Antimicrobial Hydantoin‐grafted Poly(ε‐caprolactone) by Ring‐opening Polymerization and Click Chemistry

Abstract

Novel degradable and antibacterial polycaprolactone-based polymers are reported in this work. The polyesters with pendent propargyl groups are successfully prepared by ring-opening polymerization and subsequently used to graft antibacterial hydantoin moieties via click chemistry by a copper(I)-catalyzed azide-alkyne cycloaddition reaction. The well-controlled chemical structures of the grafted copolymers and its precursors are verified by FT-IR spectroscopy, NMR spectroscopy, and GPC characterizations. According to the DSC and XRD results, the polymorphisms of these grafted copolymers are mostly changed from semicrystalline to amorphous depending on the amount of grafted hydantoin. Antibacterial assays are carried out with Bacillus subtilis and two strains of Escherichia coli and show fast antibacterial action.

Radical Copolymerization of Vinyl Ethers and Cyclic Ketene Acetals as a Versatile Platform to Design Functional Polyesters

“…Their antibacterial behavior was then tested against Gram negative Pseudomonas aeruginosa , Gram positive Staphylococcus aureus and the clinical multiresistant S. aureus strain MRSA USA300. Films coated with quaternized triethylamine functionalities presented strong antibacterial activity, with quasi‐complete bacteria killing after 10 min of exposure (Figure ) as already shown by other antimicrobial degradable materials . Unlike triethylamine, the functionalization with N , N ‐dimethyloctylamine was not conclusive and did not produce a sufficiently functionalized surface to induce efficient antibacterial activity.…”

Biodegradable Copolymer for Stimuli-Responsive Sustained Release of Doxorubicin

“…Towards this goal, the functionalization of lactones was performed in two steps ( Scheme 3 ). At first, compound 5 was synthesized 40 from cyclohexanone in the presence of LDA and propargyl bromide at −78 °C. The crude product was first purified by column chromatography, followed by distillation under reduced pressure at 160 °C, which yielded compound 5 as a colorless, viscous liquid (62%).…”

“… 9 , 10 The ring-opening polymerization (ROP) of lactones is an emerging synthetic technique because of its versatility to produce a wide range of biomedical polymers in a controlled manner. 11 − 13 , 40 − 46 However, pendent functionalizations of polycaprolactones are still a promising area of research because of their potential synthetic challenges. 14 − 16 …”

Radical Copolymerization of Vinyl Ethers and Cyclic Ketene Acetals as a Versatile Platform to Design Functional Polyesters

“…[42] This method also allowed for the simple tuning of film degradation by changing the PCL/ PMDO weight ratio.The nature of the surface was probed by contact angle (CA; Supporting Information, Figure S14) and showed an increase of CA when butyl and chloroethyl functionalities were inserted. [43][44][45] Unlike triethylamine,t he functionalization with N,N-dimethyloctylamine was not conclusive and did not produce as ufficiently functionalized surface to induce efficient antibacterial activity.I ti simportant to note that control experiments (that is, non-functionalized film dipped into N,N-dimethyloctyla-mine), did not exhibit any antibacterial activity,r uling out antibacterial activity from adsorbed/residual amines.S ince hemolysis is the main drawbacks of cationic antibacterial polymers,t he innocuity of the copolymers versus human red blood cells was also investigated (Supporting Information, Figure S16), and showed insignificant damage even after 4h of incubation. Thefilms were further washed with water and dried at 25 8 8C.…”