Postpolymerization modification using less cytotoxic activated ester polymers for the synthesis of biological active...

Area of Science:

• Polymer Chemistry
• Materials Science
• Biomaterials

Background:

• Activated ester polymers are versatile precursors for functional polymers via reaction with amine nucleophiles.
• Salicylic acid derivatives offer potential for developing less cytotoxic activated ester polymers.

Purpose of the Study:

• To synthesize and characterize novel salicylic acid-based activated ester polymers.
• To compare the reactivity and cytotoxicity of these polymers against poly(pentafluorophenyl acrylate).
• To evaluate their suitability for post-polymerization modification with amines.

Main Methods:

• Polymerization of methyl salicylate acrylate, salicyl acrylate, and tert-butyl salicylate acrylate monomers.
• Kinetic studies to compare polymer reactivities toward amines.
• In vitro cytotoxicity assays using HeLa cells for polymers and leaving groups.

Main Results:

• Three novel reactive precursor polymers based on salicylic acid derivatives were successfully synthesized.
• Salicylic acid-based polymers exhibited lower reactivity but significantly reduced cytotoxicity compared to poly(pentafluorophenyl acrylate).
• Water-soluble leaving groups (pentafluorophenol and salicylic acid) and their corresponding polymers were assessed for toxicity.

Conclusions:

• Poly(salicyl acrylate) activated esters are viable alternatives to poly(pentafluorophenyl acrylate) for synthesizing functional polyacrylamides.
• The reduced cytotoxicity of salicylic acid-based polymers makes them attractive for advanced in vivo applications.
• These findings open new avenues for developing safer functional polymeric materials.