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Carbohydrate PolymersVolume 165, 1 June 2017, Pages 384-393

Tethering antimicrobial peptides onto chitosan: Optimization of azide-alkyne “click” reaction conditions(Article)

  • aUCIBIO-REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre 687, Porto, 4169-007, Portugal
  • bi3S, Instituto de Investigação e Inovação em Saúde, Universidade do Porto, Rua Alfredo Allen, 208, Porto, 4200-135, Portugal
  • cINEB – Instituto de Engenharia Biomédica, Universidade do Porto, Rua Alfredo Allen, 208, Porto, 4200-135, Portugal
  • dFaculdade de Engenharia, Universidade do Porto, Rua Dr. Roberto Frias, s/n, Porto, 4200-465, Portugal
  • eInstituto de Ciências Biomédicas Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, Porto, 4050-313, Portugal

Abstract

Antimicrobial peptides (AMP) are promising alternatives to classical antibiotics, due to their high specificity and potency at low concentrations, and low propensity to elicit pathogen resistance. Immobilization of AMP onto biomaterials is an emergent field of research, towards creation of novel antimicrobial materials able to avoid formation of biofilms on the surfaces of medical devices. Herein, we report the chemical route towards one such material, where chitosan was used as biocompatible carrier for the covalent grafting of Dhvar-5, a well-known potent AMP, via the chemoselective (“click”) Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The material's structure, as well as peptide loading, were confirmed by Fourier-transformed infra-red (FT-IR) and X-ray photoelectron (XPS) spectroscopies, and by Amino Acid Analysis (AAA), respectively. Results herein reported demonstrate that, with proper optimization, the “click” CuAAC is an attractive approach for the tethering of AMP onto chitosan, in order to create novel antimicrobial materials potentially valuable for biomedical applications. © 2017 Elsevier Ltd

Author keywords

AntibioticsAntimicrobial peptidesAzide-alkyne couplingBiofilmsChitosanClick chemistryCuAAC

Indexed keywords

Engineering controlled terms:AntibioticsBiocompatibilityBiofilmsBiological materialsBiomaterialsBiomedical equipmentChitinChitosanGrafting (chemical)HydrocarbonsIodineMedical applicationsPeptides
Engineering uncontrolled termsAlkyne couplingAntimicrobial materialsAntimicrobial peptideAzide-alkyne cycloadditionBiomedical applicationsClick chemistryCuAACX-ray photoelectrons
Engineering main heading:Microorganisms
EMTREE drug terms:alkyneantiinfective agentazidechitosanpeptide
EMTREE medical terms:chemistryclick chemistryinfrared spectroscopyphotoelectron spectroscopy
MeSH:AlkynesAnti-Infective AgentsAzidesChitosanClick ChemistryPeptidesPhotoelectron SpectroscopySpectroscopy, Fourier Transform Infrared

Chemicals and CAS Registry Numbers:

azide, 12596-60-0, 14343-69-2; chitosan, 9012-76-4;

Alkynes; Anti-Infective Agents; Azides; Chitosan; Peptides

  • ISSN: 01448617
  • CODEN: CAPOD
  • Source Type: Journal
  • Original language: English
  • DOI: 10.1016/j.carbpol.2017.02.050
  • PubMed ID: 28363563
  • Document Type: Article
  • Publisher: Elsevier Ltd

  Gomes, P.; UCIBIO-REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre 687, Porto, Portugal;
© Copyright 2017 Elsevier B.V., All rights reserved.

Cited by 11 documents

Petrin, T.H.C. , Fadel, V. , Martins, D.B.
Synthesis and Characterization of Peptide-Chitosan Conjugates (PepChis) with Lipid Bilayer Affinity and Antibacterial Activity
(2019) Biomacromolecules
Chen, Y. , Yu, L. , Zhang, B.
Design and Synthesis of Biocompatible, Hemocompatible, and Highly Selective Antimicrobial Cationic Peptidopolysaccharides via Click Chemistry
(2019) Biomacromolecules
Muñoz-Bonilla, A. , Echeverria, C. , Sonseca, Á.
Bio-based polymers with antimicrobial properties towards sustainable development
(2019) Materials
View details of all 11 citations
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