Class Of Surfactants Research Articles

Selective access to novel aryl alkyl disulfonates via photosulfochlorination process: An eco‐benign approach to a highly active class of surfactants

AbstractIn this work we report the synthesis of a new family of surfactants based on aryl alkyl disulfonates; the latter compounds were derived from a mixture of linear alkylbenzene with the resulting disulfonate groups residing on the linear alkyl side‐chain rather than the usual aromatic ring structure. The Reed sulfochlorination reaction was successfully utilized to selectively promote the formation of disulfonates on the alkyl group. A number of analytical methods in the form of liquid chromatography–mass spectrometry (LC–MS), gas chromatography–mass spectrometry (GC–MS), Fourier‐transform infrared spectroscopy (FTIR) and nuclear magnetic resonance (NMR) were used to characterize the resulting compounds and intermediates. The critical micelle concentration, the surface tension at the critical micelle concentration, the surface excess concentration at surface tension, and the area per molecule were measured at different concentrations and temperatures. Thermodynamic parameters and Krafft temperature were also determined. The obtained results were compared to those of commercial n‐dodecylbenzene sulfonates and linear alkylbenzene sulfonates surfactants, showing that these new synthesized surfactants present good surface properties.

Phase Behaviour, Functionality, and Physicochemical Characteristics of Glycolipid Surfactants of Microbial Origin.

Growing demand for biosurfactants as environmentally friendly counterparts of chemically derived surfactants enhances the extensive search for surface-active compounds of biological (microbial) origin. The understanding of the physicochemical properties of biosurfactants such as surface tension reduction, dispersion, emulsifying, foaming or micelle formation is essential for the successful application of biosurfactants in many branches of industry. Glycolipids, which belong to the class of low molecular weight surfactants are currently gaining a lot of interest for industrial applications. For this reason, we focus mainly on this class of biosurfactants with particular emphasis on rhamnolipids and sophorolipids, the most studied of the glycolipids.

Environmental fate studies with 14C-polyoxyethylene tallow amine (POE-T) to characterize environmental exposure and inform environmental risk assessments

Polyoxyethylene tallow amine (POE-T) is a member of the polyoxyethylene alkylamine (POEA) class of nonionic surfactants and is a component of some glyphosate-based formulations. The presence of POE-T improves foliar uptake of glyphosate in weeds, thereby reducing the amount of glyphosate needed for weed control. To further characterize the environmental fate of POE-T, aerobic soil degradation, hydrolysis, adsorption/desorption, and aerobic aquatic degradation studies were conducted according to U.S. EPA and OECD pesticide regulatory testing guidelines. POE-T labeled with carbon-14 was used in the studies to aid in analysis, assess mineralization to CO2, and allow for mass balance determinations. The aerobic soil half-lives (DT50) for POE-T ranged from 20 to 166 days with DT50 values increasing with increasing soil percent organic carbon (OC). POE-T was hydrolytically stable at pH 4–9. POE-T adsorbed strongly to soil (KFocads = 17,600–114,000) with sorption generally increasing as soil percent OC increased. The aerobic aquatic (water-sediment) system DT50s for POE-T were 14–29 days, with POE-T dissipating from the water column with DT50s of 0.10–0.12 days through metabolism and adsorption to sediment. Based on these results, aquatic organisms are unlikely to be exposed to POE -T in the water column for more than a few hours following waterborne exposure and sediment is a significant sink for POE-T in aquatic systems. However, bioavailability of POE-T in sediment and soil is predicted to be low based on strong adsorption and it is not readily desorbed.

Interfacial activity and micellar morphology of an imidazolium ring containing zwitterionic surfactants

AbstractZwitterionic surfactants based on 3‐(1‐alkyl‐3‐imidazolio) propane‐sulfonate ([ImS3‐R] where R is octyl or dodecyl) is an emerging and important class of amphiphile due to their relevance as nano reactors for the synthesis of metallic nanoparticles and accelerated acid hydrolysis. The physicochemical properties of such synthesized imidazolium ring‐containing zwitterionic surfactants have been characterized by surface tension and small‐angle neutron scattering (SANS) techniques. Surface tension measurements were used to calculate several thermodynamic parameters over a range of concentrations and temperatures (298–313 K). The results obtained showed a weak signature representing the critical micelle concentration (CMC) for ImS3‐8, however, by increasing the alkyl length of the hydrophobic group to dodecyl, that is, ImS3‐8 to ImS3‐12, the signature of the CMC was much more evident. As expected, the CMC for ImS3‐12 shifted to a lower concentration. An increase in temperature increased the surface activity and decreased the CMC of both zwitterionic surfactants, although the changes were small. Compared to classical surfactants, that is, sodium dodecyl sulfate and dodecyl trimethylammonium bromide, the CMC of ImS3‐12 is much lower. Modeling of SANS data demonstrated that the morphology of the micelles formed by these amphiphiles may be described by the “classical” model, a central hydrophobic core, with a shell of hydrated headgroups. Due to their widespread applications in colloidal and interfacial science, the present study adds new insight to the fundamental understanding of these interesting imidazolium‐based surface‐active ionic liquids (ImS3‐R).

Strong synergistic interactions in zwitterionic–anionic surfactant mixtures at the air–water interface and in micelles: The role of steric and electrostatic interactions

Hypothesis: The milder interaction with biosystems makes the zwitterionic surfactants an important class of surfactants, and they are widely used in biological applications and in personal care formulations. An important aspect of those applications is their strong synergistic interaction with anionic surfactants. It is anticipated that the strong interaction will significantly affect the adsorption and self-assembly properties.Experiments: Surface tension, ST, neutron reflectivity, NR, and small angle neutron scattering, SANS, have been used here to explore the synergistic mixing in micelles and at the air–water interface for the zwitterionic surfactant, dodecyldimethylammonium propanesulfonate, C12SB, and the anionic surfactants, alkyl ester sulfonate, AES, in the absence and presence of electrolyte, 0.1 M NaCl.Findings: At the air–water interface the asymmetry of composition in the strong synergistic interaction and the changes with added electrolyte and anionic surfactant structure reflect the relative contributions of the electrostatic and steric interactions to the excess free energy of mixing. In the mixed micelles the synergy is less pronounced and indicates less severe packing constraints. The micelle structure is predominantly globular to elongated, and shows a pronounced micellar growth with composition which depends strongly upon the nature of the anionic surfactant and the addition of electrolyte.

Surfactant Protein-G in Wildtype and 3xTg-AD Mice: Localization in the Forebrain, Age-Dependent Hippocampal Dot-like Deposits and Brain Content.

The classic surfactant proteins (SPs) A, B, C, and D were discovered in the lungs, where they contribute to host defense and regulate the alveolar surface tension during breathing. Their additional importance for brain physiology was discovered decades later. SP-G, a novel amphiphilic SP, was then identified in the lungs and is mostly linked to inflammation. In the brain, it is also present and significantly elevated after hemorrhage in premature infants and in distinct conditions affecting the cerebrospinal fluid circulation of adults. However, current knowledge on SP-G-expression is limited to ependymal cells and some neurons in the subventricular and superficial cortex. Therefore, we primarily focused on the distribution of SP-G-immunoreactivity (ir) and its spatial relationships with components of the neurovascular unit in murine forebrains. Triple fluorescence labeling elucidated SP-G-co-expressing neurons in the habenula, infundibulum, and hypothalamus. Exploring whether SP-G might play a role in Alzheimer’s disease (AD), 3xTg-AD mice were investigated and displayed age-dependent hippocampal deposits of β-amyloid and hyperphosphorylated tau separately from clustered, SP-G-containing dots with additional Reelin-ir—which was used as established marker for disease progression in this specific context. Semi-quantification of those dots, together with immunoassay-based quantification of intra- and extracellular SP-G, revealed a significant elevation in old 3xTg mice when compared to age-matched wildtype animals. This suggests a role of SP-G for the pathophysiology of AD, but a confirmation with human samples is required.

TrendProbe: Time profile analysis of emerging contaminants by LC-HRMS non-target screening and deep learning convolutional neural network

Peak prioritization is one of the key steps in non-target screening of environmental samples to direct the identification efforts to relevant and important features. Occurrence of chemicals is sometimes a function of time and their presence in consecutive days (trend) reveals important aspects such as discharges from agricultural, industrial or domestic activities. This study presents a validated computational framework based on deep learning conventional neural network to classify trends of chemicals over 30 consecutive days of sampling in two sampling sites (upstream and downstream of a river). From trend analysis and factor analysis, the chemicals could be classified into periodic, spill, increasing, decreasing and false trend. The developed method was validated with list of 42 reference standards (target screening) and applied to samples. 25 compounds were selected by the deep learning and identified via non-target screening. Three classes of surfactants were identified for the first time in river water and two of them were never reported in the literature. Overall, 21 new homologous series of the newly identified surfactants were tentatively identified. The aquatic toxicity of the identified compounds was estimated by in silico tools and a few compounds along with their homologous series showed potential risk to aquatic environment.

Metallosurfactants Consisting of Amphiphilic Ligands and Transition Metals: Structure, Bonding, Reactivity, and Self-assembling Property

Metallosurfactants are emerging as a relatively new class of surfactants whose ligand moieties bind to various transition metals. Because transition metal centers are incorporated into the surfactant frameworks, they can form various self-assembled structures with metallic interfaces such as micelles, vesicles, and lyotropic liquid crystals. To reduce the lability of transition metal complexes under aqueous conditions, various amphiphilic ligands have been developed as surfactant frameworks. This review discusses some aspects of the design and chemical structures of amphiphilic ligands, as well as focus on various functions and types of chemical bonds present in metallosurfactants.

Removal of a Model Biofilm by Sophorolipid Solutions: A QCM-D Study.

Biofilms are communities of microorganisms that have been widely studied because they can cause hospital-acquired infections and skin disorders. Polysaccharides secreted by microorganisms are constituents of biofilms, contributing to their adhesion and mechanical stability. Sophorolipids are biosurfactants with the ability to disrupt and remove biofilms. Biosurfactants have been targeted as potential substitutes for classical petrochemical-based surfactants in cosmetics. In this study, we fabricate a β-glucan film as a model biofilm, and quartz crystal microbalance with dissipation monitoring (QCM-D) measurements are used to assess the biofilm removal. The viscoelasticity of the β-glucan films is monitored while sophorolipid solutions are introduced into the system, and we found that the film removal performance increases with the sophorolipid concentration. In addition, Δf (change in frequency)-ΔD (change in energy dissipation) plot analyses reveal that two processes are involved in the removal mechanism. The first process involves the adsorption of water (hydration) on the β-glucan film. The second process involves the removal of the β-glucan film from the sensor surface. Furthermore, it is suggested that sophorolipids interfere with the hydration of the β-glucan film and suppress increases in its viscosity. This is expected to be an essential factor for the removal of the β-glucan film. Sophorolipids, therefore, show potential for use in cosmetics as an eco-friendly agent for biofilm removal.

Short-chain branched sulfosuccinate as a missing link between surfactants and hydrotropes.

Surfactants aggregate in water into micelles, and these micelles incorporate organic substances to solubilize them. Hydrotropes are compounds that increase the solubility of hydrophobic substances in water without this form of aggregation. Decreasing the chain length of the classical surfactant Aerosol OT (AOT) from C8 to C5 results in a molecule with intermediate properties. Molecular dynamics simulations and surface tension measurements are performed on this short chain derivative of AOT. This compound shows high solubility and at the same time progressive weak aggregation. The hydration of head groups hinders significant plunging into a hydrophobic core, which leads to well defined liquid chain nanodomains. The transition to bicontinuous aggregates is in the concentration range of 1 mol L-1. The sulfonate group of the head groups (placed at the water interface of worm-like aggregates) rather than the aggregate-aggregate interaction is responsible for the unusual small angle X-ray scattering pattern.

Effect of Various Classes of Surfactants on Interfacial Tension Reduction and Wettability Alteration on Smart-Water-Surfactant Systems

Effect of Various Classes of Surfactants on Interfacial Tension Reduction and Wettability Alteration on Smart-Water-Surfactant Systems

Modulation of micellization behavior of imidazolium based surface active ionic liquids by aromatic anions in aqueous medium

Surface active ionic liquids (SAILs) represent a class of ionic surfactants that many times display better surface-active properties as compared to conventional ionic surfactants. The micellization of SAILs can be further tailored by the addition of salts, and aromatic salts comprising hydrotropic anions have never been explored for altering the micellization of SAILs in low concentration range. Considering this, we have investigated the effect of addition of three aromatic salts i.e. Sodium 4-hydroxy benzenesulfonate, sodium benzenesulfonate, and sodium p-toluenesulfonate on the micellization of 1-dodecyl-3-methylimidazolium chloride, [C12mim][Cl] and its amide functionalized counterpart, 3-(2-(dodecylamino)−2-oxoethyl)−1-methyl-1H-imidazol-3-ium chloride, [C12Amim][Cl]. The surface-active behavior of SAILs has been investigated by tensiometry, whereas micellization in bulk has been probed through conductivity, steady-state fluorescence, dynamic light scattering (DLS) and zeta-potential measurements. The possible location of aromatic anions adsorbed on the micellar surface has been probed using 1H NMR measurements. Isothermal titration calorimetry has been utilized to gain insights into the thermodynamic aspects of micellization. The inferences gained from different techniques have been correlated and found to be in good agreement with each other. It has been observed that the functionalization of alkyl chain length of SAIL along with relative hydrophobicity and bulkiness of the aromatic anions control the characteristic properties of micellization.

Further Studies on Cationic Gemini Amphiphiles as Carriers for Gene Delivery-The Effect of Linkers in the Structure and Other Factors Affecting the Transfection Efficacy of These Amphiphiles.

Gene therapy has the therapeutic potential to address a multitude of health problems, and it also has utility in different domains of science. However, its applications are plagued due to the absence of a suitable, safe, efficient, selective, and universal vector, which could help in delivering the desired nucleic acid cargo to the site of action. Though viral vectors are efficient, they pose various health risks. Different types of synthetic agents have been tried as nucleic acid vectors by researchers but with limited success. Gemini amphiphiles (GAs) are a class of synthetic surfactants having biscationic heads with attached hydrophilic and lipophilic groups. Herein, we synthesized two classes of GAs differing in the chemical nature and length of the linkers, head groups, and lipophilic chains. The resulting compounds were evaluated for their efficiency to transfect A549 and HeLa cell lines with a β-galactosidase reporter plasmid. A 3-oxypentyl linker, a monohydroxyethyl head group, and a tetradecyl moiety as the lipophilic chain offered the best transfection efficiency (compound 10BIII). Dioleoylphosphatidylethanolamine (DOPE) as the helper lipid improved the transfection efficacy of the GAs in the absence of serum. In the presence of serum, DOPE and cholesterol, as the helper lipids, improved the transfection efficacy of the resulting formulations. The synthesized GAs showed concentration-dependent toxicity in the MTT assay. Biodistribution studies using 99mTc-labeled lipoplexes indicated that the lipoplexes got concentrated in some vital organs such as the spleen, liver, and lungs.

An HLD framework for cationic ammonium surfactants

The Hydrophilic-Lipophilic Difference (HLD) model can be described by additive contributions accounting for the effect of the oil and surfactant nature, temperature, ionic strength, and so on. The first step to build an HLD framework for a surfactant class is to have Winsor III phase equilibria in a restricted range of formulation variables. In this respect, anionic and nonionic surfactants are well suited for an HLD study. On the contrary, it is difficult achieve for pure cationic surfactant Winsor III phase equilibria without the addition of alcohols and this has precluded the extension of the HLD to cationic surfactants. In the present contribution, we first propose a system based on a blend of single-tailed and double-tailed cationic surfactant to study the oil contribution, and then we afforded the determination of the surfactant contribution trough an experimental approach (the “HLD-titration”) that is especially tailored for systems displaying a wide range of existence of Winsor III phase equilibria. HLD-titration results confirmed the ionic strength contribution to HLD as a logarithmic function of salinity for cationic-based microemulsions similarly to anionic ones. However, the oil carbon number contribution is almost four-fold larger ( k ​= ​0.7 ​± ​0.1) with respect to anionic surfactants. A clearing point was observed in correspondence of the Winsor III phase equilibria under stirring. This approach allows us the determination of the so-called characteristic curvature ( Cc ), i.e. the term describing the surfactant nature contribution to the film curvature, of the cationic surfactant. Finally, the method was adopted to determine Cc values of 7 quaternary ammonium surfactants differing in the polar heads nature and further three amine oxide surfactant at pH ​= ​1 where they are protonated.

OLIGOMERIC GUANIDINE-CONTAINING PROTON CATIONIC IONIC LIQUID

Oligomeric ionic liquids occupy an intermediate position between low molecular weight and polymeric. They are promising as polymer electrolytes in electrochemical devices for various purposes, membranes for the separation of gas mixtures, in sensor technologies, and so on. Oligomeric guanidinium ionic liquids are practically not described in the literature. In terms of studying the effect of the structure of the epoxy component on the properties of oligomeric ionic liquids of this type, it is advisable to introduce into its composition an aliphatic oligoether component. The choice of aliphatic oligoepoxide for the synthesis of guanidinium oligomeric ionic liquids is based on the fact that it is structurally similar to poly - and oligoethylene oxides, which are known to be non-toxic, biodegradable, and reactive oligomeric ionic liquids at elevated temperatures. A new type of reactive oligomeric proton cationic ionic liquid was synthesized by the reaction of oligomeric aliphatic diepoxide with guanidine, followed by neutralization of the product with hydrochloric acid. In this study, the synthesis of proton cationic oligomeric ionic liquids was based on the introduction of guanidinium fragments as end groups of the oligoether aliphatic chain. This reaction is attractive because of the ease of opening the oxirane ring with such a strong nucleophile as guanidine.The reaction forms a fragment with an aliphatic C-N bond, which retains the high basicity of the nitrogen atom. Its structure is characterized by the presence of guanidinium groups at the ends of the aliphatic hydroxyl-containing oligoether chain. The chemical structure of this compound is characterized by IR -, 1H ,13 C NMR spectroscopy methods, and its molecular mass characteristics are determined.The average molecular weight of the synthesized oligomeric ionic liquids is 610 g / mol.The value of the coefficient of polydispersity of the synthesized oligomeric ionic liquids is equal to 1.2. Determination of the content of amino groups in the guanidine-containing oligomer in the basic form by titrometric method allowed to establish that the value found is close to the theoretically calculated value. The synthesized oligomeric proton ionic liquid is characterized by an amorphous structure with two glass transition temperatures. The first lies in the range -70 °C, the second in the region of 70 °C, and the beginning of thermal oxidative destruction is located in the region of 148 °C. The temperature dependence of the ionic conductivity for this compound is nonlinear in the Arrhenius coordinates, which indicates the realization of ionic conductivity mainly due to the free volume in the system. The proton conductivity of this compound is 6.4·10-5–1·10-2Cm/cmin the range of 20–100 °C. The obtained compound exhibits surface-active properties characteristic of classical surfactants, as evidenced by the value of the limiting surface activity – 2.8·102 Nm2 / kmol. The value of CCM is 1.8·10-2 mol/l., and the value of the minimum surface tension – 37.70 mN / m. The synthesized oligomeric ionic liquid is of interest as electrolytes operating under anhydrous conditions, surfactants, disinfectants, and starting reagents for the synthesis of ion-containing blockopolymers.

Synthetic surfactants in Swiss sewage sludges: Analytical challenges, concentrations and per capita loads

Surfactants are high-production-volume chemicals that are among the most abundant organic pollutants in municipal wastewater. In this study, sewage sludge samples of 36 Swiss wastewater treatment plants (WWTPs), serving 32% of the country's population, were analyzed for major surfactant classes by liquid chromatography mass spectrometry (LC-MS). The analyses required a variety of complementary approaches due to different analytical challenges, including matrix effects (which can affect adduct ion formation) and the lack of reference standards. The most abundant contaminants were linear alkylbenzene sulfonates (LAS; weighted mean [WM] concentration of 3700 μg g−1 dry weight), followed by secondary alkane sulfonates (SAS; 190 μg g−1). Alcohol polyethoxylates (AEO; 8.3 μg g−1), nonylphenol polyethoxylates (NPEO; 16 μg g−1), nonylphenol (NP; 3.1 μg g−1), nonylphenol ethoxy carboxylates (NPEC; 0.35 μg g−1) and tert-octylphenol (tert-OP, 1.8 μg g−1) were present at much lower concentrations. This concentration pattern agrees with the production volumes of the surfactants and their fates in WWTPs. Branched AEO homologues dominated over linear homologues, probably due to higher persistence. Sludge concentrations of LAS, SAS, and NP were positively correlated with the residence time in the anaerobic digester. Derivation of the per capita loads successfully revealed potential industrial/commercial emission sources. Comparison of recent versus historic data showed a decrease in NPEO and NP levels by one or two orders of magnitude since their ban in the 1980s. By contrast, LAS still exhibit similar concentrations compared to 30 years ago.

Alkyl glyceryl ethers as water-based lubricant additives in mixtures with xanthan gum

Water-based lubricants are greener and more environmentally friendly than comparable oil-based lubricants. However, water-based lubricants typically have a poorer performance and, thus, need to be formulated with various additives. Here, alkyl glyceryl ethers, a class of nonionic surfactants, were investigated as lubricant additives. To this purpose, aqueous solutions of newly synthesized ethers (with different alkyl chain lengths, C8, C10, C12, and C14) were formulated with xanthan gum. The lubrication performance of these formulations was then tested experimentally. Clearly, alkyl glyceryl ethers showed a significantly improved performance (higher friction reduction) with increasing the alkyl chain length. However, the ethers had to be formulated with xanthan gum, with which they formed a complex, which promoted ether dispersion and probably adsorption on the metal surface in the aqueous phase, thereby drastically reducing friction. Thus, the alkyl glyceryl ethers synthesized in this work are attractive green and highly efficient lubricant additives, which can improve the sustainability of industrial lubrication processes.

A General Approach on Surfactants Use and Properties in Drug Delivery Systems.

Surfactants are amphiphilic molecules of great interest in the pharmaceutical field which are used in combination with other adjuvants to solubilize poorly soluble drugs, improve their dissolution profile, promote permeation, improve drug delivery, enhance stabilization, among other characteristics. Literature shows that surfactants are included in several pharmaceutical compositions: tablets, solid dispersions, emulsions, microemulsions, nanoemulsions, liposomes and niosomes. This review aims to elucidate the different classes of surfactants based on their charges (cationic, anionic, nonionic, zwitterionic, and dimeric), the micelles formation process, and how surfactant molecules geometry can affect this phenomenon. Moreover, current studies regarding the benefits of surfactants in the development of formulations are presented. Finally, a discussion on how charges and chain length of surfactants can affect the stratum corneum epithelial cells leading to increased permeation or skin irritability is reported.

Diptool-A Novel Numerical Tool for Membrane Interactions Analysis, Applying to Antimicrobial Detergents and Drug Delivery Aids.

The widespread problem of resistance development in bacteria has become a critical issue for modern medicine. To limit that phenomenon, many compounds have been extensively studied. Among them were derivatives of available drugs, but also alternative novel detergents such as Gemini surfactants. Over the last decade, they have been massively synthesized and studied to obtain the most effective antimicrobial agents, as well as the most selective aids for nanoparticles drug delivery. Various protocols and distinct bacterial strains used in Minimal Inhibitory Concentration experimental studies prevented performance benchmarking of different surfactant classes over these last years. Motivated by this limitation, we designed a theoretical methodology implemented in custom fast screening software to assess the surfactant activity on model lipid membranes. Experimentally based QSAR (quantitative structure-activity relationship) prediction delivered a set of parameters underlying the Diptool software engine for high-throughput agent-membrane interactions analysis. We validated our software by comparing score energy profiles with Gibbs free energy from the Adaptive Biasing Force approach on octenidine and chlorhexidine, popular antimicrobials. Results from Diptool can reflect the molecule behavior in the lipid membrane and correctly predict free energy of translocation much faster than classic molecular dynamics. This opens a new venue for searching novel classes of detergents with sharp biologic activity.

Synthesis, antimicrobial activity and cytotoxicity of triphenylphosphonium (TPP) conjugates of 1,2,3-triazolyl nucleoside analogues

Four new triphenylphosphonium (TPP) conjugates of 1,2,3-triazolyl nucleoside analogues were synthesized by coupling with 8-bromoctyl- or 10- bromdecyltriphenylphosphonium bromide and evaluated for the in vitro antibacterial activity against S. aureus, B. cereus, E. faecalis, two MRSA strains isolated from patients and resistant to fluoroquinolone antibiotic ciprofloxacin and β-lactam antibiotic amoxicillin, E. coli, antifungal activity against T. mentagrophytes C. albicans and cytotoxicity against human cancer cell lines M−HeLa, MCF-7, A549, HuTu-80, PC3, PANC-1 and normal cell line Wi-38. In these compounds a TPP cation was attached via an octyl or a decyl linker to the N 3 atom of the heterocycle moiety (thymine, 6-methyluracil, quinazoline-2,4-dione) which was bonded with 2′,3′,5′-tri- O - acetyl-greek beta-d-ribofuranose residue by the (1,2,3-triazol-4-il)methyl bridge. All synthesized compounds showed high antibacterial activity against S. aureus within the range of MIC values 1.2–4.3 greek muM, and three of them appeared to be bactericidal with respect to tis bacterium at MBC values 4.1–4.3 greek muM. Two lead compounds showed both high antibacterial activity against the MRSA strains resistant to Ciprofloxacin and Amoxicillin within the range of MIC values 1.0–4.3 greek muM and high cytotoxicity against human cancer cell lines HuTu-80 and MCF-7 within the range of IC50 values 6.4–10.2 greek muM. This is one of the few examples when phosphonium salts exhibited both antibacterial activity and cytotoxicity against human cancer cell lines. According to the results obtained the bactericidal effect of the lead compounds, unlike classical surfactants, was not caused by a violation of the integrity of the cytoplasmic membrane of bacteria and their cytotoxic activity is most likely associated both with the induction of apoptosis along the mitochondrial pathway and the arrest of the cell cycle in the G0/G1 phase.