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Original Articles

Design and Facile Synthesis of Neoglycolipids as Lactosylceramide Mimetics and Their Transformation into Glycoliposomes

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Pages 166-178 | Received 07 Sep 2004, Accepted 28 Oct 2004, Published online: 22 May 2014

  • 1) Huwiler, A., Kolter, T., Pteilschifter, J., and Sandhoft, K., Physiology and pathophysiology of sphingolipid metabolism and signaling. Biochim. Biophys. Acta, 1485, 63–99 (2000).
  • 2) van Meer, G., and Holthuis, J. C. M., Sphingolipid transport in eukaryotic cells. Biochim. Biophys. Acta, 1486, 145–170 (2000).
  • 3) Chen, C. S., Patterson, M. C., Wheatley, C. L., O’Brien, J. F., and Pagano, R. E., Broad screening test for sphingolipid-storage diseases. Lancet, 354, 901–905 (1999).
  • 4) Iwamoto, T., Fukumoto, S., Kanaoka, K., Sakai, E., Shibata, M., Fukumoto, E., Inokuchi, J., Takamiya, K., Furukawa, K., Kato, Y., and Mizuno, A., Lactosylceramide is essential for the osteoclastogenesis mediated by macrophage-colony-stimulating factor and receptor activator of nuclear factor-κB ligand. J. Biol. Chem., 49, 46031–46038 (2001).
  • 5) Chatterjee, S., Sphingolipids in atherosclerosis and vascular biology. Arterioscler. Thromb. Vasc. Biol., 18, 1523–1533 (1998).
  • 6) Sliedregt, L. A., Rensen, P. C., Rump, E. T., van Santbrink, P. J., Bijsterbosch, M. K., Valentijn, A. R., van der Marel, G. A., van Boom, J. H., van Berkel, T. J., and Biessen, E. A., Design and synthesis of novel amphiphilic dendric galactosides for selective targeting of liposomes to the hepatic asialoglycoprotein receptor. J. Med. Chem., 42, 609–618 (1999).
  • 7) Stahn, R., and Zeisig, R., Cell adhesion inhibition by glycoliposomes: effects of vesicle diameter and ligand density. Tumor Biol., 21, 176–186 (1998).
  • 8) Murahashi, N., Ishida, H., Sakai, A., and Sakagami, M., Hepatic accumulation of glutamic acid branched neogalactosyl-lipid modified liposomes. Biol. Pharm. Bull., 29, 259–266 (1997).
  • 9) Yamauchi, H., Kikuchi, H., Sawada, M., Tomikawa, M., and Hirota, S., Characterization and tissue distribution of liposomes containing lactose mono-fatty acid derivatives. J. Microencapsulation, 11, 189–195 (1994).
  • 10) Liu, D. X., Mori, A., and Huang, L., Role of liposome size and RES blockade in controlling biodistribution and tumor uptake of GM1-containing liposomes. Biochim. Biophys. Acta, 1104, 95–101 (1992).
  • 11) Koketsu, M., Nitoda, T., Sugino, H., Juneja, L. R., Kim, M., Yamamoto, T., Abe, N., Kajimoto, T., and Wong, C.-H., Synthesis of a novel sialic acid derivative (sialyl-phospholipid) as an antirotaviral agent. J. Med. Chem., 40, 3332–3335 (1977).
  • 12) Inoki, Y., Miura, T., Kajimoto, T., Kawase, M., Kawase, Y., Yosida,Y., Tsuji, S., Kinouchi, T., Endo, H., Kagawa, Y., and Hamamoto, T., Ganglioside GD3 and its mimetics induce cytochrome c release from mitochondria. Biochem. Biophys. Res. Commun., 270, 1210–1216 (2000).
  • 13) Pohlentz, G., and Drees, B., Neoglycolipids derived from phosphatidylethanolamine serve as probes in cell studies on glycolipid metabolism. Biol. Chem., 381, 29–34 (2000).
  • 14) Stoll, M. S., Feizi, T., Loreless, R. W., Chai, W., Lawson, A. M., and Yuen, C. T., Fluorescent neoglycolipids: improved probes for oligosaccharide ligand discovery. Eur. J. Biochem., 267, 1795–1804 (2000).
  • 15) Shimizu, Y., Yamakami, K., Gomi, T., Nakata, M., Asanuma, H., Tadakuma, T., and Kojima, N., Protection against Leishmania major infection by oligomannose-coated liposomes. Bioorg. Med. Chem., 11, 1191–1195 (2003).
  • 16) Sakai, K., Katsumi, R., Ohi, H., Usui, T., and Ishido, Y., Enzymatic synthesis of N-acetyllactosamine and N-acetylallolactosamine by the use of β-D-galactosidase. J. Carbohydr. Chem., 11, 553–565 (1992).
  • 17) Yasutake, N., Totani, K., Harada, Y., Haraguchi, S., Murata, T., and Usui, T., Efficient synthesis of glyceroyl β-lactoside and its derivatives through a condensation reaction by cellulose. Biochim. Biophys. Acta, 1620, 252–258 (2003).
  • 18) Totani, K., Yasutake, N., Ohi, H., Murata, T., and Usui, T., Efficient synthesis of aliphatic β-lactosides as mimic units of glycosphingolipids by use of Trichoderma reesei cellulase. Arch. Biochem. Biophys., 385, 70–77 (2001).
  • 19) Wang, P., Schuster, M., Wang, Y.-F., and Wong, C.-H., Synthesis of phospholipids-inhibitor conjugates by enzymatic transphosphatidylation with phospholipase D. J. Am. Chem. Soc., 115, 10487–10491 (1993).
  • 20) Miura, T., Aonuma, M., Kajimoto, T., Ida, Y., Kawase, M., Kawase, Y., and Yoshida, Y., Design and synthesis of D-series ganglioside mimetics. Synlett, 6, 650–652 (1997).
  • 21) Furuike, S., Levadny, V. G., Li, S. J., and Yamazaki, M., Low pH induces an interdigitated gel to bilayer gel phase transition in dihexadecylphosphatidylcholine membrane. Biophys. J., 77, 2015–2023 (1999).
  • 22) Kinoshita, K., Furuike, S., and Yamazaki, M., Intermembrane distance in multilamellar vesicles of phosphatidylcholine depends on the interaction free energy between solvents and the hydrophilic segments of the membrane surface. Biophys. Chem., 74, 237–249 (1998).
  • 23) Tanaka, T., Tamba, S., Masum, M., Yamashita, Y., and Yamazaki, M., La3+ and Gd3+ induces shape change of giant unilamellar vesicles of phosphatidylcholine. Biochim. Biophys. Acta, 1564, 173–182 (2002).
  • 24) Oku, N., Kendall, D. A., and Macdonald, R. C., A simple procedure for the determination of the trapped volume of liposomes. Biochim. Biophys. Acta, 691, 332–340 (1982).
  • 25) Li, X.-M., Momsen, M. M., Brockman, H. L., and Brown, R. E., Lactosylceramide: effect of acyl chain structure on phase behavior and molecular packing. Biophys. J., 83, 1535–1546 (2002).
  • 26) Saxena, K., Zimmermann, P., Schmidt, R. R., and Shipley, G. G., Bilayer properties of totally synthetic C16:0-lactosyl-ceramide. Biophys. J., 78, 306–312 (2000).

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