Self-Assembly and Cellular Uptake of Degradable and Water-Soluble Polyperoxides

Abstract

Water-soluble polyperoxides (PPs) as a new type of degradable and polymeric material were synthesized by the radical alternating copolymerization of sorbic derivatives containing a tetra(ethylene oxide) unit in the ester group using molecular oxygen. The obtained PPs showed a lower critical solution temperature (LCST)-type phase separation, and the transition temperature decreased according to the content of the hydrophobic ester group in the PPs. The PPs formed nanoaggregates with a diameter of 250-370 nm in water under the LCST. These PP aggregates were revealed to include 1-anilinonaphthalene-8-sulfonic acid as the fluorescence probe and epirubicin as the anticancer drug in their hydrophobic compartment. We evaluated the cytotoxicity and cellular uptake of the PPs in order to test their ability as a carrier used for the delivery of anticancer drugs. The cell viability in the presence of the PPs was comparable to those for the other biodegradable polymers, and epirubicin was taken up into the A549 efficiently with the PPs via an endocytosis mechanism.

Composition‐dependent crystallization behavior of copolyperoxides from methyl methacrylate and 4‐vinylbenzyl stearate

“…Polyperoxides degrade highly exothermically in contrast to common polymers which usually degrade endothermically . Even though polyperoxides are very much sensitive towards heat, enzyme, light, acid, and base, they find significant academic and industrial usefulness as thermal and photo initiators for radical copolymerization, auto‐combustible fuels, curators in coating and molding compositions, dismantlable adhesion, drug delivery, etc. Recently, Sato and coworkers explored the thermal latent properties of 1‐phenyl‐3‐pyrazolidones (PhPs) with an active hydrogen towards their addition effect for sorbic ester‐based polyperoxides.…”

Liquid marble containing degradable polyperoxides for adhesion force-changeable pressure-sensitive adhesives

“…[5][6][7] Furthermore, polyperoxides and their derivatives, including branched and block copolymers, have been applied to various types of degradable functional materials, i.e., dismantlable (de-bondable) adhesives, 8,9 coatings for surface modication, 9,10 and biocompatible materials. 11,12 Matsumoto et al reported that the radical alternating copolymerization of 1,3-diene monomers with oxygen smoothly proceeded in solution under oxygen bubbling, i.e., at atmospheric pressure, in good yields. 13 Considering the fact that the synthesis of polyperoxides using general vinyl monomers requires a high oxygen pressure to increase the yield, 1 the synthesis of polyperoxides using 1,3-diene monomers is versatile, facile, and suitable for practical applications.…”

Thermally Induced Aerobic Autopolymerization of Methyl Methacrylate in Amide-Type Solvents: Simultaneous Polymerization during Induction via Direct In Situ O2 Activation

“…Interpolymerization of vinylic monomers with O 2 appears to be quite ubiquitous, as no compound containing the vinyl or vinylidene group has been found which does not readily form a peroxide upon exposure to air under ordinary conditions, which have all been found to initiate polymerization . Kishore et al reported the preparation of oligo(peroxide)s with O 2 of typical vinylic monomers, including nonsubstituted, monosubsttituted, 1,1‐disubstituted (vinylidene), 1,2‐disubstituted vinylics, and conjugated dienes form oligo(peroxide)s under the induction of ultraviolet (UV) light, visible light, heat or radicals, or catalysis of Co II complexes, in bulk or organic solvents, while Matsumoto successfully attempted the radical alternating oxidative polymerization of conjugated dienes with O 2 , leading to degradable poly(peroxide)s …”