Novel Materials From the Supramolecular Self-Assembly of Short Helical β3-Peptide Foldamers.

Ketav Kulkarni,Marie-Isabel Aguilar,Nathan Habila,Mark P Del Borgo

doi:10.3389/fchem.2019.00070

Ketav Kulkarni, Marie-Isabel Aguilar + Show 2 more

Open Access

https://doi.org/10.3389/fchem.2019.00070

Copy DOI

Abstract

Self-assembly is the spontaneous organization of small components into higher-order structures facilitated by the collective balance of non-covalent interactions. Peptide-based self-assembly systems exploit the ability of peptides to adopt distinct secondary structures and have been used to produce a range of well-defined nanostructures, such as nanotubes, nanofibres, nanoribbons, nanospheres, nanotapes, and nanorods. While most of these systems involve self-assembly of α-peptides, more recently β-peptides have also been reported to undergo supramolecular self-assembly, and have been used to produce materials—such as hydrogels—that are tailored for applications in tissue engineering, cell culture and drug delivery. This review provides an overview of self-assembled peptide nanostructures obtained via the supramolecular self-assembly of short β-peptide foldamers with a specific focus on N-acetyl-β3-peptides and their applications as bio- and nanomaterials.

Highlights

Peptide-based self-assembly is the spontaneous formation of a stable hierarchical structure via a combination of molecular interactions that include hydrogen bonding, hydrophobic interactions, electrostatic interactions, π-π stacking and van der Waals forces
Given that self-assembly of β3-peptides is unperturbed by the steric bulk of the side chain while the presence of a hydrophobic sequence further inhibits the lateral assembly resulting in uniform fiber morphology, β3-peptide amphiphiles in which a lipid chain moiety is incorporated into a β3peptide template have been synthesized and shown to undergo self-assembly
Following administration of the fluorescent hydrogels to mice via subcutaneous injection, visualization of the gel implants using real-time in vivo animal imaging showed no degradation 14 days post-implantation. These results demonstrate that β3-tripeptide fluorescent hydrogels which can be detected in vivo and functionalized with different bioactive epitopes may provide a template for the design of stable implantable materials for in vivo biomedical applications

Summary

Introduction

Peptide-based self-assembly is the spontaneous formation of a stable hierarchical structure via a combination of molecular interactions that include hydrogen bonding, hydrophobic interactions, electrostatic interactions, π-π stacking and van der Waals forces (without an external trigger). This molecular symmetry forms the core of the supramolecular self-assembly of β3-peptides and N-acetylation of β3-peptides containing at least three β3-amino acids and triggers self-assembly via a head-totail motif (Del Borgo et al, 2013; Christofferson et al, 2018).

Results

Conclusion