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<p>Chitosan (CS), a naturally derived polysaccharide, exhibits inherent biocompatibility and moderate antimicrobial activity; however, its efficacy against resistant and biofilm-forming pathogens remains limited. To enhance its bioactivity, CS was chemically modified through N-phthaloylation and O-/N-acylation with L-arginine, yielding derivatives including N-phthaloyl chitosan (Ph-CS), N-acylated chitosan (N-Arg-CS), O-acylated chitosan (O-Arg-CS), and O-N-acylated chitosan (O-N-Arg-CS). Characterization using FTIR, SEM, TEM, EDX, and TGA confirmed successful structural and morphological modifications. O-N-Arg-CS exhibited significant improvements in thermal stability, porosity, and nanoscale morphology, with particle sizes ranging from 100 to 150&#xa0;nm. Antimicrobial assays demonstrated that O-N-Arg-CS had the highest efficacy, with inhibition zones of 27&#xa0;mm against <i>Pseudomonas aeruginosa</i>, 25&#xa0;mm against <i>Klebsiella pneumoniae</i>, and 21&#xa0;mm against <i>Staphylococcus aureus</i>. It also exhibited over 100% biofilm inhibition at 300&#xa0;mg/mL for all tested pathogens. Cytoplasmic protein leakage studies indicated strong membrane-disruptive effects, with the highest leakage observed for <i>P. aeruginosa</i> (312&#xa0;µg/mL). N-Arg-CS and O-N-Arg-CS also showed dose-dependent killing efficiency, completely eradicating microbial populations within 60–90&#xa0;min at concentrations as low as 150&#xa0;mg/mL. These findings highlight the potential of O-N-Arg-CS as a highly effective and biocompatible antimicrobial agent. Its strong broad-spectrum activity, biofilm inhibition, and low toxicity make it a promising candidate for coatings on medical implants to combat biofilm-associated and multidrug-resistant infections.&#xa0;These results establish O-N-Arg-CS as a highly effective and safe antibacterial biomaterial, demonstrating significant translational potential for medical implant coatings. </p>

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Modification of chitosan biopolymer with L-arginine synthesized via click chemistry for designing promising polymeric compounds as antimicrobial coatings for medical implants

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年8月6日

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  • El-Refaie Kenawy,
  • El-Sayed M. Abdelrehim,
  • M. E. Elba,
  • Yehia A.-G. Mahmoud,
  • Yosra Mashaly,
  • Sarah Salem

摘要

Chitosan (CS), a naturally derived polysaccharide, exhibits inherent biocompatibility and moderate antimicrobial activity; however, its efficacy against resistant and biofilm-forming pathogens remains limited. To enhance its bioactivity, CS was chemically modified through N-phthaloylation and O-/N-acylation with L-arginine, yielding derivatives including N-phthaloyl chitosan (Ph-CS), N-acylated chitosan (N-Arg-CS), O-acylated chitosan (O-Arg-CS), and O-N-acylated chitosan (O-N-Arg-CS). Characterization using FTIR, SEM, TEM, EDX, and TGA confirmed successful structural and morphological modifications. O-N-Arg-CS exhibited significant improvements in thermal stability, porosity, and nanoscale morphology, with particle sizes ranging from 100 to 150 nm. Antimicrobial assays demonstrated that O-N-Arg-CS had the highest efficacy, with inhibition zones of 27 mm against Pseudomonas aeruginosa, 25 mm against Klebsiella pneumoniae, and 21 mm against Staphylococcus aureus. It also exhibited over 100% biofilm inhibition at 300 mg/mL for all tested pathogens. Cytoplasmic protein leakage studies indicated strong membrane-disruptive effects, with the highest leakage observed for P. aeruginosa (312 µg/mL). N-Arg-CS and O-N-Arg-CS also showed dose-dependent killing efficiency, completely eradicating microbial populations within 60–90 min at concentrations as low as 150 mg/mL. These findings highlight the potential of O-N-Arg-CS as a highly effective and biocompatible antimicrobial agent. Its strong broad-spectrum activity, biofilm inhibition, and low toxicity make it a promising candidate for coatings on medical implants to combat biofilm-associated and multidrug-resistant infections. These results establish O-N-Arg-CS as a highly effective and safe antibacterial biomaterial, demonstrating significant translational potential for medical implant coatings.