Synthesis of new aliphatic poly(ester‐carbonate)s bearing amino groups based on photolabile protecting group and evaluation of antibacterial property

Abstract

Amino‐functionalized six‐membered cyclic carbonate 5‐((2‐nitrobenzyl) amino)‐1,3‐dioxan‐2‐one (NBAC) was synthesized with 2‐nitrobenzyl group as photolabile protecting group. The following copolymerization was carried out by using l‐lactide as comonomer and Sn (Oct)2 as catalyst. The amino‐functionalized polymer P(LA‐co‐AC) was obtained by ultraviolet irradiation of P(LA‐co‐NBAC) to remove the protecting group. The structures of products were confirmed by 1H nuclear magnetic resonance (NMR) and 13C NMR analysis. The pendant amino groups not only resulted in an enhancement of the hydrophilicity, but also played a role of antibacterial effect due to the positive charge imparted to the material.

Biodegradable Polymers and Polymer Composites with Antibacterial Properties

“…Chen et al [ 336 ] obtained a series of copolymers with a pendant amino group by ROP initiated with a tin compound during the copolymerization of L-lactide and specially synthesized cyclic carbonate ((2-nitrobenzyl) amino)-1,-3-dioxan-2-one (NBAC). The use of carbonate with a nitrobenzyl group allowed the troublesome process of deprotection of functional groups.…”

A novel biodegradable ureteral stent with antibacterial ability to inhibit biofilm formation

“…Further, we found that the introduction of bactericidal groups such as amino cations, can not only improve the hydrophilicity, but also directly endow the material with antibacterial properties. [34][35] In this study, we synthesized a macromolecule with pendant primary amine groups named poly (L-lactide-co-5-amino-1,3-dioxan-2-one) (P(LA-co-AC)), which mimicked antimicrobial peptides (AMP) 36 . Based on reports in the literature, this AMP structure could attach to the microbial membrane via electrostatic attractions between their cationic groups and the anionic membrane's surface.…”

“…34,35 In this study, we synthesized a macromolecule with pendant primary amine groups, named poly (L-lactide-co-5-amino-1,3dioxan-2-one) (P(LA-co-AC)), which mimicked antimicrobial peptides (AMP). 36 Based on reports in the literature, this AMP structure could attach to the microbial membrane via electrostatic attractions between their cationic groups and the surface of the anionic membrane. When this occurs, hydrophobic chains intercalate into the microbial membrane to induce membrane destabilization and subsequent leakage of cytoplasmic content, leading to lysis.…”