Fluorinated Polymeric Surfactant with a Pluronic-like Structure and Its Application as a Drug Carrier

Abstract

Pluronics (PEO-PPO-PEO or PPO-PEO-PPO), as the first commercially used polymeric surfactants, designed and manufactured by BASF, have been applied in the development of many pharmaceutical formulations and drug load as well as delivery. Herein, the Williamson ether synthesis reaction was used to prepare hydrophobic monomer fluorinated epichlorohydrin (EPTF) considered as an intermediate state before. In addition, ABA triblock amphiphilic polymers (molecular weight ranging from 2083 to 8888 g/mol with the polymer dispersity index (PDI) lower than 1.52) with a Pluronic-like structure were synthesized by the living cationic polymerization of polyethylene oxide (PEO) and EPTF. The structures of EPTF and polymeric surfactants were characterized by Fourier infrared transform spectroscopy (FI-IR), nuclear magnetic resonance (NMR), and gel permeation chromatography (GPC). Moreover, these kinds of polymeric surfactants can not only reduce the surface tension of water but also self-assemble in water to form micelles with a much lower critical micelle concentration (CMC) ranging from 8.13 × 10–5 to 1.95 × 10–3 g/L. Baicalin, low-water-solubility anticancer drug, can be loaded into this polymeric surfactant to form nanomicelles by a solvent evaporation method. The particle size, colloidal stability, and loaded content were characterized by dynamic light scattering (DLS), transmission electron microscopy (TEM), and ultraviolet–visible (UV–vis) spectrometry. These results indicate that hydrophobic anticancer drugs, like baicalin, can be loaded into these kinds of surfactants with a much higher concentration (maximum 380.776 μg/mL) and excellent storage stability, overcoming their low water solubility so as to increase their therapeutic efficacy.

Polymeric Surfactants: Recent Advancement in Their Synthesis, Properties, and Industrial Applications

“…However, their high costs over conventional lowmolecular weight surfactants are still a challenge. [162][163][164][165][166][167][168][169]…”

Method: Efficient Ocular Drug Delivery Using Fluorinated Nanoparticle Laden Films

“…Travoprost is loaded in the micelles via a solvent evaporation method. We hypothesize that pentafluoroethyl groups could not incorporate into the PFPE core because fluorophilic effect of two fluorocarbons is too weak to self-assembly [28] and the steric effect of PEG prevents pentafluoroethyl groups from interacting with the core while it still could repel positively charged CPPs on the surface. Here, RGD improves micelle-membrane interactions.…”

Folate Functionalized and Evodiamine‐Loaded Pluronic Nanomicelles for Augmented Cervical Cancer Cell Killing

“…[23][24][25] Pluronics are generally known as poloxamers (structure of PEOx-PPOy-PEOx) consisted of hydrophilic head and hydrophobic core of poly ethylene oxide (PEO) and poly (propylene oxide) (PPO), respectively. [26][27][28][29][30][31] Pluronics are naturally amphiphilic, capable of self-assembling into nano micelles, and capable of encapsulating and delivering hydrophobic nutraceuticals to target areas in a pH-responsive way. [32][33][34] For the drug delivery applications, targeted drug delivery via modification or functionalization of polymers is more considerable compared to nonspecific drug delivery polymers because it enables the target specific delivery of hydrophobic drugs.…”

“…[ 23–25 ] Pluronics are generally known as poloxamers (structure of PEOx‐PPOy‐PEOx) consisted of hydrophilic head and hydrophobic core of poly ethylene oxide (PEO) and poly (propylene oxide) (PPO), respectively. [ 26–31 ] Pluronics are naturally amphiphilic, capable of self‐assembling into nano micelles, and capable of encapsulating and delivering hydrophobic nutraceuticals to target areas in a pH‐responsive way. [ 32–34 ]…”