Abstract:We synthesized nine quaternary ammonium compounds (QUATs) starting from phenylalanine, N-alkyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromides, which were prepared as optically pure substances. Five compounds were prepared as S-enantiomers and four compounds as R-enantiomers. These compounds were evaluated by their activities against bacteria and fungi. Three microbial strains were used in the study: the gram-negative bacteria Escherichia coli, the gram-positive bacteria Staphylococcus aureus and the fungi Candida albicans. The activities were expressed as minimum bactericidal or fungicidal concentrations (MBC). The most active compounds were (2S)-N-tetradecyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide and (2R)-N-tetradecyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide, with MBC values exceeding those of commercial benzalkoniumbromide (BAB) used as standard. The relationships between structure and biological activity of the tested QUATs were quantified by the bilinear model (QSAR) and are discussed.

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The present study is focused on the synthesis and investigation of the physicochemical and biological properties of silver nanoparticles stabilized with a series of cationic gemini surfactants having a polymethylene spacer of variable length. UV-VIS spectroscopy, dynamic light scattering, scanning electron microscopy and zeta potential measurements were applied to provide physicochemical characterization of the silver nanoparticles. The mean size values of the nanoparticles were found to be in the 50 to 115 nm range. From the nanoparticle size distributions and scanning electron microscopy images it results that a population of small nanoparticles with the size of several nanometers was confirmed if the nanoparticles were stabilized with gemini molecules with either a short methylene spacer (two or four −CH2− groups) or a long spacer (12 −CH2− groups). The average zeta potential value for silver nanoparticles stabilized with gemini molecules is roughly independent of gemini surfactant spacer length and is approx. +58 mV. An interaction model between silver nanoparticles and gemini molecules which reflects the gained experimental data, is suggested. Microbicidal activity determinations revealed that the silver nanoparticles stabilized with gemini surfactants are more efficient against Gram-negative bacteria and yeasts, which has a direct relation to the interaction mechanism of nanoparticles with the bacterial cell membrane and its structural composition.

: Self-assembly properties of cationic gemini surfactants with biodegradable amide or ester groups in the spacer were investigated utilising time-resolved fluorescence quenching, dynamic light scattering and zeta potential measurements. A correlation between aggregation parameters such as micelle aggregation number, micelle size and zeta potential with the structure of gemini molecules was made. For gemini molecules with medium spacer lengths, micelle aggregation number does not change much with the surfactant concentration. When the spacer is extended, a stronger aggregation tendency is observed for gemini surfactant molecules with two ester groups in the spacer and the aggregation number increases. The assumption of stronger aggregation of ester-based gemini molecules at larger spacer number values is also documented by measurements of the size and zeta potential of ester-based micelles. The explanation of the difference in aggregation ability of amide-based and ester-based gemini molecules is related to the structural features of gemini molecules, notably to the larger flexibility and denser arrangement of ester-based gemini molecules in a micelle. To support this assumption, optimised 3D models of the studied gemini molecules were constructed. Correspondingly, the calculations show smaller size and interfacial area for ester-based gemini conformers.

Directed mutagenesis was used to probe the functions of Tyr-470 and Tyr-481 of Pseudomonas aeruginosa exotoxin A (ETA) with respect to cytotoxicity, ADP-ribosylation of elongation factor 2 (EF-2), and NAD-glycohydrolase activity. Both of these residues lie in the active site cleft, close to Glu-553, a residue believed to play a direct role in catalysis of ADP-ribosylation of EF-2. Substitution of Tyr-470 with Phe caused no change in any of these activities, thus eliminating the possibility that the phenolic hydroxyl group of Tyr-470 might be directly involved in catalysis. Mutation of Tyr-481 to Phe caused an approximately 10-fold reduction in NAD:EF-2 ADP-ribosyltransferase activity and cytotoxicity but no change in NAD-glycohydrolase activity. The latter mutation did not alter the KM of NAD in the NAD-glycohydrolase reaction, which suggests that the phenolic hydroxyl of Tyr-481 does not participate in NAD binding. We hypothesize that the phenolic hydroxyl of Tyr-481 may be involved in the interaction of the toxin with substrate EF-2.

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A series of novel phospholium amphiphilic compounds with straight alkyl chains with different numbers of carbon atoms (12,14,15,16,17,18) were synthesized. The quaternary phosphorus, phosphonium cation, is incorporated into a five-membered heterocyclic ring. Their physicochemical properties were investigated by measurements of surface tension, conductivity and dynamic light scattering. The critical micelle concentration (c M ), the surface tension value at the c M (c cmc ), the surface area at the surface saturation per head group (A cmc ), the ionization degree of micelle (a), the free energy of micellization (DG°m ic ), and hydrodynamic diameter (d h ) were determined. Antimicrobial activity was tested against bacteria and yeast. The structure-activity relationship was determined. 3 J CP = 17.3 Hz, = C-CH 3 ) 22.5 (d, 1 J CP = 46.2 Hz, a CH 2 of alkyl chain), 22.6 (d, 2 J CP = 4.1 Hz, b CH 2 of alkyl chain), 22.7 (x CH 2 of alkyl chain), 29.1, 29.3, 29.4, 29.5, 29.6(0), 29.6(4), 29.7 (d-x-2 CH 2 of alkyl chain), 30.5 (d, 3 J CP = 15.6 Hz, c CH 2 of alkyl chain), 31.9 (x-1 CH 2 of alkyl chain), 113.6 (d, 1 J CP = 80.0 Hz, = CHP), 115.9 (d, 1 J CP = 83.9 Hz, Ph C 1 ), 130.0 (d, 3 J CP = 12.9 Hz, Ph C meta ), 133.6 (d, 2 J CP = 10.7 Hz, Ph C ortho ), 134.6 (d, 4 J CP = 3.0 Hz, Ph C para ), 163.2 (d, 2 J CP = 16.4 Hz, = C-CH 3 ); 31 P NMR (CDCl 3 , H 3 PO 4 ) d: 38.5; IR t max /cm -H NMR (CDCl 3 , TMS) d: 0.88 (t, 3 J H,H = 6.7 Hz, 3H, CH 3 of alkyl chain), 1.13-1.38 (m, 22H, 11 9 CH 2 of alkyl chain), 1.38-1.62 (m, 4H, b, c CH 2 of alkyl chain) 2.29 (s, 6H, 2 9 = C-CH 3 ), 3.08-3.22 (m, 2H, a CH 2 of alkyl chain), 7.08 (d, 2 J HP = 30.9 Hz, 2H, = CHP), 7.54-7.61 (m, 2H, Ph H meta ), 7.61-7.75 (m, 1H, Ph H para ), 8.15-8.23 (m, 2H, Ph H ortho ); 13 C NMR (CDCl 3 , TMS) d: 14.1 (CH 3 of alkyl chain), 18.5 (d, 3 J CP = 17.3 Hz, = C-CH 3 ) 22.5 (d, 1 J CP = 46.1 Hz, a CH 2 of alkyl chain), 22.6 (d, 2 J CP = 4.1 Hz, b CH 2 of alkyl chain), 22.7 (x CH 2 of alkyl chain), 29.1, 29.3, 29.4, 29.5, 29.6, 29.7 (d-x-2 CH 2 of alkyl chain), 30.5 (d, 3 J CP = 15.4 Hz, c CH 2 of alkyl chain), 31.9 (x-1 CH 2 of alkyl chain), 113.6 (d, 1 J CP = 80.0 Hz, = CHP), 115.8 (d, 1 J CP = 83.8 Hz, Ph C 1 ), 130.0 (d, 3 J CP = 12.9 Hz, Ph C meta ), 133.5 (d, 2 J CP = 10.4 Hz, Ph C ortho ), 134.7 (d, 4 J CP = 3.0 Hz, Ph C para ), 163.2 (d, 2 J CP = 16.5 Hz, = C-CH 3 ); 31 P NMR (CDCl 3 , H 3 PO 4 ) d: 38.5; IR t max /cm -