Antibacterial Activities of Five Cationic Gemini Surfactants with Ethylene Glycol Bisacetyl Spacers

A series of cationic gemini surfactants containing two dimethylalkylammonium chains linked by ethylene glycol bisacetyl spacers were synthesized [G_m‐AnA‐m, G = gemini surfactant, m = 12 (–C₁₂H₂₅), 14 (–C₁₄H₂₉), or 16 (–C₁₆H₃₃), A = acetyl, and n = 2, 3, or 4 is the number of ethylene glycol units in the spacers]. Because of the inductive effect of the oxygen atom in the spacer, acylation can take place using chloroacetyl chloride instead of bromoacetyl bromide which helps to limit the use of environmentally harmful reagents. Critical micelle concentrations were determined using conductivity measurements. The antibacterial activities of the surfactants against Gram‐positive bacterium Staphylococcus aureus and Gram‐negative bacterium Escherichia coli were evaluated from the minimum inhibitory concentration (MIC), minimum bacterial concentration, a time–kill study, and the inhibitory zone. Increasing the length of the spacer did not result in an obvious change of antibacterial activity. However, increasing the length of the alkyl chain apparently increased the antibacterial activity against S. aureus but decreased the antibacterial activity against E. coli. The G_{12‐A2A‐12} surfactant had the lowest CMC of 1.26 mmol L^?1 and exhibited the best antibacterial activity with a MIC of 32 μg mL^?1 toward S. aureus and 64 μg mL^?1 toward E. coli in the presence of 10⁵ CFU of bacteria. This work indicated that these cationic gemini surfactants have potential applications as antibacterial agents and emulsifiers.     

Design,Synthesis, and Dual Evaluation of Quinoline and Quinolinium Iodide Salt Derivatives as Potential Anticancer and Antibacterial Agents

A series of novel quinoline and quinolinium iodide derivatives were designed and synthesized to discover potential anticancer and antibacterial agents. With regard to anticancer properties, in vitro cytotoxicities against three human cancer cell lines (A-549, HeLa and SGC-7901) were evaluated. The antibacterial properties against two strains, Escherichia coli (ATCC 29213) and Staphylococcus aureus (ATCC 8739), along with minimum inhibitory concentration (MIC) values were evaluated. The target alkyliodine substituted compounds exhibited significant antitumor and antibacterial activity, of which compound 8-((4-(benzyloxy)phenyl)amino)-7-(ethoxycarbonyl)-5-propyl-[1,3]dioxolo[4,5-g]quinolin-5-ium ( 12 ) was found to be the most potent derivative with IC₅₀ values of 4.45±0.88, 4.74±0.42, 14.54±1.96, and 32.12±3.66 against A-549, HeLa, SGC-7901, and L-02 cells, respectively, stronger than the positive controls 5-FU and MTX. Furthermore, compound 12 had the most potent bacterial inhibitory activity. The MIC of this compound against both E. coli and S. aureus was 3.125 nmol ⋅ mL⁻¹, which was smaller than that against the reference agents amoxicillin and ciprofloxacin.     

Functionalization of halloysite nanotubes with polyethyleneimine and various ionic liquid forms with antimicrobial activity

Halloysite nanotube (HNT), a natural clay, was modified with branched polyethyleneimine (PEI) to form PEI-HNT using epichlorohydrin (ECH) as coupling agent, then protonated with HCl to obtain H-PEI-HNTs providing [NH₃]⁺[Cl]⁻ functionality for potential antimicrobial properties. Upon PEI modification, zeta potential value of HNTs was increased to +37.3 mV from −34.5 mV and to +41.1 mV for H-PEI-HNTs. Only 1.87 wt % H-element in HNT was increased to 3.03 wt % upon PEI modification along with newly generated elements of N and C at 2.99 and 9.93 wt %, respectively. Moreover, ionic liquid (IL) forms of HNTs with [NH₃]⁺[N(CN)₂]⁻, [NH₃]⁺[PF₆]⁻ and [NH₃]⁺[BF₄]⁻ functionality were generated via anion exchange of H-PEI-HNTs with sodium dicyanamide (SDC), ammonium hexafluorophosphate (AHFP), and sodium tetrafluoroborate (STFB). The antimicrobial properties of the modified, protonated, and IL forms of HNTs were determined via macro dilution, diffusion and agar screening tests against Escherichia coli ATCC 8739, Pseudomonas aeruginosa ATCC 10145, Bacillus subtilis ATCC 6633, Staphylococcus aureus ATCC 6538 strains, and Candida albicans ATCC 10231 strains. It was found that H-PEI-HNTs possesses potent antimicrobial effect compared with the other forms of HNTs with 2–4 mg mL⁻¹ MIC and 8–16 mg mL⁻¹ MBC values via the macro dilution method. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2020 , 137, 48352.     

Synthesis and Anti-Listeria Properties of Odorless Hybrid Bio-Based n-Phenolic Vegetable Branched-Chain Fatty Acids

Consumers are becoming concerned about the impact of synthetic chemicals on human health and environments, and demanding natural compounds to reduce risk of antibiotic resistance of microorganisms. However, natural compounds are often less effective than synthetic antimicrobials. This challenge may be addressed with the development of bio-based antimicrobial agents. In this study, bio-based n-phenolic branched-chain fatty acids (n-phenolic-branched chain fatty acid [BCFA]) were synthesized from vegetable oil (soybean and safflower) fatty acids and four natural phenolics (phenol, thymol, carvacrol, and creosote), and tested against Listeria innocua. Results revealed that the newly synthesized products in crude form had minimum inhibitory concentrations (MIC) against L. innocua ranging from 3.6 to 116.4 μg mL⁻¹, with phenol-BCFA products having the lowest MIC (3.6 μg mL⁻¹) and minimum bactericidal concentration (MBC) (7.3 μg mL⁻¹). The precursors (unsaturated free fatty acids and phenolics) and noncovalently bound mixture of free fatty acids and phenolics had MIC above 232.7 μg mL⁻¹. After purification by molecular fractionation, n-phenolic-BCFA in the free fatty acid/monomer form were shown to be responsible for the anti-Listeria activity with MIC of 3.6–7.3 μg mL⁻¹ and MBC of 7.3–29.1 μg mL⁻¹. These promising results pave the road for further study of this new class of bio-based compounds, which may lead to their widespread use.     

Radiation-Induced Acrylamide/4-Vinyl Pyridine Biocidal Hydrogels: Synthesis,Characterization, and Antimicrobial Activities

Acrylamide/4-vinyl pyridine hydrogels were synthesized by radiation polymerization technique using a γ-irradiator. The prepared radiation-synthesized acrylamide/4-vinyl pyridine hydrogels were then treated using a modifying agent with aromatic functional group. The modifying agent used in the modification of acrylamide/4-vinyl pyridine hydrogels was the N-aromatic alkyl quaternizing agent of chloromethyl benzene. The functional group on the modified acrylamide/4-vinyl pyridine hydrogels was confirmed with Fourier transform infrared (FTIR) spectrometry. Thermal analysis, surface morphology investigation, and swelling of the modified and unmodified hydrogels were completed. The antibacterial and antifungal activities of the modified and unmodified hydrogels were also tested against gram-positive Staphylococcus aureus (ATCC 25923); two gram-negative Escherichia coli (ATCC 25922), and Pseudomonas aeruginosa (ATCC 27853) human pathogenic bacteria and a fungal strain—Candida albicans (ATCC 10231) for their MBC values. It was found that acrylamide/4-vinyl pyridine hydrogels do not possess biocidal properties, whereas the modified form of acrylamide/4-vinyl pyridine?chloromethyl benzene showed highly bactericidal characteristics.     

Antibacterial Small Molecules That Potently Inhibit Staphylococcus aureus Lipoteichoic Acid Biosynthesis

The rise of antibiotic resistance, especially in Staphylococcus aureus, and the increasing death rate due to multiresistant bacteria have been well documented. The need for new chemical entities and/or the identification of novel targets for antibacterial drug development is high. Lipoteichoic acid (LTA), a membrane-attached anionic polymer, is important for the growth and virulence of many Gram-positive bacteria, and interest has been high in the discovery of LTA biosynthesis inhibitors. Thus far, only a handful of LTA biosynthesis inhibitors have been described with moderate (MIC=5.34 μg mL⁻¹) to low (MIC=1024 μg mL⁻¹) activities against S. aureus. Herein we describe the identification of novel compounds that potently inhibit LTA biosynthesis in S. aureus, displaying impressive antibacterial activities (MIC as low as 0.25 μg mL⁻¹) against methicillin-resistant S. aureus (MRSA). Under similar in vitro assay conditions, these compounds are 4-fold more potent than vancomycin and 8-fold more potent than linezolid against MRSA.     

Identification of a Novel Inhibition Site in Translocase MraY Based upon the Site of Interaction with Lysis Protein E from Bacteriophage ϕX174

Translocase MraY is the site of action of lysis protein E from bacteriophage ?X174. Previous genetic studies have shown that mutation F288L in transmembrane helix 9 of E. coli MraY confers resistance to protein E. Construction of a helical wheel model for transmembrane helix 9 of MraY and the transmembrane domain of protein E enabled the identification of an Arg‐Trp‐x‐x‐Trp (RWxxW) motif in protein E that might interact with Phe288 of MraY and the neighbouring Glu287. This motif is also found in a number of cationic antimicrobial peptide sequences. Synthetic dipeptides and pentapeptides based on the RWxxW consensus sequence showed inhibition of particulate E. coli MraY activity (IC₅₀ 200–600 μM ), and demonstrated antimicrobial activity against E. coli (MIC 31–125 μg mL^?1). Cationic antimicrobial peptides at a concentration of 100 μg mL^?1 containing Arg‐Trp sequences also showed 30–60 % inhibition of E. coli MraY activity. Assay of the synthetic peptide inhibitors against recombinant MraY enzymes from Bacillus subtilis, Pseudomonas aeruginosa, and Micrococcus flavus (all of which lack Phe288) showed reduced levels of enzyme inhibition, and assay against recombinant E. coli MraY F288L and an E287A mutant demonstrated either reduced or no detectable enzyme inhibition, thus indicating that these peptides interact at this site. The MIC of Arg‐Trp‐octyl ester against E. coli was increased eightfold by overexpression of mraY, and was further increased by overexpression of the mraY mutant F288L, also consistent with inhibition at the RWxxW site. As this site is on the exterior face of the cytoplasmic membrane, it constitutes a potential new site for antimicrobial action, and provides a new cellular target for cationic antimicrobial peptides.     

A cationic alternating copolymer composed of ornithine and glycine with an ordered sequence for enhanced bacterial activity

The chains and segments of unordered cationic polypeptides are complex and may produce unexpected biological activities. Herein, the Ugi's 4CC reaction is adopted to synthesize a cationic alternating copolymer comprising ornithine and glycine (poly(Orn-alter-Gly)) with an ordered sequence for enhanced bacterial resistance. In this technique, potassium isocyanate, 4-(N-carbobenzyloxyamino)-1-butyraldehyde and 1-(4-Methoxyphenyl)ethylamine react to produce MPE-substituted poly(Orn-alter-Gly) in one step without using a catalyst and then poly(Orn-alter-Gly) is obtained by removing the N-(1-p-methoxyphenethyl) (MPE) group. ¹H NMR, Fourier transform infrared spectroscopy, and automatic amino acid analysis confirm that ornithine and glycine are linked alternately in the poly(Orn-alter-Gly) chains. Both MPE-substituted poly(Orn-alter-Gly) and poly(Orn-alter-Gly) have excellent antibacterial activity against Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa as well as excellent biocompatibility. The synthesis strategy and materials provide new information on how to obtain ordered sequence cationic polypeptides.     

Functional Gelatin-Carbon Nanotubes Nanohybrids With Enhanced Antibacterial Activity

Hybrid materials with enhanced antibacterial activity were prepared by incorporation of carbon nanotubes within gelatin-fluoroquinolones bioconjugates. Gelatin bioconjugates were characterized by UV-Vis, FT-IR, and calorimetric analyses, nanohybrids by morphological analyses. Biocompatibility was evaluated on human mesenchymal stem cells, and antibacterial performance against Klebsiella pneumoniae and Escherichia coli. Minimun inhibitory concentrations from 0.025 to 0.05 µg mL^?1 and from 0.025 to 0.10 µg mL^?1, and MBC from 0.025 to 0.10 µg mL^?1 and from 0.05 to 0.20 µg mL^?1 were detected for Escherichia coli and Klebsiella pneumoniae, respectively, showing that nanotubes increase antimicrobial activity comparing to both free and gelatin-conjugated drugs.     

Synthesis,Surface Activity,and Antimicrobial Efficacy of Hydrogenated Cardanol-Derived Positively Charged Asymmetric Gemini Surfactants

Nine different hydrogenated cardanol-based quaternary ammonium compounds including one conventional single-tale single-head surfactant, one bicephalic single-tale double-head surfactant, and seven asymmetric Gemini surfactants were synthetized using a simple process with high yields. Their structures were characterized using ¹H NMR, ¹³C NMR, and high-resolution mass spectral studies. Their surface active properties were evaluated by the wilhelmy plate method at 25 °C and physical parameters like CMC, γ_CMC, π_CMC, C₂₀, τ_CMC, and A_min were calculated. The Krafft temperature values of C-BP-1, C-BP-4, and C-BP-6 are lower than 0 °C, suggesting high-potential industrial application. All synthesized compounds but C-BP-F exhibit great antimicrobial ability against Gram-positive bacteria (S. aureus [ATCC 25923] and C. glutamicum [ATCC 13032]) while inadequate antimicrobial ability against Gram negative strains (E. coli [ATCC 25922] and P. aeruginosa [ATCC 27853]).     

p(AAm/TA)‐based IPN hydrogel films with antimicrobial and antioxidant properties for biomedical applications

Interpenetrating polymer networks (IPN), either semi‐IPN (s‐IPN) or full IPN, based on a natural polymer tannic acid (TA) and synthetic poly(acrylamide) (p(AAm)) were prepared by incorporation of TA during p(AAm) hydrogel film preparation with and without crosslinking of TA simultaneously. The synthesis of p(AAm/TA) s‐IPN and IPN hydrogels with different amounts of TA were prepared by concurrent use of redox polymerization and epoxy crosslinking. The p(AAm)‐based hydrogels were completely degraded at 37.5°C within 9 and 2 days at pHs 7.4 and 9, respectively. Biocompatibility of p(AAm), s‐IPN, and IPN were tested with WST assay and double staining, they had 75% cell viability up to almost 20 μg mL^?1 concentration against L929 fibroblast cell. Antioxidant properties of IPN and s‐IPN hydrogels were investigated with FC and ABTS^? methods. Antimicrobial properties of TA‐containing s‐IPN, and IPN hydrogels were determined against three common bacterial strains, Escherichia coli ATCC 8739, Staphylococcus aureus ATCC 6538, and Bacillus subtilis ATCC 6633, and it was found that p(AAm/TA)‐based s‐IPN and IPN hydrogels are effective antimicrobial and antioxidant materials. Moreover, almost up to day‐long linear TA release profiles were obtained from IPN and s‐IPN hydrogels in phosphate buffer solution at pH 7.4 at 37.5°C. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015 , 132, 41876.     

Microemulsion polymerization in the water,aerosol-OT,tetrahydrofurfuryl methacrylate system

Summary Part of the phase diagram at low (<10%) oil content and 25°C has been mapped in the water, Aerosol-OT (AOT), tetrahydrofurfuryl methacrylate (THFM) ternary system. Sodium persulfate/sodium metabisulfite was used as a redox initiator to induce polymerization in this microemulsion system at 7.8% (w/w) THFM and 4.4% AOT. Conversions in excess of 90% were obtained. The parent microemulsion droplets have diameters on the order of 5 nm. The resulting latexes have average particle diameters of 37–39 nm. The latex particles are cross-linked as a result of radical induced opening of the tetrahydrofurfuryl ring, and exhibit nearly the same density (1.216 g/cm³) and glass transition temperature (67°C) as material (1.222 g/cm³; 62°C) produced by solution polymerization. This three-component microemulsion, and the corresponding latexes, have been imaged directly by cryo-electron microscopy. The first reports of three-component polymerized (oil in water) microemulsions, stabilized by cationic surfactants, were made by Murtagh, Ferrick, and Thomas [ACS Polymer Preprints 1987, 28, 441] and more recently by Perez-Luna, Puig, Castano, Rodriguez, Murthy, and Kaler [Langmuir 1990, 6, 1040]. this report appears to be the first such polymerization in a three-component system stabilized with an anionic surfactant. These latexes are cross-linked beads, and are the first such examples to be prepared by microemulsion polymerization.     

Novel Phenyl-Based Bis-quaternary Ammonium Compounds as Broad-Spectrum Biocides

Herein we report the synthesis and microbiological evaluation of novel phenyl based bis-quaternary ammonium compounds (bis-QACs). Using a simple 2-step synthetic route from dibromo- and dihydroxybenzenes, we obtained a structurally diverse broad panel of bis-QACs with topologically distinct bridging connections between pyridinium heads. Selected analogs possessed potent broad-spectrum biocidal activity against both bacterial and fungal pathogens: methicillin-resistant Staphylococcus aureus (ATCC 43300); Escherichia coli (ATCC 25922), Klebsiella pneumonia (ATCC 700603), Acinetobacter baumannii (ATCC 19606), Pseudomonas aeruginosa (ATCC 27853), Candida albicans (ATCC 90028), Cryptococcus neoformans var. grubii (ATCC 208821). Promising compounds displayed minimum inhibitory concentrations (MIC) values ≤0.25 μg/mL alongside improved cytotoxicity and hemolytic profiles compared to modern antiseptics. Thus, synthesized bis-QACs represent a promising class of biocides with the potential to replace existing household sanitizers.     

Synthesis and antimicrobial activities of new water‐soluble bis‐quaternary ammonium methacrylate polymers

New methacrylate monomers containing pendant quaternary ammonium moieties based on 1,4‐diazabicyclo‐[2.2.2]‐octane (DABCO) were synthesized. The DABCO group contains either a butyl or a hexyl pendant group comprising the hydrophobic segment of the monomers and one tether group to the methacrylate moiety. The monomers were homopolymerized in water by using 2,2′‐azobis(2‐methylpropionamide) dihydrochloride (V‐50) as an initiator. The monomers and polymers were characterized by elemental analysis, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), FTIR, and ¹³C‐NMR. The antimicrobial activities of the corresponding small molecules (bis‐quaternary ammonium monocarboxylates) and polymers were investigated against Staphylococcus aureus and Escherichia coli. Although the small molecules did not show any antimicrobial activity, the polymers were moderately effective against both Gram‐positive and Gram‐negative bacteria. The minimum inhibitory concentration (MIC) values of the polymers with butyl and hexyl hydrocarbon chains against S. aureus and E. coli were found to be 250 and 62.5 μg/mL, respectively. The minimum bactericidal concentration (MBC) value for the polymer with the butyl group was higher than 1 mg/mL, whereas the MBC value for the polymer with hexyl group was found to be 62.5 μg/mL. Thus, an increase of the alkyl chain length from 4 to 6 significantly increased the antimicrobial activity of the polymer. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 94: 635–642, 2004     

Biostatic Behavior of Side Chain Charged Polycations and Polymer-Ag Complexes

Summary Poly[(3-methacryloylamino)propyl]trimethylammonium)chloride (PMF'TA), and poly (2-acrylamido-2-methyl-1-propane sulfonic acid) (PAPSA) were synthesized by radical polymerization. Three copolymers of (3-methacryloylamino)propyl] trimethylammonium chloride and 2-acrylamido-2-methyl-1-propane sulfonic acid P(MPTA-co-APSA) with different feed monomer mol ratios were also synthesized by radical polymerization. These polymer materials and the commercial poly(vinylpyrro1idone-co-2-dimethylaminoethyl methacrylate) quaternized P(VP-co- DMAEM) were purified by ultrafiltration membranes and subsequently their complexes with Ag(I) were prepared. Antibacterial activity of all these polymers, was investigated against Escherichia coli (6538P), and Staphylococcus aureus (ATCC 28922), using the National Comittee for Clinical Laboratory Standards method [1]. None of these compounds exhibited biocidal or biostatic action against E. coli, and only PMTA and P(VP-co-DMAEM) exhibited some action against S. aureus.     

Synthesis of quaternary piperazine methacrylate homopolymers and their antibiofilm and anti-quorum sensing effects on pathogenic bacteria

In this work, poly(glycidyl methacrylate) (PGMA, G) homopolymers with different molecular weights (5600–21,000 gmol⁻¹) were synthesized by atom transfer radical polymerization (ATRP) method. Epoxy groups of PGMA homopolymers were converted to hydroxyl and 1-methyl piperazin residues by reacting with 1-methyl piperazine via ring-opening reaction. The obtained poly(2-hydroxy-3-methyl piperazinepropyl methacrylate) (PHMPPMA, G-P) homopolymers (from 9450 to 35,900 gmol⁻¹) were reacted with alkyl halides of different carbon chain lengths (methyl-, ethyl-, propyl-, butyl-, pentyl-iodides, hexyl bromide) and benzyl chloride (arylhalide) to form quaternary PHMPPMA homopolymers (G-QP). MIC values varied from 0.125 mg/ml to 5 mg/ml. It was found that homopolymer (1G-6QP) produced by the modification of PHMPPMA with hexyl iodide with low molecular weight had highest quorum-sensing inhibition zone ranging from 14.5 ± 0.5 mm (MIC) and 10.0 ± 0.5 mm (MIC/4) as well as best violacein inhibition 61.0 ± 2.2% (MIC) to 17.3 ± 0.6% (MIC/8). Homopolymer (1G-BzQP) produced by the modification of PHMPPMA with benzyl chloride with the lowest molecular weight had best biofilm inhibition ranging from 77.83 ± 1.60% (MIC) to 18.23 ± 0.87% (MIC/8) on S. aureus, 75.70 ± 5.20% (MIC) to 14.25 ± 1.10% (MIC/8) on E. coli and from 86.16 ± 0.83% (MIC) to 12.41 ± 0.76% (MIC/8) on C. albicans. The synthesized homopolymers can be used to combat microbial resistance and severity of infections.     

Synthesis and Antimicrobial Activities of Oximes Derived from O-Benzylhydroxylamine as FabH Inhibitors

Forty‐three oxime derivatives were synthesized by allowing O‐benzylhydroxylamines to react with primary benzaldehydes or salicylaldehydes; these products were gauged as potential inhibitors of β‐ketoacyl‐(acyl‐carrier‐protein) synthase III (FabH). Among the 43 compounds, 38 are reported herein for the first time. These compounds were assayed for antimicrobial activities against Escherichia coli, Pseudomonas aeruginosa, Pseudomonas fluorescens, Bacillus subtilis, Staphylococcus aureus, and Enterococcus faecalis. Compounds with prominent antibacterial activities were tested for their E. coli FabH inhibitory activities. 3‐((2,4‐Dichlorobenzyloxyimino)methyl)benzaldehyde O‐2,4‐dichlorobenzyl oxime ( 44 ) showed the best antibacterial activity, with minimum inhibitory concentrations of 3.13–6.25 μg mL^?1 against the tested bacterial strains, exhibiting the best E. coli FabH inhibitory activity, with an IC₅₀ value of 1.7 mM . Docking simulations were performed to position compound 44 into the E. coli FabH active site in order to determine the most probable binding conformation.     

Preparation,characterization, and antibacterial activities of para-biguanidinyl benzoyl chitosan hydrochloride

Para-biguanidinyl benzoyl chitosan hydrochloride (p-BGBC) is prepared with chitosan (CTS) and para-biguanidinyl benzoyl chloride, which is synthesized by acidchloride reaction of para-biguanidinyl benzonic acid hydrochloride (p-BGBA), as starting material in the medium consisted of MeSO₃H and dimethyl sulfoxide (DMSO). Structure of p-BGBC is characterized by FT-IR, ¹H NMR and gel permeation chromatography (GPC), and its antimicrobial activities are evaluated against a Gram-negative bacterium Escherichia coli (E. coli) and a Gram-positive bacterium Staphylococcus aureus (S. aureus). Compared with CTS hydrochloride, p-BGBC has much stronger antimicrobial activities, which increase with the increase of its degree of substitution (DS) of guanidinylation. When the DS of p-BGBC achieves or exceeds 36.8%, its antibacterial activities against the tested bacteria are higher than that of Bromo-Geramium. © 2012 Wiley Periodicals, Inc. J Appl Polym Sci, 2012     

Synthesis and Antimicrobial Activity of p-tetranitrocalix[4]arene Derivative

The present study demonstrates the synthesis and antimicrobial activity of the p-tetranitrocalix[4]arene (3). The microbial activity was determined against a variety of microorganisms, i.e., Gram-positive and Gram-negative bacterial strains such as Staphylococcus aureus ATCC 10231, Streptococcus viridans ATCC 12392, Escherichia coli ATCC 8739, as well as some fungal species including Aspergillus niger ATCC 16404, Aspergillus flavus ATCC 90906, and Candida albicans ATCC 32333. Kirby-Bauer well agar diffusion method was employed for the determination of antimicrobial activity. All the microorganisms were applied to a selective agar medium (Mueller Hinton Agar) for growth. It was observed that compound 3 is considerably effective against selected microorganisms. The MIC values were also evaluated. Thus, from the results it could be deduced that compound 3 may be a valuable addition to the therapeutic index.     

The influence of coating with aminopropyl triethoxysilane and CuO/Cu2O nanoparticles on antimicrobial activity of cotton fabrics under dark conditions

A novel impregnation process for the fabrication of cotton nanocomposite with strong antimicrobial activity against antibiotics-resistant bacteria and yeast was developed. The impregnation process includes the sol–gel treatment of fabric with (3-aminopropyl)triethoxysilane in the first step, and synthesis of the CuO/Cu₂O nanoparticles (NPs) on the fabric surface in the second step. The in situ synthesis of the CuO/Cu₂O NPs was based on the adsorption of Cu²⁺-ions by the introduced amino groups of the sol–gel coating. The adsorbed Cu²⁺-ions are subsequently reduced in the alkaline solution of NaBH₄. X-ray diffraction measurements confirmed the formation of CuO/Cu₂O NPs. Scanning electron microscopy and atomic absorption spectrometry analyses indicate that the particle size, agglomeration, and amounts of synthesized NPs were highly affected by the initial concentration of CuSO₄ solution. The toxicity of nanocomposites to human keratinocytes (HaCaT) and antimicrobial activity against Gram-negative Escherichia coli ATCC 25922, E. coli ATCC BAA 2469, and Klebsiella pneumoniae ATCC BAA 2146, and Gram-positive bacteria Staphylococcus aureus ATCC 25923, S. aureus ATCC 43300 and yeast Candida albicans ATCC 24433 strongly depended on the copper content. In addition to excellent antimicrobial activity, controlled release of Cu²⁺-ions from the fabrics into physiological saline solution was obtained.