Self-assembling glycopolymers have garnered increased attention from the scientific community as an effective solution to the complications presented by current therapeutics. Using glycopolymers to encapsulate highly toxic drugs, targeted delivery can be achieved by exploiting the enhanced permeation and retention (EPR) effect and by functionalizing polymers with sugar moieties specific to receptors present on tumor-associated cell lines. With this combination of passive and active targeting in mind, amphiphilic diblock copolymer poly(2-(a-D-mannosyloxy)ethyl methacrylate)-co-poly(tert-butyl acrylate), or pMannHEMA-co-ptBA, was synthesized using reversible addition fragmentation chain transfer (RAFT) polymerization. A critical micelle concentration of 0.00734 mg/mL was observed in 0.1 M phosphate buffer of pH 8.0. By dynamic light scattering, micelles were 31.6 nm in diameter. The binding behavior of the copolymer with concanavalin A (ConA) was also examined by measuring the turbidity change rate. Using a 1.0 mg/mL solution of pMannHEMA-co-ptBA in HEPES buffer, the copolymer displayed increased absorbance in the presence of ConA, indicating receptor recognition (Figure 1). Consequently, this work provides a general synthetic route to self-assembling glycopolymers. pMannHEMA-co-ptBA demonstrated self-assembling behavior with a low critical micelle concentration. In addition, the copolymer exhibited positive binding behavior with a mannose-binding protein, distinguishing the copolymer as a potentially clinically relevant molecule.Figure 1. Time course of optical density at 420 nm in mixtures of concavalin A and pMannHEMA-co-ptBA and copolymer structure.

Synthesis of mannose-functionalized polymeric micelles

245th National Meeting (2013)

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