Thermodynamic properties of aqueous micellar solutions of some new acetylated gluco-cationic surfactants

Fisicaro, E.; Biemmi, Mariano; Compari, Carlotta; Duce, Elenia; Peroni, Monica; Viscardi, G.; Quagliotto, Pierluigi

doi:10.1016/j.colsurfa.2006.12.033

Cited by 8 publications

(13 citation statements)

References 39 publications

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“…The experimental data are expressed in terms of apparent and partial molar quantities of the solute, as is usual in solution thermodynamics, assuming infinite dilution as the reference state. Apparent and partial molar quantities were obtained from the experimental data using methods detailed elsewhere. – …”

Section: Resultsmentioning

confidence: 99%

Thermodynamics and Biological Properties of the Aqueous Solutions of New Glucocationic Surfactants

et al. 2008

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Thermodynamic properties of aqueous solutions of newly synthesized compounds, namely, N-[2-(beta-D-glucopyranosyl)ethyl]-N,N-dimethyl-N-alkylammonium bromides with hydrophobic tails of 12 (C12DGCB) and 16 (C16DGCB) carbon atoms, determined as a function of concentration by means of direct methods, are reported here. Dilution enthalpies, densities, and sound velocities were measured at 298 K, allowing for the determination of apparent and partial molar enthalpies, volumes, and compressibilities. Changes in thermodynamic quantities upon micellization were derived using a pseudophase-transition approach. From a comparison with the corresponding acetylated compounds N-[2-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)ethyl]-N,N-dimethyl-N-dodecylammonium bromide (C12AGCB) and N-[2-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyanosyl)ethyl]-N,N-dimethyl-N-hexadecylammonium bromide (C16AGCB), the role played in the micellization process by the acetylated glycosyl moiety was inferred: it enhances the hydrophobic character of the molecule and lowers the change in enthalpy of micelle formation by about 1.5 kJ mol(-1). By comparing the volume of C12DGCB with those of DEDAB and DTAB, the volumes taken up by the (beta- d-glucopyranosyl)ethyl and beta- d-glucopyranosyl groups were found to be 133 and 99 cm3 mol(-1), respectively. Regarding the interaction with DPPC membranes, it seems that the sugar moiety of the hexadecyl deacetylated compound gives rise to hydrogen bonds with the oxygen atoms of the lipid phosphates, shifting the phase transition of DPPC from a bilayer gel to a bilayer liquid crystal to lower temperatures. C16AGCB induces significantly greater changes than C16DGCB in the structure of liposomes, suggesting the formation of domains. The interaction is strongly enhanced by the presence of water. Neither compound interacts strongly with DNA or compacts it, as shown by EMSA assays and AFM images. Only C16AGCB is able to deliver little DNA inside cells when coformulated with DOPE, as shown by the transient transfection assay. This might be related to the ability of C16AGCB to form surfactant-rich domains in the lipid structure.

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Section: Resultsmentioning

confidence: 99%

Thermodynamics and Biological Properties of the Aqueous Solutions of New Glucocationic Surfactants

et al. 2008

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“…Surfactants based on glycolipids represent the most studied group and are the most promising class for commercial production, for industrial use, as well as for biomedical applications [ 198 ]. Among the great number of different anionic, cationic, and non-ionic sugar-based surfactants described in the literature [ 199 , 200 , 201 ], all characterized by mild production conditions, lower toxicity, high biodegradability, and environmental compatibility, glucose-based amphiphiles are prominent [ 202 , 203 , 204 ].…”

Section: Applicationsmentioning

confidence: 99%

Sugar-Based Ionic Liquids: Multifaceted Challenges and Intriguing Potential

2021

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Carbohydrates represent a promising option in transitioning from oil-based chemical resources to renewable ones, with the goal of developing chemistries for a sustainable future. Cellulose, hemicellulose, and largely available monosaccharides already provide useful chemical building blocks, so-called platform chemicals, such as levulinic acid and hydroxymethyl furfural, as well as solvents like cyrene or gamma-valerolactone. Therefore, there is great anticipation for novel applications involving materials and chemicals derived from sugars. In the field of ionic liquids (ILs), sugar-based ILs have been overlooked for a long time, mainly on account of their multistep demanding preparation. However, exploring new strategies for accessing sugar-based ILs, their study, and their exploitation, are attracting increasing interest. This is due to the growing concerns about the negative (eco)toxicity profile of most ILs in conjunction with their non-sustainable nature. In the present review, a literature survey concerning the development of sugar-based ILs since 2011 is presented. Their preparation strategies and thermal behavior analyses, sorted by sugar type, make up the first two sections with the intention to provide the reader with a useful guide. A final overview of the potential applications of sugar-based ILs and their future perspectives complement the present analysis.

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“…Generally, cationic surfactants have been widely used owing to their excellent antibacterial activity, but the conventional cationic surfactants have strong irritant properties [7]. The biological activity data showed that the cationic surfactants and their nanostructure with copper and nickel nanoparticles exhibit moderate to high efficacy against the tested microorganisms.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Surface Activities and Anti-Bacterial Activity of (Copper and Nickel) Nanoparticles Stabilized by Cationic Thiol Polyurethane Surfactants

Sabbah¹

2018

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A series of cationic polyurethane surfactant [PQ14, PQ16 and PQ18] were synthesized by the reaction of alkyl bromoacetate (namely: tetradecyl-, hexadecyl-and octadecyl bromoacetate) as quaternizing agents and modified polyurethane contains tertiary amine species. Modified polyurethane was prepared by the reaction of toluene diisocyanate (TDI) and Triethanol amine mono mercaptoacetate. Grinding method is used to synthesize copper and nickel nanoparticles which stabilized by Cationic Thiol polyurethane surfactants. The chemical structures of the prepared surfactants were confirmed using elemental analysis, FTIR, UV and 1 H-NMR spectroscopy. The molecular weight measurements of the prepared polymers showed that the segments of each polymer contain average 10 units of the urethane-Triethanol amine mercaptoacetate. The surface activities of the prepared surfactants including: surface tension (γ), effectiveness (π cmc), concentration at micelle formation (CMC), efficiency (Pc 20), maximum concentration at the interface (Γ max), average area occupied by each surfactant molecule at the interface at equilibrium (A min) of surfactants solutions were established at 25°C. The surface tension and the critical micelle concentration values of the prepared surfactants were gradually decreased by the gradual increase of their alkyl chain length. Antimicrobial activity of the synthesized cationic surfactants and their nanostructure with copper and nickel nanoparticles were evaluated against pathogenic bacteria and fungi. The antimicrobial activity showed the enhancement in the antimicrobial activity of the synthesized cationic surfactants in the nanostructures form.

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Thermodynamic properties of aqueous micellar solutions of some new acetylated gluco-cationic surfactants

Cited by 8 publications

References 39 publications

Thermodynamics and Biological Properties of the Aqueous Solutions of New Glucocationic Surfactants

Thermodynamics and Biological Properties of the Aqueous Solutions of New Glucocationic Surfactants

Sugar-Based Ionic Liquids: Multifaceted Challenges and Intriguing Potential

Synthesis, Surface Activities and Anti-Bacterial Activity of (Copper and Nickel) Nanoparticles Stabilized by Cationic Thiol Polyurethane Surfactants

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