Supramolecular Amphiphiles Based on Pillar[5]arene and Meroterpenoids: Synthesis, Self-Association and Interaction with Floxuridine

In recent years, meroterpenoids have found wide biomedical application due to their synthetic availability, low toxicity, and biocompatibility. However, these compounds are not used in targeted drug delivery systems due to their high affinity for cell membranes, both healthy and in cancer cells. Using the approach of creating supramolecular amphiphiles, we have developed self-assembling systems based on water-soluble pillar[5]arene and synthetic meroterpenoids containing geraniol, myrtenol, farnesol, and phytol fragments. The resulting systems can be used as universal drug delivery systems. It was shown by turbidimetry that the obtained pillar[5]arene/synthetic meroterpenoid systems do not interact with the model cell membrane at pH = 7.4, but the associates are destroyed at pH = 4.1. In this case, the synthetic meroterpenoid is incorporated into the lipid bilayer of the model membrane. The characteristics of supramolecular self-assembly, association constants and stoichiometry of the most stable pillar[5]arene/synthetic meroterpenoid complexes were established by UV-vis spectroscopy and dynamic light scattering (DLS). It was shown that supramolecular amphiphiles based on pillar[5]arene/synthetic meroterpenoid systems form monodisperse associates in a wide range of concentrations. The inclusion of the antitumor drug 5-fluoro-2′-deoxyuridine (floxuridine) into the structure of the supramolecular associate was demonstrated by DLS, 19F, 2D DOSY NMR spectroscopy.

Di-anionic self-associating supramolecular amphiphiles (SSAs) as antimicrobial agents against MRSA and Escherichia coli

Amphiphilic agents demonstrate selective antimicrobial activity against MRSA and are shown to form interesting macrocyclic structures in the solid state.

Glutathione Sensitive Vesicles prepared from Supramolecular Amphiphiles.

Gluthatione (GSH) senstive vesicles were prepared by the self-asseembly of ampihphilic incllusions complexes. These novel chemically sensitive supramolecular amphiphiles are anticipated to have applications in drug delivery; the nanocarriers can...

Classical and non-classical melatonin receptor agonist-directed micellization of bipyridinium-based supramolecular amphiphiles in water

A series of melatonin receptor agonists prove capable of templating soft matter assemblies with concomitant enhancement of the material's surface active properties in water.

Unraveling dominant surface physicochemistry to build antimicrobial peptide coatings with supramolecular amphiphiles

Surface polarity via hydrogen bonding dominates interactions with supramolecular nanofibrillar amphiphiles formed by GL13K antimicrobial peptides.

Tuning the aggregation of an amphiphilic anionic calix[5]arene by selective host–guest interactions with bola-type dications

Bola-type dications of different length drive the formation of head-to-tail or capsular supramolecular amphiphiles and, in turn, that of the final aggregates.