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1.
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
2.
Biomed Mater ; 19(5)2024 Jul 05.
Article in English | MEDLINE | ID: mdl-38917812

ABSTRACT

Stopping postoperative soft tissue adhesions is one of the most challenging clinical problems that needs to be addressed urgently to avoid secondary injury and pain to patients. Currently, membrane materials with anti-protein adsorption and antibacterial activity are recognized as an effective and promising anti-adhesion barrier to prevent postoperative adhesion and the recurrent adhesion after adhesiolysis. Herein, poly(amino acid) (PAA), which is structurally similar to collagen, is selected as the membrane base material to successfully synthesize PAA-5 membranes with excellent mechanical and degradation properties by in-situ melt polymerization and hot-melt film-forming technology. Subsequently, the co-deposition of polydopamine/polysulfobetaine methacrylate (PDA/PSBMA) coatings induced by CuSO4/H2O2on PAA-5 membranes results in the formation of PDC-5S and PDC-10S, which exhibit excellent hemocompatibility, protein antifouling properties, and cytocompatibility. Additionally, PDC-5S and PDC-10S demonstrated significant antibacterial activity againstEscherichia coliandStaphylococcus aureus, with an inhibition rate of more than 90%. As a result, this study sheds light on newly discovered PAA membranes with anti-protein adsorption and antibacterial activity can sever as one of the promising candidates for the prevention of postoperative peritoneum adhesions.


Subject(s)
Anti-Bacterial Agents , Escherichia coli , Hydrogen Peroxide , Indoles , Membranes, Artificial , Methacrylates , Polymers , Staphylococcus aureus , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Polymers/chemistry , Adsorption , Indoles/chemistry , Indoles/pharmacology , Methacrylates/chemistry , Escherichia coli/drug effects , Staphylococcus aureus/drug effects , Humans , Hydrogen Peroxide/chemistry , Animals , Materials Testing , Amino Acids/chemistry , Biofouling/prevention & control , Coated Materials, Biocompatible/chemistry , Coated Materials, Biocompatible/pharmacology , Betaine/chemistry , Betaine/analogs & derivatives , Tissue Adhesions/prevention & control
3.
J Mater Chem B ; 12(22): 5455-5464, 2024 Jun 05.
Article in English | MEDLINE | ID: mdl-38742282

ABSTRACT

Polyurethane (PU) catheters are commonly used in clinical treatment. However, the hydrophobic nature of the PU catheter surface leads to adhesion or adsorption to platelets, proteins, bacteria, and other molecules when used in human treatment. To achieve a surface with strong hydrophilicity, high stability and excellent biocompatibility, it is necessary to functionalize the PU catheters. In this paper, a coating with antifouling function was constructed on the surface of PU catheters using plasma technology and an amide coupling reaction. A series of characterization methods, including X-ray photoelectron spectroscopy (XPS), water contact angles (WCA), and atomic force microscopy (AFM), were used to prove the successful modification of the polymer coatings. The coatings showed good stability under conditions such as PBS (pH 7.4, 720 h), 75% ethanol (6 h) and 1 wt% SDS (10 min). Additionally, the coatings exhibit excellent hemocompatibility and antibacterial properties. The PU/PEI/PCSB coating has the best anti-fouling performance among them, which means that using the PCSB copolymer has the potential to modify different clinical catheters into highly effective antifouling coatings.


Subject(s)
Betaine , Surface Properties , Humans , Betaine/chemistry , Betaine/analogs & derivatives , Betaine/pharmacology , Polyurethanes/chemistry , Polyurethanes/pharmacology , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/chemical synthesis , Coated Materials, Biocompatible/chemistry , Coated Materials, Biocompatible/pharmacology , Biofouling/prevention & control , Staphylococcus aureus/drug effects , Escherichia coli/drug effects , Animals , Materials Testing , Polymers/chemistry , Polymers/pharmacology
4.
Contact Dermatitis ; 91(2): 139-145, 2024 Aug.
Article in English | MEDLINE | ID: mdl-38783163

ABSTRACT

BACKGROUND: Chemical hair relaxers are widely utilized by black women, yet little research exists on the allergens present in these products. OBJECTIVE: This study aims to investigate allergen prevalence in the most popular chemical hair relaxers. METHODS: We analysed 41 products from five major retailers, identifying allergens through ingredient lists and comparing them to the 2020 American Contact Dermatitis Group Core allergen series. RESULTS: The most common contact allergens in chemical relaxers include propylene glycol, cetyl steryl alcohol, fragrance, D/L-a-tocopherol, tea tree oil and cocamidopropyl betaine. CONCLUSION: Understanding allergen exposure in products used by individuals with textured hair is needed for managing contact dermatitis in diverse populations. This analysis underscores the presence of potential allergens in hair relaxers, emphasizing the importance of dermatologists' awareness and patient scrutiny of ingredient lists.


Subject(s)
Allergens , Dermatitis, Allergic Contact , Hair Preparations , Humans , Hair Preparations/adverse effects , Hair Preparations/chemistry , Allergens/adverse effects , Allergens/analysis , Dermatitis, Allergic Contact/etiology , Betaine/analogs & derivatives , Betaine/adverse effects , Betaine/analysis , Tea Tree Oil/adverse effects , Tea Tree Oil/analysis , Perfume/adverse effects , Perfume/analysis , Propylene Glycol/adverse effects , Propylene Glycol/analysis , Female
5.
Int J Mol Sci ; 25(10)2024 May 17.
Article in English | MEDLINE | ID: mdl-38791538

ABSTRACT

Various studies have shown that Hypogymnia physodes are a source of many biologically active compounds, including lichen acids. These lichen-specific compounds are characterized by antioxidant, antiproliferative, and antimicrobial properties, and they can be used in the cosmetic and pharmaceutical industries. The main aim of this study was to optimize the composition of natural deep eutectic solvents based on proline or betaine and lactic acid for the extraction of metabolites from H. physodes. The design of the experimental method and the response surface approach allowed the optimization of the extraction process of specific lichen metabolites. Based on preliminary research, a multivariate model of the experiment was developed. For optimization, the following parameters were employed in the experiment to confirm the model: a proline/lactic acid/water molar ratio of 1:2:2. Such a mixture allowed the efficient extraction of three depsidones (i.e., physodic acid, physodalic acid, 3-hydroyphysodic acid) and one depside (i.e., atranorin). The developed composition of the solvent mixtures ensured good efficiency when extracting the metabolites from the thallus of H. physodes with high antioxidant properties.


Subject(s)
Depsides , Lactones , Depsides/chemistry , Depsides/isolation & purification , Depsides/pharmacology , Lactones/chemistry , Lactones/isolation & purification , Lactones/pharmacology , Deep Eutectic Solvents/chemistry , Antioxidants/chemistry , Antioxidants/pharmacology , Antioxidants/isolation & purification , Proline/chemistry , Lichens/chemistry , Lactic Acid/chemistry , Green Chemistry Technology/methods , Betaine/chemistry , Betaine/analogs & derivatives , Betaine/pharmacology , Solvents/chemistry , Dibenzoxepins , Hydroxybenzoates
6.
Biomater Adv ; 160: 213839, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38579521

ABSTRACT

Pulmonary delivery of protein therapeutics poses significant challenges that have not been well addressed in the research literature or practice. In fact, there is currently only one commercial protein therapeutic that is delivered through aerosolization and inhalation. In this study, we propose a drug delivery strategy that enables a high-concentration dosage for the pulmonary delivery of antibodies as an aerosolizable solid powder with desired stability. We utilized zwitterionic polymers for their promising properties as drug delivery vehicles and synthesized swellable, biodegradable poly(sulfo-betaine) (pSB) microparticles. The microparticles were loaded with Immunoglobulin G (IgG) as a model antibody. We quantified the microparticle size and morphology, and the particles were found to have an average diameter of 1.6 µm, falling within the optimal range (~1-5 µm) for pulmonary drug delivery. In addition, we quantified the impact of the crosslinker to monomer ratio on particle morphology and drug loading capacity. The results showed that there is a trade-off between desired morphology and drug loading capacity as the crosslinker density increases. In addition, the particles were aerosolized, and our data indicated that the particles remained intact and retained their initial morphology and size after aerosolization. The combination of morphology, particle size, antibody loading capacity, low cytotoxicity, and ease of aerosolization support the potential use of these particles for pulmonary delivery of protein therapeutics.


Subject(s)
Aerosols , Betaine , Betaine/analogs & derivatives , Particle Size , Betaine/chemistry , Humans , Administration, Inhalation , Immunoglobulin G/chemistry , Immunoglobulin G/administration & dosage , Drug Delivery Systems/methods , Polymers/chemistry , Drug Carriers/chemistry , Animals , Antibodies/chemistry , Microspheres
7.
Int J Pharm ; 657: 124160, 2024 May 25.
Article in English | MEDLINE | ID: mdl-38663642

ABSTRACT

Addressing the pervasive issue of bacteria and biofilm infections is crucial in the development of advanced antifouling wound dressings. In this study, a novel wound healing treatment using sulfobetaine (SBMA) decorated electrospun fibrous membrane based on polycaprolactone (PCL)/nitric oxide (NO) donors was developed. The fabrication involved a dual strategy, first integrating NO donors into mesoporous polydopamine (MPDA) and complexed with PCL/PEI to electrospin nanofibers. The fibrous membrane exhibited a potent antibacterial response upon irradiation at 808 nm, owing to a combination of NO and photothermal effect that effectively targets bacteria and disrupts biofilms. Surface functionalization of the membrane with PEI allowed for the attachment of SBMA via Michael addition, fabricating a zwitterionic surface, which significantly hinders protein adsorption and reduces biofilm formation on the wound dressing. In vitro and in vivo assessments confirmed the rapid bactericidal capabilities and its efficacy in biofilm eradication. Combining photothermal activity, targeted NO release and antifouling surface, this multifaceted wound dressing addresses key challenges in bacterial infection management and biofilm eradication, promoting efficient wound healing.


Subject(s)
Anti-Bacterial Agents , Bandages , Betaine , Biofilms , Indoles , Nanofibers , Polyesters , Wound Healing , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/administration & dosage , Biofilms/drug effects , Animals , Wound Healing/drug effects , Polyesters/chemistry , Indoles/chemistry , Indoles/pharmacology , Betaine/chemistry , Betaine/pharmacology , Betaine/analogs & derivatives , Nanofibers/chemistry , Polymers/chemistry , Nitric Oxide/metabolism , Staphylococcus aureus/drug effects , Biofouling/prevention & control , Nitric Oxide Donors/pharmacology , Nitric Oxide Donors/chemistry , Mice , Surface Properties , Escherichia coli/drug effects , Polyethyleneimine/chemistry
8.
J Control Release ; 369: 39-52, 2024 May.
Article in English | MEDLINE | ID: mdl-38508523

ABSTRACT

The emergence of multidrug-resistant bacteria along with their resilient biofilms necessitates the development of creative antimicrobial remedies. We designed versatile fluorinated polymer micelles with surface-charge-switchable properties, demonstrating enhanced efficacy against Methicillin-Resistant Staphylococcus Aureus (MRSA) in planktonic and biofilm states. Polymethacrylate diblock copolymers with pendant fluorocarbon chains and carboxyl betaine groups were prepared using reversible addition-fragmentation chain transfer polymerization. Amphiphilic fluorinated copolymers self-assembled into micelles, encapsulating ciprofloxacin in their cores (CIP@FCBMs) for antibacterial and antibiofilm applications. As a control, fluorine-free copolymer micelles loaded with ciprofloxacin (CIP@BCBMs) were prepared. Although both CIP@FCBMs and CIP@BCBMs exhibited pH-responsive surface charges and lipase-triggered drug release, CIP@FCBMs exhibited powerful antimicrobial and antibiofilm activities in vitro and in vivo, attributed to superior serum stability, higher drug loading, enhanced fluorination-facilitated cellular uptake, and lipase-triggered drug release. Collectively, reversing surface charge, on-demand antibiotic release, and fluorination-mediated nanoparticles hold promise for treating bacterial infections and biofilms.


Subject(s)
Anti-Bacterial Agents , Betaine , Biofilms , Ciprofloxacin , Lipase , Methicillin-Resistant Staphylococcus aureus , Staphylococcal Infections , Methicillin-Resistant Staphylococcus aureus/drug effects , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/administration & dosage , Anti-Bacterial Agents/chemistry , Biofilms/drug effects , Lipase/metabolism , Hydrogen-Ion Concentration , Animals , Betaine/chemistry , Betaine/administration & dosage , Betaine/analogs & derivatives , Staphylococcal Infections/drug therapy , Ciprofloxacin/pharmacology , Ciprofloxacin/administration & dosage , Ciprofloxacin/chemistry , Fluorocarbons/chemistry , Fluorocarbons/pharmacology , Micelles , Drug Liberation , Polymers/chemistry , Humans , Polymethacrylic Acids/chemistry
10.
Physiol Plant ; 176(1): e14206, 2024.
Article in English | MEDLINE | ID: mdl-38356346

ABSTRACT

Aroma or fragrance in rice is a genetically controlled trait; Its high appreciation by consumers increases the rice market price. Previous studies have revealed that the rice aroma is controlled by a specific gene called BETAINE ALDEHYDE DEHYDROGENASE (OsBADH2), and mutation of this gene leads to the accumulation of an aromatic substance 2-acetyl-1-pyrroline (2-AP). The use of genetic engineering to produce aroma in commercial and cultivated hybrids is a contemporary need for molecular breeding. The current study reports the generation of aroma in the three-line hybrid restorer line Shu-Hui-313 (SH313). We created knock-out (KO) lines of OsBADH2 through the CRISPR/Cas9. The analysis of KO lines revealed a significantly increased content of 2AP in the grains compared with the control. However, other phenotypic traits (plant height, seed setting rate, and 1000-grain weight) were significantly decreased. These KO lines were crossed with a non-aromatic three-line hybrid rice male sterile line (Rong-7-A) to produce Rong-7-You-626 (R7Y626), R7Y627 and R7Y628. The measurement of 2-AP revealed significantly increased contents in these cross combinations. We compared the content of 2-AP in tissues at the booting stage. Data revealed that young spike stalk base contained the highest content of 2-AP and can be used for identification (by simple chewing) of aromatic lines under field conditions. In conclusion, our dataset offers a genetic source and illustrates the generation of aroma in non-aromatic hybrids, and outlines a straightforward identification under field conditions.


Subject(s)
Betaine/analogs & derivatives , Oryza , Oryza/genetics , CRISPR-Cas Systems/genetics , Odorants , Genes, Plant
11.
Int J Biol Macromol ; 260(Pt 1): 129465, 2024 Mar.
Article in English | MEDLINE | ID: mdl-38242394

ABSTRACT

Chitosan exhibits a wide source, non-toxic and biodegradable, and is the optimal functional raw material for preparing food packaging materials. However, the pure chitosan film has some disadvantages such as limited antibacterial activity and weak mechanical properties. In this study, sulfobetaines modified chitosan (CS-SBMA) was synthesized by grafting copolymerized betaine methacrylate sulfonate onto the chain of chitosan to improve the anti-bacterial adhesion and antibacterial properties of chitosan, aiming to develop antibacterial and anti-bacterial adhesion films based on CS-SBMA and polyvinyl alcohol (PVA) by the casting method. The structure of CS-SBMA was characterized by 1H NMR and FTIR. The appropriate proportion of CS-SBMA/PVA was determined to be 1/1 and 1/2, by characterizing the composite films with FTIR, XRD, SEM, mechanical, optical, and water resistance behaviors. In addition, CS-SBMA/PVA films showed excellent antibacterial, anti-bacterial adhesion and biofilm control function. The colonies number of E. coli and S. aureus on the surface of CS-SBMA/PVA 1/1 film decreased 94.15 % and 94.27 %, respectively, and 92.93 % of S. aureus and 94.87 % of E. coli colonies were inactivated within 60 min contact. These results indicate that CS-SBMA/PVA film exhibits potential antibacterial and anti-bacterial adhesion properties, which is suitable for food packaging materials.


Subject(s)
Betaine/analogs & derivatives , Chitosan , Chitosan/chemistry , Polyvinyl Alcohol/chemistry , Staphylococcus aureus , Escherichia coli , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Food Packaging/methods
12.
Environ Sci Pollut Res Int ; 31(2): 2314-2326, 2024 Jan.
Article in English | MEDLINE | ID: mdl-38057675

ABSTRACT

Water treatment for most public pools involves disinfection with active chlorine leading to the formation of disinfection by-products (DBPs). Among them, nitrogen-containing compounds (N-DBPs) having increased toxicity and adverse effects on human health are of the greatest concern. Being the major component of various body washers for swimmers, cocamidopropyl betaine (CAPB) represents a potential and still underestimated anthropogenic precursor of N-DBPs in pool water. The purpose of this study was to investigate CAPB transformation pathways and mechanisms under the aqueous chlorination conditions. High-performance liquid and two-dimensional gas chromatography hyphenated with high-resolution mass spectrometry were used for the search and tentative identification of the primary and final CAPB transformation products. A wide range of DBPs containing up to five chlorine atoms including these in combination with hydroxyl and additional carbonyl groups has been revealed in model chlorination experiments for the first time. The proposed mechanism of their formation involves nucleophilic substitution of the secondary amide hydrogen atom at the first stage with subsequent free radical and electrophilic addition reactions resulting in non-selective introduction of halogen atoms and hydroxyl groups in the alkyl chain. The deep transformation products include short-chain chlorinated hydrocarbons and their oxidation products as well as dimethylcarbamoyl chloride possessing high toxicity and carcinogenic properties. Targeted analysis of real swimming pool water samples confirmed the results of model experiments enabling semi-quantitative determination of CAPB (0.8 µg L-1) and 18 primary DBPs, including 10 chlorine-containing compounds with the total concentration of 0.1 µg L-1. Among them, monochloro (50%) and hydroxydichloro (25%) derivatives predominate. The toxicity and health of the main DBPs has been estimated using QSAR/QSTR approach. Thus, the possibility of formation of new classes of potentially toxic chlorine-containing DBPs associated with the widespread use of detergents and cosmetics was shown.


Subject(s)
Betaine/analogs & derivatives , Chlorine Compounds , Disinfectants , Hydrocarbons, Chlorinated , Swimming Pools , Water Pollutants, Chemical , Water Purification , Humans , Disinfection , Disinfectants/chemistry , Chlorine/chemistry , Nitrogen/analysis , Hydrocarbons, Chlorinated/analysis , Chlorine Compounds/analysis , Halogenation , Nitrogen Compounds , Chlorides , Water Pollutants, Chemical/analysis
13.
ACS Appl Bio Mater ; 7(1): 144-153, 2024 01 15.
Article in English | MEDLINE | ID: mdl-38150303

ABSTRACT

Cell migration is an essential dynamic process for most living cells, mainly driven by the reorganization of actin cytoskeleton. To control actin dynamics, a molecular architecture that can serve as a nucleator has been designed by polymerizing sulfobetaine methacrylate. The synthesized zwitterionic polymer, poly(sulfobetaine methacrylate) (PZI), effectively nucleates the polymerization process of G-actin and substantially accelerates the rate of polymerization. Isothermal titration calorimetry (ITC) and bioinformatics analysis indicated binding between PZI and monomeric G-actin. Thus, in vitro actin dynamics was studied by dynamic light scattering (DLS), pyrene-actin polymerization assay, and total internal reflection fluorescence microscopy (TIRFM). Furthermore, a 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) fluorophore-containing monomeric unit was incorporated into the sulfobetaine zwitterionic architecture to visualize the effect of polymer in the cellular environment. The BODIPY-containing zwitterionic sulfobetaine polymer (PZI-F) successfully penetrated the cell and remained in the lysosome with minimal cytotoxicity. Confocal microscopy revealed the influence of this polymer on the cellular actin cytoskeleton dynamics. The PZI-F polymer was successfully able to inhibit the collective migration of the human cervical cancer cell line (HeLa cell) and breast cancer cell line (MDA-MB-231 cell), as confirmed by a wound healing assay. Therefore, polyzwitterionic sulfobetaine could be explored as an inhibitor of cancer cell migration.


Subject(s)
Actins , Betaine/analogs & derivatives , Boron Compounds , Neoplasms , Humans , Actins/metabolism , HeLa Cells , Actin Cytoskeleton/metabolism , Cell Movement
14.
Phys Chem Chem Phys ; 24(37): 22679-22690, 2022 Sep 28.
Article in English | MEDLINE | ID: mdl-36106535

ABSTRACT

Mixtures of sulfobetaine based lipids with phosphocholine phospholipids are of interest in order to study the interactions between zwitterionic surfactants and the phospholipids present in cell membranes. In this study we have investigated the structure of mixed monolayers of sulfobetaines and phosphocholine phospholipids. The sulfobetaine used has a single 18-carbon tail, and is referred to as SB3-18, and the phospholipid used is DMPC. Surface pressure-area isotherms of the samples were used to determine whether any phase transitions were present during the compression of the monolayers. Neutron and X-ray reflectometry were then used to investigate the structure of these monolayers perpendicular to the interface. We found that the average headgroup and tail layer thickness was reasonably consistent across all mixtures, with a variation of less than 3 Å reported in the total thickness of the monolayers at each surface pressure. However, by selective deuteration of the two components of the monolayers, it was found that the two components have different tail layer thicknesses. For the mixture with equal compositions of DMPC and SB3-18 or with a higher composition of DMPC the tail tilts were found to be constant, resulting in a greater tail layer thickness for SB3-18 due to its longer tail. For the mixture higher in SB3-18 this was not the case, the tail tilt angle for the two components was found to be different and DMPC was found to have a greater tail layer thickness than SB3-18 as a result.


Subject(s)
Phospholipids , Water , Betaine/analogs & derivatives , Carbon , Dimyristoylphosphatidylcholine/chemistry , Phospholipids/chemistry , Phosphorylcholine , Surface Properties , Surface-Active Agents , Water/chemistry
15.
J Mater Chem B ; 10(39): 7979-7994, 2022 10 12.
Article in English | MEDLINE | ID: mdl-36093922

ABSTRACT

Antibacterial wound dressing is essential for inflammation control and accelerated wound healing. This study investigates polyzwitterion-functionalized silver nanoparticles (AgNPs) with enhanced antibacterial performance in an injectable wound dressing hydrogel. A mussel-inspired poly(sulfobetaine methacrylate-co-dopamine methacrylamide) (PSBDA) copolymer consisting of sulfobetaine and catechol moieties is developed and used in the stabilizing strategy for a facile one-step synthesis of AgNPs. The catechol moieties in PSBDA reduce AgNO3 in an alkaline solution and anchor PSBDA onto the surface of AgNPs. The zwitterionic AgNPs exhibit a uniform size profile and significantly improved stability, which are critical for maintaining antibacterial efficiency in a physiological environment. An injectable wound dressing hydrogel is developed by incorporating zwitterionic AgNPs into the mixed precursors of gelatin methacryloyl (GelMA) and poly(vinyl alcohol) (PVA). The hydrogel precursors exhibit good injectability and rapidly respond to UV-induced in situ gelation. The zwitterionic AgNP-incorporating hydrogel demonstrates significantly improved antibacterial efficiency compared to the non-zwitterionic counterpart both in vitro and in vivo. The zwitterionic modification also provides enhanced hemocompatibility and biocompatibility. The as-developed hydrogel dressing facilitates the resolution of inflammation and results in a rapid re-epithelization for the accelerated wound healing process in a rat full-thickness wound model.


Subject(s)
Metal Nanoparticles , Silver , Animals , Anti-Bacterial Agents/pharmacology , Betaine/analogs & derivatives , Catechols , Dopamine/pharmacology , Gelatin , Hydrogels/pharmacology , Inflammation , Methacrylates/pharmacology , Polyvinyl Alcohol/pharmacology , Rats , Silver/pharmacology , Wound Healing
16.
J Alzheimers Dis ; 89(4): 1439-1452, 2022.
Article in English | MEDLINE | ID: mdl-36057823

ABSTRACT

BACKGROUND: Animal studies suggest that gut microbiome metabolites such as trimethylamine N-oxide (TMAO) may influence cognitive function and dementia risk. However potential health effects of TMAO and related metabolites remain unclear. OBJECTIVE: We examined prospective associations of TMAO, γ-butyrobetaine, crotonobetaine, carnitine, choline, and betaine with risk of cognitive impairment and dementia among older adults aged 65 years and older in the Cardiovascular Health Study (CHS). METHODS: TMAO and metabolites were measured in stored plasma specimens collected at baseline. Incident cognitive impairment was assessed using the 100-point Modified Mini-Mental State Examination administered serially up to 7 times. Clinical dementia was identified using neuropsychological tests adjudicated by CHS Cognition Study investigators, and by ICD-9 codes from linked Medicare data. Associations of each metabolite with cognitive outcomes were assessed using Cox proportional hazards models. RESULTS: Over a median of 13 years of follow-up, 529 cases of cognitive impairment, and 522 of dementia were identified. After multivariable adjustment for relevant risk factors, no associations were seen with TMAO, carnitine, choline, or betaine. In contrast, higher crotonobetaine was associated with 20-32% higher risk of cognitive impairment and dementia per interquintile range (IQR), while γ-butyrobetaine was associated with ∼25% lower risk of the same cognitive outcomes per IQR.∥Conclusion:These findings suggest that γ-butyrobetaine, crotonobetaine, two gut microbe and host metabolites, are associated with risk of cognitive impairment and dementia. Our results indicate a need for mechanistic studies evaluating potential effects of these metabolites, and their interconversion on brain health, especially later in life.


Subject(s)
Cognitive Dysfunction , Dementia , Animals , Betaine/analogs & derivatives , Betaine/metabolism , Carnitine/metabolism , Choline , Cognitive Dysfunction/epidemiology , Dementia/epidemiology , Medicare , Methylamines/metabolism , United States/epidemiology
17.
J Chromatogr A ; 1681: 463442, 2022 Oct 11.
Article in English | MEDLINE | ID: mdl-36058078

ABSTRACT

We have coated a typical C18 column with the pH cationic charge controllable zwitterionic synthetic surfactant, cocamidopropyl betaine (CAPB), in order to generate a mixed mode reversed phase weak ion exchange column. As determined by the Thomas model, the column has an adsorbed surfactant capacity of 0.557 mmoles. The addition of 8.8 × 10-4 M CAPB to the totally aqueous mobile phase ensured stability of the surfactant on the column and permitted separation of the four component sulfonamide mixture with micellar liquid chromatography (MLC) in under 11 min. Comparatively, with a dilute H2SO4 mobile phase with no CAPB, the separation time for the sulfonamide mixture reached an excessive run time of an hour on the bare C18 chains. With CAPB in the mobile phase (no organic solvent present), a seven component sulfonamide mixture could be separated in less than 45 min. A five component short chain carboxylic acid mixture, separated in 20 min, was used to examine the ion exchange character of the column in pH environments of 2.3 and 4.6. Three phase MLC equilibrium analysis was also done in these pH environments with the sulfa drug and carboxylic acid mixtures to determine partition coefficients. Finally, a quite high molecular weight (70,000) anionic polystyrene sulfonate polymer was characterized by MLC with only CAPB and variable pH mobile phases; the optimal pH was determined to be 5.6. A totally aqueous mobile phase without CAPB was not suitable for profiling this polymer.


Subject(s)
Micelles , Surface-Active Agents , Betaine/analogs & derivatives , Carboxylic Acids , Chromatography, Liquid , Polymers , Solvents/chemistry , Sulfonamides , Surface-Active Agents/chemistry , Water/chemistry
18.
Biomacromolecules ; 23(10): 4349-4356, 2022 10 10.
Article in English | MEDLINE | ID: mdl-36049071

ABSTRACT

Inspired by the melanogenesis occurring in nature, we report tyrosinase-mediated antifouling surface coating by synthesizing a tyrosine-conjugated sulfobetaine derivative (Tyr-SB). Synthetic Tyr-SB contains zwitterionic sulfobetaine and tyrosine, whose phenolic amine group acts as a dormant coating precursor. In contrast to catecholamine derivatives, tyrosine derivatives are stable against auto-oxidation and are enzymatically oxidized only in the presence of tyrosinase to initiate melanin-like oxidation. When the surface of interest was applied during the course of Tyr-SB oxidation, a superhydrophilic poly(Tyr-SB) film was coated on the surfaces, thereby showing antifouling performance against proteins or adherent cells. Because the oxidation of Tyr-SB occurred under mild aqueous conditions (pH 6-7) without the use of any chemical oxidants, such as sodium periodate or ammonium persulfate, we anticipate that the coating method described herein will serve as a biocompatible tool in the field of biosensors, cell surface engineering, and medical devices, whose interfaces differ in chemistry.


Subject(s)
Biofouling , Monophenol Monooxygenase , Betaine/analogs & derivatives , Biofouling/prevention & control , Catecholamines , Melanins , Oxidants , Tyrosine
19.
Soft Matter ; 18(35): 6618-6628, 2022 Sep 14.
Article in English | MEDLINE | ID: mdl-36000279

ABSTRACT

The ubiquitous nature of microorganisms, especially of biofilm-forming bacteria, makes biofouling a prevalent challenge in many settings, including medical and industrial environments immersed in liquid and subjected to shear forces. Recent studies have shown that zwitterionic groups are effective in suppressing bacteria and protein adhesion as well as biofilm growth. However, the effect of zwitterionic groups on the removal of surface-bound bacteria has not been extensively studied. Here we present a microfluidic approach to evaluate the effectiveness in facilitating bacteria detachment by shear of an antifouling surface treatment using (3-(dimethyl;(3-trimethoxysilyl)propyl)ammonia propane-1-sulfonate), a sulfobetaine silane (SBS). Control studies show that SBS-functionalized surfaces greatly increase protein (bovine serum albumin) removal upon rinsing. On the same surfaces, enhanced bacteria (Pseudomonas aeruginosa) removal is observed under shear. To quantify this enhancement a microfluidic shear device is employed to investigate how SBS-functionalized surfaces promote bacteria detachment under shear. By using a microfluidic channel with five shear zones, we compare the removal of bacteria from zwitterionic and glass surfaces under different shear rates. At times of 15 min, 30 min, and 60 min, bacteria adhesion on SBS-functionalized surfaces is reduced relative to the control surface (glass) under quiescent conditions. However, surface-associated bacteria on the SBS-functionalized glass and control show similar percentages of live cells, suggesting minimal intrinsic biocidal effect from the SBS-functionalized surface. Notably, when exposed to shear rates ranging from 104 to 105 s-1, significantly fewer bacteria remain on the SBS-functionalized surfaces. These results demonstrate the potential of zwitterionic sulfobetaine as effective antifouling coatings that facilitate the removal of bacteria under shear.


Subject(s)
Bacterial Adhesion , Biofouling , Bacteria , Betaine/analogs & derivatives , Betaine/chemistry , Betaine/pharmacology , Biofouling/prevention & control , Surface Properties
20.
Acta Biomater ; 151: 290-303, 2022 10 01.
Article in English | MEDLINE | ID: mdl-35995406

ABSTRACT

Zwitterionic polymers have shown promising results in non-fouling and preventing thrombosis. However, the lack of controlled surface coverage hinders their application for biomedical devices. Inspired by the natural biological surfaces, a facile zwitterionic microgel-based coating strategy is developed by the co-deposition of poly (sulfobetaine methacrylate-co-2-aminoethyl methacrylate) microgel (SAM), polydopamine (PDA), and sulfobetaine-modified polyethyleneimine (PES). The SAMs were used to construct controllable morphology by using the PDA combined with PES (PDAS) as the intermediate layer, which can be easily modulated via adjusting the crosslinking degree and contents of SAMs. The obtained SAM/PDAS coatings exhibit high anti-protein adhesive properties and can effectively inhibit the adhesion of cells, bacteria, and platelet through the synergy of high deposition density and controllable morphology. In addition, the stability of SAM/PDAS coating is improved owing to the anchoring effects of PDAS to substrate and SAMs. Importantly, the ex vivo blood circulation test in rabbits suggests that the SAM/PDAS coating can effectively decrease thrombosis without anticoagulants. This study provides a versatile coating method to address the integration of zwitterionic microgel-based coatings with high deposition density and controllable morphology onto various substrates for wide biomedical device applications. STATEMENT OF SIGNIFICANCE: Thrombosis is a major cause of medical device implantation failure, which results in significant morbidity and mortality. In this study, inspired by natural biological surfaces (fish skin and vascular endothelial layer) and the anchoring ability of mussels, we report a convenient and efficient method to firmly anchor zwitterionic microgels using an oxidative co-deposition strategy. The prepared coating has excellent antifouling and antithrombotic properties through the synergistic effect of physical morphology and chemical composition. This biomimetic surface engineering strategy is expected to provide new insights into the clinical problems of blood-contacting devices related to thrombosis.


Subject(s)
Microgels , Animals , Anticoagulants , Betaine/analogs & derivatives , Fibrinolytic Agents , Methacrylates , Polyethyleneimine/pharmacology , Polymers/chemistry , Rabbits , Surface Properties
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