Sulfonic Salt Research Articles

Intranasal administration of liposomes: Potential brain delivery with prospective ophthalmic reach

The low efficacy of drug transportation from the bloodstream to specific tissues remains a challenge in drug delivery to the central nervous system (CNS), primarily because of the presence of the blood-brain and blood-retinal barriers. There is a need for non-invasive drug delivery techniques to the CNS given the intrusive nature of and potential patient burden associated with intraventricular, intrathecal, and intravitreal administration. Recently, the focus has shifted towards intranasal (i.e., nose-to-brain) drug delivery. Furthermore, there have been reports indicating that the use of drug nanocarriers, such as liposomes, facilitates efficient drug delivery via the intranasal pathway. This study investigates the brain penetration capabilities of intranasally administered liposomes using the hydrophobic fluorescent molecule, 1,1′-dioctadecyl-3,3,3′,3′-tetramethyl lindodicarbocyanine, 4-chlorobenzene sulfonate salt (DiD), as a model compound. The primary objective of this study was to elucidate the penetration of intranasally administered liposomes into the CNS, including the eyes. An examination of DiD distribution in the dissected brain and ocular tissues showed that DiD concentrations were elevated specifically at the limbus of the ocular tissue when surface-modified liposomes were employed. These findings suggest that intranasal liposome administration can deliver drugs to the posterior ophthalmic region, specifically the optic nerve, in addition to the brain.

Hydrogen-bonding interactions in the salts 2,4,6-triaminopyrimidin-1-ium sorbate dihydrate, 2,4,6-triaminopyrimidin-1-ium N-phenylantharanilate and 2,4,6-triaminopyrimidin-1-ium p-toluenesulfonate.

Three salts, namely, 2,4,6-triaminopyrimidin-1-ium sorbate dihydrate, C4H8N5+·C6H7O2-·2H2O, (I), 2,4,6-triaminopyrimidin-1-ium N-phenylanthranilate, C4H8N5+·C13H10NO2-, (II), and 2,4,6-triaminopyrimidin-1-ium p-toluenesulfonate, C4H8N5+·C7H7O3S-, (III), were synthesized, characterized by X-ray diffraction techniques and their supramolecular interactions investigated. In all three crystal structures, protonation of the pyrimidine moiety occurs at the N1 position and is reflected in a widening of the C-N-C bond angle. In salts (I)-(III), the primary acid-base interaction occurs through a pair of N-H...O hydrogen bonds to give a heterodimeric R22(8) synthon. Salts (II) and (III) form a discrete centrosymmetric base pair that produces a homodimeric R22(8) synthon and salt (I) forms a water-mediated base pair resulting in a tetrameric R44(12) synthon. The supramolecular patterns exhibited by sulfonate salt (III) mimic the patterns of carboxylate salt (II) and both exhibit a DADA array (D = donor and A = acceptor) quadruple hydrogen-bonded pattern. The crystal structures of salts (I) and (III) are stabilized by offset and face-to-face aromatic π-π stacking interactions, respectively. The resulting architectures in salts (I)-(III) are a supramolecular sheet with a rosette-like architecture in (I), a supramolecular sheet-like architecture in (II) and a three-dimensional supramolecular network in (III).

Zwitterionic and vinyl-N-imidazolium ionic liquids

In this paper, we present employing our own and literature data the results of investigation of the thermal behavior and ion transport properties of vinyl and alkyl imidazolium zwitterions containing an alkane sulfonic acid group and salts on their basis. For comparison, we present the results of investigation the respective vinyl and alkyl imidazolium ILs without these functional groups. The phase behavior of zwitterionic and vinyl imidazolium ionic liquids is studied by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA).

1, 3, 6, 8-pyrene sulfonic acid tetrasodium fluorescent pigment synthesis and security ink production

Colorants used in security inks are special pigments that radiate in the UV region or IR region. Obtained pigments can be from valuable rare earth elements or they can be organic based. Organic-based pigments are generally insoluble in water, which limits their use. For this purpose, an organic-based UV-radiating pigment was synthesized and made water-soluble by forming its salt. With the obtained salt-formed pigment, inkjet ink that can be used in counterfeiting was applied and its printability and resistance properties were determined. In this study, 1, 3, 6, 8-pyrene sulfonic acid tetrasodium salt was synthesized and water-based inkjet inks with hydroxy ethyl cellulose binder were produced. The prepared inks were printed on the paper surface. The color and gloss of the prints obtained were measured both in the visible region and in the UV region. Its optical properties were detected by UV spectroscopy. Strength properties such as light fastness, nitro resistance, alkali resistance, acid resistance, rub resistance, drying time, adhesion and dry film weight of the prints were determined. As a result; Inkjet ink with 1, 3, 6, 8-pyrene sulfonic acid tetrasodium salt was produced and it was concluded that it has good resistance properties.

Ferrocene Bis(Sulfonate) Salt as Redoxmer for Fast and Steady Redox Flow Desalination.

Desalination is considered a promising solution to alleviate water shortages, yet current methods are often restricted, due to challenges like high energy consumption, significant cost, or limited desalination capacity. In this study, we present a novel approach of redox flow desalination (RFD) utilizing the highly aqueous-soluble and reversible redox-active compound, potassium 1,1'-bis(sulfonate) ferrocene (1,1'-FcDS). This water-soluble organic compound yielded stable and rapid desalination, sustaining extended operation without notable decay and achieving an impressive desalination rate of up to 457.5 mmol·h-1·m-2 and energy consumption as low as 40.2 kJ·molNaCl-1. Specifically, the RFD device effectively desalinated a 50 mM NaCl solution to potable standards within 6000 s using 1,1'-FcDS. It maintained an average energy consumption of 178.16 kJ·molNaCl-1 and exhibited negligible deterioration in desalination rate, energy efficiency, and charge efficiency throughout a rigorous 12,000 s cycling test. Furthermore, the versatility of this method was demonstrated by effectively treating saline water with varying initial concentrations from 10 mM to 50 mM, showcasing its potential across a broad spectrum of applications.

Adsorption of spray droplets reduced adsorption of dicamba spray droplets on leaves as droplet size increases

Abstract Off-target movement of growth regulator herbicides can cause severe injury to susceptible plants. Apart from not spraying on windy days or at excessive boom heights, making herbicide applications using nozzles that produce large droplets is the preferred method for reducing herbicide drift. Although large droplets maintain a higher velocity and are more likely to reach the leaf surface in windy conditions, their ability to remain on the leaf surface is poorly understood. Upon impact with the leaf surface, droplets may shatter, bounce, roll-off, or be retained on a leaf surface. We examined how different nozzles, pressures, and adjuvants impact spray droplet adsorption on the leaf surface of common lambsquarters and soybean. Plants were grown in a greenhouse and sprayed in a spray chamber. Three nozzles (XR, AIXR, and TTI) were evaluated at 138, 259, and 379 kPa. Dicamba (0.14 kg ae ha⁻¹) was applied alone and with methylated seed oil (MSO), a non-ionic surfactant, silicone-based adjuvant, crop oil concentrate, or a drift reduction adjuvant. A 1, 3, 6, 8-pyrene tetra sulfonic acid tetra sodium salt was added as a tracer. Dicamba spray droplet adsorption when using the XR nozzle, which produced the smallest spray droplets, was 1.75 times greater than when applied with the TTI nozzle with the largest spray droplets. Applying dicamba with MSO increased adsorption on leaf surfaces nearly four times the amount achieved without an adjuvant. The lowest application pressure (138 kPa) increased dicamba spray volume adsorbed more than 10% compared to the higher pressures 259 and 379 kPa. By understanding the impacts of these application parameters on dicamba spray droplet adsorption, applicators can select application parameters, equipment, and adjuvants that will maximize the amount of dicamba spray volume retained on the target leaf surface while minimizing dicamba spray drift.

Experimental and kinetic analysis of the fluorocarbon structures and coal particles at the microscale

Understanding the dynamic wetting process between liquid droplets and coal dust particles is crucial. Compared to other substances, coal possesses a more intricate microscale molecular chemical structure, with coal's molecular chemical and physical structural characteristics being the primary microscale factors influencing its wetting properties. To enhance the wetting and permeability performance of coal dust, an analysis of the microstructural influences on the wetting process of coal dust through experiments and simulations with five different structured fluorocarbon solutions: perfluorooctane sulfonate sodium (A1), perfluoroisopropyl acrylate (A2), perfluorooctane sulfonic acid ammonium salt (A3), perfluorooctyl alcohol polyoxyethylene ether (N1), and perfluorohexyl ethanol polyoxyethylene ether (N2), was conducted. A wetting theory model (collision–adsorption–immersion) was proposed based on experiments with different concentrations and types of surface tension, and wetting experiments were conducted based on this theory model. The results indicate that smaller coal particle sizes facilitate solution penetration, with the N2 solution demonstrating the best wetting and permeation effects. Microstructural experimental analysis revealed that N2 has more polar functional group structures than the other four fluorocarbon solutions. To further investigate the forces of different structures on coal particles, a molecular dynamics model was employed, and the simulation results indicated that the interaction forces and the number of hydrogen bonds representing the adsorption capacity in the N2 system were the highest.

Biological responses in Danio rerio by the disinfectant SDBS in SARS-CoV-2 pandemic

The use of disinfectants, such as Sodium Dodecylbenzene Sulfonic acid salt (SDBS), has grown since the SARS-CoV-2 pandemic, with environmentally unknown consequences. The present study analyzed SDBS effects in the fish species Danio rerio, using a combination of biomarkers. Our data reported that larvae had their total locomotor activity increased when exposed to 1 mg/L of SDBS, but this parameter was decreased in fish exposed to 5 mg/L. A significant increment of erratic movements was reported in fish exposed to 1 and 5 mg/L of SDBS. These concentrations inhibited CYP1A1/CYP1A2, and of GSTs inhibition, suggesting SDBS is not preferentially biotransformed by these routes. Results concerning the antioxidant defense biomarkers (CAT and GPx) showed no straightforward pattern, suggesting SDBS exposure may have resulted in changes in redox balance. Finally, acetylcholinesterase activity increased. In summary, increased use of SDBS in a near future may result in deleterious effects in environmentally exposed fish.

Optimization and Characterization of Protein Extraction from Asparagus Leafy By-Products.

Asparagus production generates significant amounts of by-products during the summer and post-harvest growth period. By-products can be good sources of nutrients and phytochemicals. The interest in increasing the availability of proteins for human consumption has led to the use of new plant sources rich in proteins. The objective of this study was to use response surface methodology (RSM) to optimize the aqueous extraction process of proteins from asparagus leafy by-products, for the production of new protein ingredients. The optimum extraction condition was at pH 9, with 40 min of extraction at 50 °C, and the concentration was fixed at 5 g·L-1. The isolate obtained presented 90.48% protein with 43.47% protein yield. Amino acids such as alanine, proline, valine, leucine/isoleucine, asparagine, and phenylalanine were identified, and the antioxidant activity for 2,2 AZINO BIS (3-ethylbenzo thiazoline 6 sulfonic acid diammonium salt) was 145.76 equivalent to Trolox μmol.100g-1 and for DPPH 65.21 equivalent to Trolox μmol.100g-1. The product presented favorable technological properties (water absorption capacity 4.49 g·g-1 and oil absorption capacity 3.47 g·g-1) and the color tended towards dark green (L* 31.91, a* -1.01, b* -2.11). The protein isolate obtained through the extraction optimization process showed high potential to be used as a protein ingredient.

Determination of perfluorinated compounds in Eichhornia crassipes (Mart.) Solms using LC-MS/MS in combination with sample preparation by ultrasound-assisted extraction and solid-phase extraction

Fifteen perfluorinated compounds, including perfluorocarboxylic acids and perfluoroalkyl sulfonate salts (with 4 to 12 carbon atoms in their structure) in Eichhornia crassipes (Mart.) Solms samples underwent analysis using Liquid Chromatography- tandem Mass Spectrometry (LC-MS/MS). This analysis was conducted alongside sample preparation employing ultrasound-assisted extraction and solid-phase extraction. The optimization of solvent extraction involved the use of 5 ml of methyl tert-butyl ether (MTBE), 10 minutes of sonication, and three repeated extraction cycles. The weak anion exchange (WAX) cartridge was selected after evaluating and comparing the solid-phase extraction efficiencies of both WAX and C18 cartridges. The evaluated method demonstrated successful analysis of all 15 PFCs in plant samples, achieving favorable recoveries ranging from 71 to 116% (with a coefficient of variation of 1.2-6.6%). The quantification limits for these 15 PFCs in Eichhornia crassipes (Mart.) Solms samples ranged between 0.30 to 0.54 ng/g.
 ® 2023 Journal of Science and Technology - NTTU

Study on the effects of carbon nanotubes and xanthan gum on the performance of hydrocarbon surfactant foam systems

To improve the foam stability and fire extinguishing efficiency of fluorine-free foam (FFF) extinguishing agents, xanthan gum (XG) and carbon nanotubes (CNTs) were selected as the foam stabilizer agents in this study to investigate their effects on the physical and chemical properties and fire suppression effectiveness of FFF system. The effects of the four factors, namely, α-olefin sulfonic acid Salts (AOS), YT-Y762, XG, and CNTs, on the foam performance were investigated using L9(34) orthogonal design method. Three FFF solutions were selected based on the following four parameters: surface tension, 25% drainage time, foam height, and viscosity. The physicochemical properties, fire extinguishing, and burnback performance of the three FFF solutions were investigated. The results indicated that XG and CNTs have synergistic effects on the FFF solution, and the addition of 0.2 wt% of XG and 0.4 wt% of CNTs increased the 25 % drainage time by 81.40 %. The fire extinguishing performance was effectively improved. The results show the potential application of carbon nanotubes in FFF extinguishing agents.

Synthesis and properties of polythiophenes bearing alkylsulfonic acid esters at the side chain

Electric conductivity improves as the side-chain substituents of polythiophenes are transformed into alkyl sulfonate esters, sulfonic acid alkali metal salts and alkyl sulfonic acids.

Development and Validation of a Novel Analytical Method (Ion Pair HPLC) For Separating and Determining Bisoprolol Fumarate and Carvedilol in Pure and Their Pharmaceutical Forms.

This work shows a new analytical method (ion pair HPLC) for the analysis of Bisoprolol Fumarate (BIS) and Carvedilol (CAR) in bulk and tablet. The developed analytical method has been carried out on an Inertsil ODS-3 5µL column 4.6 X 250 mm (w), as stationary phase using a mobile phase {Acetonitrile/ water 50/50 (v/v) containing sodium heptane sulfonic salt 0.001M as Ion pair agent}. The detection wavelength was 223 nm and the flow rate was 1.5 mL /min. Retention times were 3.5 min of BIS and 5.8 min of CAR. The analytical method has been validated by ICH guidelines. The developed method gave linearity in the concentration range of 20–60 µg/ mL accuracy with mean recovery values between 98-102 % (99.73% for BIS and 101.2% for CAR). The developed method is useful for separating and determining Bisoprolol Fumarate and Carvedilol in their pharmaceutical forms.

Synthesis of Sulfonic Acid Salts and Sulfonic Acids by Advanced Cross‐Coupling Reaction of Vinyl Sulfonates

AbstractThe present work describes an advanced cross‐coupling reaction of vinyl sulfonates for the synthesis of sulfonic acid salts and sulfonic acids under mild reaction conditions. The regioselectivity of the double Negishi reaction was achieved by means of the different reactivity of the C−Br and activated C−O bonds. The cross‐coupling reaction leads to a mixture of alkenes and sulfonic acid salts. The separation of alkenes and sulfonic acid salts is achieved through the low solubility of sulfonic acid sodium salts after workup. In addition, the developed procedure is also used for the atom‐economical preparation of cyclooxygenase‐2 inhibitors (COX‐2).

An effective oxygen vacancy restrain method for flexible perovskite solar cells with enhanced performance and bending resistance

Flexible perovskite solar cells (F-PSCs) are currently a research hotspot due to their lightweight, solution processability, and low cost. However, oxygen vacancies in SnO2 would deteriorate the crystallization of perovskite, especially in F-PSCs due to the low temperature of SnO2 preparation with flexible substrates, thus inducing poor performance and decreased bending resistance. Here, trichlorobenzene sulfonic acid potassium salt (TSAPS) is used as an effective oxygen vacancy restrain additive on the SnO2 surface for F-PSCs. The oxygen vacancies are reduced from 68.40% to 45.26% after TSAPS modification. Meanwhile, the interfacial defects are suppressed by the synergistic passivation of individual ions in TSAPS, thus the carrier extraction and transportation are effectively improved. As a result, the PCE of the F-PSCs greatly increased from 15.22% to 18.63%. In addition, the unencapsulated SnO2/TSAPS-based flexible device can maintain 84% of its initial efficiency after 3000 bending cycles, exhibiting superior mechanical stability, while the control one decreased to only 9%. This work demonstrates a dependable method for improving the quality of the interface between the ETL and perovskite layer, resulting in enhanced bending resistance and performance for flexible PSCs.

Sulfonato Complex Formation Rather than Sulfonate Binding in the Extraction of Base Metals with 2,2′-Biimidazole: Extraction and Complexation Studies

The application of a bidentate aromatic N,N’-donor ligand, 2,2′-biimidazole (BIIMH2), as an extractant in the form of 1-octyl-2,2′-biimidazole (OBIIMH) and related derivatives in the solvent extraction of base metal ions (Mg2+, Mn2+, Fe3+, Fe2+, Co2+, Ni2+, Cu2+ and Zn2+) from an acidic sulfonate medium using dinonylnaphthalene disulfonic acid (DNNDSA) as a synergist was investigated. OBIIMH with DNNDSA as a co-extractant showed a lack of selectivity for base metals ions (Mg2+, Mn2+, Fe3+, Fe2+, Co2+, Ni2+, Cu2+ and Zn2+) despite its similarity with a related bidentate aromatic ligand, 2,2′-pyridylimidazole, which showed preference for Ni(II) ions. The nickel(II) specificity, through stereochemical “tailor-making”, was not achieved as expected and the extracted species were isolated to study the underlying chemistry. The homemade metal sulfonate salts, M(RSO3)2·6H2O (R = Toluene and M2+ = Co2+, Ni2+, Cu2+ and Zn2+), were used as precursors of the metal complexes of BIIMH2 using toluene-4-sulfonic acid as the representative sulfonate. Spectroscopic analysis and single-crystal X-ray analysis supported the formation of similar neutral distorted octahedral sulfonato complexes through the bis coordination of BIIMH2 and two sulfonate ions rather than the formation of cationic complex species with anion coordination of sulfonates. We attributed the observation of similar complex species and the similar stability constants of the bis-complexes in solution as the cause for the lack of pH-metric separation of the later 3d metal ions.

Structural analysis and properties of three novel sulfonic acid-based pharmaceutical salts of paliperidone

Three novel paliperidone sulfonate salts, including salt 1 (paliperidone methanesulfate), salt 2 (paliperidone benzenesulfate), and salt 3 (paliperidone p-toluenesulfate), were successfully designed and synthesized using a slow solvent evaporation method. Through TGA-DSC (thermogravimetric analysis-differential scanning calorimetry) testing, it was observed that the decomposition temperatures of these newly developed pharmaceutical salts were increased by 90 K, highlighting their enhanced thermal stability compared with paliperidone. The formation of these salts was primarily attributed to intermolecular hydrogen bonding interactions, as revealed by single-crystal structure analyses. Furthermore, the analyses of 3D dnorm Hirshfeld surface and 2D fingerprint plots demonstrated that the molecular stability was further enhanced by the interactions of H···H and H···O. Salt 1 showed a 10-fold increase in solubility and an approximately 200-fold increase in dissolution rate in a variety of simulated human body fluid environments. The confirmation of the formation of paliperidone drug salts and the high purity of the synthesized salts were further supported by PXRD (powder X-ray diffraction) and IR (infrared spectroscopy) analysis. Notably, this study represents the first reported investigation of paliperidone sulfonate salts, potentially providing valuable insights for the improvement of paliperidone pharmaceutical formulations.

Effect of addition of polyether amine and TiO2 nanofibers on the properties of PEO based sodium ion conducting composites

Sodium ion conducting polymer composite films have been prepared using the blend of poly (ethylene oxide) and polyetheramine (JEFFAMINE ED2003) in which sodium trifluoromethane sulfonate (NaTf) salt and varying amounts of inorganic filler (TiO2 nanofibers) have been added. The effect of TiO2 nanofibers addition has been seen in terms of improved ionic conductivity and electrochemical stability of the nanocomposite film. Highest ionic conductivity of ∼3.5 × 10⁻⁵ Scm⁻1 (at room temperature) along with an electrochemical stability up to ∼2.6 V has been obtained for PEO-Jeffamine blend based solid polymer electrolyte (SPE) with 10 wt% of NaTf salt and a small amount (0.2 wt%) of TiO2 nanofibers. A non monotonic variation in the room temperature ionic conductivity and intensity of XRD peaks has been seen for composite films with increasing concentration of TiO2 nanofibers. Uniform distribution of salt (Na, F and S) and TiO2 nanofibers in the prepared composite film has been obtained in the elemental mapping. FTIR results have given evidence of interaction between the blended polymers, salt and TiO2. The wavelength and duration of exposure of UV radiation have altered the electrical properties of film. Increase in the number of ionic charge carriers has been attained on exposure to UV radiation.

Antiviral Activity of Zinc Oxide Nanoparticles against SARS-CoV-2.

The highly contagious SARS-CoV-2 virus is primarily transmitted through respiratory droplets, aerosols, and contaminated surfaces. In addition to antiviral drugs, the decontamination of surfaces and personal protective equipment (PPE) is crucial to mitigate the spread of infection. Conventional approaches, including ultraviolet radiation, vaporized hydrogen peroxide, heat and liquid chemicals, can damage materials or lack comprehensive, effective disinfection. Consequently, alternative material-compatible and sustainable methods, such as nanomaterial coatings, are needed. Therefore, the antiviral activity of two novel zinc-oxide nanoparticles (ZnO-NP) against SARS-CoV-2 was investigated in vitro. Each nanoparticle was produced by applying highly efficient "green" synthesis techniques, which are free of fossil derivatives and use nitrate, chlorate and sulfonate salts as starting materials and whey as chelating agents. The two "green" nanomaterials differ in size distribution, with ZnO-NP-45 consisting of particles ranging from 30 nm to 60 nm and ZnO-NP-76 from 60 nm to 92 nm. Human lung epithelial cells (Calu-3) were infected with SARS-CoV-2, pre-treated in suspensions with increasing ZnO-NP concentrations up to 20 mg/mL. Both "green" materials were compared to commercially available ZnO-NP as a reference. While all three materials were active against both virus variants at concentrations of 10-20 mg/mL, ZnO-NP-45 was found to be more active than ZnO-NP-76 and the reference material, resulting in the inactivation of the Delta and Omicron SARS-CoV-2 variants by a factor of more than 106. This effect could be due to its greater total reactive surface, as evidenced by transmission electron microscopy and dynamic light scattering. Higher variations in virus inactivation were found for the latter two nanomaterials, ZnO-NP-76 and ZnO-NP-ref, which putatively may be due to secondary infections upon incomplete inactivation inside infected cells caused by insufficient NP loading of the virions. Taken together, inactivation with 20 mg/mL ZnO-NP-45 seems to have the greatest effect on both SARS-CoV-2 variants tested. Prospective ZnO-NP applications include an antiviral coating of filters or PPE to enhance user protection.

Pyridinium ferrocene sulfonate salts: Highly soluble materials for electrochemical applications

Aqueous redox flow batteries (ARFBs) are devices that use water-soluble electroactive compounds for scalable energy storage. Energy storage capacity is maximized when anolytes and catholytes are highly soluble. In this paper, we present a series of pyridinium salts of the ferrocene bis(sulfonate) dianion as highly soluble candidates for ARFB applications. Four compounds with different alkyl chains on pyridinium cations were synthesized and evaluated for their electrochemical properties as well as their efficacy in ARFB devices. Although these compounds were highly soluble, resulting in potentially large energy densities, they suffer from the same stability issues as seen in the related imidazolium ferrocene bis(sulfonate) salt systems.