A Study of the Interaction between a Family of Gemini Amphiphilic Pseudopeptides and Model Monomolecular Film Membranes Formed with a Cardiolipin

Gorczyca, M; Korchowiec, Beata; Korchowiec, Jacek; Trojan, S; Rubio‐Magnieto, Jenifer; Luis, Santiago V.; Rogalska, Ewa

doi:10.1021/acs.jpcb.5b02575

Cited by 12 publications

(7 citation statements)

References 64 publications

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“…The side-chain conformation of the water-annealed films was analyzed using the IR absorption of the CH 2 group. The symmetric ( ν s ) and asymmetric ( ν a ) CH 2 stretching modes are frequently used to discuss the conformations of hydrocarbons. − The ν s and ν a modes appear at 2848 ± 1 and 2918 ± 1 cm –1 , respectively, when the hydrocarbon chains adopt on an all-trans zigzag conformation. These peaks are shifted to higher wavenumbers with increased prevalence of gauche conformations .…”

Section: Resultsmentioning

confidence: 99%

Nanophase Separation of Poly(N-alkyl acrylamides): The Dependence of the Formation of Lamellar Structures on Their Alkyl Side Chains

et al. 2019

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In this study, poly(N-alkyl acrylamides) [(pAlkylAms)], which contain alkyl side chains that differ with respect to the chain length (n; n = 4− 18), were synthesized and the formation of lamellar structures via nanophase separation was examined. Differential scanning calorimetry (DSC) measurements indicated that p(AlkylAms) (n = 4−15) powders are amorphous at 20 °C, whereas p(AlkylAms) (n ≥ 16) contain partially crystalized side chains. The Xray diffraction (XRD) patterns of the spin-coated films of p(AlkylAms) (n = 4− 15) exhibited broad diffraction peaks that correspond to the nanosegregated alkyl side chain domains (q nd ), while the spectra of the polymer films of p(AlkylAms) (n ≥ 16) exhibited both q nd and diffraction corresponding to crystalized side chains (q ca ). The spin-coated films were annealed in water (water annealing) for 12 h to induce nanophase separation and then characterized using XRD. The XRD results for the water-annealed films were categorized into three groups. The first group comprised of p(AlkylAms) (n = 4−7), which showed XRD patterns similar to those of the pristine films. The second group contained p(AlkylAms) (n = 8−14), which exhibited strong Bragg diffraction peaks that correspond to lamellar structures (q lm ). The last group was composed of p(AlkylAms) (n ≥ 15), which exhibited not only q lm but also q ca . The results indicate that in p(AlkylAms) (n ≥ 8), the nanosegregation force between the hydrophilic main chain and the hydrophobic side chains is sufficient to produce an amorphous film with a lamellar structure. Furthermore, based on a comparison of the lamellar structure of p(AlkylAms) (n = 18) prepared by conventional thermal annealing with the structure obtained using water annealing, we concluded that nanosegregation competes with side-chain crystallization.

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Section: Resultsmentioning

confidence: 99%

Nanophase Separation of Poly(N-alkyl acrylamides): The Dependence of the Formation of Lamellar Structures on Their Alkyl Side Chains

et al. 2019

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“…The outer membrane of Gram-negative bacteria such as E. coli includes porins, which allow the passage of small hydrophilic molecules across the membrane, and lipopolysaccharide molecules that extend into extracellular space. Thus, the observed trend in the activity results could be explained by the relative lipophilicity of the compounds combined with their capacity to disrupt the cell membrane [39,40]. The relative lipophilicity of the compounds was determined theoretically using VCCLab and Molinspiration softwares (LogP values Table 1) and experimentally (retention time values from HPLC, Table 1, Figures S3-S8).…”

Section: Antibacterial and Cytotoxicity Studiesmentioning

confidence: 99%

Imidazole and Imidazolium Antibacterial Drugs Derived from Amino Acids

et al. 2020

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The antibacterial activity of imidazole and imidazolium salts is highly dependent upon their lipophilicity, which can be tuned through the introduction of different hydrophobic substituents on the nitrogen atoms of the imidazole or imidazolium ring of the molecule. Taking this into consideration, we have synthesized and characterized a series of imidazole and imidazolium salts derived from L-valine and L-phenylalanine containing different hydrophobic groups and tested their antibacterial activity against two model bacterial strains, Gram-negative E. coli and Gram-positive B. subtilis. Importantly, the results demonstrate that the minimum bactericidal concentration (MBC) of these derivatives can be tuned to fall close to the cytotoxicity values in eukaryotic cell lines. The MBC value of one of these compounds toward B. subtilis was found to be lower than the IC50 cytotoxicity value for the control cell line, HEK-293. Furthermore, the aggregation behavior of these compounds has been studied in pure water, in cell culture media, and in mixtures thereof, in order to determine if the compounds formed self-assembled aggregates at their bioactive concentrations with the aim of determining whether the monomeric species were in fact responsible for the observed antibacterial activity. Overall, these results indicate that imidazole and imidazolium compounds derived from L-valine and L-phenylalanine—with different alkyl lengths in the amide substitution—can serve as potent antibacterial agents with low cytotoxicity to human cell lines.

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“…To obtain a better understanding of the experimental measurements, molecular dynamics simulations were used [ 39 , 40 , 41 , 42 ], which allowed the properties of the model membranes and molecular interaction within the system containing GOTCAB molecules to be studied at an atomic level.…”

Section: Resultsmentioning

confidence: 99%

The Molecular Bases of the Interaction between a Saponin from the Roots of Gypsophila paniculata L. and Model Lipid Membranes

Korchowiec

Kwiecińska

et al. 2022

IJMS

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In view of the possible medical applications of saponins, the molecular structure of a GOTCAB saponin from the roots of Gypsophila paniculata L. was determined by NMR. The biological activity of saponins may depend on the interaction with cell membranes. To obtain more insight in the mechanism of membrane-related saponin function, an experimental and theoretical study was conducted. Ternary lipid systems composed of sphingomyelin, 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine, and cholesterol were used as models of mammalian cell membranes. The membrane–saponin interaction was studied experimentally by monitoring surface pressure in the monomolecular films formed at the air–aqueous subphase interface. The behavior of GOTCAB saponin in a water box and model monolayer systems was characterized by molecular dynamics simulations. The results obtained showed that, in the systems used, cholesterol had a decisive effect on the interaction between GOTCAB and phosphocholine or sphingomyelin as well as on its location within the lipid film.

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A Study of the Interaction between a Family of Gemini Amphiphilic Pseudopeptides and Model Monomolecular Film Membranes Formed with a Cardiolipin

Cited by 12 publications

References 64 publications

Nanophase Separation of Poly(N-alkyl acrylamides): The Dependence of the Formation of Lamellar Structures on Their Alkyl Side Chains

Nanophase Separation of Poly(N-alkyl acrylamides): The Dependence of the Formation of Lamellar Structures on Their Alkyl Side Chains

Imidazole and Imidazolium Antibacterial Drugs Derived from Amino Acids

The Molecular Bases of the Interaction between a Saponin from the Roots of Gypsophila paniculata L. and Model Lipid Membranes

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