11 research outputs found

    Antimicrobial Properties and Cytotoxic Effect of Imidazolium Geminis with Tunable Hydrophobicity

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    Antimicrobial, membranotropic and cytotoxic properties of dicationic imidazolium surfactants of n-s-n (Im) series with variable length of alkyl group (n = 8, 10, 12, 14, 16) and spacer fragment (s = 2, 3, 4) were explored and compared with monocationic analogues. Their activity against a representative range of Gram-positive and Gram-negative bacteria, and also fungi, is characterized. The relationship between the biological activity and the structural features of these compounds is revealed, with the hydrophobicity emphasized as a key factor. Among dicationic surfactants, decyl derivatives showed highest antimicrobial effect, while for monocationic analogues, the maximum activity is observed in the case of tetradecyl tail. The leading compounds are 2–4 times higher in activity compared to reference antibiotics and prove effective against resistant strains. It has been shown that the antimicrobial effect is not associated with the destruction of the cell membrane, but is due to specific interactions of surfactants and cell components. Importantly, they show strong selectivity for microorganism cells while being of low harm to healthy human cells, with a SI ranging from 30 to 100

    Enhanced Herbicidal Action of Clopyralid in the Form of a Supramolecular Complex with a Gemini Surfactant

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    Surfactants are often added to herbicidal formulations to improve the delivery of the herbicide into plants. In this study a new herbicidal formulation was formed based on the clopyralid with 0.01% gemini surfactant hexanediyl-1,6-bis(dimethylcetylammonium bromide) (16-6-16) as an adjuvant. The increase in the efficiency of the formulation was associated with the formation of a supramolecular surfactant–herbicide complex (SMC), which has improved wetting properties, provides high clopyralid concentration on the leaf surface, and has higher penetrating ability compared to surfactant-free clopyralid solutions. Comparison of the herbicidal action of clopyralid–16-6-16 SMC with two commercial formulations of the same concentration of clopyralid was performed using digital phenotyping of the model weed plant cocklebur (Xanthium strumarium). Based on the spectral indices NDVI (normalized differential vegetation index) and PSRI (plant senescence reflectance index) and key morphological indexes of the leaf angle, plant height, and leaf area, we showed that clopyralid formulations strongly affected the plants and that the strongest and most durable effect was exerted by the clopyralid–16-6-16 SMC formulation

    Micellization and Catalytic Properties of Cationic Surfactants with Head Groups Functionalized with a Hydroxyalkyl Fragment

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    The catalytic activity of two homological series of cationic surfactants bearing a hydroxyalkyl fragment in the head groups R­(CH<sub>3</sub>)<sub>2</sub>N<sup>+</sup>(CH<sub>2</sub>CH<sub>2</sub>OH)­Br<sup>–</sup> and R­(CH<sub>3</sub>)<sub>2</sub>N<sup>+</sup>(CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH)­Br<sup>–</sup> toward the cleavage of the <i>p</i>-nitrophenyl esters of carbonic acids of different hydrophobicity (acetate, caprilate, caprinate, laurate, myristate) is shown to exceed that of typical cationic surfactants with the trimethylammonium (TMA) headgroup. The catalytic effect increases with the alkyl chain length of surfactants and nonmonotonous changes in the series: acetate < caprilate < myristate < laurate < caprinate, reaching 750 times. NMR and IR spectroscopy studies and the surface potential calculations revealed that the higher catalytic effect of hydroxyalkylated surfactants is not due to their higher surface potential and binding capacity toward substrates. This is in line with finding that binding constants for TMA series are higher than for their hydroxyalkylated analogues, which was demonstrated by the fitting of kinetic data in terms of the pseudophase model. The microenvironment factor rather than concentrating effect is responsible for the advanced catalytic properties of hydroxyalkylated surfactants in the micellar phase

    Polyelectrolyte Capsules with Tunable Shell Behavior Fabricated by the Simple Layer-by-Layer Technique for the Control of the Release and Reactivity of Small Guests

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    A novel simple protocol for the layer-by-layer coating of uncharged organic substrates (hydrophobic carboxylic acid esters, CAEs) and control of their loading/release behavior has been developed. The approach involves the preliminary treatment of CAEs with the cationic surfactant cetyltrimethylammonium bromide followed by poly­(acrylic acid)/polyethyleneimine alternate deposition. The basic hydrolysis of the substrates is used to spectrophotometrically control the loading/release behavior through monitoring the absorbency of the reaction product <i>p</i>-nitrophenolate ion. Unlike the reactivity of free CAEs, highly sensitive to the solution pH, and the presence of micellar catalysts, the reaction rate of the loaded substrates is unaffected by reaction conditions and can be administered by the capsule design (numbers of deposition cycles, adjusted pH, ultrasonication). The developed protocol makes it possible to omit the use of the sacrificial template and stages of its removal. Capsules corresponding to the biorelevant size criterion, with diameter of ≤200 nm, are obtained. They can be successfully applied for sustaining the dosage of different specimens with the desirable rate and for the control of the guest reactivity by tuning the shell permeability
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