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Issue 10, 2014
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Chirality effects at each amino acid position on tripeptide self-assembly into hydrogel biomaterials

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Abstract

Hydrogels formed by ultrashort peptides are emerging as cost-effective materials for cell culture. However, L-peptides are labile to proteases, while their D-isomers are thought to not support cell growth as well. In contrast, the self-assembly behaviour and biological performance of heterochiral peptides (i.e., made of both D and L amino acids) are largely unknown. In this study, we evaluate the effects of amino acid chirality on tripeptide self-assembly and hydrogelation at physiological pH, and cytocompatibility in fibroblast cell culture. A series of uncapped hydrophobic tripeptides with all combinations of D, L amino acids was prepared, tested for self-assembly under physiological conditions, and analysed by circular dichroism, FT-IR, cryo-TEM, AFM, and Thioflavin T fluorescence imaging. Amino acid chirality has a profound effect on the peptides' supramolecular behaviour. Only selected isomers form hydrogels, and of amyloid structure, as confirmed by rheology and XRD. Importantly, they are able to maintain the viability and proliferation of fibroblasts in vitro. This study identifies two heterochiral gels that perform well in cell culture and will assist in the design of innovative and cost-effective peptide gel biomaterials.

Graphical abstract: Chirality effects at each amino acid position on tripeptide self-assembly into hydrogel biomaterials

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Publication details

The article was received on 20 Dec 2013, accepted on 05 Mar 2014 and first published on 07 Mar 2014


Article type: Paper
DOI: 10.1039/C3NR06752A
Citation: Nanoscale, 2014,6, 5172-5180
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    Chirality effects at each amino acid position on tripeptide self-assembly into hydrogel biomaterials

    S. Marchesan, C. D. Easton, K. E. Styan, L. J. Waddington, F. Kushkaki, L. Goodall, K. M. McLean, J. S. Forsythe and P. G. Hartley, Nanoscale, 2014, 6, 5172
    DOI: 10.1039/C3NR06752A

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