Search Results (16)

Food packaging films play a vital role in preserving and protecting food. The focus has gradually shifted to safety and sustainability in the preparation of functional food packaging materials. In this study, a bisquaternary ammonium salt of tannic acid (BQTA) was synthesized, and the bioplastics based on BQTA and polyvinyl alcohol (PVA) were created for packaging applications. The impact of BQTA on antibacterial effect, antioxidant capacity, opacity, ultraviolet (UV) protective activity, mechanical strength, thermal stability, and anti-fog of the resultant bioplastics was examined. In vitro antibacterial experiments confirmed that BQTA possesses excellent antimicrobial properties, and only a trace amount addition of BQTA in PVA composite film could inhibit about 100% of Escherichia coli and Staphylococcus aureus. Compared to BQTA/PVA bioplastics with pure PVA, the experiment findings demonstrate that BQTA/PVA bioplastics show strong antioxidant and UV protection action and the performance of fruit preservation. It also revealed a small improvement in thermal stability and tensile strength. The small water contact angle, even at low BQTA concentrations, gave BQTA/PVA bioplastics good anti-fog performance. Based on the findings, bioplastics of BQTA/PVA have the potential to be used to create packaging, and they can be applied as the second (inner) layer of the primary packaging to protect food freshness and nutrition due to their antioxidant activity and biocompatibility. Full article

The rational synthesis of zeolites with designed morphology is a highly challenging task. In this study, we propose 1,5-bis(methylpiperidine)pentylammonium hydroxide (BMPPAOH) as an organic structure-directing agent (OSDA) based on theoretical calculations. The morphology of zeolite samples is characterized by XRD, SEM, TEM, N₂ sorption isotherms, and UV Raman spectroscopy. This simple bis-quaternary ammonium salt favored the formation of spiral morphology in Beta zeolite spheres (S-Beta). The crystallization of zeolite in the presence of BMMPAOH is a two-stage process, where nanoparticles agglomerate into spheres in the early stages followed by the emergence of S-Beta crystals with spiral morphology. The synthesized Pt-S-Beta catalysts show higher catalytic activity in VOC abatement compared with other Pt-Beta samples. Full article

A cellulose-based matrix for monitoring milk freshness (MF) was produced from rice straw particles (RSPs) in a 0.125–0.150 mm that was bis-quaternized to attach bromocresol purple (BP) as a sensor. Under alkali conditions, the obstinate structure of the rice straw had opened, thereby improving the accessibility of the cellulose. Bis-quaternization created more adsorption sites for BP. The maximum adsorption capacity was 97.68 mg/g. The sensors were interwoven with cellulosic fibers to form the cellulose-based label with a relatively loose three-dimensional structure via hydrogen bonds. As the proportion of BP-BCRPs was increased from 10% to 40%, the air permeability of the label increased from 3.76 to 15.01 mm/s, which increased the response to the tested gases (10.12 s for 1 mL of acetic acid). The intelligent label exhibited excellent sensitivity at pH values of 3–9 with highly saturated color changes. During the storage period, the label color shifted from blue-purple to yellow as acidity was increased from 17.24 to 19.8 °T due to capillarity action, providing a timely warning to consumers. The prepared colorimetric porous intelligent cellulose-based label is suitable for monitoring of MF. Full article

Developing a water-soluble supramolecular system for the detection and removal of Hg²⁺ is extremely needed but remains challenging. Herein, we reported the facile construction of a fluorescent supramolecular system (H⊃G) in 100% water through the self-assembly of carboxylatopillar[5]arene sodium salts (H) and diketopyrrolopyrrole-bridged bis(quaternary ammonium) guest (G) by host–guest interaction. With the addition of Hg²⁺, the fluorescence of H⊃G could be efficiently quenched. Since Hg²⁺ showed synergistic interactions (coordination and Hg²⁺- cavity interactions with G and H, respectively), crosslinked networks of H⊃G@Hg²⁺ were formed. A sensitive response to Hg²⁺ with excellent selectivity and a low limit of detection (LOD) of 7.17 × 10⁻⁷ M was obtained. Significantly, the quenching fluorescence of H⊃G@Hg²⁺ can be recovered after a simple treatment with Na₂S. The reusability of H⊃G for the detection of Hg²⁺ ions was retained for four cycles, indicating the H⊃G could be efficiently used in a reversible manner. In addition, the H⊃G could efficiently detect Hg²⁺ concentration in real samples (tap water and lake water). The developed supramolecular system in 100% water provides great potential in the treatment of Hg²⁺ detection and removal for environmental sustainability. Full article

In recent years, the phenomenon of antibiotic resistance in hospitals, communities and the environment has increasingly grown, so antibiotic resistance has become an urgent problem that requires a decisive and global intervention. Incorrect/unnecessary use of antibiotics contributes to increase the ability of microorganisms to develop resistance faster and faster. Research efforts must, therefore, be made to ensure a future in which antibiotic drugs will still be useful in combating infectious diseases. The search for new antibacterial compounds is fundamental. In this study, the antimicrobial activity of the compounds was evaluated against selected bacterial strains from food and environmental matrices by using the Agar Well Diffusion Assay. A total of thirty-six Gram-positive and Gram-negative bacteria were employed to determine the action spectrum and the antimicrobial effectiveness of a small series of thiourea derivatives. Results showed that the highest activities were found for compounds 1 and 4. The important role of the alkyl chain length and/or guanidine moiety in the width of action spectrum was evidenced. Further studies will allow evaluating the efficacy of the inhibiting action and the molecular mechanisms underlying this activity in order to identify compounds capable of counteracting the phenomenon of antibiotic resistance and to identify possible future applications of these newly synthesized compounds that have shown a high bactericidal action potential. Full article

The present study provides a solvent-free organic synthesis of quaternary ammonium salts: bis(2-hydroxyethyl)dimethylammonium taurate ([BHEDMA][Tau]) and bis(2-hydroxyethyl)dimethylammonium acetate ([BHEDMA][OAc]). These ionic compounds are promising materials for carbon dioxide capture processes, as mono sorbents, supplemental components in the conventional process of chemical absorption, and in the combined membrane approach for improving sorption efficiency. The synthesized compounds were characterized by ¹H NMR and FT-IR spectroscopies and elemental analysis. Afterward, the sorption properties of the compounds were evaluated using the inverse gas chromatography (IGC) method, and their thermodynamic parameters were calculated in the temperature range of 303.15–333.15 K. The enthalpy change (∆_sH) was less than 80 kJ·mol⁻¹, indicated by the physical nature of sorption and also proved by FT-IR. Henry’s law constant in regard to carbon dioxide at 303.15 K was equal to 4.76 MPa for [BHEDMA][Tau], being almost 2.5 lower than for [BHEDMA][OAc] (11.55 MPa). The calculated carbon dioxide sorption capacity for [BHEDMA][Tau] and [BHEDMA][OAc] amounted to 0.58 and 0.30 mmol·g⁻¹, respectively. The obtained parameters are comparable with the known solid sorbents and ionic liquids used for CO₂ capture. However, the synthesized compounds, combining the advantages of both alkanolamines and ionic liquids, contain no fluorine in their structure and thus match the principles of environmental care. Full article

A novel series of 1-[3-{3,5-bis(benzylidene)-4-oxo-1-piperidino}-3-oxopropyl]-4-piperidone oximes 3a–h and related quaternary ammonium salts 4a–h were prepared as candidate antineoplastic agents. Evaluation against neoplastic Ca9-22, HSC-2 and HSC-4 cells revealed the compounds in series 3 and 4 to be potent cytotoxins with submicromolar CC₅₀ values in virtually all cases. In contrast, the compounds were less cytocidal towards HGF, HPLF and HPC non-malignant cells revealing their tumour-selective toxicity. Quantitative structure–activity relationships revealed that, in general, both cytotoxic potency and selectivity index figures increased as the magnitude of the Hammett sigma values rose. In addition, 3a–h are cytotoxic towards a number of leukemic and colon cancer cells. 4b,c lowered the mitochondrial membrane potential in CEM cells, and 4d induced transient G2/M accumulation in Ca9-22 cells. Five compounds, namely 3c,d and 4c–e, were identified as lead molecules that have drug-like properties. Full article

Microbial multidrug resistance presents a real problem to human health. Therefore, water-soluble polymers based on poly(aspartate-co-succinimide) were synthesized via reaction of poly(aspartate-co-succinimide) with bis-quaternary ammonium or quaternary salts. The resultant copolymers were characterized by various techniques such as FTIR, TGA, ¹HNMR, ¹³CNMR and elemental microanalysis. Antimicrobial activities of the new onium salts were investigated against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Salmonella typhi, and the fungi; Candida albicans,Aspergillus niger, Cryptococcus neoformans and Aspergillus flavus by agar diffusion method. Antimicrobial activity was studied in terms of inhibition zone diameters, in addition to the estimation of minimal inhibitory concentration (MIC) of the prepared compounds. A. niger and E. coli were the most affected microorganisms among the tested microorganisms with an inhibition zone of 19–21 (mm) in case of biocides, (V) and (VII). The obtained results showed that the quaternary onium salts have higher activity compared to the aspartate copolymer with MIC concentrations of 25 mg/mL for (VII) and (V) and 50 mg/mL for (VI) and (IV). Full article

A series of 108 novel quaternary bis-ammonium pyridoxine derivatives carrying various substituents at the quaternary nitrogen’s and acetal carbon was synthesized. Thirteen compounds exhibited antibacterial and antifungal activity (minimum inhibitory concentration (MIC) 0.25–16 µg/mL) comparable or superior than miramistin, benzalkonium chloride, and chlorhexidine. A strong correlation between the lipophilicity and antibacterial activity was found. The most active compounds had logP values in the range of 1–3, while compounds with logP > 6 and logP < 0 were almost inactive. All active compounds demonstrated cytotoxicity comparable with miramistin and chlorhexidine on HEK-293 cells and were three-fold less toxic when compared to benzalkonium chloride. The antibacterial activity of leading compound 5c₁₂ on biofilm-embedded Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli or Pseudomonas aeruginosa was comparable or even higher than that of the benzalkonium chloride. In vivo 5c₁₂ was considerably less toxic (LD₅₀ 1705 mg/kg) than benzalkonium chloride, miramistine, and chlorhexidine at oral administration on CD-1 mice. An aqueous solution of 5c₁₂ (0.2%) was shown to be comparable to reference drugs efficiency on the rat’s skin model. The molecular target of 5c₁₂ seems to be a cellular membrane as other quaternary ammonium salts. The obtained results make the described quaternary bis-ammonium pyridoxine derivatives promising and lead molecules in the development of the new antiseptics with a broad spectrum of antimicrobial activity. Full article

Three new cationic gemini surfactants with ester spacer type 2-2′-(ethane-1,2-diyl bis(oxy)) bis(N-(2-alkanamidoethyl)-N,N-dimethyl-2-oxoethan-1-aminium)) dichloride) (CGSES12, CGSES14 and CGSES16), based on N,N-dimethyl fatty amido ethylamine, were produced. These gemini quaternary ammonium salts were synthesized using a three-step reaction method, starting from th/e condensation of the fatty acid chloride (RCOCl) of various hydrophobic chain lengths (R, C₁₁H₂₃, C₁₃H₂₇, C₁₅H₃₁) with N,N-dimethyl ethylene diamine, followed by the quaternization of the tertiary amino group formed with the spacer of the ester group formed in the second step. The chemical configuration of the surfactants was established by FT-IR, ¹HNMR, ¹³CNMR and Mass spectroscopies. The inhibition performance of three surfactants was studied by weight loss and electrochemical measurements. The results show that CGSES12, CGSES14 and CGSES16 behave as effective inhibitors and surface agents. The maximum efficiency was higher than 94% at 2.5 mM, and the inhibition order was CGSES16 > CGSES14 > CGSES12. This was due to the increment in hydrophobicity of the gemini surfactants. Their adsorption on a mild steel surface followed the Langmuir isotherm. CGSES12, CGSES14 and CGSES16 can be considered mixed-type inhibitors. The presence of CGSES12, CGSES14 and CGSES16 increased charge transfer resistance and decreased the corrosion rate. The adsorption focused on heteroatoms and the surface properties of cationic gemini surfactants. Full article

Polyhedral oligomeric silsesquioxanes (POSSs), Am-POSS(x,y), prepared by hydrolytic condensation, contains two types of ammonium side-chain groups, where the numbering of x and y represents the type of ammonium ions in the POSS structure, corresponding to primary (1), secondary (2), tertiary (3), and quaternary (4) ammonium ions. Mixtures of the two starting materials selected from organotrialkoxysilanes containing primary, secondary, and tertiary amines and a quaternary ammonium salt [(RO)₃Si(CH₂)₃R′, R = CH₃ or CH₂CH₃, R′ = NH₂, NHCH₃, N(CH₃)₂, and N(CH₃)₃Cl] were dissolved in dimethyl sulfoxide (DMSO). The hydrolytic condensation was performed in the presence of bis(trifluoromethansulfonyl)imide (HNTf₂) and water. All Am-POSS(x,y) structures consisted of a cage-type octamer (T₈-POSS), as confirmed by ²⁹Si NMR spectrometry and matrix-assisted laser desorption ionization-time of flight mass spectrometry (MALDI-TOF MS). Differential scanning calorimetry (DSC) and X-ray diffraction (XRD) analyses indicated that Am-POSS(1,3), Am-POSS(1,4), and Am-POSS(2,4) had amorphous structures. These POSSs have two or three differences in the number of methyl groups between the two types of ammonium side-chains. Conversely, Am-POSS(1,2), Am-POSS(2,3), and Am-POSS(3,4) had crystalline structures. The difference in the number of methyl groups between the two types of ammonium side-chains in these POSSs is only one. Therefore, the crystalline-amorphous structure of Am-POSS(x,y) is controlled by the side-chain group combinations. Furthermore, Am-POSS(1,3), Am-POSS(1,4), and Am-POSS(2,4) are protic ionic liquids with relatively low flow temperatures. Full article

A family of fifteen quaternary ammonium salts (QAs), bearing the 1,2-bis(4-pyridyl)ethane core, were obtained using for the first time two different green methods, such as microwave (MW) and ultrasounds (US) irradiation, with very good yields and in much shorter times compared to the classical method, and an assay on their antimicrobial action against Escherichia coli (E. coli) was carried out. While 12 to 24 h were required for complete alkylation of 1,2-bis(4-pyridyl)ethane by reactive halogenated derivatives in anhydrous solvent under reflux conditions, MW and US irradiation reduced the reaction time and the desired products were achieved in a few min. One of the aims of this study was to evaluate the antibacterial potential of the synthesized QAs against pathogenic bacteria, along with their impact on germination activity of wheat seeds (Triticum aestivum L.). The antibacterial activity of the QAs against Escherichia coli was explored by determining the minimum inhibitory concentration (MIC). The MIC values varied from 0.312 to 2.5 mg/mL, highlighting the lowest values attained for the derivatives containing methoxy, chlorine and benzofurane functional groups. The viability of aerobic bacteria was determined with the Tetrazolium/Formazan Test, a method that was found to be the best alternative approach with respect to the difuzimetric method. Seeds of Triticum aestivum L. were used for the evaluation of the germination indicators, such as seed germination (SG), the relative seed germination (RSG), the relative radicle growth (RRG), and the seed germination index (GI). The toxicity studies of QAs 1, 4 and 7, at two different concentrations, showed no inhibitory effect on seed germination. Full article

The comparative effect of two quaternary ammonium salts from 1,2-bis(4-pyridyl)ethane (PyQAs), namely N,N′-diphenacyl-1,2-bis(4-pyridinium)ethane dibromide (PyQAs1) and N,N′-di(p-methoxyphenacyl)-1,2-bis(4-pyridinium)ethane dibromide (PyQAs2), upon the size and photoluminescence of zinc oxide nanoparticles (ZnO NPs) was investigated. The formation of ZnO NPs took place in the presence of variable amounts of the two PyQAs species (1, 2.5, and 5%), according to the chemical precipitation of zinc(II) acetate with potassium hydroxide in ethanol under reflux. The obtained ZnO NPs were structurally characterized by means of X-ray powder diffraction, infrared, and Raman spectroscopy. The fluorescence of all supernatant solutions, observed under ultraviolet light, determined us to make an investigation of the solutions by means of liquid chromatography coupled with electrospray ionization mass spectrometry (LC-MS-ESI) in order to elucidate the identity of the newly formed fluorescent species. Such an occurrence thus allowed the invocation of the catalytic effect of zinc(II) ions towards the organic transformation of both nonfluorescent PyQAs surfactants into new fluorescent organic species. Full article

New dimeric, trimeric and tetrameric quaternary ammonium salts were accomplished by reaction of tertiary alkyldimethyl amines with appropriate bromomethylbenzene derivatives. A series of new cationic surfactants contain different alkyl chain lengths (C4–C18), aromatic spacers and different numbers of quaternary nitrogen atoms. The structure of the products was confirmed by spectral analysis (FT-IR, ¹H-NMR, ¹³C-NMR and 2D-NMR), mass spectroscopy (ESI-MS), elemental analysis, as well as PM5 semiempirical methods. Compound (21) was also analyzed using X-ray crystallography. Critical micelle concentration (CMC) of 1,4-bis-[N-(1-alkyl)-N,N-dimethylammoniummethyl]benzene dibromides (3–9) was determined to characterize the aggregation behavior. The antimicrobial properties of novel QACs (Quaternary Ammonium Salts) were examined to set their minimal inhibitory concentration (MIC) values against fungi Aspergillus niger, Candida albicans, Penicillium chrysogenum and bacteria Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa. Full article

Chiral tertiary and quaternary amine solvating agents for NMR spectroscopy were synthesized from the wood resin derivative (+)-dehydroabietylamine (2). The resolution of enantiomers of model compounds [Mosher’s acid (3) and its n-Bu₄N salt (4)] (guests) by (+)-dehydroabietyl-N,N-dimethylmethanamine (5) and its ten different ammonium salts (hosts) was studied. The best results with 3 were obtained using 5 while with 4 the best enantiomeric resolution was obtained using (+)-dehydroabietyl-N,N-dimethylmethanaminium bis(trifluoromethane-sulfonimide) (6). The compounds 5 and 6 showed a 1:1 complexation behaviour between the host and guest. The capability of 5 and 6 to recognize the enantiomers of various α-substituted carboxylic acids and their n-Bu₄N salts in enantiomeric excess (ee) determinations was demonstrated. A modification of the RES-TOCSY NMR pulse sequence is described, allowing the enhancement of enantiomeric discrimination when the resolution of multiplets is insufficient. Full article