Surfactant Effect on the Physicochemical Characteristics of Solid Lipid Nanoparticles Based on Pillar[5]arenes.

Anastasia Nazarova,Luidmila Yakimova,Darya Filimonova,Ivan Stoikov

doi:10.3390/ijms23020779

Anastasia Nazarova, Luidmila Yakimova + Show 2 more

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https://doi.org/10.3390/ijms23020779

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Abstract

Novel monosubstituted pillar[5]arenes containing both amide and carboxyl functional groups were synthesized. Solid lipid nanoparticles based on the synthesized macrocycles were obtained. Formation of spherical particles with an average hydrodynamic diameter of 250 nm was shown for pillar[5]arenes containing N-(amidoalkyl)amide fragments regardless of their concentration. It was established that pillar[5]arene containing N-alkylamide fragments can form spherical particles with two different sizes (88 and 223 nm) depending on its concentration. Mixed solid lipid nanoparticles based on monosubstituted pillar[5]arenes and surfactant (dodecyltrimethylammonium chloride) were obtained for the first time. The surfactant made it possible to level the effect of the macrocycle concentration. It was found that various types of aggregates are formed depending on the macrocycle/surfactant ratio. Changing the macrocycle/surfactant ratio allows to control the charge of the particles surface. This controlled property will lead to the creation of molecular-scale porous materials that selectively interact with various types of substrates, including biopolymers.

Highlights

Molecular-scale porous materials are used to recognize, separate and storage molecules, including proteins and oligopeptides in recent years [1,2,3]
We have successfully synthesized new monosubstituted pillar[5]arenes containing both amide and terminal carboxylic fragments and showed that these macrocycles could assemble in the different supramolecular forms in CDCl3, DMSO depending on the structure of the substituent
The formation of a stable solid lipid nanoparticles (SLN) system depends on the initial concentration of macrocycle

Summary

Introduction

Molecular-scale porous materials are used to recognize, separate and storage molecules, including proteins and oligopeptides in recent years [1,2,3]. Macrocyclic compounds are promising candidates for the creation of generation of molecular-scale porous materials due to their cavity [10,11,12]. Pillar[5]arenes are able to form various types of self-organizing structures depending on the used solvent: supramolecular polymers, supramolecular nodes and rotaxanes [21,22,23,24,25,26], and solid lipid nanoparticles (SLN) [27,28]. SLN are prepared from mixtures of lipids (hydrophobic or amphiphilic molecule, soluble in organic solvents) with, if needed, the presence of cosurfactants [29]. The choice of surfactant molecules primarily depends on the chosen lipid, since they must be physicochemically compatible [37]

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