Thiol-Norbornene Photoclick Chemistry for Grafting Antimicrobial Peptides onto Chitosan to Create Antibacterial Biomaterials

• Type: Article in International Scientific Journal
• Date: 2022

Authors

Alves, PM (Author) Other; Pereira, RF (Author) Other; Costa, B (Author) Other; Tassi, N (Author) Other; Teixeira, C (Author) Other; Leiro, V (Author) Other; Monteiro, C (Author) Other; Paula Gomes (Author) FCUP; Costa, F (Author) Other; Martins, MCL (Author) Other

Journal

Title: ACS Applied Polymer Materials

Vol. 4

Pages: 5012-5026

Publisher: American Chemical Society

Indexing

ISI Web of Knowledge - 5 Citations

Scopus - 5 Citations

Other information

Authenticus ID: P-00W-PPS

DOI: 10.1021/acsapm.2c00563

Abstract (EN): 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 toward 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 mu mol of Dhvar5/g) were achieved, while in NorChit-Ct-Dhvar5 conjugation yield was 30% (55 mu mol of Dhvar5/g). Finally, NorChit-Dhvar5 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 toward the fabrication of antibacterial biomaterials.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 15