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

•Chitosan’s amines were converted into azides via the diazo-transfer reagent ISA.HCl.•An alkyne-modified derivative of the potent antimicrobial peptide Dhvar-5 was produced.•Peptide was tethered onto chitosan via copper-catalyzed alkyne-azide coupling (CuAAC).•THPTA and aminoguanidine hydrochloride...

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Bibliographic Details
Published in:Carbohydrate polymers 2017-06, Vol.165, p.384-393
Main Authors: Barbosa, Mariana, Vale, Nuno, Costa, Fabíola M.T.A., Martins, M. Cristina L., Gomes, Paula
Format: Article
Language:English
Subjects:
Antibiotics
Antimicrobial peptides
Azide-alkyne coupling
Biofilms
Chitosan
Click chemistry
CuAAC
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Summary:•Chitosan’s amines were converted into azides via the diazo-transfer reagent ISA.HCl.•An alkyne-modified derivative of the potent antimicrobial peptide Dhvar-5 was produced.•Peptide was tethered onto chitosan via copper-catalyzed alkyne-azide coupling (CuAAC).•THPTA and aminoguanidine hydrochloride additives were critical for the success of the CuAAC.•FTIR and XPS confirmed success of all reaction steps, and a peptide load of 2mg per gram of chitosan was achieved. 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.
ISSN:0144-8617
1879-1344
DOI:10.1016/j.carbpol.2017.02.050