Fabrication and Characterization of π–π Stacking Peptide-Contained Double Network Hydrogels

Abstract

Since the physical properties are similar to native extracellular matrices, double network (DN) hydrogels have been studied extensively in the tissue engineering. However, the double chemical crosslinked DN hydrogel is limited by poor fatigue resistance. π–π stacking is a non-covalent bonding interaction, which is essential to maintain and self-assemble the three-dimensional structure of biological proteins and nucleic acids. In this study, a robust polyethylene glycol diacrylate (PEGDA)/FFK hybrid DN hydrogel was prepared by Michael addition and π–π stacking. The hybrid DN hydrogels with π–π stacking interactions have excellent mechanical strength and fatigue resistance. The DN FFK/PEGDA hydrogels reveal great biocompatibility and hemocompatibility. The DN hydrogels containing π–π stacking have the potential to fabricate robust hybrid DN hydrogels in drug release and tissue engineering.

Applications of self-assembled peptide hydrogels in anti-tumor therapy

“…Molecules containing aromatic ring structures tend to pile up on each other through π–π-stacking, forming organized fibers or nanostructures that facilitate the formation of self-assembled hydrogels. 22 …”

Therapeutic Peptides, Proteins and their Nanostructures for Drug Delivery and Precision Medicine

“…For instance, diphenylalanine (FF) is a well‐known peptide sequence for its ability to self‐assemble into nanotubes [66] . In one example, a double network hydrogel suitable for drug delivery applications was synthesized by chemically cross‐linking a Phe‐Phe‐Lys peptide to polyethylene glycol diacrylate polymers via Michael addition [67] . Because of the π‐π stacking interactions of FF, a second layer of cross‐linked network resulted in a hybrid double network hydrogel.…”

“…[66] In one example, a double network hydrogel suitable for drug delivery applications was synthesized by chemically cross-linking a Phe-Phe-Lys peptide to polyethylene glycol diacrylate polymers via Michael addition. [67] Because of the π-π stacking interactions of FF, a second layer of crosslinked network resulted in a hybrid double network hydrogel. Preliminary data suggested that the hydrogel maintained favorable characteristics (mechanical properties, slow degradation) even in blood and in vitro cell culture, supporting the potential use in drug delivery and other applications such as tissue engineering.…”

Dichotomy of π-stacking-directing noncovalent forces in organic–inorganic planar assemblies: the case of halo-substituted benzoquinones π-stacked with a platinum(ii) square-plane

“…π-Stacking (or simply stacking) interactions, i.e. noncovalent attractive interactions between two planar moieties, play an important role in supramolecular organic, 1–4 organometallic 5–8 and bioorganic 9–11 chemistry, molecular recognition, 12,13 and materials science. 14–18 In the vast majority of relevant studies, aromatic compounds are applied as stacking coformers, while hybrid stacking, which occurred between organic and organometallic or organic and inorganic planes, has received very little attention.…”