Abstract
Liposome surface functionalization facilitates the enormous potential applications of liposomes, such as stabilizing and targeting carrier systems for delivering active molecules in biomedical research and applications. Cell surface carbohydrates have been an attractive model system for liposome surface functionalization for enhanced biomedical applications, such as site-specific and ligand-directed drug and gene delivery, multivalent inhibition, and vaccine adjuvant applications. The present protocol describes an efficient and chemically selective liposome surface glyco-functionalization method based on Staudinger ligation performed in phosphate-buffered saline buffer (pH 7.4) at room temperature. Specifically, a carbohydrate derivative carrying a spacer with an azide group is conjugated onto the surface of preformed liposomes carrying terminal triphenylphosphine groups. The compatibility of the reaction conditions for liposome surface functionalization was confirmed with dynamic light scattering and kinetic experiments monitoring the leakage of entrapped 5,6-carboxyfluorescein.
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References
Philippot, J. R. and Schuber F. (1995) Liposomes as Tools in Basic Research and Industry, CRC Press, Boca Raton.
Allen, T. M. and Cullis, P. R. (2004) Drug delivery systems: Entering the mainstream. Science 303, 1818–1822.
Torchilin, V. P. (2005) Recent advances with liposomes as pharmaceutical carriers. Nat. Rev. Drug Discov. 4, 145–160.
Allen, T. M., Hansen C., Martin F., Redemann C., and Young, A.Y. (1991) Liposomes containing synthetic lipid derivatives of poly ethylene glycol show prolonged circulation half-lives in vivo. Biochim. Biophys. Acta 1066, 29–36.
Sihorkar, V., Vyas, S. P. (2001) Potential of polysaccharide anchored liposome in drug delivery, targeting and immunization. J. Pharmceut. Sci. 4, 138–158.
Mehvar, R. (2003) Recent Trends in the use of polysaccharides for improved delivery of therapeutic agents: Pharmacokinetic and pharmacodynamic perspectives. Curr. Pharm. Biotechnol. 4, 283–302.
Stahn, R., Grittner, C., Zeisig, R., Karsten, U., Wenzel, F. (2001) 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.
Sun, X. L., Kanie Y., Guo, C. T., Kanie O., Suzuki, Y. and Wong, C. H. (2000) Syntheses of C-3 modified sialylglycosides as selective inhibitors of influenza hemagglutinin and neuraminidase. Eur. J. Org. Chem. 14, 2643–2653.
Kuboki, N., Yokoyama, N., Namangala, B., Okamura, M., Inoue, N., Takagi, H., Nakayama, T., Nishikawa, Y., Ikehara, Y., Kojima, N. (2008) Adjuvant effect of oligomannose-coated liposome-based platform for vaccine against African trypanosomosis. J. Protozool. Res. 18, 1–10.
Sapra, P. and Allen, T. M. (2003) Ligand-targeted liposomal anticancer drugs. Prog. Lipid Res. 42, 439–462.
Nobs, L., Buchegger, F., Gurny, R. and Allemann E. (2004) Current methods for attaching targeting ligands to liposomes and nanoparticles. J. Pharm. Sci. 93, 1980–1982.
Kung, V. T. and Redemann, C. T. (1986) Synthesis of carboxyacyl derivatives of phosphatidylethanolamine and use as an efficient method for conjugation of protein to liposomes. Biochim. Biophys. Acta 862, 435–439.
Schelte, P., Boeckler, C., Frisch, B. and Schuber, F. (2000) Differential reactivity of maleimide and bromoacetyl functions with thiols: application to the preparation of liposomal diepitope constructs. Bioconjug. Chem. 11, 118–123.
Nakano, Y., Mori, M., Nishinohara, S., Takita, Y., Naito, S., Kato, H., Taneichi, M., Komuro, K., Uchoda, T. (2001) Surface-linked liposomal antigen induces IgE-selective unresponsiveness regardless of the lipid components of liposomes. Bioconjug. Chem. 12, 391–395.
Bourel-Bonnet, L., Pecheur, E. I., Grandjean, C., Blanpain, A., Baust, T., Melnyk, O., Hoflack, B., Gras-Masse, H. (2005) Anchorage of synthetic peptides onto liposomes via hydrazone and alpha-oxo hydrazone bonds. preliminary functional investigations. Bioconjug. Chem. 16, 450–457.
Hassane, F. S., Frisch, B., Schuber, F. (2006) Targeted liposomes: convenient coupling of ligands to preformed vesicles using “click chemistry”. Bioconjug. Chem. 17, 849–854.
Sun, X. L., Stabler, C, Cazalis, C., Chaikof, E. L. (2006) Carbohydrates and protein immobilization onto solid surface by sequential Diels-Alder and azide-alkyne cycloaddition. Bioconjug. Chem. 17, 52–57.
Kiick, K. L.; Saxon, E.; Tirrell, D. A.; Bertozzi, C. R. (2002) Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation. Proc. Natl. Acad. Sci. USA 99, 19–24.
Prescher, J. A., Dube, D. H., Bertozzi, C. R. (2004) Chemical remodeling of cell surfaces in living animals. Nature 430, 873–877.
Zhang, H., Ma, Y., Sun, X.-L. (2009) Chemically-selective surface glyco-functionalization of liposomes through Staudinger ligation. Chem. Commun. 3032–3034.
Seo, T. S., Wang, C., Li, Z. M., Ruparel, H., Ju. J. Y. (2003) Site-specific fluorescent labeling of DNA using Staudinger ligation. Bioconjug. Chem. 14, 697–701.
Sun, X. L., Grande, D., Baskaran, S., and Chaikof, E. L. (2002) Glycosaminoglycan-mimetic biomaterials 4: Synthesis of sulfated lactose-based glycopolymers that exhibit anticoagulant activity. Biomacromolecules 3, 1065–1070.
Saha, S.K., Brewer, C.F. (1994) Determination of the concentrations of oligosaccharides, complex type carbohydrates, and glycoproteins using the phenol-sulfuric acid method. Carbohydr. Res. 254, 157–167.
Barbet, J., Machy, P., Truneh, A. and Leserman, L. D. (1984) Weak acid-induced release of liposome-encapsulated carboxyfluorescein. Biochim. Biophys. Acta 772, 347–356.
Acknowledgments
The authors acknowledge financial support under grants from the American Health Assistance Foundation (AHAF-H2007027), from NIH-NHLBI (1R01HL102604-01), and from the Startup Fund from Cleveland State University. Thanks to Dr. Dale Ray at CCSB for the NMR studies and Dr. Xiang Zhou at CSU for the mass spectrometry studies.
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Zhang, H., Ma, Y., Sun, XL. (2011). Chemically Selective Liposome Surface Glyco-functionalization. In: Mark, S. (eds) Bioconjugation Protocols. Methods in Molecular Biology, vol 751. Humana Press. https://doi.org/10.1007/978-1-61779-151-2_16
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DOI: https://doi.org/10.1007/978-1-61779-151-2_16
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