Effect of Peptide Sequences on Supramolecular Interactions of Naphthaleneimide/Tripeptide Conjugates

Abstract

In this study, we reported a significant difference in the supramolecular hydrogelation of newly discovered NI-GFF (NI-Gly-l-Phe-l-Phe) and NI-FFG (NI-l-Phe-l-Phe-Gly) on the basis of their phase diagrams. With a small difference in the peptide chain between NI-GFF and NI-FFG, we observed a significant difference in their self-assembly properties; NI-GFF formed a stable gel at neutral pH, whereas NI-FFG did not, under the same conditions. From spectroscopic and computational studies, intermolecular π-π interactions and extended hydrogen bonding interactions might reinforce the intermolecular interactions of NI-GFF, which may facilitate the formation of the self-assembled nanostructures and the hydrogel. In addition, the aggregation-induced emission (AIE)-active NI-GFF reveals relatively good biocompatibility compared with that of NI-FFG for two commonly used cell lines, suggesting that it is a promising candidate for use as a supramolecular material in biomedical applications. Our results highlight the importance of tripeptide sequences in a self-assembling hydrogel system.

Ultrashort Peptide Self-Assembly: Front-Runners to Transport Drug and Gene Cargos

“…Further exploration on naphthaleneimide (NI) conjugates; NI-Gly-Phe-Phe-OH and NI-Phe-Phe-Gly-OH supramolecular hydrogels, articulated the good biocompatibility of NI-Gly-Phe-Phe-OH with cell lines. The observations could suggest that these supramolecular materials are promising candidates for their use in biomedical applications (Yeh et al, 2016).…”

Enzyme Instructed Self‐assembly of Naphthalimide‐dipeptide: Spontaneous Transformation from Nanosphere to Nanotubular Structures that Induces Hydrogelation

“…[26] Recently we reported a NI-based supramolecular hydrogelator, which exhibits AIE phenomenon. [27][28][29] Particularly, we have shown the self-assembly of NIÀ F that results in the formation of AIE-active microfibers which facilitate the high contrast visualization of 3D live cell imaging. [27] In this work, our focus is to study the selfassembly of phosphate-based NI derivatives.…”

“…To gain more insights into the intermolecular interactions that are responsible for the self-assembly and hydrogelation process, we carried out UV-Vis absorption, and fluorescence emission measurements. [28] Compound NI-FY exhibited a strong absorption band at around 340 nm which can be attributed to the electronic transition of NI chromophore ( Figure S11). Emission spectra of the NI-FY dipeptide in aqueous buffer is shown in Figure 8.…”

Guiding principles for peptide nanotechnology through directed discovery

“…35,73, These systems can then be modified, for example through the systematic substitution of an amino acid in the peptide sequence, analogous to the experimental approaches discussed in the previous section, to determine how these modifications affect the structure and properties of the resulting nanostructure. 73,103 The alternative approach to systematic variation of a given sequence is the screening of potential combinations of building blocks to determine whether the resulting systems have the desired properties. 31,43,45 While this process can, in principle, result in an outright prediction of the "best" system, the nature of these predictions typically results in a small selection of systems that are predicted to be of interest for further experimental testing.…”