Hydrolysis and Antibacterial Activity of Polymers Containing 8-Quinolinyl Acrylate

Abstract

The hydrolytic release of 5-chloro-8-hydroxyquinoline (HQ) from 5-chloro-8-quinolinylacrylate (AQ) containing polymers was studied under physiological under conditions (pH 7.2 and 37°C) as well as in acidic and alkaline medium. The hydrolysis rate was influenced by autocatalytic process with participation by quinolinyl groups as well as by neighboring groups. For copolymers of AQ and acrylamide (AM), the release rate increased with increasing pH, temperature, and the content of hydrophilic monomer. Copolymers of AQ and N-vinylpyrrolidone (VP) exhibit a lower rate of HQ release because of steric hindrance of the hydrolysis site and the influence of the alternating VP-AQ sequences which contribute to the enhanced hydrophobicity of the copolymer. The antimicrobial activity of the copolymers was found to be related to their hydrolysis behavior. The attachment of a biologically active agent to a macromolecular carrier can prolong its effect.