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Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems
The self-assembly of nanometric structures from molecular building blocks is an effective way to make new functional materials for biological and technological applications. In this work, four symmetrical bolaamphiphiles based on dehydrodipeptides (phenylalanyldehydrophenylalanine and tyrosyldehydro...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162347/ https://www.ncbi.nlm.nih.gov/pubmed/33946932 http://dx.doi.org/10.3390/gels7020052 |
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author | Amorim, Carolina Veloso, Sérgio R. S. Castanheira, Elisabete M. S. Hilliou, Loic Pereira, Renato B. Pereira, David M. Martins, José A. Jervis, Peter J. Ferreira, Paula M. T. |
author_facet | Amorim, Carolina Veloso, Sérgio R. S. Castanheira, Elisabete M. S. Hilliou, Loic Pereira, Renato B. Pereira, David M. Martins, José A. Jervis, Peter J. Ferreira, Paula M. T. |
author_sort | Amorim, Carolina |
collection | PubMed |
description | The self-assembly of nanometric structures from molecular building blocks is an effective way to make new functional materials for biological and technological applications. In this work, four symmetrical bolaamphiphiles based on dehydrodipeptides (phenylalanyldehydrophenylalanine and tyrosyldehydrophenylalanine) linked through phenyl or naphthyl linkers (terephthalic acid and 2,6-naphthalenedicarboxylic acid) were prepared, and their self-assembly properties were studied. The results showed that all compounds, with the exception of the bolaamphiphile of tyrosyldehydrophenylalanine and 2,6-naphthalene dicarboxylic acid, gave self-standing hydrogels with critical gelation concentrations of 0.3 wt % and 0.4 wt %, using a pH trigger. The self-assembly of these hydrogelators was investigated using STEM microscopy, which revealed a network of entangled fibers. According to rheology, the dehydrodipeptide bolaamphiphilic hydrogelators are viscoelastic materials with an elastic modulus G′ that falls in the range of native tissue (0.37 kPa brain–4.5 kPa cartilage). In viability and proliferation studies, it was found that these compounds were non-toxic toward the human keratinocyte cell line, HaCaT. In sustained release assays, we studied the effects of the charge present on model drug compounds on the rate of cargo release from the hydrogel networks. Methylene blue (MB), methyl orange (MO), and ciprofloxacin were chosen as cationic, anionic, and overall neutral cargo, respectively. These studies have shown that the hydrogels provide a sustained release of methyl orange and ciprofloxacin, while methylene blue is retained by the hydrogel network. |
format | Online Article Text |
id | pubmed-8162347 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-81623472021-05-29 Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems Amorim, Carolina Veloso, Sérgio R. S. Castanheira, Elisabete M. S. Hilliou, Loic Pereira, Renato B. Pereira, David M. Martins, José A. Jervis, Peter J. Ferreira, Paula M. T. Gels Article The self-assembly of nanometric structures from molecular building blocks is an effective way to make new functional materials for biological and technological applications. In this work, four symmetrical bolaamphiphiles based on dehydrodipeptides (phenylalanyldehydrophenylalanine and tyrosyldehydrophenylalanine) linked through phenyl or naphthyl linkers (terephthalic acid and 2,6-naphthalenedicarboxylic acid) were prepared, and their self-assembly properties were studied. The results showed that all compounds, with the exception of the bolaamphiphile of tyrosyldehydrophenylalanine and 2,6-naphthalene dicarboxylic acid, gave self-standing hydrogels with critical gelation concentrations of 0.3 wt % and 0.4 wt %, using a pH trigger. The self-assembly of these hydrogelators was investigated using STEM microscopy, which revealed a network of entangled fibers. According to rheology, the dehydrodipeptide bolaamphiphilic hydrogelators are viscoelastic materials with an elastic modulus G′ that falls in the range of native tissue (0.37 kPa brain–4.5 kPa cartilage). In viability and proliferation studies, it was found that these compounds were non-toxic toward the human keratinocyte cell line, HaCaT. In sustained release assays, we studied the effects of the charge present on model drug compounds on the rate of cargo release from the hydrogel networks. Methylene blue (MB), methyl orange (MO), and ciprofloxacin were chosen as cationic, anionic, and overall neutral cargo, respectively. These studies have shown that the hydrogels provide a sustained release of methyl orange and ciprofloxacin, while methylene blue is retained by the hydrogel network. MDPI 2021-04-29 /pmc/articles/PMC8162347/ /pubmed/33946932 http://dx.doi.org/10.3390/gels7020052 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Amorim, Carolina Veloso, Sérgio R. S. Castanheira, Elisabete M. S. Hilliou, Loic Pereira, Renato B. Pereira, David M. Martins, José A. Jervis, Peter J. Ferreira, Paula M. T. Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems |
title | Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems |
title_full | Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems |
title_fullStr | Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems |
title_full_unstemmed | Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems |
title_short | Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems |
title_sort | bolaamphiphilic bis-dehydropeptide hydrogels as potential drug release systems |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162347/ https://www.ncbi.nlm.nih.gov/pubmed/33946932 http://dx.doi.org/10.3390/gels7020052 |
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