Synthesis and Degradation Study of Cationic Polycaprolactone-Based Nanoparticles for Biomedical and Industrial Applications

Abstract

Positively charged polymers have increased in importance in the last years because of the possibility of being used in many different applications, from gene delivery to polymer flooding applications and as flocculants in wastewater treatment. In all cases, the possibility of obtaining biodegradable colloidal products leads to great advantages. In this work, positively charged nanoparticles (NPs) have been produced via free radical emulsion polymerization (FREP). This synthetic route was selected since it is widely used in industry and it facilitates large scale production along with control of some key features of the final NPs such as their size, surface charge, and particle size distribution dispersity. NP synthesis was carried out by a four-step process: the synthesis of biodegradable esterbased macromonomers obtained through the ring-opening polymerization of the ε-caprolactone, the reaction among the obtained macromonomer and succinic anhydride, the final condensation with choline chloride to obtain the positively charged macromonomer, and the FREP polymerization of the produced macromonomer. The effects of reaction conditions on NP characteristics were studied, and the tunable behavior of the obtained charged NPs has been proven, also in terms of degradation time.

Preformed Biodegradable Zwitterionic Nanoparticles as Tunable Excipients for the Formulation of Therapeutics Directly at the Point of Care

“…34,35 In addition, these macromonomers can be provided with a charged functional moiety by exploiting the reactivity of their hydroxyl end-group. 36 We now exploit these latest advances in the synthesis of highly controllable colloids to produce biodegradable zwitterionic NPs that, with minimal effort, can be adapted for the efficient loading and controlled release of different drugs. In particular, we realized this synthesis by combining the ROP and RAFT emulsion polymerization to produce amphiphilic block copolymers self-assembled into NPs directly in water and with minimal use of organic solvents.…”

“…However, the advent of the reversible addition–fragmentation chain transfer (RAFT) emulsion polymerization has allowed the production of highly tunable NPs composed of block copolymers directly in aqueous media. , To make these NPs biodegradable, oligoester-based macromonomers can be adopted to synthesize the hydrophobic portion of the copolymers and hence to drive their simultaneous self-assembly . These macromonomers are produced via ring opening polymerization (ROP) of lactones (e.g., caprolactone or lactide) in the presence of a primary alcohol comprising a vinyl group (e.g., hydroxyethyl methacrylate, HEMA). , In addition, these macromonomers can be provided with a charged functional moiety by exploiting the reactivity of their hydroxyl end-group …”

PEGylated Amine-Functionalized Poly(ε-caprolactone) for the Delivery of Plasmid DNA

“…As compared with PLA, PCL as a biodegradable polyester has very slow hydrolytic degradation, and literature reports that it takes more than a year for either bulk or nanostructured PCL to start showing major degradations under aqueous environments at 37 • C [38], although the degradation of PCL becomes faster at elevated temperatures [39,40]. The hydrolytic stability of PCL relative to PLA is among the key considerations for us to design CPCL-based polymers for gene delivery applications.…”

Fabrication of a Cu Nanoparticles/Poly(ε-caprolactone)/Gelatin Fiber Membrane with Good Antibacterial Activity and Mechanical Property via Green Electrospinning

“…Compared with other biodegradable polymers, PCL has nontoxicity, good biocompatibility, excellent elasticity and mechanical property, and adjustable physicochemical property. Thus, PCL has been widely applied in various fields. , However, the poor hydrophilicity of PCL limits its further application. For example, such property may lead to the low load of cells and the reduction of cell adhesion, proliferation, and differentiation.…”

“…Thus, PCL has been widely applied in various fields. 11,12 However, the poor hydrophilicity of PCL limits its further application. For example, such property may lead to the low load of cells and the reduction of cell adhesion, proliferation, and differentiation.…”