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

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. Usi...

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Published in:International journal of molecular sciences Vol. 22; no. 15; p. 7950
Main Authors: Akhmedov, Alan A., Shurpik, Dmitriy N., Padnya, Pavel L., Khadieva, Alena I., Gamirov, Rustem R., Panina, Yulia V., Gazizova, Asiya F., Grishaev, Denis Yu, Plemenkov, Vitaliy V., Stoikov, Ivan I.
Format: Journal Article
Language:English
Published: Basel MDPI AG 01-08-2021
MDPI
Subjects:
Alcohol
associations
Biocompatibility
Biomedical materials
Cell membranes
Drug delivery
Drug delivery systems
Farnesol
floxuridine
host-guest systems
Light scattering
Lipid bilayers
Lipids
macrocyclic systems
Magnetic resonance spectroscopy
NMR
NMR spectroscopy
Nuclear magnetic resonance
Photon correlation spectroscopy
Phytol
pillararenes
Self-assembly
Self-association
Solvents
Stoichiometry
terpenoids
Toxicity
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Summary: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.
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ISSN:1422-0067
1661-6596
1422-0067
DOI:10.3390/ijms22157950