Self-Assembly Mechanism of a Peptide-Based Drug Delivery Vehicle

Abstract

We report the mechanism of the concentration-dependent self-assembly of a tetrapeptide. Peptide Boc-Trp-Leu-Trp-Leu-OMe self-assembles to form discrete nanospheres at a low concentration. Tryptophan side chains point outwards of the nanospheres while leucine side chains point towards the core of the nanospheres. The nanospheres fuse together to become microspheres with the increase in the peptide concentration. At higher concentrations of the peptide, the microspheres start clustering. This is stabilized by the aromatic interactions between the side chains of the tryptophan residues that cover the outer surface of the peptide microspheres. In addition to behaving like the conventional hollow sphere-based drug delivery vehicles which entraps the drug and performs stimuli-responsive release, this prototype can interact, stabilize, and intercalate hydrophobic dye carboxyfluorescein and anti-cancer drug curcumin even on the surface through aromatic interactions. The dye/drug can be released in acidic pH and in the presence of physiologically relevant ions such as potassium.

Self-assembled hydrophobic Ala-Aib peptide encapsulating curcumin: a convenient system for water insoluble drugs

“…5b, dashed line). 37,42 On the other hand, the dimension of the aggregates containing curcumin, measured by DLS, showed relevant differences with respect to the control peptide (average dimensions of aggregates 308 AE 78 nm, Fig. SI4 †).…”

“…[32][33][34][35][36][37][38][39] Nevertheless few works regarding the use of peptides as curcumin delivery vehicles have been reported until now. [40][41][42][43][44] In this work we show that the short peptide 7 aggregate represents a very useful tool that successfully encapsulates the curcumin. To demonstrate our results, uorescence emission and confocal microscopy studies are reported.…”

The Investigation of a Multi‐Functional Peptide as Gelator, Dyes Separation Agent and Metal Ions Adsorbent

“…The scaffold of gel can be formed by various of gelators, among which, peptides are a kind of rising materials for the fabrication of gels because of their biocompatibility and their molecule structures can be rationally designed . Large numbers of peptide gels have been reported for the functions of tissue engineering, nanoreactors, drug delivery vehicle, antibacterial agent and regenerative medicine . Phenylalanine‐phenylalanine (FF) dipeptide is usually used as the core recognition of the β‐amyloid fiber and may be the simplest peptide with kinds of self‐assembled structures driven by the π‐π stacking interaction between the benzene rings .…”

“…[4][5][6] Large numbers of peptide gels have been reported for the functions of tissue engineering, nanoreactors, drug delivery vehicle, antibacterial agent and regenerative medicine. [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] Phenylalanine-phenylalanine (FF) dipeptide is usually used as the core recognition of the β-amyloid fiber and may be the simplest peptide with kinds of self-assembled structures driven by the π-π stacking interaction between the benzene rings. [22,23] However, most of the peptides consisting of FF can hardly dissolve in water.…”

Self-assembled pearl-necklace patterned upconverting nanocrystals with highly efficient blue and ultraviolet emission: femtosecond laser based upconversion properties

“…and they have myriad applications in biomedicals for developing articial membranes and for various biofunctions. [18][19][20] Self-assembly of various inorganic (metals/hybrids) nanoparticles is well known. [21][22][23] The formation of self-assembled necklace type nanostructures is very much interesting in the area of modern nanotechnology.…”