Fatty Acids/Tetraphenylethylene Conjugates: Hybrid AIEgens for the Preparation of Peptide-Based Supramolecular Gels

Abstract

Aggregation-induced emissive materials are gaining particular attention in the last decades due to their wide application in different fields, from optical devices to biomedicine. In this work, compounds having these kinds of properties, composed of tetraphenylethylene scaffold combined with fatty acids of different lengths, were synthesized and characterized. These molecules were found able to self-assemble into different supramolecular emissive structures depending on the chemical composition and water content. Furthermore, they were used as N-terminus capping agents in the development of peptide-based materials. The functionalization of a 5-mer laminin-derived peptide led to the obtainment of luminescent fibrillary materials that were not cytotoxic and were able to form supramolecular gels in aqueous environment.

Aggregation-Induced Enhanced Emission of Tetraphenylethene-phenylalanine Hybrids: Synthesis and Characterization

“…τ is the measured multiexponential lifetime of the samples; lifetimes were fitted with multiexponential decay curves, and in brackets is indicated the contribution percentage to the decay; the average lifetime was calculated according to τ av = falsefalse ∑ bold-italicn = bold1 m α n τ n 2 falsefalse ∑ bold-italicn = bold1 m α n τ n , where m is the n th component of the fitted decay and α is the pre-exponential value of the n th component. K r = QY/τ av …”

“…The high signal-to-noise ratio of the probe demonstrated the absence of known lacking limitations of conventional fluorogenic probes and could be used for in vitro diagnostic applications in neurodegenerative diseases. Recently, in our research group, fatty acid/TPE chimera molecules have been developed and used for the preparation of AIE peptide-based supramolecular gels and for the selective delivery of anticancer drugs . Moreover, an alternative to peptide/protein labeling is the development of unnatural fluorescent amino acids (FlAAs), characterized by the presence of luminescent scaffolds on their side chains.…”

Stereochemical Behavior of Pyrrolo-Pyrazole Peptidomimetics Promoting Phase-Selective Supramolecular Organogels

“…A particularly intriguing topic is the development of supramolecular gels, in which semi-solid materials are formed by entrapping large amounts of solvents in ordered 3D networks formed by the assembly of small molecules and peptides [5,6].…”

Tetraphenylethylene-Based Photoluminescent Self-Assembled Nanoparticles: Preparation and Biological Evaluation

“…Due to this interesting behavior, AIEgens have been increasingly applied in the design of materials involving such aggregation states, e.g., nanoparticles . Examples of AIE nanoparticles are present in literature, mainly as diagnostic tools , but also for drug delivery because of their multiple functions including bioluminescence, drug release monitoring, and low biological toxicity. ,, Recently, we showed that the conjugation of fatty acids with the 4-amino TPE leads to the formation of supramolecular aggregates that are able to self-assemble into different supramolecular emissive structures depending on the chemical composition and water content . Here, we exploited the same approach in order to obtain emissive self-assembling drug conjugates.…”

“… 17 , 20 , 21 Recently, we showed that the conjugation of fatty acids with the 4-amino TPE leads to the formation of supramolecular aggregates that are able to self-assemble into different supramolecular emissive structures depending on the chemical composition and water content. 22 Here, we exploited the same approach in order to obtain emissive self-assembling drug conjugates. This would make possible an easy preparation of fluorescent NPs, an important tool to follow the dynamics of drug internalization.…”