Synthesis of Zwitterionic Pluronic Analogs
journal contributionposted on 19.07.2018, 18:49 by Matthew Skinner, Brandon M. Johnston, Yalin Liu, Brenton Hammer, Ryan Selhorst, Ioanna Xenidou, Sarah L. Perry, Todd Emrick
Novel polymer amphiphiles with chemical structures designed as zwitterionic analogs of Pluronic block copolymers were prepared by controlled free radical polymerization of phosphorylcholine (PC) or choline phosphate (CP) methacrylate monomers from a difunctional poly(propylene oxide) (PPO) macroinitiator. Well-defined, water-dispersible zwitterionic triblock copolymers, or “zwitteronics”, were prepared with PC content ranging from 5 to 47 mol percent and composition-independent surfactant characteristics in water, which deviate from the properties of conventional Pluronic amphiphiles. These PC-zwitteronics assembled into nanoparticles in water, with tunable sizes and critical aggregation concentrations (CACs) based on their hydrophilic–lipophilic balance (HLB). Owing to the lower critical solution temperature (LCST) miscibility of the hydrophobic PPO block in water, PC-zwitteronics exhibited thermoreversible aqueous solubility tuned by block copolymer composition. The chemical versatility of this approach was demonstrated by embedding functionality, in the form of alkyne groups, directly into the zwitterion moieties. These alkynes proved ideal for cross-linking the zwitteronic nanoparticles and for generating nanoparticle-cross-linked hydrogels using UV-initiated thiol–yne “click” chemistry.
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Pluronic block copolymersmethacrylate monomerszwitteronic nanoparticlesLCSTzwitterion moietieswater-dispersible zwitterionic triblock copolymersPC contentHLBPC-zwitteronicembedding functionalityPPO blockzwitterionic analogschemical structuresZwitterionic Pluronic Analogs Novel polymer amphiphilesPluronic amphiphilesnanoparticle-cross-linked hydrogelssolution temperaturealkyne groupsblock copolymer compositionCPcomposition-independent surfactant characteristicsCACaggregation concentrationschemical versatilitytunable sizes47 mol percentcholine phosphate