Multivalent glycoliposomes and micelles to study carbohydrate–protein and carbohydrate–carbohydrate interactions

Abstract

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.

Mannosylated Liposomes with Built-in Peptidoglycan Based Immunomodulators for Subunit Vaccine Formulations

“…Chemical synthesis, purification and characterization of such amphiphilic compounds is a very complex process. [17] Synthesis of new glycosyl lipoconjugates provides many advantages with respect to the design of carbohydrate ligands having specific structural characteristics and their binding on different lipophilic anchors such as fatty acids [31] and cholesterol. [42] In our previous research, we have shown how adamantane can be used as a membrane anchor in lipid bilayer for different carbohydrate molecules which are exposed on liposome surface.…”

“…[12,40] The glycosylation as well as mannosylation of liposome surface can be accomplished in several ways. [17] The most used methods encompasses adsorption of different glycopolimers or a chemical reaction between the glycosylconjugate and liposome. [41] Although simple, these methods are constrained regarding the stability of liposomes in the reaction mixture.…”

“…Various strategies have been developed to achive adequate surface decoration of liposomes with the mannose ligands in order to obtain efficient recognition by MRs. [17] It was shown that mannose density on the surface of liposomes as well as stereochemical arrangement of mannosyl epitopes, valency and type of linker used, significantly affect recognition and binding by MRs. [18][19][20] Efficiency of mannosylated liposomes in targeted drug delivery has been demonstrated in numerous studies. [21][22][23][24][25][26][27] Our previous studies have been focused on the synthesis of novel immunomodulators and potent adjuvant formulations with improved activity.…”

Detecting Protein–Glycolipid Interactions Using Glycomicelles and CaR-ESI-MS

“…An alternative approach is to incorporate the GLs in a lipid monolayer or bilayer, such that the protein-GL interactions can be studied in a more native-like environment [10]. For such studies, a variety of different model membranes have been used to solubilize the GLs, including supported lipid bilayers, liposomes, micelles, bicelles, nanodiscs, and picodiscs [11][12][13][14], and the protein-GL interactions probed using diverse analytical techniques (e.g., fluorescence, nuclear magnetic resonance (NMR), and SPR spectroscopy) [15][16][17][18].between water-soluble lectins and GLs, solubilized using nanodiscs (NDs), have been detected using the catch-andrelease (CaR)-ESI-MS assay [19,20]. Nanodiscs are discoidal phospholipid bilayers surrounded by two copies of an amphipathic membrane scaffold protein [12,13].…”

Design and syntheses of mono and multivalent mannosyl-lipoconjugates for targeted liposomal drug delivery

“…Mannosylated liposomes have been recognized as promising non-live vectors for targeted delivery purposes. In the past few decades several strategies have been developed to promote an adequate coating of liposomes, used as drug or antigen carrier, with the mannose derivative that specifically recognizes MR receptor (Irache et al, 2008;Jayaraman et al, 2013;Schuster et al, 2003). To study carbohydrate-protein interactions, or the mechanism of lectin action, a variety of methods can be used.…”