New self-assembled supramolecular hydrogels based on dehydropeptides

Supramolecular hydrogels rely on small molecules that self-assemble in water as a result of the cooperative effect of several relatively weak intermolecular interactions. Peptide-based low molecular weight hydrogelators have attracted enormous interest owing to the simplicity of small molecules comb...

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Bibliographic Details
Published in:Journal of materials chemistry. B, Materials for biology and medicine Materials for biology and medicine, 2015-08, Vol.3 (3), p.6355-6367
Main Authors: Vilaça, H, Pereira, G, Castro, T. G, Hermenegildo, B. F, Shi, J, Faria, T. Q, Micaêlo, N, Brito, R. M. M, Xu, B, Castanheira, E. M. S, Martins, J. A, Ferreira, P. M. T
Format: Article
Language:English
Subjects:
Amino acids
Dichroism
Fluorescence
Hydrogels
Molecular dynamics
Naproxen
Peptides
Self assembly
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Summary:Supramolecular hydrogels rely on small molecules that self-assemble in water as a result of the cooperative effect of several relatively weak intermolecular interactions. Peptide-based low molecular weight hydrogelators have attracted enormous interest owing to the simplicity of small molecules combined with the versatility and biocompatibility of peptides. In this work, naproxen, a well known non-steroidal anti-inflammatory drug, was N -conjugated with various dehydrodipeptides to give aromatic peptide amphiphiles that resist proteolysis. Molecular dynamics simulations were used to obtain insight into the underlying molecular mechanism of self-assembly and to rationalize the design of this type of hydrogelators. The results obtained were in excellent agreement with the experimental observations. Only dehydrodipeptides having at least one aromatic amino acid gave hydrogels. The characterization of the hydrogels was carried out using transmission electron microscopy (TEM), circular dichroism (CD), fluorescence spectroscopy and also rheological assays. New hydrogelators based on dehydrodipeptides N -conjugated with naproxen were prepared and characterized. These compounds gave hydrogels that resist proteolysis.
ISSN:2050-750X
2050-7518
DOI:10.1039/c5tb00501a