Abstract
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 C3-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.
Highlights
Hydrogels, consisting of a large amount of water and an entangled fibrous network, are attractive materials which have been reported to have potential applications in many areas such as tissue engineering[1,2,3,4], catalysis[5,6], wound healing[7], and cell culture[8]
In this work anthranilamide-based short peptides were synthesised and their ability to form antibacterial hydrogel through self-assembly, were investigated. These anthranilamide-based short peptides can be generated in solution, which is beneficial in terms of scalability and access to chemical diversity
The library of anthranilamide-based short peptides was designed based on three main modifications, which include modifying the acyl group R1, introducing substituents at the 5 position of the capping group, and incorporation of anthranilamide-based short peptides into the bola amphiphile (BA) scaffold Fig. 2
Summary
Hydrogels, consisting of a large amount of water and an entangled fibrous network, are attractive materials which have been reported to have potential applications in many areas such as tissue engineering[1,2,3,4], catalysis[5,6], wound healing[7], and cell culture[8] Such hydrogels can be created through the self-assembly of small molecules, referred to as low molecular weight gelators (LMWG), forming a viscoelastic three-dimensional network that immobilizes water and results in hydrogel formation. In this work anthranilamide-based short peptides were synthesised and their ability to form antibacterial hydrogel through self-assembly, were investigated. Anthranilamide-based short peptides were incorporated in other self-assembled systems such as bola amphiphile (BA) and C3-symmetric molecules
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