Multivalent glycoliposomes and micelles to study carbohydrate-protein and carbohydrate-carbohydrate interactions.

This tutorial review describes multivalent carbohydrate-protein and carbohydrate-carbohydrate interaction studies that utilize self-assembled aggregates of thermodynamically stable liposomes and micelles. Strategies to prepare multivalent glycoliposomes and micelles include: (i) insertion of synthetic glycolipids into matrix lipids; (ii) preparation of glycolipids that aggregate to liposomes and micelles and (iii) modification of the hydrophilic surfaces with desired sugars. Several design strategies have been developed in order to obtain constituent glycolipids, having multivalent sugar moieties and their subsequent interactions with proteins were assessed in relation to the type of linkers that connect the hydrophilic and lipophilic segments. Lipophilic segments other than alkyl chains have also been developed. Polymer based glycoliposomes and micelles form an emphasis. Further, glycoliposomes facilitate studies of carbohydrate-carbohydrate interactions. An overview of the various types of glycoliposomes and micelles used to study carbohydrate-protein and carbohydrate-carbohydrate recognition phenomena is presented.

[1]  S. Šegota,et al.  Surface modified liposomes by mannosylated conjugates anchored via the adamantyl moiety in the lipid bilayer. , 2012, Biochimica et biophysica acta.

[2]  Marta Fernández-García,et al.  Glycopolymers obtained by chemical modification of well‐defined block copolymers , 2012 .

[3]  V. Soldi,et al.  Self-assembled carbohydrate-based micelles for lectin targeting , 2011 .

[4]  M. Assali,et al.  Copper-catalyzed azide-alkyne cycloaddition in the synthesis of polydiacetylene: "click glycoliposome" as biosensors for the specific detection of lectins. , 2011, Chemistry.

[5]  Sung You Hong,et al.  Design, synthesis and biological evaluation of carbohydrate-functionalized cyclodextrins and liposomes for hepatocyte-specific targeting. , 2010, Organic & biomolecular chemistry.

[6]  Yan Zhao,et al.  Facile Synthesis of Multivalent Water-Soluble Organic Nanoparticles via ``Surface Clicking'' of Alkynylated Surfactant Micelles , 2010 .

[7]  R. Roy,et al.  Design and Creativity in Synthesis of Multivalent Neoglycoconjugates , 2010, Advances in Carbohydrate Chemistry and Biochemistry.

[8]  J. Voskuhl,et al.  Sugar-decorated sugar vesicles: lectin-carbohydrate recognition at the surface of cyclodextrin vesicles. , 2010, Chemistry.

[9]  N. Jayaraman.  Multivalent ligand presentation as a central concept to study intricate carbohydrate-protein interactions. , 2009, Chemical Society reviews.

[10]  L. Billon,et al.  Lectin Recognizable Biomaterials Synthesized via Nitroxide-Mediated Polymerization of a Methacryloyl Galactose Monomer , 2009 .

[11]  H. Amenitsch,et al.  Self-organization of synthetic cholesteryl oligoethyleneglycol glycosides in water. , 2009, Langmuir : the ACS journal of surfaces and colloids.

[12]  Xue-Long Sun,et al.  Chemically-selective surface glyco-functionalization of liposomes through Staudinger ligation. , 2009, Chemical communications.

[13]  Jiahuai Han,et al.  Multivalent mannose-displaying nanoparticles constructed from poly{styrene-co-[(maleic anhydride)-alt-styrene]}. , 2009, Organic & biomolecular chemistry.

[14]  D. Danino,et al.  Carbohydrate modified catanionic vesicles: probing multivalent binding at the bilayer interface. , 2009, Journal of the American Chemical Society.

[15]  Gaojian Chen,et al.  Synthesis of thiol-linked neoglycopolymers and thermo-responsive glycomicelles as potential drug carrier. , 2009, Chemical communications.

[16]  B. Frisch,et al.  Influence of ligand valency on the targeting of immature human dendritic cells by mannosylated liposomes. , 2008, Bioconjugate chemistry.

[17]  G. Sprott,et al.  Synthesis of archaeal glycolipid adjuvants-what is the optimum number of sugars? , 2008, Carbohydrate research.

[18]  L. Legnani,et al.  Synthesis, Conformational Studies, Binding Assessment and Liposome Insertion of a Thioether‐Bridged Mimetic of the Antigen GM3 Ganglioside Lactone , 2007, Chembiochem : a European journal of chemical biology.

[19]  S. Yokoyama,et al.  Monovalent Gb3-/Gb2-derivatives conjugated with a phosphatidyl residue: a novel class of Shiga toxin-neutralizing agent. , 2007, Biological & pharmaceutical bulletin.

[20]  S. Hakomori,et al.  Self-recognition of N-linked glycans with multivalent GlcNAc, determined as ceramide mimetic conjugate. , 2007, Glycobiology.

[21]  A. Imberty,et al.  Mannosylated poly(ethylene oxide)-b-poly(epsilon-caprolactone) diblock copolymers: synthesis, characterization, and interaction with a bacterial lectin. , 2007, Biomacromolecules.

[22]  Jie Xue,et al.  Biomimetic glycoliposomes as nanocarriers for targeting P-selectin on activated platelets. , 2007, Bioconjugate chemistry.

[23]  B. N. Murthy,et al.  Evaluation of alpha-D-mannopyranoside glycolipid micelles-lectin interactions by surface plasmon resonance method. , 2006, Glycobiology.

[24]  Q. Cheng,et al.  Manipulating FRET with polymeric vesicles: development of a "mix-and-detect" type fluorescence sensor for bacterial toxin. , 2006, Langmuir : the ACS journal of surfaces and colloids.

[25]  Jason E Gestwicki,et al.  Synthetic multivalent ligands as probes of signal transduction. , 2006, Angewandte Chemie.

[26]  M. Hashida,et al.  Influence of cholesterol composition on the association of serum mannan-binding proteins with mannosylated liposomes. , 2006, Biological & pharmaceutical bulletin.

[27]  S. Sampath,et al.  Synthesis and Langmuir studies of bivalent and monovalent α-d-mannopyranosides with lectin Con A , 2005 .

[28]  H. Shinohara,et al.  Preparation and Supramolecular Properties of Unadulterated Glycosyl Liposomes from a Bis(α‐D‐mannopyranosyl)[60]Fullerene Conjugate , 2005, Chemistry & biodiversity.

[29]  R. Marchant,et al.  Pentaerythritol as the core of multivalent glycolipids: synthesis of a glycolipid with three SO3Lea ligands. , 2005, Organic letters.

[30]  M. Yamazaki,et al.  Design and Facile Synthesis of Neoglycolipids as Lactosylceramide Mimetics and Their Transformation into Glycoliposomes , 2005, Bioscience, biotechnology, and biochemistry.

[31]  A. Mazzaglia,et al.  Multivalent binding of galactosylated cyclodextrin vesicles to lectin. , 2004, Organic & biomolecular chemistry.

[32]  I. Fichtner,et al.  Effect of sialyl Lewis X-glycoliposomes on the inhibition of E-selectin-mediated tumour cell adhesion in vitro. , 2004, Biochimica et biophysica acta.

[33]  Y. Aoyama,et al.  Macrocyclic glycoclusters. Self-aggregation and phosphate-induced agglutination behaviors of calix[4]resorcarene-based quadruple-chain amphiphiles with a huge oligosaccharide pool. , 2003, Journal of the American Chemical Society.

[34]  D. Thompson,et al.  Size and structure of spontaneously forming liposomes in lipid/PEG-lipid mixtures. , 2002, Biophysical journal.

[35]  Y. Nagasaki,et al.  Sugar-installed block copolymer micelles: their preparation and specific interaction with lectin molecules. , 2001, Biomacromolecules.

[36]  H. Gabius,et al.  Plant lectins: Occurrence, biochemistry, functions and applications , 2001, Glycoconjugate Journal.

[37]  C. Bertozzi,et al.  Polymerized liposome assemblies: bifunctional macromolecular selectin inhibitors mimicking physiological selectin ligands. , 2001, Biochemistry.

[38]  H. Kitano,et al.  Dehydration Effect on the Recognition of Amphiphiles with Many Pendent Mannose Residues by Concanavalin A , 2001 .

[39]  Long Jiang,et al.  Influence of the Spacer Length of Glycolipid Receptors in Polydiacetylene Vesicles on the Colorimetric Detection of Escherichia coli , 2000 .

[40]  Chi‐Huey Wong,et al.  Syntheses of C‐3‐Modified Sialylglycosides as Selective Inhibitors of Influenza Hemagglutinin and Neuraminidase , 2000 .

[41]  N. Bovin,et al.  Antitumour activity of cytotoxic liposomes equipped with selectin ligand SiaLe(X), in a mouse mammary adenocarcinoma model. , 2000, European journal of cancer.

[42]  Carolyn R. Bertozzi,et al.  Essentials of Glycobiology , 1999 .

[43]  R. Schmidt,et al.  Carbohydrate-Carbohydrate Recognition between LewisX Glycoconjugates. , 1999, Angewandte Chemie.

[44]  G. A. van der Marel,et al.  Design and synthesis of novel amphiphilic dendritic galactosides for selective targeting of liposomes to the hepatic asialoglycoprotein receptor. , 1999, Journal of medicinal chemistry.

[45]  George M Whitesides,et al.  Polyvalent Interactions in Biological Systems: Implications for Design and Use of Multivalent Ligands and Inhibitors. , 1998, Angewandte Chemie.

[46]  R. Stahn,et al.  Multivalent sialyl Lewis x ligands of definite structures as inhibitors of E-selectin mediated cell adhesion. , 1998, Glycobiology.

[47]  R. Lemieux,et al.  HOW WATER PROVIDES THE IMPETUS FOR MOLECULAR RECOGNITION IN AQUEOUS SOLUTION , 1996 .

[48]  Luke S. S. Guo,et al.  Sialyl Lewis x Liposomes as a Multivalent Ligand and Inhibitor of E-Selectin Mediated Cellular Adhesion , 1996 .

[49]  Yuan-chuan Lee,et al.  Carbohydrate-Protein Interactions: Basis of Glycobiology , 1995 .

[50]  J. Davis,et al.  Oligosaccharide behavior of complex natural glycosphingolipids in multicomponent model membranes. , 1995, Biochemistry.

[51]  M. Bednarski,et al.  Direct colorimetric detection of a receptor-ligand interaction by a polymerized bilayer assembly. , 1993, Science.

[52]  D. Connolly,et al.  Binding and endocytosis of cluster glycosides by rabbit hepatocytes. Evidence for a short-circuit pathway that does not lead to degradation. , 1982, The Journal of biological chemistry.

[53]  T. Dam,et al.  Multivalent lectin-carbohydrate interactions energetics and mechanisms of binding. , 2010, Advances in carbohydrate chemistry and biochemistry.

[54]  P. Johannis,et al.  The Sweet Love between Marine Sponge Cells , 2008 .

[55]  Toyoaki Akino,et al.  Antigenicity of the carbohydrate moiety of ganglioside GM3 having 3-O-acetyl ceramide , 2004, Glycoconjugate Journal.

[56]  F. Pincet,et al.  Specific and non specific interactions involving LeX determinant quantified by lipid vesicle micromanipulation , 2004, Glycoconjugate Journal.

[57]  A. Engel,et al.  Influence of Spacer Length on Interaction of Mannosylated Liposomes with Human Phagocytic Cells , 2004, Pharmaceutical Research.

[58]  A. Basu,et al.  Studies of the carbohydrate-carbohydrate interaction between lactose and GM3 using Langmuir monolayers and glycolipid micelles , 2004, Glycoconjugate Journal.

[59]  R. Nagarajan,et al.  Molecular Packing Parameter and Surfactant Self-Assembly: The Neglected Role of the Surfactant Tail† , 2002 .

[60]  H. Kitano,et al.  Recognition of novel lipopolypeptides with many pendent sugar residues by lectin. , 2001, Bioconjugate chemistry.

[61]  K. Rice,et al.  Enzymatic synthesis of N-linked oligosaccharides terminating in multiple sialyl-Lewis(x) and GalNAc-Lewis(x) determinants: clustered glycosides for studying selectin interactions. , 1998, Carbohydrate research.