New amphiphilic glycopolymers by click functionalization of random copolymers – application to the colloidal stabilisation of polymer nanoparticles and their interaction with concanavalin A lectin

Otman Otman,Paul Boullanger,Thierry Hamaide,Eric Drockenmuller

doi:10.3762/bjoc.6.58

Abstract

Glycopolymers with mannose units were readily prepared by click chemistry of an azido mannopyranoside derivative and a poly(propargyl acrylate-co-N-vinyl pyrrolidone). These glycopolymers were used as polymer surfactants, in order to obtain glycosylated polycaprolactone nanoparticles. Optimum stabilization for long time storage was achieved by using a mixture of glycopolymers and the non-ionic triblock copolymer Pluronic® F-68. The mannose moieties are accessible at the surface of nanoparticles and available for molecular recognition by concanavalin A lectin. Interaction of mannose units with the lectin were evaluated by measuring the changes in nanoparticles size by dynamic light scattering in dilute media.

Highlights

Over the last decades, research efforts in pharmaceutical, food and cosmetics technologies have been directed towards the syntheses of new bioactive entities or medicines, and towards new formulations that can enhance the activity of drugs, as well as the elaboration of new drug delivery systems.The main objectives are the transport of active hydrophilic or lipophilic substances, while minimizing drug degradation, increasing drug availability and localization in the required organ
This paper reports the first results on another class of glycopolymers obtained from the functionalization of poly(propargyl acrylate-co-N-vinyl pyrrolidone) by click chemistry with ω-mannopyranoside
All the observations that will be described were true for crude suspensions as well as re-suspended pellets the supernatants are more homogenous and the more abundant fractions, and contain about 65 % of nanoparticles. This time increasing amounts of concanavalin A (con A) were added to the supernatant fraction of colloidal suspensions of nanoparticles stabilized by the mixture of Pluronic® F-68 (PF-68) and NVP-PA-Man

Summary

Introduction

Research efforts in pharmaceutical, food and cosmetics technologies have been directed towards the syntheses of new bioactive entities or medicines, and towards new formulations that can enhance the activity of drugs, as well as the elaboration of new drug delivery systems.The main objectives are the transport of active hydrophilic or lipophilic substances, while minimizing drug degradation, increasing drug availability and localization in the required organ. We recently reported the synthesis and characterization of amphiphilic copolymers bearing carbohydrate and oligocaprolactone side chains, obtained via copolymerization of a PCL macromonomer and maleic anhydride, and further functionalization by ring opening of the anhydride moiety with amino mannopyranoside. These copolymers were used as polymer surfactants for the stabilization of PCL nanoparticles coated with carbohydrate on their surface [12].

Results

Conclusion