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https://hdl.handle.net/10216/142702
Author(s): | Alves, PM Pereira, RF Costa, B Tassi, N Teixeira, C Leiro, V Monteiro, C Gomes, P Costa, F Martins, MCL |
Title: | Thiol-Norbornene Photoclick Chemistry for Grafting Antimicrobial Peptides onto Chitosan to Create Antibacterial Biomaterials |
Publisher: | American Chemical Society |
Issue Date: | 2022-06-30 |
Abstract: | Covalent conjugation of antimicrobial peptides (AMP) is considered an effective approach to overcome their potential degradation in vivo. As the high cost of AMP-based therapies is one of the major hurdles towards their clinical application, it is urgently needed to explore high yield reactions. Herein, the highly efficient thiol-norbornene photoclick chemistry (TNPC) was explored for AMP grafting onto chitosan. Norbornenes were introduced onto chitosan (NorChit) in an aqueous/organic system, followed by UV-triggered conjugation of N- and C-terminus cysteine-modified Dhvar5 (NorChit-Dhvar5). Up to 0.38 norbornene groups per chitosan repeating unit and up to 43% conjugation yield in NorChit-Nt-Dhvar5 (80 μmol of Dhvar5/g) were achieved, while in NorChit-Ct-Dhvar5 conjugation yield was 30% (55 μmol of Dhvar5/g). Finally, NorChitDhvar5 ultrathin films showed up to a 35% reduction of total adhered Gram-positive Staphylococcus epidermidis and increased the adhesion and killing of Gram-negative Pseudomonas aeruginosa compared to unmodified chitosan. Moreover, NorChit-Dhvar5 was noncytotoxic to human neonatal dermal fibroblasts, according to ISO 10993-1. Overall, our findings indicate TNPC as a high yield strategy for AMP grafting onto norbornene-functionalized biopolymers towards the fabrication of antibacterial biomaterials. |
Subject: | Peptidopolysaccharides Surface modification Covalent conjugation Thiol-ene Peptide tethering Dhvar5 |
URI: | https://hdl.handle.net/10216/142702 |
Series: | ACS Applied Polymer Materials |
Document Type: | Artigo em Revista Científica Internacional |
Rights: | embargoedAccess |
Embargo End Date: | 2023-06-30 |
Appears in Collections: | I3S - Artigo em Revista Científica Internacional |
Files in This Item:
File | Description | Size | Format | |
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Alves P - ACS Appl Polym Mater 2022 .pdf | 2.36 MB | Adobe PDF | View/Open | |
Alves P - ACS Appl Polym Mater 2022 - supplementary info.pdf | 1.32 MB | Adobe PDF | View/Open |
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