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BioMed Research International
Volume 2015, Article ID 350580, 8 pages
http://dx.doi.org/10.1155/2015/350580
Research Article

Macrophage-Targeting Gene Delivery Using a Micelle Composed of Mannose-Modified Lipid with Triazole Ring and Dioleoyl Trimethylammonium Propane

1Department of Chemistry and Biochemistry, The University of Kitakyushu, 1-1 Hibikino, Wakamatsu-ku, Kitakyushu, Fukuoka 808-0135, Japan
2NexTEP, Japan Science and Technology Agency, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan

Received 9 March 2015; Accepted 28 May 2015

Academic Editor: Hojae Bae

Copyright © 2015 Ichiki Fukuda et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. S. Kawakami, Y. Higuchi, and M. Hashida, “Nonviral approaches for targeted delivery of plasmid DNA and oligonucleotide,” Journal of Pharmaceutical Sciences, vol. 97, no. 2, pp. 726–745, 2008. View at Publisher · View at Google Scholar · View at Scopus
  2. G. Y. Wu and C. H. Wu, “Receptor-mediated in vitro gene transformation by a soluble DNA carrier system,” Journal of Biological Chemistry, vol. 262, no. 10, pp. 4429–4432, 1987. View at Google Scholar · View at Scopus
  3. M. Hashimoto, M. Morimoto, H. Saimoto, Y. Shigemasa, and T. Sato, “Lactosylated chitosan for DNA delivery into hepatocytes: the effect of lactosylation on the physicochemical properties and intracellular trafficking of pDNA/chitosan complexes,” Bioconjugate Chemistry, vol. 17, no. 2, pp. 309–316, 2006. View at Publisher · View at Google Scholar · View at Scopus
  4. J. C. Perales, G. A. Grossmann, M. Molas et al., “Biochemical and functional characterization of DNA complexes capable of targeting genes to hepatocytes via the asialoglycoprotein receptor,” The Journal of Biological Chemistry, vol. 272, no. 11, pp. 7398–7407, 1997. View at Publisher · View at Google Scholar · View at Scopus
  5. M. Sakashita, S. Mochizuki, and K. Sakurai, “Hepatocyte-targeting gene delivery using a lipoplex composed of galactose-modified aromatic lipid synthesized with click chemistry,” Bioorganic & Medicinal Chemistry, vol. 22, no. 19, pp. 5212–5219, 2014. View at Publisher · View at Google Scholar
  6. S. Asayama, M. Nogawa, Y. Takei, T. Akaike, and A. Maruyama, “Synthesis of novel polyampholyte comb-type copolymers consisting of a poly(L-lysine) backbone and hyaluronic acid side chains for a DNA carrier,” Bioconjugate Chemistry, vol. 9, no. 4, pp. 476–481, 1998. View at Publisher · View at Google Scholar · View at Scopus
  7. Y. Takei, A. Maruyama, A. Ferdous et al., “Targeted gene delivery to sinusoidal endothelial cells: DNA nanoassociate bearing hyaluronan-glycocalyx,” The FASEB Journal, vol. 18, no. 6, pp. 699–701, 2004. View at Google Scholar · View at Scopus
  8. M. Hashimoto, M. Morimoto, H. Saimoto et al., “Gene transfer by DNA/mannosylated chitosan complexes into mouse peritoneal macrophages,” Biotechnology Letters, vol. 28, no. 11, pp. 815–821, 2006. View at Publisher · View at Google Scholar · View at Scopus
  9. K. Un, S. Kawakami, M. Yoshida et al., “The elucidation of gene transferring mechanism by ultrasound-responsive unmodified and mannose-modified lipoplexes,” Biomaterials, vol. 32, no. 20, pp. 4659–4669, 2011. View at Publisher · View at Google Scholar · View at Scopus
  10. M. Leist, F. Gantner, S. Jilg, and A. Wendel, “Activation of the 55 kDa TNF receptor is necessary and sufficient for TNF- induced liver failure, hepatocyte apoptosis, and nitrite release,” Journal of Immunology, vol. 154, no. 3, pp. 1307–1316, 1995. View at Google Scholar · View at Scopus
  11. D. K. Podolsky, “Inflammatory bowel disease,” The New England Journal of Medicine, vol. 347, no. 6, pp. 417–429, 2002. View at Publisher · View at Google Scholar · View at Scopus
  12. R. J. Xavier and D. K. Podolsky, “Unravelling the pathogenesis of inflammatory bowel disease,” Nature, vol. 448, no. 7152, pp. 427–434, 2007. View at Publisher · View at Google Scholar · View at Scopus
  13. R. Townsend and P. Stahl, “Isolation and characterization of a mannose/N-acetylglucosamine/fucose-binding protein from rat liver,” Biochemical Journal, vol. 194, no. 1, pp. 209–214, 1981. View at Google Scholar · View at Scopus
  14. T. B. H. Geijtenbeek and S. I. Gringhuis, “Signalling through C-type lectin receptors: shaping immune responses,” Nature Reviews Immunology, vol. 9, no. 7, pp. 465–479, 2009. View at Publisher · View at Google Scholar · View at Scopus
  15. K. Koiwai, K. Tokuhisa, R. Karinaga et al., “Transition from a normal to inverted cylinder for an amidine-bearing lipid/pDNA complex and its excellent transfection,” Bioconjugate Chemistry, vol. 16, no. 6, pp. 1349–1351, 2005. View at Publisher · View at Google Scholar · View at Scopus
  16. S. Mochizuki, Y. Kamikawa, K. Nishina et al., “Relationship between DNA-transfection efficiency and chemical structures of aromatic cationic lipids,” Bulletin of the Chemical Society of Japan, vol. 85, no. 3, pp. 354–359, 2012. View at Publisher · View at Google Scholar · View at Scopus
  17. K. D. Bodine, D. Y. Gin, and M. S. Gin, “Synthesis of readily modifiable cyclodextrin analogues via cyclodimerization of an alkynyl-azido trisaccharide,” Journal of the American Chemical Society, vol. 126, no. 6, pp. 1638–1639, 2004. View at Publisher · View at Google Scholar · View at Scopus
  18. T. Tanaka, H. Nagai, M. Noguchi, A. Kobayashi, and S.-I. Shoda, “One-step conversion of unprotected sugars to beta-glycosyl azides using 2-chloroimidazolinium salt in aqueous solution,” Chemical Communications, no. 23, pp. 3378–3379, 2009. View at Publisher · View at Google Scholar · View at Scopus
  19. A. V. Delgado, F. González-Caballero, R. J. Hunter, L. K. Koopal, and J. Lyklema, “Measurement and interpretation of electrokinetic phenomena,” Journal of Colloid and Interface Science, vol. 309, no. 2, pp. 194–224, 2007. View at Publisher · View at Google Scholar · View at Scopus
  20. K. Ewert, N. L. Slack, A. Ahmad et al., “Cationic lipid-DNA complexes for gene therapy: understanding the relationship between complex structure and gene delivery pathways at the molecular level,” Current Medicinal Chemistry, vol. 11, no. 2, pp. 133–149, 2004. View at Publisher · View at Google Scholar · View at Scopus
  21. I. Koltover, T. Salditt, J. O. Rädler, and C. R. Safinya, “An inverted hexagonal phase of cationic liposome-DNA complexes related to DNA release and delivery,” Science, vol. 281, no. 5373, pp. 78–81, 1998. View at Publisher · View at Google Scholar · View at Scopus
  22. K. K. Ewert, H. M. Evans, A. Zidovska, N. F. Bouxsein, A. Ahmad, and C. R. Safinya, “A columnar phase of dendritic lipid-based cationic liposome-DNA complexes for gene delivery: hexagonally ordered cylindrical micelles embedded in a DNA honeycomb lattice,” Journal of the American Chemical Society, vol. 128, no. 12, pp. 3998–4006, 2006. View at Publisher · View at Google Scholar · View at Scopus
  23. F. Yeh, E. L. Sokolov, A. R. Khokhlov, and B. Chu, “Nanoscale supramolecular structures in the gels of poly (diallyldimethylammonium chloride) interacting with sodium dodecyl sulfate,” Journal of the American Chemical Society, vol. 118, no. 28, pp. 6615–6618, 1996. View at Publisher · View at Google Scholar · View at Scopus
  24. F. Yeh, E. L. Sokolov, A. R. Khokhlov, and B. Chu, “Nanoscale supramolecular structures in the gels of poly(diallyldimethylammonium chloride) interacting with sodium dodecyl sulfate,” Journal of the American Chemical Society, vol. 118, no. 28, pp. 6615–6618, 1996. View at Publisher · View at Google Scholar · View at Scopus
  25. M. Schwarz, L. Spector, A. Gargir et al., “A new kind of carbohydrate array, its use for profiling antiglycan antibodies, and the discovery of a novel human cellulose-binding antibody,” Glycobiology, vol. 13, no. 11, pp. 749–754, 2003. View at Publisher · View at Google Scholar · View at Scopus
  26. Y. C. Lee, R. R. Townsend, M. R. Hardy et al., “Binding of synthetic oligosaccharides to the hepatic Gal/GalNAc lectin. Dependence on fine structural features,” The Journal of Biological Chemistry, vol. 258, no. 1, pp. 199–202, 1983. View at Google Scholar · View at Scopus
  27. R. T. Lee, P. Lin, and Y. C. Lee, “New synthetic cluster ligands for galactose/N-acetylgalactosamine-specific lectin of mammalian liver,” Biochemistry, vol. 23, no. 18, pp. 4255–4261, 1984. View at Publisher · View at Google Scholar · View at Scopus
  28. J. Zhang, J. Zhu, X. Bu et al., “Cdc42 and RhoB activation are required for mannose receptor-mediated phagocytosis by human alveolar macrophages,” Molecular Biology of the Cell, vol. 16, no. 2, pp. 824–834, 2005. View at Publisher · View at Google Scholar · View at Scopus
  29. J. L. Miller, B. J. M. DeWet, L. Martinez-Pomares et al., “The mannose receptor mediates dengue virus infection of macrophages,” PLoS Pathogens, vol. 4, no. 2, article e17, 2008. View at Publisher · View at Google Scholar · View at Scopus
  30. S. Yamasaki, E. Ishikawa, M. Sakuma, H. Hara, K. Ogata, and T. Saito, “Mincle is an ITAM-coupled activating receptor that senses damaged cells,” Nature Immunology, vol. 9, no. 10, pp. 1179–1188, 2008. View at Publisher · View at Google Scholar · View at Scopus
  31. S. Yamasaki, M. Matsumoto, O. Takeuchi et al., “C-type lectin Mincle is an activating receptor for pathogenic fungus, Malassezia,” Proceedings of the National Academy of Sciences of the United States of America, vol. 106, no. 6, pp. 1897–1902, 2009. View at Publisher · View at Google Scholar · View at Scopus
  32. A. S. J. Marshall, J. A. Willmen, H.-H. Lin, D. L. Williams, S. Gordon, and G. D. Brown, “Identification and characterization of a novel human myeloid inhibitory C-type lectin-like receptor (MICL) that is predominantly expressed on granulocytes and monocytes,” Journal of Biological Chemistry, vol. 279, no. 15, pp. 14792–14802, 2004. View at Publisher · View at Google Scholar · View at Scopus
  33. C. H. Chen, H. Floyd, N. E. Olson et al., “Dendritic-cell-associated C-type lectin 2 (DCAL-2) alters dendritic-cell maturation and cytokine production,” Blood, vol. 107, no. 4, pp. 1459–1467, 2006. View at Publisher · View at Google Scholar · View at Scopus