Cationic Imidazolium Amphiphiles Bearing a Methoxyphenyl Fragment: Synthesis, Self-Assembly Behavior, and Antimicrobial Activity

Abstract

Novel cationic amphiphiles of the 3-alkyl-1-(4methoxyphenyl)-1H-imidazol-3-ium bromide series bearing methoxyphenyl fragments (MPI-n) have been synthesized. Their aggregation properties in aqueous solutions, solubilization capacity, and hemolytic and antimicrobial activities have been investigated by a number of physicochemical methods. Using tensiometry, conductometry, and fluorescence spectroscopy, it was shown that the MPI-n have lower CMCs than their nonfunctionalized counterparts. The unusual alkyl-chain-length-dependent morphology of aggregates is testified for this homological series. Amphiphiles with 12, 14, and 16 alkyl tails are characterized by the formation of micellar aggregates, while a surfactant with a decyl tail is characterized by the formation of larger aggregates with lower surface curvature. The MPI-10 aggregate morphology was rationalized in terms of the packing parameter consideration and was supported by size measurements and the fluorescence probe techniques, which showed that vesicle-like aggregates in closepacking mode probably occur. MPI-n aggregates have exhibited a high solubilization capacity toward hydrophobic azo dye Orange OT. Importantly, amphiphiles studied showed (i) high bacteriostatic activity at the level of ciprofloxacin; (ii) high bactericidal action against all Gram-positive bacteria, including methicillin-resistant strains; (iii) bactericidal properties against Gram-negative bacteria; and (iv) low hemolytic activity.

Enhancement of the Transdermal Delivery of Nonsteroidal Anti-inflammatory Drugs Using Liposomes Containing Cationic Surfactants

“…The solutions were diluted to 1 mM and measured five times . The ζ potential was calculated using the Smoluchowski equation where ζ is the zeta potential, η is the dynamic viscosity of a solvent, μ is the particle electrophoretic mobility, and ε is the dielectric constant . Electrophoretic mobility for all samples is given in the Supporting Information (Tables S1–S2, Figure S1).…”

Complexation of Oligo- and Polynucleotides with Methoxyphenyl-Functionalized Imidazolium Surfactants

“…The homologous series of MPI-n (n = 10, 12, 14, 16) was obtained via the reaction of 1-(4-methoxyphenyl)imidazole with the corresponding alkyl bromide [47,48]. Briefly: the mixture of 1-(4-methoxyphenyl)-1H-imidazole (1 mol) and corresponding alkyl bromide (1.1 mol) was stirred in dry acetonitrile under heating.…”

“…Moreover, the system acted more selectively on M-HeLa cancer cells (IC 50 = 4.8 µM) than on A549 (IC 50 = 7.1 µM). It should be noted that, in some cases, the use of surfactant/ONu complexes can significantly reduce the effective cytotoxic concentration compared with individual surfactant systems [47]. For example, for individual MPI-12, the IC 50 is 18 µM toward M-HeLa and 23.7 µM toward A549, while in the complex, this concentration decreases to 4.8 µM and 7.1 µM, respectively.…”

“…The cytotoxic effect of MPI-n amphiphiles, MPI-n/ONu and MPI-n/pK18 binary systems toward normal and tumor human cell lines (surfactant/ONu molar ratio is 1:1; surfactant/DNA molar ratio is 3:1). [47] 18.0 ± 1.4 23.7 ± 1.9 13.2 ± 1.1 MPI-14 [47] 6.3 ± 0.5 22.4 ± 1.7 10.0 ± 0.9 MPI-16 [47] 11.5 ± 0.9 27.8 ± 2.2 13.1 ± 1.2 a M-HeLa is a human cervix epitheloid carcinoma; b A549 is an adenocarcinomic human alveolar basal epithelial cell line; c Chang liver is normal human liver cells. The experiments were repeated three times.…”

Role of Polyanions and Surfactant Head Group in the Formation of Polymer–Colloid Nanocontainers

“…surfactant–PE nanostructures may be of interest as carriers due to the ease of their formation. According to the literature data, including our studies, mixed systems based on amphiphiles and PE can be used as nanocontainers for the delivery of hydrophobic substances, specifically medicines [ 3 , 11 , 12 , 13 , 27 , 28 ]; Polymer–surfactant complexes are biomimetic systems, and their study makes it possible to simulate the interaction of charged amphiphiles with natural biopolymers (nucleic acids, proteins, polysaccharides) and lipids [ 29 , 30 ], factors of enzyme catalysis [ 31 ], etc. Moreover, they may be considered the simplest models for studying membrane–drug interactions (e.g., antimicrobial preparations exert their effects by interacting with biological membranes) [ 32 ].…”