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Conjugation of Ctx(Ile(21))-Ha Antimicrobial Peptides to Chitosan Ultrathin Films by N-Acetylcysteine Improves Peptide Physicochemical Properties and Enhances Biological Activity

[Image: see text] The importance of obtaining new compounds with improved antimicrobial activity is a current trend and challenge. Some polymers such as chitosan have shown promising bactericidal properties when they are structurally modified, which is due to the binding versatility provided by thei...

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Autores principales: Roque-Borda, Cesar Augusto, Antunes, Bruna Fernandes, Toledo Borgues, Anna Beatriz, Costa de Pontes, Janaína Teixeira, Meneguin, Andréia Bagliotti, Chorilli, Marlus, Trovatti, Eliane, Teixeira, Silvio Rainho, Pavan, Fernando Rogério, Vicente, Eduardo Festozo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9386805/
https://www.ncbi.nlm.nih.gov/pubmed/35990469
http://dx.doi.org/10.1021/acsomega.2c02570
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author Roque-Borda, Cesar Augusto
Antunes, Bruna Fernandes
Toledo Borgues, Anna Beatriz
Costa de Pontes, Janaína Teixeira
Meneguin, Andréia Bagliotti
Chorilli, Marlus
Trovatti, Eliane
Teixeira, Silvio Rainho
Pavan, Fernando Rogério
Vicente, Eduardo Festozo
author_facet Roque-Borda, Cesar Augusto
Antunes, Bruna Fernandes
Toledo Borgues, Anna Beatriz
Costa de Pontes, Janaína Teixeira
Meneguin, Andréia Bagliotti
Chorilli, Marlus
Trovatti, Eliane
Teixeira, Silvio Rainho
Pavan, Fernando Rogério
Vicente, Eduardo Festozo
author_sort Roque-Borda, Cesar Augusto
collection PubMed
description [Image: see text] The importance of obtaining new compounds with improved antimicrobial activity is a current trend and challenge. Some polymers such as chitosan have shown promising bactericidal properties when they are structurally modified, which is due to the binding versatility provided by their free amines. Likewise, antimicrobial peptides (AMPs) have received attention in recent years because of their bactericidal activity that is similar to or even better than that of conventional drugs, and they exhibit a low induction rate of antimicrobial resistance. Herein, the modified AMP Ctx(Ile(21))-Ha-Ahx-Cys was conjugated to chitosan using N-acetylcysteine as an intermediate by the carbodiimide method. Films were prepared using protonated chitosan in 1% acetic acid and Ctx(Ile(21))-Ha-Ahx-Cys AMP dissolved in N-acetylcysteine-chitosan; 1.6 mmol of ethylcarbodiimide hydrochloride, 1.2 mmol of N-hydroxysulfosucchimide, and 0.1 mol L (–1)of N-morpholino)ethanesulfonic acid buffer at pH 6.5 by continuous stirring at 100 × g for 10 min at 37 °C. Physicochemical properties were evaluated by Fourier-transform infrared spectroscopy, differential scanning calorimetry/thermogravimetric analysis, and X-ray diffraction to determine the mechanical properties, solubility, morphology, and thickness. Furthermore, the antimicrobial activities of chitosan-based conjugated films were evaluated againstStaphylococcus aureus,Pseudomonas aeruginosa,SalmonellaTyphimurium, andEscherichia coli. The results showed that the conjugation of a potent AMP could further increase its antibacterial activity and maintain its stable physicochemical properties. Therefore, the developed peptide–chitosan conjugate could be applied as an additive in surgical procedures to prevent and combat bacterial infection.
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spelling pubmed-93868052022-08-19 Conjugation of Ctx(Ile(21))-Ha Antimicrobial Peptides to Chitosan Ultrathin Films by N-Acetylcysteine Improves Peptide Physicochemical Properties and Enhances Biological Activity Roque-Borda, Cesar Augusto Antunes, Bruna Fernandes Toledo Borgues, Anna Beatriz Costa de Pontes, Janaína Teixeira Meneguin, Andréia Bagliotti Chorilli, Marlus Trovatti, Eliane Teixeira, Silvio Rainho Pavan, Fernando Rogério Vicente, Eduardo Festozo ACS Omega [Image: see text] The importance of obtaining new compounds with improved antimicrobial activity is a current trend and challenge. Some polymers such as chitosan have shown promising bactericidal properties when they are structurally modified, which is due to the binding versatility provided by their free amines. Likewise, antimicrobial peptides (AMPs) have received attention in recent years because of their bactericidal activity that is similar to or even better than that of conventional drugs, and they exhibit a low induction rate of antimicrobial resistance. Herein, the modified AMP Ctx(Ile(21))-Ha-Ahx-Cys was conjugated to chitosan using N-acetylcysteine as an intermediate by the carbodiimide method. Films were prepared using protonated chitosan in 1% acetic acid and Ctx(Ile(21))-Ha-Ahx-Cys AMP dissolved in N-acetylcysteine-chitosan; 1.6 mmol of ethylcarbodiimide hydrochloride, 1.2 mmol of N-hydroxysulfosucchimide, and 0.1 mol L (–1)of N-morpholino)ethanesulfonic acid buffer at pH 6.5 by continuous stirring at 100 × g for 10 min at 37 °C. Physicochemical properties were evaluated by Fourier-transform infrared spectroscopy, differential scanning calorimetry/thermogravimetric analysis, and X-ray diffraction to determine the mechanical properties, solubility, morphology, and thickness. Furthermore, the antimicrobial activities of chitosan-based conjugated films were evaluated againstStaphylococcus aureus,Pseudomonas aeruginosa,SalmonellaTyphimurium, andEscherichia coli. The results showed that the conjugation of a potent AMP could further increase its antibacterial activity and maintain its stable physicochemical properties. Therefore, the developed peptide–chitosan conjugate could be applied as an additive in surgical procedures to prevent and combat bacterial infection. American Chemical Society 2022-08-05 /pmc/articles/PMC9386805/ /pubmed/35990469 http://dx.doi.org/10.1021/acsomega.2c02570 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Roque-Borda, Cesar Augusto
Antunes, Bruna Fernandes
Toledo Borgues, Anna Beatriz
Costa de Pontes, Janaína Teixeira
Meneguin, Andréia Bagliotti
Chorilli, Marlus
Trovatti, Eliane
Teixeira, Silvio Rainho
Pavan, Fernando Rogério
Vicente, Eduardo Festozo
Conjugation of Ctx(Ile(21))-Ha Antimicrobial Peptides to Chitosan Ultrathin Films by N-Acetylcysteine Improves Peptide Physicochemical Properties and Enhances Biological Activity
title Conjugation of Ctx(Ile(21))-Ha Antimicrobial Peptides to Chitosan Ultrathin Films by N-Acetylcysteine Improves Peptide Physicochemical Properties and Enhances Biological Activity
title_full Conjugation of Ctx(Ile(21))-Ha Antimicrobial Peptides to Chitosan Ultrathin Films by N-Acetylcysteine Improves Peptide Physicochemical Properties and Enhances Biological Activity
title_fullStr Conjugation of Ctx(Ile(21))-Ha Antimicrobial Peptides to Chitosan Ultrathin Films by N-Acetylcysteine Improves Peptide Physicochemical Properties and Enhances Biological Activity
title_full_unstemmed Conjugation of Ctx(Ile(21))-Ha Antimicrobial Peptides to Chitosan Ultrathin Films by N-Acetylcysteine Improves Peptide Physicochemical Properties and Enhances Biological Activity
title_short Conjugation of Ctx(Ile(21))-Ha Antimicrobial Peptides to Chitosan Ultrathin Films by N-Acetylcysteine Improves Peptide Physicochemical Properties and Enhances Biological Activity
title_sort conjugation of ctx(ile(21))-ha antimicrobial peptides to chitosan ultrathin films by n-acetylcysteine improves peptide physicochemical properties and enhances biological activity
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9386805/
https://www.ncbi.nlm.nih.gov/pubmed/35990469
http://dx.doi.org/10.1021/acsomega.2c02570
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