Sequential post-polymerization modification of a pentafluorophenyl ester-containing homopolymer: a convenient route to effective pH-responsive nanocarriers for anticancer drugs

Abstract

Effective pH-responsive anticancer drug nanocarriers can be simply prepared through post-polymerization modification of a single pentafluorophenyl ester-containing polymer.

Electrochemically-initiated polymerization of reactive monomers via 4-fluorobenzenediazonium salts

“…In the case of 2,6-difluorophenyl acrylate and PFPA, the reactive polymers are based on active ester side groups, which can be transformed into the respective amide. 39,[45][46][47] Poly(glycidyl methacrylate) (PGMA) on the other hand bears an epoxide functional group, which can be ring-opened by a nucleophile. 48 Details are discussed in the following.…”

“…Polymer Chemistry employed for PPM. 39,[45][46][47] It was obtained in a similar fashion to 2,6-difluorophenyl acrylate from acryloyl chloride as mentioned above. First polymerization attempts applying a constant current of −4 mA until 4 F mol −1 passed through the system turned out to deliver polymeric material, however the 19 F NMR spectrum exhibited signals arising from potential decomposition reactions (Fig.…”

Playing construction with the monomer toy box for the synthesis of multi‐stimuli responsive copolymers by reversible deactivation radical polymerization protocols

“…O′Reilly's group has recently obtained redox‐responsive polymeric micelles through postpolymerization modification of PEG‐ b ‐P(pentafluorophenyl methacrylate) with a reductant‐sensitive diamine 128 . Hoven's group 122,124 obtained pH‐ or redox‐ responsive polymeric nano‐aggregates by nucleophilic displacement of poly(pentafluorophenyl acrylate) with 1‐amino‐2‐propanol for hydrophilicity, sequentially followed by displacement of the residual pentafluorophenyl groups by the amino group of 1‐(3‐aminopropyl)imidazole for pH responsivity. Roth, P.J.…”

Chemiluminescent self-reporting supramolecular transformations on macromolecular scaffolds

“…polybutadiene 42 ) can be decorated with a broad variety of functionalities to obtain innovative macromolecules with tailor-made properties. Among the different reactions enabling PPMs (copper-catalyzed azidealkyne cycloaddition (CuAAC), 43 thiol-ene addition, 44 Michael addition, 45 or electrophilic cascade reactions 42 ), active esters, such as pentafluorophenyl (PFP) esters, [46][47][48] are considerably attractive functional units to deliver well-defined multi-functionalized polymers. Especially the possibility to modify active PFP ester groups within a copolymer backbone in a precise and orthogonal manner is highly beneficial.…”