Supramolecular Systems Based on Novel Amphiphiles and a Polymer: Aggregation and Selective Solubilization

Abstract

Supramolecular systems based on novel triazole‐containing and pyrimidine‐containing amphiphiles bearing OH‐groups and a hydrophilic polymer (polyethyleneimine, PEI) were fabricated. Aggregation threshold of individual amphiphile solutions and a surfactant/polymer binary mixture were determined to be equal to 2 and 0.05 mM, respectively, using tensiometry and conductometry techniques. It was found, that PEI addition to surfactant aqueous solutions induces the transition from open to closed association mode accompanying the decrease of mean hydrodynamic diameter of particles (D H) from 100 nm to D H ≤ 5 nm. Polymer addition to the system results in the leveling of pH decrease with surfactant concentration and increase of the electrokinetic potential values from 10 mV up to 40 mV. It was established that solubilization capacity of the supramolecular system formed could be increased by transition from surfactant individual solutions to the amphiphile/polymer binary system. The solubilization properties of the system strongly depend on the nature of the hydrophobic guest solubilized and differ by two orders of magnitude for hydrophobic azodye and lipophilic oxime.

Self-Assembly of Amphiphilic Compounds as a Versatile Tool for Construction of Nanoscale Drug Carriers

“…Besides, the specific architecture of nucleolipid molecules and their biocompatibility allows their use for biomedical purposes as neurotracers [ 99 ], drugs against glioblastoma [ 100 ] and carriers for potential anti-malarial drugs [ 101 ]. Systematic studies [ 102 , 103 , 104 , 105 ] have focused on charged representatives of this type of amphiphilic compounds ( Figure 4 ), exemplified by a series of cationic nucleolipids bearing a pyrimidine moiety, which allows revealing quantitative structure–activity relationships. For example, it has been established that these nucleolipids have unique aggregation behavior in aqueous solutions [ 102 ], solubilization properties toward model hydrophobic compounds [ 103 ], marked membranotropic properties [ 104 ] and substrate-specific effects on the catalysis of ecotoxicants of various hydrophobicity [ 105 ].…”

“…Systematic studies [102][103][104][105] have focused on charged representatives of this type of amphiphilic compounds (Figure 4), exemplified by a series of cationic nucleolipids bearing a pyrimidine moiety, which allows revealing quantitative structure-activity relationships. For example, it has been established that these nucleolipids have unique aggregation behavior in aqueous solutions [102], solubilization properties toward model hydrophobic compounds [103], marked membranotropic properties [104] and substrate-specific effects on the catalysis of ecotoxicants of various hydrophobicity [105]. nucleolipids bearing a pyrimidine moiety, which allows revealing quantitative structure-activity relationships.…”

“…nucleolipids bearing a pyrimidine moiety, which allows revealing quantitative structure-activity relationships. For example, it has been established that these nucleolipids have unique aggregation behavior in aqueous solutions [102], solubilization properties toward model hydrophobic compounds [103], marked membranotropic properties [104] and substrate-specific effects on the catalysis of ecotoxicants of various hydrophobicity [105]. A comparative analysis of collected data for nucleolipids of various structure (Table 3) was conducted in order to establish the functional significance in their amphiphilic structures.…”