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Article

Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems

1
Center of Chemistry, University of Minho, 4710-057 Braga, Portugal
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Center of Physics, University of Minho, 4710-057 Braga, Portugal
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Institute for Polymers and Composites, University of Minho, 4800-058 Guimarães, Portugal
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REQUIMTE/LAQV, Laboratório de Farmacognosia, Departamento de Química, Faculdade de Farmácia, Universidade do Porto, R. Jorge Viterbo Ferreira, n 228, 4050-313 Porto, Portugal
*
Authors to whom correspondence should be addressed.
Academic Editor: Maria Valentina Dinu
Received: 24 March 2021 / Revised: 20 April 2021 / Accepted: 24 April 2021 / Published: 29 April 2021
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. View Full-Text
Keywords: bolaamphiphiles; dehydropeptide; self-assembly; supramolecular hydrogels; drug delivery bolaamphiphiles; dehydropeptide; self-assembly; supramolecular hydrogels; drug delivery
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MDPI and ACS Style

Amorim, C.; Veloso, S.R.S.; Castanheira, E.M.S.; Hilliou, L.; Pereira, R.B.; Pereira, D.M.; Martins, J.A.; Jervis, P.J.; Ferreira, P.M.T. Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems. Gels 2021, 7, 52. https://doi.org/10.3390/gels7020052

AMA Style

Amorim C, Veloso SRS, Castanheira EMS, Hilliou L, Pereira RB, Pereira DM, Martins JA, Jervis PJ, Ferreira PMT. Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems. Gels. 2021; 7(2):52. https://doi.org/10.3390/gels7020052

Chicago/Turabian Style

Amorim, Carolina, Sérgio R.S. Veloso, Elisabete M.S. Castanheira, Loic Hilliou, Renato B. Pereira, David M. Pereira, José A. Martins, Peter J. Jervis, and Paula M.T. Ferreira. 2021. "Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems" Gels 7, no. 2: 52. https://doi.org/10.3390/gels7020052

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