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1.
Proc Natl Acad Sci U S A ; 121(25): e2403273121, 2024 Jun 18.
Article in English | MEDLINE | ID: mdl-38865266

ABSTRACT

In secondary active transporters, a relatively limited set of protein folds have evolved diverse solute transport functions. Because of the conformational changes inherent to transport, altering substrate specificity typically involves remodeling the entire structural landscape, limiting our understanding of how novel substrate specificities evolve. In the current work, we examine a structurally minimalist family of model transport proteins, the small multidrug resistance (SMR) transporters, to understand the molecular basis for the emergence of a novel substrate specificity. We engineer a selective SMR protein to promiscuously export quaternary ammonium antiseptics, similar to the activity of a clade of multidrug exporters in this family. Using combinatorial mutagenesis and deep sequencing, we identify the necessary and sufficient molecular determinants of this engineered activity. Using X-ray crystallography, solid-supported membrane electrophysiology, binding assays, and a proteoliposome-based quaternary ammonium antiseptic transport assay that we developed, we dissect the mechanistic contributions of these residues to substrate polyspecificity. We find that substrate preference changes not through modification of the residues that directly interact with the substrate but through mutations peripheral to the binding pocket. Our work provides molecular insight into substrate promiscuity among the SMRs and can be applied to understand multidrug export and the evolution of novel transport functions more generally.


Subject(s)
Quaternary Ammonium Compounds , Substrate Specificity , Quaternary Ammonium Compounds/metabolism , Quaternary Ammonium Compounds/chemistry , Crystallography, X-Ray , Bacterial Proteins/metabolism , Bacterial Proteins/genetics , Bacterial Proteins/chemistry , Biological Transport , Membrane Transport Proteins/metabolism , Membrane Transport Proteins/chemistry , Membrane Transport Proteins/genetics , Drug Resistance, Multiple, Bacterial/genetics , Anti-Infective Agents, Local/metabolism , Anti-Infective Agents, Local/pharmacology , Anti-Infective Agents, Local/chemistry , Models, Molecular
2.
Pediatr Dent ; 46(3): 204-208, 2024 May 15.
Article in English | MEDLINE | ID: mdl-38822497

ABSTRACT

Purpose: The purpose of this study was to investigate the microleakage of atraumatic glass ionomer restorations with and without silver diammine fluoride (SDF) application. Restorations with SDF are termed silver-modified atraumatic restorations (SMART). Methods: Sixty carious extracted permanent teeth were randomly allocated to two SMART groups and two control groups (n equals 15 per group) for a total of four groups. After selective caries removal, test specimens were treated with 38 percent SDF and polyacrylic acid conditioner was applied and rinsed; teeth were restored with Fuji IX GP® glass ionomer (n equals 15) or with SMART Advantage™ glass ionomer (SAGI; n equals 15). For control groups, specimens were restored with their respective GI material after selective caries removal, both without SDF. Restored teeth were placed in Dulbecco's Phosphate-Buffered Saline solution at 37 degrees Celsius for 24 hours. Teeth were thermocycled between five and 55 degrees Celsius for 1,000 cycles, stained with two percent basic fuchsin, sectioned, and visually inspected for microleakage utilizing stereomicroscopy on a four-point scale. Data were statistically analyzed using Kruskal-Wallis one-way analysis of variance on ranks using Dunn's method (P<0.05). Results: Microleakage between the two SMART restoration groups was insignificant. SAGI alone demonstrated significantly more microleakage than all other groups. There was no statistical significance between the Fuji IX GP® control group and the two SMART restoration groups. Conclusions: This in vitro study indicated that silver diammine fluoride placed before glass ionomer restoration does not increase microleakage. Polyacrylic acid may be used after SDF placement without increasing microleakage.


Subject(s)
Dental Atraumatic Restorative Treatment , Dental Caries , Dental Leakage , Fluorides, Topical , Glass Ionomer Cements , Silver Compounds , Dental Leakage/prevention & control , Humans , Silver Compounds/chemistry , Glass Ionomer Cements/chemistry , Dental Atraumatic Restorative Treatment/methods , Fluorides, Topical/chemistry , Dental Caries/prevention & control , Cariostatic Agents/chemistry , Quaternary Ammonium Compounds/chemistry , Viscosity , Acrylic Resins/chemistry , Dental Restoration, Permanent/methods
3.
Pediatr Dent ; 46(3): 192-198, 2024 May 15.
Article in English | MEDLINE | ID: mdl-38822501

ABSTRACT

Purpose: The purposes of this study were to evaluate the effect of silver diammine fluoride (SDF) on the shear bond strength (SBS) of pink opaquer (PO) compared to resin-modified glass ionomer (RMGI) and conventional composite (COMP) on demineralized dentin, and also to investigate the mode of failure (MOF). Methods: Sixty extracted third molars were prepared, demineralized for 14 days, and divided into four groups: (1) COMP; (2) SDF+PO; (3) SDF+RMGI; and (4) SDF+COMP (restoration size: two by two mm). SBS, MOF, modified adhesive remnant index (MARI), and remnant adhesive volume (RAV) were evaluated using an Instron® machine, light microscopy, 3D digital scanner ( 3Shape©), and GeoMagic Wrap© software. Results: There was no significant difference in SBS (MPa) among the COMP mean??standard deviation (2.5±1.59), SDF+COMP (2.28±1.05), SDF+PO (3.31±2.63), and SDF+RMGI groups (3.74±2.34). There was no significant difference in MOF and MARI among the four groups (P>0.05). There was no significant difference in RAV (mm3) among the COMP (0.5±0.33), SDF+COMP (0.39±0.44), SDF+PO (0.42±0.38), and SDF+RMGI groups (0.42±0.38; P>0.05). A significant correlation existed between MOF and RAV (R equals 0.721; P<0.001). MOF, MARI, and RAV did not show any correlations with SBS (P>0.05). Conclusions: Silver diammine fluoride does not affect shear bond strength between carious dentinal surface and tooth color restorative materials. The amount of material left on the interface is not related to the amount of shear force needed to break the restoration.


Subject(s)
Composite Resins , Dental Bonding , Dentin , Fluorides, Topical , Shear Strength , Silver Compounds , Humans , Silver Compounds/chemistry , Dentin/drug effects , Composite Resins/chemistry , Glass Ionomer Cements/chemistry , Quaternary Ammonium Compounds/chemistry , Materials Testing , Dental Restoration, Permanent/methods , Dental Materials/chemistry , Dental Stress Analysis , Tooth Demineralization/prevention & control , In Vitro Techniques , Acrylic Resins/chemistry , Color
4.
Int J Mol Sci ; 25(11)2024 May 25.
Article in English | MEDLINE | ID: mdl-38891947

ABSTRACT

Esterquats constitute a unique group of quaternary ammonium salts (QASs) that contain an ester bond in the structure of the cation. Despite the numerous advantages of this class of compounds, only two mini-reviews discuss the subject of esterquats: the first one (2007) briefly summarizes their types, synthesis, and structural elements required for a beneficial environmental profile and only briefly covers their applications whereas the second one only reviews the stability of selected betaine-type esterquats in aqueous solutions. The rationale for writing this review is to critically reevaluate the relevant literature and provide others with a "state-of-the-art" snapshot of choline-type esterquats and betaine-type esterquats. Hence, the first part of this survey thoroughly summarizes the most important scientific reports demonstrating effective synthesis routes leading to the formation of both types of esterquats. In the second section, the susceptibility of esterquats to hydrolysis is explained, and the influence of various factors, such as the pH, the degree of salinity, or the temperature of the solution, was subjected to thorough analysis that includes quantitative components. The next two sections refer to various aspects associated with the ecotoxicity of esterquats. Consequently, their biodegradation and toxic effects on microorganisms are extensively analyzed as crucial factors that can affect their commercialization. Then, the reported applications of esterquats are briefly discussed, including the functionalization of macromolecules, such as cotton fabric as well as their successful utilization on a commercial scale. The last section demonstrates the most essential conclusions and reported drawbacks that allow us to elucidate future recommendations regarding the development of these promising chemicals.


Subject(s)
Betaine , Cations , Choline , Betaine/chemistry , Betaine/analogs & derivatives , Choline/chemistry , Choline/analogs & derivatives , Cations/chemistry , Esters/chemistry , Quaternary Ammonium Compounds/chemistry , Humans
5.
Int J Biol Macromol ; 272(Pt 2): 132933, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38862322

ABSTRACT

Quaternary-ammonium chitosan (CT-CTA) is a popular water treatment agent, and its electropositivity and cation strength are improved compared with chitosan. The use of CT-CTA is widely advocated to remove suspended particles and organic matter from wastewater. However, the solubility of CT-CTA is an important factor affecting the performance of CT-CTA, which is a neglected problem in previous studies. In the study, CT-CTA with different solubilities were prepared by adjusting pH from 2 to 7 in preparation, and their applications were explored in wastewater. When the pH was 2, 2.5, or 3, the obtained CT-CTA was a dissolved state. The turbidity and color removal were 95 % - 98 % and 60 % - 74 %, respectively. When the pH was 4, 5, 6, or 7, the obtained CT-CTA was a solid state. The turbidity and color removal were 30 % - 63 % and 90 % - 97 %, respectively. For domestic-wastewater treatment, CT-CTA in a dissolved state removed 92 % of turbidity and 50 % of chemical oxygen demand (COD). CT-CTA in a solid state removed 86 % of turbidity and 64 % of COD with poly aluminum chloride (PAC). The results illustrated the performance of CT-CTA with different solubilities, which can broaden its application in wastewater treatment.


Subject(s)
Chitosan , Solubility , Wastewater , Water Purification , Chitosan/chemistry , Wastewater/chemistry , Water Purification/methods , Hydrogen-Ion Concentration , Quaternary Ammonium Compounds/chemistry , Biological Oxygen Demand Analysis , Water Pollutants, Chemical/chemistry
6.
ACS Appl Mater Interfaces ; 16(23): 29867-29875, 2024 Jun 12.
Article in English | MEDLINE | ID: mdl-38825754

ABSTRACT

Antimicrobial surfaces limit the spread of infectious diseases. To date, there is no antimicrobial coating that has widespread use because of short-lived and limited spectrum efficacy, poor resistance to organic material, and/or cost. Here, we present a paint based on waterborne latex particles that is supramolecularly associated with quaternary ammonium compounds (QACs). The optimal supramolecular pairing was first determined by immobilizing selected ions on self-assembled monolayers exposing different groups. The QAC surface loading density was then increased by using polymer brushes. These concepts were adopted to develop inexpensive paints to be applied on many different surfaces. The paint could be employed for healthcare and food production applications. Its slow release of QAC allows for long-lasting antimicrobial action, even in the presence of organic material. Its efficacy lasts for more than 90 washes, and importantly, once lost, it can readily be restored by spraying an aqueous solution of the QAC. We mainly tested cetyltrimethylammonium as QAC as it is already used in consumer care products. Our antimicrobial paint is broad spectrum as it showed excellent antimicrobial efficiency against four bacteria and four viruses.


Subject(s)
Quaternary Ammonium Compounds , Quaternary Ammonium Compounds/chemistry , Quaternary Ammonium Compounds/pharmacology , Anti-Infective Agents/pharmacology , Anti-Infective Agents/chemistry , Paint , Surface Properties , Latex/chemistry , Latex/pharmacology , Microbial Sensitivity Tests , Bacteria/drug effects
7.
Sci Rep ; 14(1): 14110, 2024 06 19.
Article in English | MEDLINE | ID: mdl-38898117

ABSTRACT

Newly synthesized gemini quaternary ammonium salts (QAS) with different counterions (bromide, hydrogen chloride, methylcarbonate, acetate, lactate), chain lengths (C12, C14, C16) and methylene linker (3xCH2) were tested. Dihydrochlorides and dibromides with 12 carbon atoms in hydrophobic chains were characterized by the highest biological activity against planktonic forms of yeast and yeast-like fungi. The tested gemini surfactants also inhibited the production of filaments by C. albicans. Moreover, they reduced the adhesion of C. albicans cells to the surfaces of stainless steel, silicone and glass, and slightly to polystyrene. In particular, the gemini compounds with 16-carbon alkyl chains were most effective against biofilms. It was also found that the tested surfactants were not cytotoxic to yeast cells. Moreover, dimethylcarbonate (2xC12MeCO3G3) did not cause hemolysis of sheep erythrocytes. Dihydrochlorides, dilactate and diacetate showed no mutagenic potential.


Subject(s)
Antifungal Agents , Biofilms , Candida albicans , Quaternary Ammonium Compounds , Biofilms/drug effects , Quaternary Ammonium Compounds/pharmacology , Quaternary Ammonium Compounds/chemistry , Quaternary Ammonium Compounds/chemical synthesis , Antifungal Agents/pharmacology , Antifungal Agents/chemical synthesis , Antifungal Agents/chemistry , Candida albicans/drug effects , Animals , Sheep , Surface-Active Agents/pharmacology , Surface-Active Agents/chemical synthesis , Surface-Active Agents/chemistry , Hemolysis/drug effects , Erythrocytes/drug effects , Microbial Sensitivity Tests , Cell Adhesion/drug effects , Stainless Steel/chemistry
8.
Talanta ; 276: 126290, 2024 Aug 15.
Article in English | MEDLINE | ID: mdl-38805755

ABSTRACT

A very sensitive electrochemical biosensor, with haemoglobin (Hb) as its basis, has been created to quantify hydrogen peroxide (H2O2), an essential marker in environmental monitoring, food safety, and medical diagnosis. The sensor uses a simple, eco-friendly preparation method. Hb was immobilised on manganese dioxide nanostructure/gold nanoparticles/poly-diallydimethylammonium chloride-functionalised multiwalled carbon nanotubes (PDDA-MWCNT/AuNP/MnO2), characterised using various techniques: amperometry, voltammetry, X-ray diffraction (XRD), and transmission electron microscopy (TEM). Nafion was used as a binder membrane to preserve the biological and electrochemical properties of the protein on the modified electrode. In comparison to earlier research, the novel biosensor had a lower detection limit (1.83 µM) and a limit of quantification (6.11 µM) (S/N = 3) for H2O2. It also exhibited notable reproducibility, long-term stability, and repeatability. It was effectively used to measure the amount of H2O2 in cow milk and orange juice, yielding recoveries in the order of 98.90-99.53 % with RSDs less than 5.0 %, which makes it a promising biosensor for food control.


Subject(s)
Biosensing Techniques , Electrochemical Techniques , Gold , Hemoglobins , Hydrogen Peroxide , Manganese Compounds , Metal Nanoparticles , Milk , Nanotubes, Carbon , Oxides , Quaternary Ammonium Compounds , Hydrogen Peroxide/chemistry , Hydrogen Peroxide/analysis , Gold/chemistry , Hemoglobins/analysis , Hemoglobins/chemistry , Biosensing Techniques/methods , Manganese Compounds/chemistry , Metal Nanoparticles/chemistry , Quaternary Ammonium Compounds/chemistry , Nanotubes, Carbon/chemistry , Oxides/chemistry , Electrochemical Techniques/methods , Milk/chemistry , Animals , Polyethylenes/chemistry , Cattle , Fruit and Vegetable Juices/analysis , Limit of Detection , Electrodes
9.
Colloids Surf B Biointerfaces ; 239: 113932, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38749165

ABSTRACT

Quaternary ammonium salts (QAS) are widely used in medicine, industry and agriculture as disinfectants, biocides, and fungicides. QAS have the ability to coat various surfaces, prevent adhesion of microorganisms to them and inhibit the formation of biofilm. A group of surfactants derived from benzoic acid with different chemical structures was tested: monomeric QAS with different alkyl chain lengths (C12, C14, C16), gemini QAS containing 12-carbon alkyl chains and linkers of various lengths (3,4,6 methylene groups), as well as multifunctional QAS. Among the tested surfactants, monomeric QAS showed the highest bactericidal and fungicidal activity. All three groups of tested compounds inhibited the filamentation of C. albicans. The best antimicrobial activity was demonstrated by the monomeric surfactant C12AA, while the multifunctional equivalent (2xC12AA) was characterized by good anti-adhesive activity. All tested compounds are non-mutagenic and cause low hemolysis of sheep erythrocytes. Multifunctional and gemini surfactants are also non-toxic.


Subject(s)
Candida albicans , Hemolysis , Microbial Sensitivity Tests , Surface-Active Agents , Surface-Active Agents/pharmacology , Surface-Active Agents/chemistry , Surface-Active Agents/chemical synthesis , Sheep , Animals , Candida albicans/drug effects , Hemolysis/drug effects , Erythrocytes/drug effects , Biofilms/drug effects , Anti-Infective Agents/pharmacology , Anti-Infective Agents/chemistry , Anti-Infective Agents/chemical synthesis , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/chemical synthesis , Quaternary Ammonium Compounds/chemistry , Quaternary Ammonium Compounds/pharmacology , Quaternary Ammonium Compounds/chemical synthesis , Antifungal Agents/pharmacology , Antifungal Agents/chemical synthesis , Antifungal Agents/chemistry
10.
Sci Rep ; 14(1): 12496, 2024 05 31.
Article in English | MEDLINE | ID: mdl-38821995

ABSTRACT

Designing materials capable of disinfecting water without releasing harmful by-products is an ongoing challenge. Here, we report a novel polycationic sponge material synthesized from chitosan derivatives and cellulose fibers, exhibiting antibacterial properties. The design of such material is based on three key principles. First, the formation of a highly porous structure through cryogelation for an extensive surface area. Second, the incorporation of cationic quaternary ammonium moieties onto chitosan to enhance bacterial adsorption and antibacterial activity. Lastly, the reinforcement of mechanical properties through integration of cellulose fibers. The presented sponge materials exhibit up to a 4-log (99.99%) reduction within 6 h against both gram-positive B. subtilis and gram-negative E. coli. Notably, QCHI90/Cell, with the highest surface charge, exhibits a 2-4.5 log reduction within 1 h of incubation time. The eco-friendly synthesis from water and readily available biomaterials, along with cost-effectiveness and simplicity, underscores its versatility and feasibility of upscaling. Together with its outstanding antibacterial activity, this macroporous biomaterial emerges as a promising candidate for water disinfection applications.


Subject(s)
Anti-Bacterial Agents , Biocompatible Materials , Cellulose , Chitosan , Escherichia coli , Water Purification , Escherichia coli/drug effects , Biocompatible Materials/chemistry , Cellulose/chemistry , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Water Purification/methods , Chitosan/chemistry , Water Microbiology , Bacillus subtilis/drug effects , Porosity , Quaternary Ammonium Compounds/chemistry , Quaternary Ammonium Compounds/pharmacology , Adsorption
11.
Int J Biol Macromol ; 269(Pt 2): 132153, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38729494

ABSTRACT

Hollow vesicles are promising in water treatment due to their unique structure of the membrane and inner cavity. However, the adsorption capacity needs to be improved for targeted pollutants. Herein, millimeter-scale hollow vesicles were prepared with a one-step process of sequential stirring and grafting using chitosan, diallyldimethylammonium chloride, and sodium alginate as raw materials with the purpose of efficient removal of anionic dyes from wastewater. The composite vesicles were characterized using scanning electron microscopy, Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy, and X-ray diffraction. The hollow vesicles showed the structure of the cationic membrane and the inner cavity, facilitating the dye adsorption. The adsorption capacity for the anionic dye Reactive Black 5 reached 698.1 mg/g, more than twice that of the binary composite vesicles without graft. The adsorption kinetics and isotherm data coincided with the pseudo-second-order and Langmuir models, respectively, and the adsorption mechanism was monolayer chemisorption. Moreover, the vesicles worked well in wide ranges of environment pH, temperature, and co-existing pollutants. They also possessed excellent cyclic regeneration performance, in which 93 % of the initial adsorption capacity was maintained after four cycles. These results indicate that the millimeter-scale hollow vesicles exhibit broad application prospects for wastewater purification.


Subject(s)
Alginates , Chitosan , Coloring Agents , Quaternary Ammonium Compounds , Water Pollutants, Chemical , Water Purification , Chitosan/chemistry , Alginates/chemistry , Adsorption , Quaternary Ammonium Compounds/chemistry , Water Pollutants, Chemical/chemistry , Coloring Agents/chemistry , Water Purification/methods , Kinetics , Anions/chemistry , Hydrogen-Ion Concentration , Wastewater/chemistry , Naphthalenesulfonates/chemistry , Allyl Compounds
12.
J Chromatogr A ; 1727: 465011, 2024 Jul 19.
Article in English | MEDLINE | ID: mdl-38776604

ABSTRACT

Chiral enantiomers, especially the enantiomers of chiral drugs often exhibit different pharmacological activity, metabolism and toxicity, thus it is of great research significance to scientifically and reasonably develop single chiral drugs with low toxicity and high efficiency. Among them, high performance liquid chromatographic techniques based on chiral stationary phases (CSPs) has become one of the most attractive methods used to evaluate the enantiomeric purity of single-enantiomers compound of pharmacological relevance. In this work, pillar[5]arene functionalized with L- and D-histidine, respectively, were modified on the surface of mesoporous silica as novel chiral stationary phases called L/DHis-BP5-Sil. Notably, L/D-histidine had the characteristics of low steric hindrance and easy derivatization. Although the π-π interaction of imidazole group was weaker than that of benzene ring, the benzene ring bonding imidazole-conjugated ring in the structure produced better enantioseparation effect. The results showed that L/DHis-BP5-Sil can separate a variety of complex structural enantiomers with excellent reproducibility, thermal stability and separation performance. Hence, the unique advantage of the highly selective separation of L/DHis-BP5-Sil provides new insights into the enantioseparation field.


Subject(s)
Calixarenes , Histidine , Silicon Dioxide , Stereoisomerism , Silicon Dioxide/chemistry , Calixarenes/chemistry , Histidine/chemistry , Chromatography, High Pressure Liquid/methods , Porosity , Reproducibility of Results , Quaternary Ammonium Compounds/chemistry
13.
ACS Nano ; 18(20): 12905-12916, 2024 May 21.
Article in English | MEDLINE | ID: mdl-38721835

ABSTRACT

For most frequent respiratory viruses, there is an urgent need for a universal influenza vaccine to provide cross-protection against intra- and heterosubtypes. We previously developed an Escherichia coli fusion protein expressed extracellular domain of matrix 2 (M2e) and nucleoprotein, named NM2e, and then combined it with an aluminum adjuvant, forming a universal vaccine. Although NM2e has demonstrated a protective effect against the influenza virus in mice to some extent, further improvement is still needed for the induction of immune responses ensuring adequate cross-protection against influenza. Herein, we fabricated a cationic solid lipid nanoadjuvant using poly(lactic acid) (PLA) and dimethyl-dioctadecyl-ammonium bromide (DDAB) and loaded NM2e to generate an NM2e@DDAB/PLA nanovaccine (Nv). In vitro experiments suggested that bone marrow-derived dendritic cells incubated with Nv exhibited ∼4-fold higher antigen (Ag) uptake than NM2e at 16 h along with efficient activation by NM2e@DDAB/PLA Nv. In vivo experiments revealed that Ag of the Nv group stayed in lymph nodes (LNs) for more than 14 days after initial immunization and DCs in LNs were evidently activated and matured. Furthermore, the Nv primed T and B cells for robust humoral and cellular immune responses after immunization. It also induced a ratio of IgG2a/IgG1 higher than that of NM2e to a considerable extent. Moreover, NM2e@DDAB/PLA Nv quickly restored body weight and improved survival of homo- and heterosubtype influenza challenged mice, and the cross-protection efficiency was over 90%. Collectively, our study demonstrated that NM2e@DDAB/PLA Nv could offer notable protection against homo- and heterosubtype influenza virus challenges, offering the potential for the development of a universal influenza vaccine.


Subject(s)
Adjuvants, Immunologic , Influenza Vaccines , Polyesters , Quaternary Ammonium Compounds , Influenza Vaccines/immunology , Influenza Vaccines/chemistry , Influenza Vaccines/administration & dosage , Animals , Mice , Polyesters/chemistry , Adjuvants, Immunologic/chemistry , Adjuvants, Immunologic/pharmacology , Quaternary Ammonium Compounds/chemistry , Female , Mice, Inbred BALB C , Orthomyxoviridae Infections/prevention & control , Orthomyxoviridae Infections/immunology , Nanoparticles/chemistry , Cross Protection/immunology , Adjuvants, Vaccine/chemistry , Viral Matrix Proteins/immunology
14.
J Chromatogr A ; 1726: 464965, 2024 Jul 05.
Article in English | MEDLINE | ID: mdl-38733925

ABSTRACT

Aristolochic acids (AAs) naturally occurring in the herbal genus Aristolochia are associated with a high risk of kidney failure, multiple tumors and cancers. However, approaches with high selectivity and rapidity for measuring AAs in biological samples are still inadequate. Inspired by the mechanism of AAs-induced nephrotoxicity, we designed a hybrid magnetic polymer-porous agarose (denoted as MNs@SiO2M@DNV-A), mimicking the effect of basic and aromatic residues of organic anion transporter 1 (OAT1) for efficient enriching aristolochic acid I (AA I) and aristolochic acid II (AA II) in the plasma. The monomers of vinylbenzyl trimethylammonium chloride (VBTAC), N-vinyl-2-pyrrolidinone (NVP) and divinylbenzene (DVB) were employed to construct the polymer layer, which provided a selective adsorption for AAs by multiple interactions. The porous agarose shell contributed to remove interfering proteins in the plasma samples. A magnetic solid-phase extraction (MSPE) based on the proposed composite enhanced the selectivity toward AA I and AA II in the plasma samples. In combination of HPLC analysis, the proposed method was proved to be applicable to fast and specific quantification of AAs in blood samples, which was characterized by a good linearity, high sensitivity, acceptable recovery, excellent repeatability and satisfactory reusability.


Subject(s)
Aristolochic Acids , Quaternary Ammonium Compounds , Sepharose , Solid Phase Extraction , Aristolochic Acids/chemistry , Aristolochic Acids/isolation & purification , Aristolochic Acids/blood , Sepharose/chemistry , Solid Phase Extraction/methods , Quaternary Ammonium Compounds/chemistry , Chromatography, High Pressure Liquid/methods , Porosity , Limit of Detection , Animals , Humans , Polymers/chemistry , Adsorption , Reproducibility of Results
15.
Org Biomol Chem ; 22(20): 4135-4144, 2024 05 22.
Article in English | MEDLINE | ID: mdl-38712466

ABSTRACT

Herein, we present an innovative synthetic approach for producing a diverse set of biobased oligomers. This method begins with olive oil and employs a wide variety of commercially available amino acids (AAs) as bio-organocatalysts, in addition to tetrabutylammonium iodide (TBAI) as a cocatalyst, to synthesize various biobased oligomers. These biobased oligomers were strategically prepared starting from epoxidized olive oil (EOO) and a variety of cyclic anhydrides (phthalic, PA; maleic, MA; succinic, SA; and glutaric, GA). Among the amino acids tested as bio-organocatalysts, L-glutamic acid (L-Glu) showed the best performance for the synthesis of both poly(EOO-co-PA) and poly(EOO-co-MA), exhibiting 100% conversion at 80 °C in 2 hours, whereas the formation of poly(EOO-co-SA) and poly(EOO-co-GA) required more extreme reaction conditions (72 hours under toluene reflux conditions). Likewise, we have succeeded in obtaining the trans isomer exclusively for the MA based-oligomer within the same synthetic framework. The obtained oligomers were extensively characterized using techniques including NMR, FT-IR, GPC and TGA. A series of computational simulations based on density functional theory (DFT) and post-Hartree Fock (post-HF) methods were performed to corroborate our experimental findings and to obtain an understanding of the reaction mechanisms.


Subject(s)
Amino Acids , Polymerization , Catalysis , Amino Acids/chemistry , Amino Acids/chemical synthesis , Green Chemistry Technology , Plant Oils/chemistry , Polymers/chemistry , Polymers/chemical synthesis , Molecular Structure , Quaternary Ammonium Compounds/chemistry , Quaternary Ammonium Compounds/chemical synthesis
16.
Biomed Mater ; 19(4)2024 Jun 20.
Article in English | MEDLINE | ID: mdl-38810617

ABSTRACT

Dental caries, a chronic infectious disease characterized by tooth mineral loss caused by plaque, is one of the major global public health problems. Silver diamine fluoride (SDF) has been proven to be a highly effective anti-caries drug due to its high bacterial inhibition and remineralization ability. However, the SDF solution is unstable, which immensely limits its clinical application. Therefore, new silver-load clay named AgF@Hec was designed by replacing the NH3with hectorite in this study. Fourier transform infrared spectroscopy and x-ray diffraction spectroscopy were employed to confirm the structure of AgF@Hec. Dynamic light scattering analysis was used to reveal the effect of different hectorite concentrations on the stability of AgF@Hec. Moreover, AgF@Hec exhibits significant remineralization and hardness recovery of the initial carious lesions. Bacteriostatic experiments also proved that it has a significant inhibitory effect onA. Viscosus, S. mutans, S. sanguinis, S. salivarius, Lactobacillus sp.and both gram-positive and gram-negative bacteria. We therefore believed that AgF@Hec should be a promising biomaterial that can be applied in the prevention of dental caries.


Subject(s)
Clay , Dental Caries , Quaternary Ammonium Compounds , Silver Compounds , Silver , X-Ray Diffraction , Dental Caries/prevention & control , Clay/chemistry , Silver Compounds/chemistry , Silver Compounds/pharmacology , Spectroscopy, Fourier Transform Infrared , Quaternary Ammonium Compounds/chemistry , Quaternary Ammonium Compounds/pharmacology , Silver/chemistry , Silver/pharmacology , Fluorides/chemistry , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Tooth Remineralization/methods , Streptococcus mutans/drug effects , Humans , Hardness , Materials Testing , Animals , Microbial Sensitivity Tests , Biocompatible Materials/chemistry , Biocompatible Materials/pharmacology , Fluorides, Topical
17.
Int J Biol Macromol ; 271(Pt 2): 132672, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38810855

ABSTRACT

Wound infection not only hinders the time sequence of tissue repair, but also may lead to serious complications. Multifunctional wound dressings with biocompatibility, excellent mechanical properties and antibacterial properties can promote wound healing during skin infection and reduce the use of antibiotics. In this study, a multifunctional dual-network antibacterial hydrogel was constructed based on the electrostatic interaction of two polyelectrolytes, hydroxypropyl trimethyl ammonium chloride chitosan (HACC) and sodium alginate (SA). Attributing to the suitable physical crosslinking between HACC and SA, the hydrogel not only has good biocompatibility, mechanical property, but also has broad-spectrum antibacterial properties. In vivo results showed that the hydrogel could regulate M2 polarization, promote early vascular regeneration, and create a good microenvironment for wound healing. Therefore, this hydrogel is an effective multifunctional wound dressing. Consequently, we propose a novel hydrogel with combined elements to expedite the intricate repair of wound infection.


Subject(s)
Alginates , Anti-Bacterial Agents , Chitosan , Hydrogels , Wound Healing , Wound Healing/drug effects , Hydrogels/chemistry , Hydrogels/pharmacology , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Chitosan/chemistry , Chitosan/pharmacology , Chitosan/analogs & derivatives , Animals , Alginates/chemistry , Alginates/pharmacology , Mice , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/chemistry , Quaternary Ammonium Compounds/chemistry , Quaternary Ammonium Compounds/pharmacology , Bacterial Infections/drug therapy , Male , Bandages , Staphylococcus aureus/drug effects
18.
Int J Mol Sci ; 25(9)2024 Apr 24.
Article in English | MEDLINE | ID: mdl-38731869

ABSTRACT

This review provides a comprehensive overview of recent advancements in the design and synthesis of biologically active quaternary ammonium compounds (QACs). The covered scope extends beyond commonly reviewed antimicrobial derivatives to include synthetic agents with antifungal, anticancer, and antiviral properties. Additionally, this review highlights examples of quaternary ammonium compounds exhibiting activity against protozoa and herbicidal effects, as well as analgesic and anesthetic derivatives. The article also embraces the quaternary-ammonium-containing cholinesterase inhibitors and muscle relaxants. QACs, marked by their inherent permanent charge, also find widespread usage across diverse domains such as fabric softeners, hair conditioners, detergents, and disinfectants. The effectiveness of QACs hinges greatly on finding the right equilibrium between hydrophilicity and lipophilicity. The ideal length of the alkyl chain varies according to the unique structure of each QAC and its biological settings. It is expected that this review will provide comprehensive data for medicinal and industrial chemists to design and develop novel QAC-based products.


Subject(s)
Quaternary Ammonium Compounds , Quaternary Ammonium Compounds/chemistry , Quaternary Ammonium Compounds/chemical synthesis , Quaternary Ammonium Compounds/pharmacology , Humans , Animals , Anti-Infective Agents/pharmacology , Anti-Infective Agents/chemical synthesis , Anti-Infective Agents/chemistry , Cholinesterase Inhibitors/chemical synthesis , Cholinesterase Inhibitors/pharmacology , Cholinesterase Inhibitors/chemistry
19.
Biomacromolecules ; 25(6): 3731-3740, 2024 Jun 10.
Article in English | MEDLINE | ID: mdl-38712827

ABSTRACT

Interface engineering is essential for cellulosic fiber-reinforced polymer composites to achieve high strength and toughness. In this study, carboxymethyl cellulose (CMC) functionalized with hydrophobic quaternary ammonium ions (QAs) were utilized to modify the interface between holocellulose fibers (HF) and acrylic resin. The wet HF/CMC papers were prepared by vacuum filtration, akin to papermaking, followed by cationic ion exchange with different hydrophobic QAs. Subsequently, the modified papers were dried, impregnated with an acrylic resin monomer, and cured to produce transparent composite films. The effect of the hydrophobic QA moieties on the structure and optical and mechanical properties of the HF/CMC/acrylic resin composites were investigated. The composite film with cetyltrimethylammonium (CTA)-functionalized CMC showed high optical transmittance (87%) with low haze (43%), while the composite film with phenyltrimethylammonium (PTMA)-functionalized CMC demonstrated high Young's modulus of 7.6 GPa and high tensile strength of 180 MPa. These properties are higher than those of the composites prepared through covalent interfacial modification strategies. The results highlighted the crucial role of hydrophobic functionalized CMCs in facilitating homogeneous resin impregnation in the HF fiber network, producing a composite with enhanced interfacial adhesion strength, increased optical transparency, and mechanical strength. This facile use of hydrophobic CMCs as interfacial compatibilizers provides an energy-efficient route for preparing transparent, thin, and flexible composite films favorable in optoelectronic applications.


Subject(s)
Acrylic Resins , Carboxymethylcellulose Sodium , Hydrophobic and Hydrophilic Interactions , Tensile Strength , Carboxymethylcellulose Sodium/chemistry , Acrylic Resins/chemistry , Quaternary Ammonium Compounds/chemistry , Cellulose/chemistry , Elastic Modulus
20.
Int J Biol Macromol ; 271(Pt 2): 132345, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38750848

ABSTRACT

As an important source of green cleaning flame retardants, bio-based materials have been widely studied by researchers. However, the development of efficient biobased flame retardants and convenient finishing methods was of great significance for the functional finishing of materials. Herein, a convenient and efficient flame retardant cotton fabric was prepared via layer by layer self-assembly (LbL) by alternating precipitation of a novel bio-based flame retardant phosphorylated sodium alginate (PSA) and alkylammonium functionalized siloxane (A-POSS). The effect of coating number on flame retardancy and thermal properties of coated cotton fabric was systematically studied. Thermogravimetric analysis (TGA) results showed that residual char contents of AP/PS-15BL under air and N2 atmospheres increased by 252.0% and 225.2%, respectively, compared with control cotton. In vertical flammability tests, both the AP/PS-10BL and AP/PS-15BL showed self-extinguishing behavior and successfully passed the UL-94 V-0 rating. More importantly, the LOI value of AP/PS-15BL was significantly increased to 35.0% from 20.0% of pure cotton fabric. Additionally, coated samples showed good mechanical properties and washable resistance. In CONE test, the peak heat release rate (PHRR) and total heat release rate (THR) of AP/PS-15BL decreased by 89.3% and 49.3% respectively, compared with control cotton. Therefore, this green and convenient flame-retardant finishing method has great application potential in the multi-functional finishing of cotton fabrics.


Subject(s)
Alginates , Cotton Fiber , Flame Retardants , Alginates/chemistry , Phosphorylation , Organosilicon Compounds/chemistry , Textiles , Thermogravimetry , Quaternary Ammonium Compounds/chemistry
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