roche: Gene transfer by DNA/glycosylated polylysine complexes into human blood monocyte-derived macrophages. Hum Gene Ther 7, 721-729 (1996) (Pubitemid 26125842)
57. W. Liang, X. Shi, D. Deshpande, C. Malanga and Y. Rojanasakul: Oligonucleotide targeting to alveolar macrophages by mannose receptor-mediated endocytosis. Biochim Biophys Acta 1279, 227-234 (1996) (Pubitemid 26080854)
58. T. Ferkol, J. Perales, F. Mularo and R. Hanson: Receptor-mediated gene transfer into macrophages. Proc Natl Acad Sci U S A 93, 101-105 (1996) (Pubitemid 26038110)
59. M. Nishikawa, S. Takemura, F. Yamashita, Y. Takakura, D. Meijer, M. Hashida and P. Swart: Pharmacokinetics and in vivo gene transfer of plasmid DNA complexed with mannosylated poly(L-lysine) in mice. J Drug Target 8, 29-38 (2000) (Pubitemid 30189691)
60. S. Kawakami, A. Sato, M. Nishikawa, F. Yamashita and M. Hashida: Mannose receptor-mediated gene transfer into macrophages using novel mannosylated cationic liposomes. Gene Ther 7, 292-299 (2000) (Pubitemid 30119732)
61. Y. Kuramoto, S. Kawakami, S. Zhou, K. Fukuda, F. Yamashita and M. Hashida: Mannosylated cationic liposomes/CpG DNA complex for the treatment of hepatic metastasis after intravenous administration in mice. J Pharm Sci 98, 1193-1197 (2009)
62. Y. Hattori, S. Kawakami, K. Nakamura, F. Yamashita and M. Hashida: Efficient gene transfer into macrophages and dendritic cells by in vivo gene delivery with mannosylated lipoplex via the intraperitoneal route. J Pharmacol Exp Ther 318, 828-834 (2006) (Pubitemid 44061257)
63. Y. Higuchi, S. Kawakami, F. Yamashita and M. Hashida: The potential role of fucosylated cationic liposome/NFkappaB decoy complexes in the treatment of cytokine-related liver disease. Biomaterials 28, 532-539 (2007) (Pubitemid 44602230)
64. Wassana Wijagkanalan, Shigeru Kawakami, Yuriko Higuchi, Fumiyoshi Yamashita, and Mitsuru Hashida: Intratracheally instilled mannosylated cationic liposome/NFκB decoy complexes for effective prevention of LPS-induced lung inflammation, J Control Release, 149 (1), 42-50 (2011)
65. W. Yu, C. Liu, Y. Liu, N. Zhang and W. Xu: Mannan-modified solid lipid nanoparticles for targeted gene delivery to alveolar macrophages. Pharm Res 27, 1584-1596 (2010)
66. K. Un, S. Kawakami, R. Suzuki, K. Maruyama, F. Yamashita and M. Hashida: Enhanced transfection efficiency into macrophages and dendritic cells by a combination method using mannosylated lipoplexes and bubble liposomes with ultrasound exposure. Hum Gene Ther 21, 65-74 (2010)
67. K. Wada, H. Arima, T. Tsutsumi, Y. Chihara, K. Hattori, F. Hirayama and K. Uekama: Improvement of gene delivery mediated by mannosylated dendrimer/alpha-cyclodextrin conjugates. J Control Release 104, 397-413 (2005) (Pubitemid 40724937)
68. H. Arima, Y. Chihara, M. Arizono, S. Yamashita, K. Wada, F. Hirayama and K. Uekama: Enhancement of gene transfer activity mediated by mannosylated dendrimer/alpha-cyclodextrin conjugate (generation 3, G3). J Control Release 116, 64-74 (2006) (Pubitemid 44792299)
69. L. Dong, S. Xia, Y. Luo, H. Diao, J. Zhang and J. Chen: Targeting delivery oligonucleotide into macrophages by cationic polysaccharide from Bletilla striata successfully inhibited the expression of TNFalpha. J Control Release 134, 214-220 (2009)
70. Y. Hattori, S. Kawakami, Y. Lu, K. Nakamura, F. Yamashita and M. Hashida: Enhanced DNA vaccine potency by mannosylated lipoplex after intraperitoneal administration. J Gene Med 8, 824-834 (2006) (Pubitemid 44097138)
71. K. Un, S. Kawakami, R. Suzuki, K. Maruyama, F. Yamashita and M. Hashida: Development of an ultrasoundresponsive and mannose-modified gene carrier for DNA vaccine therapy. Biomaterials 31, 7813-7826 (2010)
72. Y. Hattori, S. Kawakami, S. Suzuki, F. Yamashita and M. Hashida: Enhancement of immune responses by DNA vaccination through targeted gene delivery using mannosylated cationic liposome formulations following intravenous administration in mice. Biochem Biophys Res Commun 317, 992-999 (2004) (Pubitemid 38496408)
73. Y. Lu, S. Kawakami, F. Yamashita and M. Hashida: Development of an antigen-presenting cell-targeted DNA vaccine against melanoma by mannosylated liposomes. Biomaterials 28, 3255-3262 (2007) (Pubitemid 46654220)
74. C. Tang, J. Lodding, G. Minigo, D. Pouniotis, M. Plebanski, A. Scholzen, I. McKenzie, G. Pietersz and V. Apostolopoulos: Mannan-mediated gene delivery for cancer immunotherapy. Immunology 120, 325-335 (2007) (Pubitemid 46232907)
75. X. Zhou, B. Liu, X. Yu, X. Zha, X. Zhang, Y. Chen, X. Wang, Y. Jin, Y. Wu, Y. Shan, J. Liu, W. Kong and J. Shen: Controlled release of PEI/DNA complexes from mannose-bearing chitosan microspheres as a potent delivery system to enhance immune response to HBV DNA vaccine. J Control Release 121, 200-207 (2007) (Pubitemid 47214651)
76. H. Salman, J. Irache and C. Gamazo: Immunoadjuvant capacity of flagellin and mannosamine-coated poly(anhydride) nanoparticles in oral vaccination. Vaccine 27, 4784-4790 (2009)
77. R. Srinivas, P. Karmali, D. Pramanik, A. Garu, Y. Mahidhar, B. Majeti, S. Ramakrishna, G. Srinivas and A. Chaudhuri: Cationic amphiphile with shikimic acid headgroup shows more systemic promise than its mannosyl analogue as DNA vaccine carrier in dendritic cell based genetic immunization. J Med Chem 53, 1387-1391 (2010)
78. P. de Bleser, P. Jannes, S. van Buul-Offers, C. Hoogerbrugge, C. van Schravendijk, T. Niki, V. Rogiers, J. van den Brande, E. Wisse and A. Geerts: Insulinlike growth factor-II/mannose 6-phosphate receptor is expressed on CCl4-exposed rat fat-storing cells and facilitates activation of latent transforming growth factor-beta in cocultures with sinusoidal endothelial cells. Hepatology 21, 1429-1437 (1995)
79. Z. Ye, K. Cheng, R. Guntaka and R. Mahato: Targeted delivery of a triplex-forming oligonucleotide to hepatic stellate cells. Biochemistry 44, 4466-4476 (2005) (Pubitemid 40403989)
80. Z. Ye, K. Cheng, R. Guntaka and R. Mahato: Receptormediated hepatic uptake of M6P-BSA-conjugated triplex-forming oligonucleotides in rats. Bioconjug Chem 17, 823-830 (2006) (Pubitemid 43794394)
81. N. Yang, Z. Ye, F. Li and R. Mahato: HPMA polymerbased site-specific delivery of oligonucleotides to hepatic stellate cells. Bioconjug Chem 20, 213-221 (2009)
82. I. Fajac, P. Briand, M. Monsigny and P. Midoux: Sugar-mediated uptake of glycosylated polylysines and gene transfer into normal and cystic fibrosis airway epithelial cells. Hum Gene Ther 10, 395-406 (1999) (Pubitemid 29097318)
83. W. Kollen, P. Midoux, P. Erbacher, A. Yip, A. Roche, M. Monsigny, M. Glick and T. Scanlin: Gluconoylated and glycosylated polylysines as vectors for gene transfer into cystic fibrosis airway epithelial cells. Hum Gene Ther 7, 1577-1586 (1996) (Pubitemid 26302212)
84. S. Grosse, Y. Aron, I. Honoré, G. Thévenot, C. Danel, A. Roche, M. Monsigny and I. Fajac: Lactosylated polyethylenimine for gene transfer into airway epithelial cells: role of the sugar moiety in cell delivery and intracellular trafficking of the complexes. J Gene Med 6, 345-356 (2004) (Pubitemid 40228052)
85. T. Montier, P. Delépine, T. Benvegnu, V. Ferrières, M. Miramon, S. Dagorn, C. Guillaume, D. Plusquellec and C. Férec: Efficient gene transfer into human epithelial cell lines using glycosylated cationic carriers and neutral glycosylated co-lipids. Blood Cells Mol Dis 32, 271-282 (2004) (Pubitemid 38296691)
86. M. Issa, M. Köping-Höggård, K. Tømmeraas, K. Vårum, B. Christensen, S. Strand and P. Artursson: Targeted gene delivery with trisaccharide-substituted chitosan oligomers in vitro and after lung administration in vivo. J Control Release 115, 103-112 (2006) (Pubitemid 44415074)
87. D. Klink, S. Chao, M. Glick and T. Scanlin: Nuclear translocation of lactosylated poly-L-lysine/cDNA complex in cystic fibrosis airway epithelial cells. Mol Ther 3, 831-841 (2001) (Pubitemid 32611292)
88. H. Gabius: Animal lectins. Eur J Biochem 243, 543-576 (1997) (Pubitemid 27073422)
89. M. Hirai, H. Minematsu, N. Kondo, K. Oie, K. Igarashi and N. Yamazaki: Accumulation of liposome with Sialyl Lewis X to inflammation and tumor region: application to in vivo bio-imaging. Biochem Biophys Res Commun 353, 553-558 (2007) (Pubitemid 46048704)
90. N. Hashida, N. Ohguro, N. Yamazaki, Y. Arakawa, E. Oiki, H. Mashimo, N. Kurokawa and Y. Tano: Highefficacy site-directed drug delivery system using sialyl-Lewis X conjugated liposome. Exp Eye Res 86, 138-149 (2008) (Pubitemid 350212886)
91. T. Murohara, J. Margiotta, L. Phillips, J. Paulson, S. DeFrees, S. Zalipsky, L. Guo and A. Lefer: Cardioprotection by liposome-conjugated sialyl Lewisxoligosaccharide in myocardial ischaemia and reperfusion injury. Cardiovasc Res 30, 965-974 (1995)
92. R. Stahn, C. Grittner, R. Zeisig, U. Karsten, S. Felix and K. Wenzel: Sialyl Lewis(x)-liposomes as vehicles for site-directed, E-selectin-mediated drug transfer into activated endothelial cells. Cell Mol Life Sci 58, 141-147 (2001) (Pubitemid 32143969)
93. T. Katav, L. Liu, T. Traitel, R. Goldbart, M. Wolfson and J. Kost: Modified pectin-based carrier for gene delivery: cellular barriers in gene delivery course. J Control Release 130, 183-191 (2008)
94. T. Kasuya, J. Jung, H. Kadoya, T. Matsuzaki, K. Tatemastu, T. Okajima, E. Miyoshi, K. Tanizawa and S. Kuroda: In vivo delivery of bio-nanocapsules displaying L4-PHA isolectin to malignant tumors overexpressing Nacetylglucosaminyltransferase V. Hum Gene Ther 19, 887-895 (2008)
95. F. van den Brûle, S. Califice and V. Castronovo: Expression of galectins in cancer: a critical review. Glycoconj J 19, 537-542 (2004)
96. T. Handerson and J. Pawelek: Beta1,6-branched oligosaccharides and coarse vesicles: a common, pervasive phenotype in melanoma and other human cancers. Cancer Res 63, 5363-5369 (2003) (Pubitemid 37139852)
97. R. Cummings, I. Trowbridge and S. Kornfeld: A mouse lymphoma cell line resistant to the leukoagglutinating lectin from Phaseolus vulgaris is deficient in UDPGlcNAc: alpha-D-mannoside beta 1,6 Nacetylglucosaminyltransferase. J Biol Chem 257, 13421-13427 (1982) (Pubitemid 13188958)
98. A. Kichler, C. Leborgne, E. Coeytaux and O. Danos: Polyethylenimine- mediated gene delivery: a mechanistic study. J Gene Med 3, 135-144 (2001) (Pubitemid 33685440)
99. D. Pack, A. Hoffman, S. Pun and P. Stayton: Design and development of polymers for gene delivery. Nat Rev Drug Discov 4, 581-593 (2005) (Pubitemid 40975711)
100. I. Fajac, G. Thévenot, L. Bédouet, C. Danel, M. Riquet, M. Merten, C. Figarella, J. Dall'Ava-Santucci, M. Monsigny and P. Briand: Uptake of plasmid/glycosylated polymer complexes and gene transfer efficiency in differentiated airway epithelial cells. J Gene Med 5, 38-48 (2003) (Pubitemid 40310366)
101. S. Grosse, A. Tremeau-Bravard, Y. Aron, P. Briand and I. Fajac: Intracellular rate-limiting steps of gene transfer using glycosylated polylysines in cystic fibrosis airway epithelial cells. Gene Ther 9, 1000-1007 (2002)
102. C. Gonçalves, C. Pichon, B. Guérin and P. Midoux: Intracellular processing and stability of DNA complexed with histidylated polylysine conjugates. J Gene Med 4, 271-281 (2002) (Pubitemid 40268363)
103. K. Shigeta, S. Kawakami, Y. Higuchi, T. Okuda, H. Yagi, F. Yamashita and M. Hashida: Novel histidineconjugated galactosylated cationic liposomes for efficient hepatocyte-selective gene transfer in human hepatoma HepG2 cells. J Control Release 118, 262-270 (2007) (Pubitemid 46329736)
104. K. Nakamura, Y. Kuramoto, H. Mukai, S. Kawakami, Y. Higuchi and M. Hashida: Enhanced gene transfection in macrophages by histidine-conjugated mannosylated cationic liposomes. Biol Pharm Bull 32, 1628-1631 (2009)
105. M. Nishikawa, M. Yamauchi, K. Morimoto, E. Ishida, Y. Takakura and M. Hashida: Hepatocytetargeted in vivo gene expression by intravenous injection of plasmid DNA complexed with synthetic multi-functional gene delivery system. Gene Ther 7, 548-555 (2000) (Pubitemid 30175557)
106. A. Kichler, I. Freulon, V. Boutin, R. Mayer, M. Monsigny and P. Midoux: Glycofection in the presence of anionic fusogenic peptides: a study of the parameters affecting the peptide-mediated enhancement of the transfection efficiency. J Gene Med 1, 134-143 (1999) (Pubitemid 129631070)
107. Y. Hattori, S. Suzuki, S. Kawakami, F. Yamashita and M. Hashida: The role of dioleoylphosphatidylethanolamine (DOPE) in targeted gene delivery with mannosylated cationic liposomes via intravenous route. J Control Release 108, 484-495 (2005) (Pubitemid 41608679)
108. S. Grosse, G. Thévenot, M. Monsigny and I. Fajac: Which mechanism for nuclear import of plasmid DNA complexed with polyethylenimine derivatives? J Gene Med 8, 845-851 (2006) (Pubitemid 44097140)
109. S. Grosse, G. Thévenot, Y. Aron, E. Duverger, M. Abdelkarim, A. Roche, M. Monsigny and I. Fajac: In vivo gene delivery in the mouse lung with lactosylated polyethylenimine, questioning the relevance of in vitro experiments. J Control Release 132, 105-112 (2008)
110. D. Klink, Q. Yu, M. Glick and T. Scanlin: Lactosylated poly-L-lysine targets a potential lactose receptor in cystic fibrosis and non-cystic fibrosis airway epithelial cells. Mol Ther 7, 73-80 (2003) (Pubitemid 36305360)
111. T. Masuda, H. Akita, T. Nishio, K. Niikura, K. Kogure, K. Ijiro and H. Harashima: Development of lipid particles targeted via sugar-lipid conjugates as novel nuclear gene delivery system. Biomaterials 29, 709-723 (2008) (Pubitemid 350181035)
112. T. Bettinger, J. Remy and P. Erbacher: Size reduction of galactosylated PEI/DNA complexes improves lectin-mediated gene transfer into hepatocytes. Bioconjug Chem 10, 558-561 (1999) (Pubitemid 29355232)
113. M. Ogris, P. Steinlein, M. Kursa, K. Mechtler, R. Kircheis and E. Wagner: The size of DNA/transferrin-PEI complexes is an important factor for gene expression in cultured cells. Gene Ther 5, 1425-1433 (1998) (Pubitemid 28482671)
114. Y. Rahman, E. Cerny, K. Patel, E. Lau and B. Wright: Differential uptake of liposomes varying in size and lipid composition by parenchymal and kupffer cells of mouse liver. Life Sci 31, 2061-2071 (1982) (Pubitemid 13213518)
115. K. Ogawara, M. Yoshida, K. Higaki, T. Kimura, K. Shiraishi, M. Nishikawa, Y. Takakura and M. Hashida: Hepatic uptake of polystyrene microspheres in rats: effect of particle size on intrahepatic distribution. J Control Release 59, 15-22 (1999) (Pubitemid 29187189)
116. F. Yuan, M. Dellian, D. Fukumura, M. Leunig, D. Berk, V. Torchilin and R. Jain: Vascular permeability in a human tumor xenograft: molecular size dependence and cutoff size. Cancer Res 55, 3752-3756 (1995)
117. J. Yang and L. Huang: Overcoming the inhibitory effect of serum on lipofection by increasing the charge ratio of cationic liposome to DNA. Gene Ther 4, 950-960 (1997) (Pubitemid 27437721)
118. M. Ogris, S. Brunner, S. Schüller, R. Kircheis and E. Wagner: PEGylated DNA/transferrin-PEI complexes: reduced interaction with blood components, extended circulation in blood and potential for systemic gene delivery. Gene Ther 6, 595-605 (1999) (Pubitemid 29192668)
119. F. Sakurai, T. Nishioka, F. Yamashita, Y. Takakura and M. Hashida: Effects of erythrocytes and serum proteins on lung accumulation of lipoplexes containing cholesterol or DOPE as a helper lipid in the single-pass rat lung perfusion system. Eur J Pharm Biopharm 52, 165-172 (2001) (Pubitemid 32755895)
120. S. Fumoto, F. Nakadori, S. Kawakami, M. Nishikawa, F. Yamashita and M. Hashida: Analysis of hepatic disposition of galactosylated cationic liposome/plasmid DNA complexes in perfused rat liver. Pharm Res 20, 1452-1459 (2003) (Pubitemid 37164054)
121. S. Kawakami, Y. Hattori, Y. Lu, Y. Higuchi, F. Yamashita and M. Hashida: Effect of cationic charge on receptor-mediated transfection using mannosylated cationic liposome/plasmid DNA complexes following the intravenous administration in mice. Pharmazie 59, 405-408 (2004) (Pubitemid 38720351)
122. S. Fumoto, S. Kawakami, K. Shigeta, Y. Higuchi, F. Yamashita and M. Hashida: Interaction with blood components plays a crucial role in asialoglycoprotein receptormediated in vivo gene transfer by galactosylated lipoplex. J Pharmacol Exp Ther 315, 484-493 (2005) (Pubitemid 41500711)
123. S. Fumoto, S. Kawakami, Y. Ito, K. Shigeta, F. Yamashita and M. Hashida: Enhanced hepatocyte-selective in vivo gene expression by stabilized galactosylated liposome/plasmid DNA complex using sodium chloride for complex formation. Mol Ther 10, 719-729 (2004) (Pubitemid 39272861)
124. V. Shepherd, M. Konish and P. Stahl: Dexamethasone increases expression of mannose receptors and decreases extracellular lysosomal enzyme accumulation in macrophages. J Biol Chem 260, 160-164 (1985) (Pubitemid 15165296)
125. M. Stein, S. Keshav, N. Harris and S. Gordon: Interleukin 4 potently enhances murine macrophage mannose receptor activity: a marker of alternative immunologic macrophage activation. J Exp Med 176, 287-292 (1992)
126. V. Shepherd, R. Abdolrasulnia, M. Garrett and H. Cowan: Down-regulation of mannose receptor activity in macrophages after treatment with lipopolysaccharide and phorbol esters. J Immunol 145, 1530-1536 (1990) (Pubitemid 20255064)
127. N. Harris, M. Super, M. Rits, G. Chang and R. Ezekowitz: Characterization of the murine macrophage mannose receptor: demonstration that the downregulation of receptor expression mediated by interferon-gamma occurs at the level of transcription. Blood, 80, 2363-2373 (1992)
128. H. Koziel, Q. Eichbaum, B. Kruskal, P. Pinkston, R. Rogers, M. Armstrong, F. Richards, R. Rose and R. Ezekowitz: Reduced binding and phagocytosis of Pneumocystis carinii by alveolar macrophages from persons infected with HIV-1 correlates with mannose receptor downregulation. J Clin Invest 102, 1332-1344 (1998) (Pubitemid 28467561)
129. S. Manna, S. Sarkar, J. Barr, K. Wise, E. Barrera, O. Jejelowo, A. Rice-Ficht and G. Ramesh: Single-walled carbon nanotube induces oxidative stress and activates nuclear transcription factor-kappaB in human keratinocytes. Nano Lett 5, 1676-1684 (2005) (Pubitemid 41396145)
130. N. Kam and H. Dai: Carbon nanotubes as intracellular protein transporters: generality and biological functionality. J Am Chem Soc 127, 6021-6026 (2005) (Pubitemid 40577658)
131. C. Gao, S. Muthukrishnan, W. Li, J. Yuan, Y. Xu and A. Muller: Linear and hyperbranched glycopolymerfunctionalized carbon nanotubes: Synthesis, Kinetics, and Characterization. Macromolecules 40, 1803-1815 (2007)
132. M. Ahmed, X. Jiang, Z. Deng and R. Narain: Cationic glyco-functionalized single-walled carbon nanotubes as efficient gene delivery vehicles. Bioconjug Chem 20, 2017-2022 (2009)
133. P. Eaton, A. Ragusa, C. Clavel, C. Rojas, P. Graham, R. Durán and S. Penadés: Glyconanoparticle-DNA interactions: an atomic force microscopy study. IEEE Trans Nanobioscience 6, 309-318 (2007) (Pubitemid 350210546)
134. M. Ahmed, Z. Deng, S. Liu, R. Lafrenie, A. Kumar and R. Narain: Cationic glyconanoparticles: their complexation with DNA, cellular uptake, and transfection efficiencies. Bioconjug Chem 20, 2169-2176 (2009)
135. B. Selvi, D. Jagadeesan, B. Suma, G. Nagashankar, M. Arif, K. Balasubramanyam, M. Eswaramoorthy and T. Kundu: Intrinsically fluorescent carbon nanospheres as a nuclear targeting vector: delivery of membrane-impermeable molecule to modulate gene expression in vivo. Nano Lett 8, 3182-3188 (2008)
136. X. Chen, U. Tam, J. Czlapinski, G. Lee, D. Rabuka, A. Zettl and C. Bertozzi: Interfacing carbon nanotubes with living cells. J Am Chem Soc 128, 6292-6293 (2006) (Pubitemid 43727247)
137. H. Sudibya, J. Ma, X. Dong, S. Ng, L. Li, X. Liu and P. Chen: Interfacing glycosylated carbon-nanotube-network devices with living cells to detect dynamic secretion of biomolecules. Angew Chem Int Ed Engl 48, 2723-2726 (2009)
138. S. Hong, G. Tobias, K. Al-Jamal, B. Ballesteros, H. Ali-Boucetta, S. Lozano-Perez, P. Nellist, R. Sim, C. Finucane, S. Mather, M. Green, K. Kostarelos and B. Davis: Filled and glycosylated carbon nanotubes for in vivo radioemitter localization and imaging. Nat Mater 9, 485-490 (2010)
139. X. Wang, D. Sarkar, P. Mani, C. Steer, Y. Chen, C. Guha, V. Chandrasekhar, A. Chaudhuri, N. Roy-Chowdhury, B. Kren and J. Roy-Chowdhury: Long-term reduction of jaundice in Gunn rats by nonviral liver-targeted delivery of Sleeping Beauty transposon. Hepatology 50, 815-824 (2009)
140. Z. Izsvák and Z. Ivics: Sleeping beauty transposition: biology and applications for molecular therapy. Mol Ther 9, 147-156 (2004) (Pubitemid 38256540)
141. M. Edelstein, M. Abedi and J. Wixon: Gene therapy clinical trials worldwide to 2007-an update. J Gene Med 9, 833-842 (2007) (Pubitemid 47543250)
142. W. Anderson: Human gene therapy. Nature 392, 25-30 (1998) (Pubitemid 28215190)
143. U. S. National Institutes of Health: Clinical Trials Database. Available: http://clinicaltrials.gov/
144. A. Avraméas, D. McIlroy, A. Hosmalin, B. Autran, P. Debré, M. Monsigny, A. Roche and P. Midoux: Expression of a mannose/fucose membrane lectin on human dendritic cells. Eur J Immunol 26, 394-400 (1996) (Pubitemid 26060247)
145. V. Shepherd, H. Freeze, A. Miller and P. Stahl: Identification of mannose 6-phosphate receptors in rabbit alveolar macrophages. J Biol Chem 259, 2257-2261 (1984) (Pubitemid 14190340)
146. M. Stein, J. Zijderhand-Bleekemolen, H. Geuze, A. Hasilik and K. von Figura: Mr 46,000 mannose 6-phosphate specific receptor: its role in targeting of lysosomal enzymes. EMBO J 6, 2677-2681 (1987)
147. B. Brandley, S. Swiedler and P. Robbins: Carbohydrate ligands of the LEC cell adhesion molecules. Cell 63, 861-863 (1990) (Pubitemid 120034927)
148. I. Moutsatsos, M. Wade, M. Schindler and J. Wang: Endogenous lectins from cultured cells: nuclear localization of carbohydrate-binding protein 35 in proliferating 3T3 fibroblasts. Proc Natl Acad Sci U S A 84, 6452-6456 (1987)
149. H. Schröder, P. Facy, M. Monsigny, K. Pfeifer, A. Bek and W. Müller: Purification of a glucose-binding protein from rat liver nuclei. Evidence for a role in targeting of nuclear mRNP to nuclear pore complex. Eur J Biochem 205, 1017-1025 (1992)
150. C. Rousseau, M. Felin, M. Doyennette-Moyne and A. Sève: CBP70, a glycosylated nuclear lectin. J Cell Biochem 66, 370-385 (1997) (Pubitemid 27332870)