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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...

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Autores principales: 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.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
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.
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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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