EDC‐Mediated Grafting of Quaternary Ammonium Salts onto Chitosan for Antibacterial and Thermal Properties Improvement

Oyervides–Muñoz, Ernesto; Avérous, Luc; Sosa‐Santillán, Gerardo de Jesús; Pollet, Éric; Pérez‐Aguilar, Nancy Verónica; Rojas‐Caldera, Claudia Maribel; Fuentes‐Avilés, José Guadalupe; García‐Astrain, Clara

doi:10.1002/macp.201800530

Cited by 13 publications

(8 citation statements)

References 52 publications

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“…In recent years, our research team has devoted extensive efforts on the preparation of functional biobased polymers derivatives by different routes for quaternary ammonium grafting, in order to increase their bioactivities such as antibacterial, biocompatibility, and proliferation inhibition properties of different types of cancer [33][34][35] as a continuation of successful attempts in the search for biologically active biobased polymer derivatives.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and antibacterial activities of novel starch derivatives against E. coli and S. aureus

et al. 2022

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Three novel starch derivatives with antibacterial properties are synthesized through a rather simple multistep synthesis route. In a first step, sodium periodate oxidation of the hydroxyl groups (C2–C3) of starch yields a di‐aldehyde structure, which is used to attach N,N‐dimethylbenzylamine by Schiff base formation. Then, the amino groups of aminated starch are quaternized with three different ammonium salts (4‐bromobutyl‐pyridinium bromide, 4‐bromobutyl‐benzalkonium bromide, and 4‐bromobutyl‐quinolinium bromide). The different resulting products are fully characterized by FTIR, 1H NMR, and SEC analysis. Their antibacterial properties are evaluated against Escherichia coli and Staphylococcus aureus in vitro to obtain minimum inhibitory and bactericidal concentrations. All the starch derivatives show strong antibacterial activities against Gram‐negative E. coli strain and Gram‐positive S. aureus. Finally, hemolysis assays show that two of the starch derivatives obtained have no significant hemolytic effect on isolated human red cells.

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and antibacterial activities of novel starch derivatives against E. coli and S. aureus

et al. 2022

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“…29 In this field, important advances have been made in previous work on the grafting of quaternary ammonium salts onto different polymers, which proved to be a promising strategy for granting these polymers with antiseptic properties and the ability to decrease the cell proliferation of cervical, breast and murine cancer cell lines. [30][31][32] Quaternary ammonium salts are cationic molecules commonly used in herbicides and antiseptic products, which have been identified to be effective against bacteria and viruses such as SARS-CoV-2. 33 As far as polymers based on aspartic acid are concerned, there is only a study on the antibacterial properties of the material obtained after the copolymerization of aspartic acid with citric acid, 34 attesting for the interest in considering giving additional antibacterial properties to PAspNa.…”

Section: Introductionmentioning

confidence: 99%

“…This work thus deals with the chemical grafting of quaternary ammonium salts like 1-(carboxypentyl) pyridinium bromide (PA-COOH), 1-(carboxypentyl) benzalkonium bromide (BK-COOH), and 1-(carboxypentyl) quinolinium bromide (QA-COOH) onto sodium polyaspartate macromolecular chains since these salts have already been successfully used and grafted on other polymers as antibacterial agents. 32 It is hypothesized that the introduction of these quaternary ammonium salts through an acid-base reaction along the PAspNa backbone chains could grant antibacterial properties while maintaining the biocompatibility and low cytotoxicity of PAspNa. The corresponding chemical structures of the PAspNa derivatives have been characterized by FT-IR and 1 H-NMR spectroscopy and thermogravimetric analysis (TGA).…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial and anticancer potential of novel polyaspartate derivatives synthesized via quaternary ammonium grafting

Torres‐Rodriguez

Avérous

Pollet

et al. 2022

J of Applied Polymer Sci

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Three novel polyaspartate derivatives with antibacterial properties and low hemolytic effects are synthesized by the reaction of sodium polyaspartate (PAspNa) with different quaternary ammonium salts with a carboxylic end‐group, subsequently these are tested in vitro against different cancer and normal cell lines. 1‐(carboxypentyl) pyridinium bromide, 1‐(carboxypentyl) benzalkonium bromide, and 1‐(carboxypentyl) quinolinium bromide are synthesized from a quaternization reaction between 6‐bromohexanoic acid and the respective tertiary amines (pyridine, N,N‐dimethylbenzylamine, and quinoline). Then, these ammonium salts are chemically grafted along the sodium polyaspartate macromolecular chains through an acid–base reaction. Three different polyaspartate derivatives are obtained and their chemical structures analyzed and confirmed by FT‐IR and 1H NMR, the corresponding thermal stability is analyzed by thermogravimetric analysis. The antibacterial efficiency of these PAspNa derivatives against Escherichia coli is determined by measuring the minimum inhibitory concentration and the minimum bactericidal concentration. Hemolysis assays are performed on isolated human erythrocytes and finally the cell proliferation is studied by 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide (MTT) analysis. All the PAspNa derivatives show antibacterial activities, low hemolytic effects, and antiproliferative effect in some concentrations evaluated in murine fibroblast (3T3), and cancer cell lines of cervix (HeLa), breast (4T1), and liver (HepG2) cells lines.

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“…Oyervides-Muñoz et al . [ 20 ] synthesized three different ammonium salts with a carboxylic acid end group through a quaternization reaction and chemically grafted them along the chitosan backbone using 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide as a carboxyl-activating agent for coupling with the primary amine groups, which significantly improved the antibacterial activity against Pseudomonas aeruginosa . Xu et al .…”

Section: Introductionmentioning

confidence: 99%

Improved antibacterial activity of hemp fibre by covalent grafting of quaternary ammonium groups

et al. 2021

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In this study, a novel antibacterial hemp fibre grafted with quaternary ammonium groups (HF–GTA), were prepared by alkalization, oxidation, amination and quaternization multistage reactions. The chemical structure and micromorphology of the fibre were characterized by Fourier-transform infrared spectroscopy, scanning electron microscopy, X-ray photoelectron spectroscopy, thermogravimetric analysis and X-ray diffraction. The grafting and reaction mechanism proved to be successful, which indicated that the grafting reaction primarily occurred on the hydroxyl group of cellulose and hemicellulose in the hemp fibre, where it retained good fibrous morphology, thermal stability and hygroscopicity. HF–GTA exhibited the best antibacterial activity, where the antibacterial ratios against Escherichia coli and Staphylococcus aureus were 95.41% and 99.64%, respectively. Even after washing 30 times, the antibacterial activity was retained at 89.78% and 91.12%, indicating that HF–GTA was endowed with good washing resistance. The antibacterial activity was owing to the electrostatic reaction reducing the electrochemical potential on the cell membrane, leading to the release of cytoplasmic substances and the dissolution of cells. This study is significantly important for guaranteeing textile quality and preventing disease transmission.

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EDC‐Mediated Grafting of Quaternary Ammonium Salts onto Chitosan for Antibacterial and Thermal Properties Improvement

Cited by 13 publications

References 52 publications

Synthesis, characterization, and antibacterial activities of novel starch derivatives against E. coli and S. aureus

Synthesis, characterization, and antibacterial activities of novel starch derivatives against E. coli and S. aureus

Antimicrobial and anticancer potential of novel polyaspartate derivatives synthesized via quaternary ammonium grafting

Improved antibacterial activity of hemp fibre by covalent grafting of quaternary ammonium groups

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