Multifunctional Poly(Vinyl Amine)s Bearing Azetidinium Groups: One Pot Preparation in Water and Antimicrobial Properties

Abstract

A simple, robust one pot procedure for the preparation of waterborne multifunctional poly(vinyl amine)s (PVAms) is presented. By post-polymerization modification of PVAm with a bifunctional coupler and functional couplers cationic, reactive azetidinium groups, and alkyl chains are introduced in the side chains of PVAms. The structure-activity relations (effect of hydrophobic and cationic modifications) of these antimicrobial polymers are studied; the minimum inhibitory concentration (MIC) against both (Gram positive and Gram negative bacteria) of the library of multifunctional poly(vinyl amine)s are determined to identify the candidates with the highest efficacy. Furthermore, the hemolytic activity-the effective concentration at which 50 and 10% of red blood cells are killed (HC50 and HC10 )-of selected polymers is determined. The ability of the polymers prepared to differentiate between microorganisms (Gram positive and Gram negative bacteria) and mammalian cells (red blood cells) is understood by comparing MIC and HC values. Finally, as an example, the best polymer is used to prepare an antimicrobial surface.

Controlling macromolecular structures towards effective antimicrobial polymers

“…Polymers with cations directly attached to the hydrophobe were more effective against bacteria, compared to segregated polymers and polymers with cation and hydrophobe linked with an alkyl chain. In a more recent study, they synthesized azetidinium functionalized poly(vinyl amine) copolymers (Table 1D) via a one-pot post-polymerization modification approach using suitable functional couplers [72]. When the hexyl chain in the hydrophobic group was replaced by a decyl chain, antimicrobial activity against S. aureus and Escherichia coli increased significantly.…”

Recent Developments in Antimicrobial Polymers: A Review

“…The microstructures containing the hydrophobic segment attached directly to the segment with cationic groups showed higher efficiency against bacteria than the one with cationic groups that are not attached to the alkyl chain [150]. Later, the same group tested multifunctional poly(vinyl amines) (PVAms), with cationic, reactive azetidinium and alkyl chain groups introduced in the side chains of PVAms, against bacteria (Figure 8) [151]. The antimicrobial efficacy of the polymers was improved by increasing the hydrophobic moiety, namely by replacing the hexyl group by the decyl group.…”

“…In addition, a higher content of cationic groups has also led to a significant increase of the antimicrobial efficiency. The results suggested that the PVAms samples containing 11% of hydrophobic and 5%–14% of cationic groups presented the best antimicrobial efficacy [151]. …”

“…Chemical structure of poly(vinyl amine) with cationic, azetidinium and alkyl groups on the side chain [151]. …”

Azetidinium Functionalized Polytetrahydrofurans: Antimicrobial Properties in Solution and Application to Prepare Non Leaching Antimicrobial Surfaces

“…To prepare polymer coated antimicrobial surfaces in the current work, we focused on the application of azetidinium functionalized polymers. The advantages of azetidinium groups in this application are: (a) inhibition of bacterial growth via interaction with cell components due to the cationic nature of this group [15,16] and (b) improving the adhesion via both (i) ionic interaction and (ii) covalent linkage. The four membered rings attached to the polymers react with the functional groups on the surface forming covalent bonds [17].…”