Surface modified liposomes by mannosylated conjugates anchored via the adamantyl moiety in the lipid bilayer

Abstract

The aim of the present study was to encapsulate mannosylated 1-aminoadamantane and mannosylated adamantyltripeptides, namely [(2R)-N-(adamant-1-yl)-3-(α,β-d-mannopyranosyloxy)-2-methylpropanamide and (2R)-N-[3-(α-d-mannopyranosyloxy)-2-methylpropanoyl]-d,l-(adamant-2-yl)glycyl-l-alanyl-d-isoglutamine] in liposomes. The characterization of liposomes, size and surface morphology was performed using dynamic light scattering (DLS) and atomic force microscopy (AFM). The results have revealed that the encapsulation of examined compounds changes the size and surface of liposomes. After the concanavalin A (ConA) was added to the liposome preparation, increase in liposome size and their aggregation has been observed. The enlargement of liposomes was ascribed to the specific binding of the ConA to the mannose present on the surface of the prepared liposomes. Thus, it has been shown that the adamantyl moiety from mannosylated 1-aminoadamantane and mannosylated adamantyltripeptides can be used as an anchor in the lipid bilayer for carbohydrate moiety exposed on the liposome surface.

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

“…[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. [30,43] The obtained results have confirmed that Con A successfully recognized mannosyl ligands exposed on liposome surface and exhibits higher affinity to multivalent mannosyl ligands. [31] Here, we report preparation and characterization of mannosylated liposomes with/without built-in peptidoglycan based immunomodulators, PGM or Ad2TP2, and with entrapped model antigen, ovalbumin.…”

“…[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. [28][29][30] In recently published paper we described the synthesis of mono-, di-and tetramannosyllipoconjugate, used for mannosylation of liposomes, and studies of interaction of prepared mannosylated liposomes with model lectine, concanavaline A (Con A) by quartz crystal microbalance (QCM). [31] Here we report preparation of mannosylated liposomes with built-in peptidoglycan based immunomodulators, peptidoglycan monomer surface.…”

Adamantyl ferrocene derivatives: Antioxidant abilities and effects on model lipid membranes

“…Our previous research of biologically active adamantoylated compounds has been focused on their interaction with model biological membrane . Although the effect of ferrocene on liposome has not been studied intensively, several recent papers have described the application of oxidized ferrocene as an organometallic amphiphile and ferrocene‐modified phospholipid in preparation of the redox‐modified liposomes .…”

“…Our previous research of adamantane derivatives of biologically active peptidoglycan fragments has shown their strong interaction with lipid membrane . Furthermore, we have shown that the adamantyl moiety can be employed as an anchor in the lipid bilayer while the polar part of the molecule, a carbohydrate mannose or guanidine residue, is exposed on the liposome surface …”

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

“…Our previous studies of chemical syntheses and characterization of mannosyl derivatives of biologically active peptidoglycan fragments, namely adamantyltripeptides , have shown their strong interaction with cell membranes and the potential for preparation of glycosylated carriers for drug delivery Štimac et al, 2012). In the continuation of our studies our interest is in finding a potent targeted delivery vehicle for drugs, especially for subunit vaccines with built-in small molecule immunopotentiators.…”