Novel Amphiphilic Degradable Poly(ε‐caprolactone)‐graft‐poly(4‐vinyl pyridine), Poly(ε‐caprolactone)‐graft‐poly(dimethylaminoethyl methacrylate) and Water‐Soluble Derivatives

Abstract

New amphiphilic graft copolymers that have a poly(ε‐caprolactone) (PCL) biodegradable hydrophobic backbone and poly(4‐vinylpyridine) (P4VP) or poly(2‐(N,N‐dimethylamino)ethyl methacrylate) (PDMAEMA) hydrophilic side chains have been prepared by anionic polymerization of the corresponding 4VP and DMAEMA monomers using a PCL‐based macropolycarbanion as initiator. The water solubility of these amphiphilic copolymers is improved by quaternization, which leads to fully water‐soluble cationic copolymers that give micellar aggregates in deionized water with diameters ranging from 65 to 125 nm. In addition, to improve the hydrophilicity of PCL‐g‐P4VP, grafting of poly(ethylene glycol) (PEG) segments has been carried out to give a water‐soluble double grafted PCL‐g‐(P4VP;PEG) terpolymer.

Synthesis, self‐assembly, and cytotoxicity of well‐defined trimethylated chitosan‐O‐poly(ε‐caprolactone): Effect of chitosan molecular weight

“…6 There were several types of cationic polymers having been used for constructing micelles with positively charged surface. These include poly (ethyleneimine) (PEI), 7 poly(2-(dimethylamino)ethyl methacrylate) (PDMAEMA), 8 poly(4-vinyl pyridine), 9 polylysine, 10 poly(N-methyldietheneamine sebacate), 11 poly(amino ester), 12 chitosan, and so forth. Among the earlier mentioned polycations, chitosan (CS) displays several advantages, such as cost-effectiveness, biocompatibility, biodegradability, and low cytotoxicity.…”

Poly(ε-caprolactone)-graft-poly(2-(N, N-dimethylamino) ethyl methacrylate) nanoparticles: pH dependent thermo-sensitive multifunctional carriers for gene and drug delivery

“…3 In terms of the special growth microenvironment of tumor tissue with lower pH (5.7-7.8) and higher temperature than that of normal tissues, several kinds of thermo-sensitive, pH-sensitive and dual-sensitive copolymer NPs have been prepared by incorporating pH and/or temperature-sensitive components. 16,17 This property is expected to be very useful for the stabiliy of nanocarriers in vivo. [12][13][14][15] Amphiphilic cationic copolymers can self-assemble into stable, size-controlled and dispersive NPs with a hydrophobic core and a cationic shell with a high surface charge density.…”

Poly(ε‐caprolactone)‐graft‐poly(2‐(dimethylamino)ethyl methacrylate) Amphiphilic Copolymers Prepared via a Combination of ROP and ATRP: Synthesis, Characterization, and Self‐Assembly Behavior

“…Poly(2‐(dimethylamino) ethyl methacrylate) (PDMAEMA), as a kind of hydrophilic, pH‐, and thermo‐sensitive polymer, has been frequently used as non‐viral DNA vector due to its cationic nature 10–12. Well‐defined amphiphilic copolymers with PDMAEMA as hydrophilic segments and PCL as hydrophobic moieties have been reported and may be useful as a potential drug and gene delivery system 13–21. As an important index for drug delivery systems, the critical association concentrations (CAC) of PCL‐ g ‐PDMAEMA was much lower than that of corresponding block polymers, which meant that the nanoparticles composed of PCL‐ g ‐PDMAEMA were more stable in aqueous media 9, 18…”

“…PCL‐based macropolycarbanion was prepared by using a non‐nucleophilic base (lithium diisopropyl amide) to remove the proton of the methylene group in ester carbonyl. This process was always performed at low temperature (−80 °C) to reduce the decomposition of main chain 8, 18. However, chain scissions of PCL are inevitable so it is difficult to control the graft density.…”