Saccharide modified pharmaceutical nanocarriers for targeted drug and gene delivery

Current Pharmaceutical Design

Volumn 15, Issue 32, 2009, Pages 3826-3836

  Yu, Wangyang ^a   Zhang, Na ^a   Li, Changjun ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

Active targeting; Drug and gene delivery; Nanocarriers; Saccharide ligands; Surface modification

Indexed keywords

ANION; ASIALOGLYCOPROTEIN RECEPTOR; BASIC FIBROBLAST GROWTH FACTOR; CARBOHYDRATE; CATION; CHITOSAN; CIPROFLOXACIN; CPG DNA COMPLEX; DISACCHARIDE; DNA VACCINE; DOXORUBICIN; GALACTOSYLATED NANOCARRIER; GLYCOLIPID; IMMUNOSTIMULATING AGENT; LACTOSYLATED NANOCARRIER; LECTIN; LIGAND; LIPOSOME; MANNAN BINDING LECTIN; MANNOSE RECEPTOR; MANNOSYLATED DENDRIMER; MANNOSYLATED NANOCARRIER; MONOSACCHARIDE; MURAMYL DIPEPTIDE; NANOCARRIER; NANOPARTICLE; POLYSACCHARIDE; PROBUCOL; STAVUDINE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; BINDING AFFINITY; CHEMICAL MODIFICATION; DRUG DELIVERY SYSTEM; DRUG DISTRIBUTION; DRUG EFFICACY; DRUG STABILITY; GENE TARGETING; GLYCOCALYX; GLYCOSYLATION; IN VIVO GENE TRANSFER; LIGAND BINDING; LIVER METASTASIS; LIVER PARENCHYMA; NONHUMAN; PARASITOSIS; PERITONEUM METASTASIS; PRIORITY JOURNAL; RESPIRATORY TRACT INFECTION; REVIEW; TARGET CELL;

ANIMALS; CARBOHYDRATES; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; GENE TARGETING; GENE THERAPY; GENE TRANSFER TECHNIQUES; GENETIC VECTORS; HUMANS; LIGANDS; NANOPARTICLES;

EID: 70449645181     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: 10.2174/138161209789649547     Document Type: Review

References (79)

1. Torchilin VP. Targeted pharmaceutical nanocarriers for cancer therapy and imaging. AAPS J 2007; 9: E128-47.
2. Yu WY, Liu CX, Ye JS, Zou WW, Zhang N, Xu WF. Novel cationic SLN containing a synthesized single-tailed lipid as a modifier for gene delivery. Nanotechnology 2009; 20: 215102.
3. Beduneau A, Saulnier P, Benoit JP. Active targeting of brain tumors using nanocarriers. Biomaterials 2007; 28: 4947-4967 (Pubitemid 47362345)
4. Yu WY, Zhang N. Surface modification of nanocarriers for cancer therapy. Curr Nanosci 2009; 5: 123-134
5. Wang SN, Deng YH, Xu H, Wu HB, Qiu YK, Chen DW. Synthesis of a novel galactosylated lipid and its application to the hepatocyte-selective targeting of liposomal doxorubicin. Eur J Pharm Biopharm 2006; 62: 32-38 (Pubitemid 41736022)
6. Wijagkanalan W, Kawakami S, Takenaga M, Igarashi R, Yamashita F, Hashida M. Efficient targeting to alveolar macrophages by intratracheal administration of mannosylated liposomes in rats. J Control Release 2008; 125: 121-130 (Pubitemid 350299608)
7. Grosse S, Aron Y, Honore I, Thevenot G, Danel C, Roche AC, et al. 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 2004; 6: 345-356 (Pubitemid 40228052)
8. Zhang XQ, Wang XL, Zhang PC, Liu ZL, Zhuo RX, Mao HQ, et al. Galactosylated ternary DNA/polyphosphoramidate nanoparticles mediate high gene transfection efficiency in hepatocytes. J Control Release 2005; 102: 749-763
9. Seo SJ, Moon HS, Guo DD, Kim SH, Akaike T, Cho CS. Receptor-mediated delivery of all-trans-retinoic acid (ATRA) to hepatocytes from ATRA-loaded poly(N-p-vinylbenzyl-4-o-beta-D-galactopyranosyl-D-gluconamide) nanoparticles. Mat Sci Eng CBiomimetic Supramol Syst 2006; 26: 136-141
10. Wu GY, Wu CH. Receptor-mediated gene delivery and expression in vivo. J Biol Chem 1988; 263: 14621-14624
11. Opanasopit P, Sakai M, Nishikawa M, Kawakami S, Yamashita F, Hashida M. Inhibition of liver metastasis by targeting of immunomodulators using mannosylated liposome carriers. J Control Release 2002; 80: 283-294 (Pubitemid 34273766)
12. Mitra M, Mandal AK, Chatterjee TK, Das N. Targeting of mannosylated liposome incorporated benzyl derivative of Penicillium nigricans derived compound MT81 to reticuloendothelial systems for the treatment of visceral leishmaniasis. J Drug Target 2005; 13: 285-293 (Pubitemid 41283162)
13. Copland MJ, Baird MA, Rades T, McKenzie JL, Becker B, Reck F, et al. Liposomal delivery of antigen to human dendritic cells. Vaccine 2003; 21: 883-890 (Pubitemid 36126422)
14. Horiuchi S, Aoyama Y. Systematic lactose-functionalization of amphiphilic octaamine macrocycle as a gene carrier. Optimization of the charge, size, toxicity, and receptor factors for hepatocyte targeting. J Control Release 2006; 116: 107-114 (Pubitemid 44854280)
15. Espuelas S, Haller P, Schuber F, Frisch B. Synthesis of an amphiphilic tetraantennary mannosyl conjugate and incorporation into liposome carriers. Bioorg Med Chem Lett 2003; 13: 2557-2560 (Pubitemid 36830772)
16. Hattori Y, Suzuki S, Kawakami S, Yamashita F, Hashida M. The role of dioleoylphosphatidylethanolamine (DOPE) in targeted gene delivery with mannosylated cationic liposomes via intravenous route. J Control Release 2005; 108: 484-495 (Pubitemid 41608679)
17. Opanasopit P, Hyoudou K, Nishikawa M, Yamashita F, Hashida M. Serum mannan binding protein inhibits mannosylated liposome-mediated transfection to macrophages. Biochim Biophys Acta 2002; 1570: 203-209 (Pubitemid 34518602)
18. Sharon N. Lectins: past, present and future. Biochem Soc Trans 2008; 36: 1457-1460
19. Monsigny M, Quetard C, Bourgerie S, Delay D, Pichon C, Midoux P, et al. Glycotargeting: the preparation of glyco-amino acids and derivatives from unprotected reducing sugars. Biochimie 1998; 80: 99-108. (Pubitemid 28185048)
20. Roseman S. Reflections on glycobiology. J Biol Chem 2001; 276: 41527-41542
21. Zhu J, Xue J, Guo Z, Zhang L, Marchant RE. Biomimetic glycoliposomes as nanocarriers for targeting P-selectin on activated platelets. Bioconjug Chem 2007; 18: 1366-1369 (Pubitemid 47464040)
22. Sihorkar V, Vyas SP. Potential of polysaccharide anchored liposomes in drug delivery, targeting and immunization. J Pharm Pharm Sci 2001; 4: 138-158 (Pubitemid 34305606)
23. Engel A, Chatterjee SK, Al-arifi A, Riemann D, Langner J, Nuhn P. Influence of spacer length on interaction of mannosylated liposomes with human phagocytic cells. Pharm Res 2003; 20: 51-57 (Pubitemid 36152917)
24. Engel A, Chatterjee SK, Al-Arifi A, Nuhn P. Influence of spacer length on the agglutination of glycolipid-incorporated liposomes by ConA as model membrane. J Pharm Sci 2003; 92: 2229-2235 (Pubitemid 37356696)
25. Tamiaki H, Azefu Y, Shibata R, Sato R, Toma K. Oligomethylene spacer length dependent interaction of synthetic galactolipids incorporated in phospholipid layers with ricin. Colloids Surf B Biointerfaces 2006; 53: 87-93. (Pubitemid 44584634)
26. Managit C, Kawakami S, Yamashita F, Hashida M. Effect of galactose density on asialoglycoprotein receptor-mediated uptake of galactosylated liposomes. J Pharm Sci 2005; 94: 2266-2275 (Pubitemid 41665286)
27. Yeeprae W, Kawakami S, Yamashita F, Hashida M. Effect of mannose density on mannose receptor-mediated cellular uptake of mannosylated O/W emulsions by macrophages. J Control Release 2006; 114: 193-201. (Pubitemid 44291840)
28. Yang JP, Huang L. Overcoming the inhibitory effect of serum on lipofection by increasing the charge ratio of cationic liposome to DNA. Gene Ther 1997; 4: 950-960 (Pubitemid 27437721)
29. Kawakami S, Fumoto S, Nishikawa M, Yamashita F, Hashida M. In vivo gene delivery to the liver using novel galactosylated cationic liposomes. Pharm Res 2000; 17: 306-313
30. Kawakami S, Hattori Y, Lu Y, Higuchi Y, Yamashita F, Hashida M. Effect of cationic charge on receptor-mediated transfection using mannosylated cationic liposome/plasmid DNA complexes following the intravenous administration in mice. Pharmazie 2004; (Pubitemid 38720351) 59: 405-408
31. Fumoto S, Nakadori F, Kawakami S, Nishikawa M, Yamashita F, Hashida M. Analysis of hepatic disposition of galactosylated cationic liposome/plasmid DNA complexes in perfused rat liver. Pharm Res 2003; 20: 1452-1459 (Pubitemid 37164054)
32. Jeong YI, Seo SJ, Park IK, Lee HC, Kang IC, Akaike T, et al. Cellular recognition of paclitaxel-loaded polymeric nanoparticles composed of poly(gamma-benzul L-glutamate) and poly(ethylene glycol) diblock copolymer endcapped with galactose moiety. Int J Pharm 2005; 296: 151-161 (Pubitemid 40693384)
33. Wakebayashi D, Nishiyama N, Yamasaki Y, Itaka K, Kanayama N, Harada A, et al. Lactose-conjugated polyion complex micelles incorporating plasmid DNA as a targetable gene vector system: their preparation and gene transfecting efficiency against cultured HepG2 cells. J Control Release 2004; 95: 653-664 (Pubitemid 38340512)
34. Diaz C, Vargas E, Gatjens-Boniche O. Cytotoxic effect induced by retinoic acid loaded into galactosyl-sphingosine containing liposomes on human hepatoma cell lines. Int J Pharm 2006; 325: 108-115 (Pubitemid 44573704)
35. Akiyama E, Morimoto N, Kujawa P, Ozawa Y, Winnik FM, Akiyoshi K. Self-assembled nanogels of cholesteryl-modified polysaccharides: effect of the polysaccharide structure on their association characteristics in the dilute and semidilute regimes. Biomacromolecules 2007; 8: 2366-2373 (Pubitemid 47316975)
36. Kawakami S, Wong J, Sato A, Hattori Y, Yamashita F, Hashida M. Biodistribution characteristics of mannosylated, fucosylated, and galactosylated liposomes in mice. Biochim Biophys Acta 2000; 1524: 258-265
37. Zhu J, Yan F, Guo Z, Marchant RE. Surface modification of liposomes by saccharides: vesicle size and stability of lactosyl liposomes studied by photon correlation spectroscopy. J Colloid Interface Sci 2005; 289: 542-550 (Pubitemid 41169889)
38. Lin WJ, Chen MH. Synthesis of multifunctional chitosan with galactose as a targeting ligand for glycoprotein receptor. Carbohydr Polym 2007; 67: 474-480
39. Hattori Y, Kawakami S, Suzuki S, Yamashita F, Hashida M. 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 2004; 317: 992-999 (Pubitemid 38496408)
40. Lu Y, Kawakami S, Yamashita F, Hashida M. Development of an antigen-presenting cell-targeted DNA vaccine against melanoma by mannosylated liposomes. Biomaterials 2007; 28: 3255-3262 (Pubitemid 46654220)
41. Hattori Y, Kawakami S, Yamashita F, Hashida M. Controlled biodistribution of galactosylated liposomes and incorporated probucol in hepatocyte-selective drug targeting. J Control Release 2000; 69: 369-377 (Pubitemid 30845481)
42. Murao A, Nishikawa M, Managit C, Wong J, Kawakami S, Yamashita F, et al. Targeting efficiency of galactosylated liposomes to hepatocytes in vivo: effect of lipid composition. Pharm Res 2002; 19: 1808-1814
43. Kawakami S, Munakata C, Fumoto S, Yamashita F, Hashida M. Novel galactosylated liposomes for hepatocyte-selective targeting of lipophilic drugs. J Pharm Sci 2001; 90: 105-113 (Pubitemid 32158038)
44. Aoki H, Sun CQ, Fuji k, Miyajima K. Disposition kinetics of liposomes modified with synthetic aminoglycolipids in rats. Int J Pharm 1995; 115: 183-191
45. Carafa M, Marianecci C, Annibaldi V, Di Stefano A, Sozio P, Santucci E. Novel O-palmitoylscleroglucan-coated liposomes as drug carriers: development, characterization and interaction with leuprolide. Int J Pharm 2006; 325: 155-162 (Pubitemid 44573698)
46. Lemarchand C, Gref R, Lesieur S, Hommel H, Vacher B, Besheer A, et al. Physico-chemical characterization of polysaccharide-coated nanoparticles. J Control Release 2005; 108: 97-111.
47. Na K, Park KH, Kim SW, Bae YH. Self-assembled hydrogel nanoparticles from curdlan derivatives: characterization, anticancer drug release and interaction with a hepatoma cell line (HepG2). J Control Release 2000; 69: 225-236 (Pubitemid 30813444)
48. Pun SH, Bellocq NC, Liu AJ, Jensen G, Machemer T, Quijano E, et al. Cyclodextrin-modified polyethylenimine polymers for gene delivery. Bioconjug Chem 2004; 15: 831-840 (Pubitemid 38981958)
49. Gonzalez H, Hwang SJ, Davis ME. New class of polymers for the delivery of macromolecular therapeutics. Bioconjug Chem 1999; 10: 1068-1074
50. Roessler BJ, Bielinska AU, Janczak K, Lee I, Baker JR. Substituted beta-cyclodextrins interact with PAMAM dendrimer-DNA complexes and modify transfection efficiency. Biochem Biophys Res Commun 2001; 283: 124-129 (Pubitemid 32912547)
51. Park IY, Kim IY, Yoo MK, Choi YJ, Cho MH, Cho CS. Mannosylated polyethylenimine coupled mesoporous silica nanoparticles for receptor-mediated gene delivery. Int J Pharm 2008; 359: 280-287
52. Kawakami S, Sato A, Nishikawa M, Yamashita F, Hashida M. Mannose receptor-mediated gene transfer into macrophages using novel mannosylated cationic liposomes. Gene Ther 2000; 7: 292-299 (Pubitemid 30119732)
53. Cui Z, Hsu CH, Mumper RJ. Physical characterization and macrophage cell uptake of mannan-coated nanoparticles. Drug Dev Ind Pharm 2003; 29: 689-700. (Pubitemid 36835162)
54. Kim TH, Nah JW, Cho MH, Park TG, Cho CS. Receptor-mediated gene delivery into antigen presenting cells using mannosylated chitosan/DNA nanoparticles. J Nanosci Nanotechnol 2006; 6: 2796-2803
55. Akbari O, Panjwani N, Garcia S, Tascon R, Lowrie D, Stockinger B. DNA vaccination: Transfection and activation of dendritic cells as key events for immunity. J Exp Med 1999; 189: 169-177 (Pubitemid 29047036)
56. Diebold SS, Plank C, Cotten M, Wagner E, Zenke M. Mannose receptor-mediated gene delivery into antigen presenting dendritic cells. Somatic Cell Mol Genet 2002; 27: 65-74.
57. Kim TH, Jin H, Kim HW, Cho MH, Cho CS. Mannosylated chitosan nanoparticle-based cytokine gene therapy suppressed cancer growth in BALB/c mice bearing CT-26 carcinoma cells. Mol Cancer Ther 2006; 5: 1723-1732 (Pubitemid 44323240)
58. Sato A, Takagi M, Shimamoto A, Kawakami S, Hashida M. Small interfering RNA delivery to the liver by intravenous administration of galactosylated cationic liposomes in mice. Biomaterials 2007; 28: 1434-1442 (Pubitemid 44959042)
59. Kawakami S, Higuchi Y, Hashida M. Nonviral approaches for targeted delivery of plasmid DNA and oligonucleotide. J Pharm Sci 2008; 97: 726-745 (Pubitemid 351293877)
60. Zhang XQ, Wang XL, Zhang PC, Liu ZL, Zhuo RX, Mao HQ, et al. Galactosylated ternary DNA/polyphosphoramidate nanoparticles mediate high gene transfection efficiency in hepatocytes. J Control Release 2005; 102: 749-763
61. Kawakami S, Yamashita F, Nishikawa M, Takakura Y, Hashida M. Asialoglycoprotein receptor-mediated gene transfer using novel galactosylated cationic liposomes. Biochem Biophys Res Commun 1998; 252: 78-83.
62. White KL, Rades T, Furneaux RH, Tyler PC, Hook S. Mannosylated liposomes as antigen delivery vehicles for targeting to dendritic cells. J Pharm Pharmacol 2006; 58: 729-737 (Pubitemid 43836160)
63. Sheng KC, Kalkanidis M, Pouniotis DS, Esparon S, Tang CK, Apostolopoulos V, et al. Delivery of antigen using a novel mannosylated dendrimer potentiates immunogenicity in vitro and in vivo. Eur J Immunol 2008; 38: 424-436
64. Lemarchand C, Gref R, Lesieur S, Hommel H, Vacher B, Besheer A, et al. Physico-chemical characterization of polysaccharide-coated nanoparticles. J Control Release 2005; 108: 97-111.
65. Gou M, Dai M, Li X, Yang L, Huang M, Wang Y, et al. Preparation of mannan modified anionic PCL-PEG-PCL nanoparticles at one-step for bFGF antigen delivery to improve humoral immunity. Colloids Surf B Biointerfaces 2008; 64: 135-139
66. Garg M, Dutta T, Jain NK. Reduced hepatic toxicity, enhanced cellular uptake and altered pharmacokinetics of stavudine loaded galactosylated liposomes. Eur J Pharm Biopharm 2007; 67: 76-85. (Pubitemid 46991319)
67. Garg M, Garg BR, Jain S, Mishra P, Sharma RK, Mishra AK, et al. Radiolabeling, pharmacoscintigraphic evaluation and antiretroviral efficacy of stavudine loaded 99mTc labeled galactosylated liposomes. Eur J Pharm Sci 2008; 33: 271-281
68. Kuramoto Y, Kawakami S, Zhou S, Fukuda K, Yamashita F, Hashida M. Use of mannosylated cationic liposomes/ immunostimulatory CpG DNA complex for effective inhibition of peritoneal dissemination in mice. J Gene Med 2008; 10: 392-399
69. Kato Y, Hosokawa T, Hayakawa E, Ito K. Influence of liposomes on tryptic digestion of insulin. Biol Pharm Bull 1993; 16: 457-461 (Pubitemid 23208662)
70. Lee CM, Lee HC, Lee KY. O-palmitoylcurdlan sulfate (OPCurS)-coated liposomes for oral drug delivery. J Biosci Bioeng 2005; 100: 255-259
71. Salman HH, Gamazo C, Campanero MA, Irache JM. Bioadhesive mannosylated nanoparticles for oral drug delivery. J Nanosci Nanotechnol 2006; 6: 3203-3209 (Pubitemid 44580001)
72. Jain S, Singh P, Mishra V, Vyas SP. Mannosylated niosomes as adjuvant-carrier system for oral genetic immunization against hepatitis B. Immunol Lett 2005; 101: 41-49 (Pubitemid 41297497)
73. Chono S, Tanino T, Seki T, Morimoto K. Efficient drug targeting to rat alveolar macrophages by pulmonary administration of ciprofloxacin incorporated into mannosylated liposomes for treatment of respiratory intracellular parasitic infections. J Control Release 2008; 127: 50-58
74. Chono S, Tanino T, Seki T, Morimoto K. Uptake characteristics of liposomes by rat alveolar macrophages: influence of particle size and surface mannose modification. J Pharm Pharmacol 2007; 59: 75-80. (Pubitemid 46133045)
75. Fujimoto K, Miyata T, Aoyama Y. Saccharide-directed cell recognition and molecular delivery using macrocyclic saccharide clusters: masking of hydrophobicity to enhance the saccharide specificity. J Am Chem Soc 2000; 122: 3558-3559 (Pubitemid 30211146)
76. Hayashida O, Mizuki K, Akagi K, Matsuo A, Kanamori T, Nakai T, et al. Macrocyclic glycoclusters. Self-aggregation and phosphate-induced agglutination behaviors of calix[4]resorcarene-based quadruple-chain amphiphiles with a huge oligosaccharide pool. J Am Chem Soc 2003; 125: 594-601.
77. Debbage P. Targeted drugs and nanomedicine: present and future. Curr Pharm Des 2009; 15(2): 153-172
78. Larson SM. Cancer drug development with the help of radiopharmaceuticals: academic experience. Curr Pharm Des 2009; 15(9): 950-956
79. Patil RR, Guhagarkar SA, Devarajan PV. Engineered nanocarriers of doxorubicin: a current update. Crit Rev Ther Drug Carrier Syst 2008; 25(1): 1-61.