Abstract

Antibiotic resistance is an emerging threat to public health. The development of a new generation of antimicrobial compounds is therefore currently required. Here we report a novel antimicrobial polymer of chitosan/polypropylene carbonate nanoparticles (CS/PPC NPs). These were designed and synthesized from readily available chitosan and a reactive oligomer polypropylene carbonate (PPC)-derived epoxy intermediate. By employing a simple and efficient functionalized strategy, a series of micelle-like chitosan-graft-polypropylene carbonate (CS-g-PPC) polymers and chitosan–polypropylene carbonate (CS–PPC) microgels were prepared by reacting mono-/bis-epoxy capped PPC with chitosan. The chemical structure, particle size, and surface charge of the newly synthesized polymers were characterized by infrared (IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, dynamic light scattering (DLS), and zeta potential measurements. The antimicrobial activities of these nanoparticles were determined in both Gram-positive bacteria (S. aureus) and Gram-negative bacteria (E. coli). Minimum inhibitory concentration (MIC), the nanoparticle concentration needed to completely inhibit the bacterial growth, was found at 128 μg mL−1 to 1024 μg mL−1, strongly depending both on the nature of the epoxy-imine network formed from the functional groups (mono- or bis-capped epoxy groups reacting with amine groups) and the feed ratio of the functional groups (-epoxy/-NH2) between the functionalized PPC and chitosan. No hemolysis was observed at concentrations well in excess of the effective bacteria-inhibiting concentrations. These findings provide a novel strategy to fabricate a new type of nanoantibiotic for antimicrobial applications.

Highlights

  • Antibiotic resistance of life-threatening bacteria is a major threat to public health.[1]

  • Chitosan is a linear polysaccharide copolymer consisting of b-1,4-linked D-glucosamine and N-acetyl-glucosamine, which is obtained by partial alkaline N-deacetylation of chitin.[8]

  • A series of CS-polypropylene carbonate (PPC) microgels was synthesized by adjusting the molar feed ratio of EP-PPC (EP-PPC-EP)/NH2 of chitosan ([-EP]/[-NH2]) from 0.01 to 2 and they were labeled as G1 to G7 (Scheme 1 and Table 1)

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Summary

Introduction

Chitosan is a linear polysaccharide copolymer consisting of b-1,4-linked D-glucosamine and N-acetyl-glucosamine, which is obtained by partial alkaline N-deacetylation of chitin.[8] Chitosan has recently attracted attention due to its signi cant antimicrobial properties and the advantages of being nontoxic, biodegradable and biocompatible.[9,10] A number of commercial applications of chitosan bene t from its antimicrobial activity, including its use in food preservation, in dentistry and ophthalmology, as well as in the manufacture of wounddressings, and antimicrobial- nished textiles.[11,12] the antimicrobial properties of chitosan are mostly limited to pH below pKa (about 6.5), since chitosan begins to lose its cationic properties and its solubility at higher pH values This can limit its applications at physiological conditions. These nanoparticles were tested for hemolytic activities against red blood cells, and the selectivity against bacteria was evaluated

Experimental
Characterization
Chemical structure analysis
Results and discussion
Conclusion
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