Postpolymerization Modification Using Less Cytotoxic Activated Ester Polymers for the Synthesis of Biological Active Polymers

Activated ester polymers, pioneered by Ferruti and Ringsdorf in the 1970s, are attractive polymeric materials because they can easily be converted into functional polymers by reacting with amine nucleophiles. In the present study, methyl salicylate acrylate, salicyl acrylate, and tert-butyl salicylate acrylate monomers were polymerized yielding three novel reactive precursors suitable for the postpolymerization modification with primary and secondary amines. The reactivities of poly­(pentafluorophenyl acrylate), poly­(methyl salicylate acrylic ester), and poly­(salicyl acrylate) toward amines were compared by kinetic studies and revealed the practical applicability of salicylic acid based derivatives for efficient postpolymerization modifications. In addition, in vitro cytotoxicity of water-soluble leaving groups, pentafluorophenol and salicylic acid, as well as water-soluble polymers containing the respective activated ester groups were investigated using HeLa cells. In short, compared to the frequently used poly­(pentafluorophenyl acrylate), poly­(salicyl acrylate) activated ester feature a lower reactivity, but exhibit less cytotoxicity. In this respect, poly­(salicyl acrylate) as reactive precursor polymers may become alternative routes for the synthesis of functional polyacrylamides when it comes to advanced applications in vivo.