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Anthranilamide-based Short Peptides Self-Assembled Hydrogels as Antibacterial Agents

In this study, we describe the synthesis and molecular properties of anthranilamide-based short peptides which were synthesised via ring opening of isatoic anhydride in excellent yields. These short peptides were incorporated as low molecular weight gelators (LMWG), bola amphiphile, and C(3)-symmetr...

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Autores principales: Aldilla, Vina R., Chen, Renxun, Martin, Adam D., Marjo, Christopher E., Rich, Anne M., Black, David StC., Thordarson, Pall, Kumar, Naresh
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6972728/
https://www.ncbi.nlm.nih.gov/pubmed/31964927
http://dx.doi.org/10.1038/s41598-019-57342-6
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author Aldilla, Vina R.
Chen, Renxun
Martin, Adam D.
Marjo, Christopher E.
Rich, Anne M.
Black, David StC.
Thordarson, Pall
Kumar, Naresh
author_facet Aldilla, Vina R.
Chen, Renxun
Martin, Adam D.
Marjo, Christopher E.
Rich, Anne M.
Black, David StC.
Thordarson, Pall
Kumar, Naresh
author_sort Aldilla, Vina R.
collection PubMed
description In this study, we describe the synthesis and molecular properties of anthranilamide-based short peptides which were synthesised via ring opening of isatoic anhydride in excellent yields. These short peptides were incorporated as low molecular weight gelators (LMWG), bola amphiphile, and C(3)-symmetric molecules to form hydrogels in low concentrations (0.07–0.30% (w/v)). The critical gel concentration (CGC), viscoelastic properties, secondary structure, and fibre morphology of these short peptides were influenced by the aromaticity of the capping group or by the presence of electronegative substituent (namely fluoro) and hydrophobic substituent (such as methyl) in the short peptides. In addition, the hydrogels showed antibacterial activity against S. aureus 38 and moderate toxicity against HEK cells in vitro.
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spelling pubmed-69727282020-01-27 Anthranilamide-based Short Peptides Self-Assembled Hydrogels as Antibacterial Agents Aldilla, Vina R. Chen, Renxun Martin, Adam D. Marjo, Christopher E. Rich, Anne M. Black, David StC. Thordarson, Pall Kumar, Naresh Sci Rep Article In this study, we describe the synthesis and molecular properties of anthranilamide-based short peptides which were synthesised via ring opening of isatoic anhydride in excellent yields. These short peptides were incorporated as low molecular weight gelators (LMWG), bola amphiphile, and C(3)-symmetric molecules to form hydrogels in low concentrations (0.07–0.30% (w/v)). The critical gel concentration (CGC), viscoelastic properties, secondary structure, and fibre morphology of these short peptides were influenced by the aromaticity of the capping group or by the presence of electronegative substituent (namely fluoro) and hydrophobic substituent (such as methyl) in the short peptides. In addition, the hydrogels showed antibacterial activity against S. aureus 38 and moderate toxicity against HEK cells in vitro. Nature Publishing Group UK 2020-01-21 /pmc/articles/PMC6972728/ /pubmed/31964927 http://dx.doi.org/10.1038/s41598-019-57342-6 Text en © The Author(s) 2020 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Aldilla, Vina R.
Chen, Renxun
Martin, Adam D.
Marjo, Christopher E.
Rich, Anne M.
Black, David StC.
Thordarson, Pall
Kumar, Naresh
Anthranilamide-based Short Peptides Self-Assembled Hydrogels as Antibacterial Agents
title Anthranilamide-based Short Peptides Self-Assembled Hydrogels as Antibacterial Agents
title_full Anthranilamide-based Short Peptides Self-Assembled Hydrogels as Antibacterial Agents
title_fullStr Anthranilamide-based Short Peptides Self-Assembled Hydrogels as Antibacterial Agents
title_full_unstemmed Anthranilamide-based Short Peptides Self-Assembled Hydrogels as Antibacterial Agents
title_short Anthranilamide-based Short Peptides Self-Assembled Hydrogels as Antibacterial Agents
title_sort anthranilamide-based short peptides self-assembled hydrogels as antibacterial agents
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6972728/
https://www.ncbi.nlm.nih.gov/pubmed/31964927
http://dx.doi.org/10.1038/s41598-019-57342-6
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