Fully degradable antibacterial poly(ester-phosphoester)s by ring-opening polymerization, “click” chemistry, and quaternization

Fully degradable cationic poly(ester-phosphoester)s with antibacterial properties were prepared by a combination of ring-opening polymerization (ROP) and “click” reaction. First, poly(ester-phosphoester)s-bearing alkynyl groups were synthesized by the ring-opening copolymerization of 2-(2-propynyloxy)−2-oxo-1,3,2-dioxaphospholane (propynyl ethylene phosphate, PEP) and ε-caprolactone (CL) using lanthanum tris(2,6-di-tert-butyl-4-methylphenolate)s (La(DBMP) 3 ) as the catalyst. 2-Azido-N,N-dimethylethanamine (DMEAN 3 ) was then attached to the copolymers by “click” reaction, resulting in poly(ester-phosphoester)s with pendant tertiary amines. After the quaternization reactions between the copolymer and various alkyl bromides, cationic poly(ester-phosphoester)s containing ammonium groups were obtained. Optical density (OD) measurement shows that the cationic copolymers have excellent antibacterial activity, which makes them potential candidates as biomaterials. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015 , 132 , 42647.