Original method for synthesis of chitosan-based antimicrobial agent by quaternary ammonium grafting

Oyervides–Muñoz, Ernesto; Pollet, Éric; Ulrich, Gilles; Sosa‐Santillán, Gerardo de Jesús; Avérous, Luc

doi:10.1016/j.carbpol.2016.11.081

Cited by 68 publications

(29 citation statements)

References 57 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Meanwhile, all the chitosan derivatives showed a much more limited weight loss between 350 and 600 °C and a final degradation step from 600 to 780 °C. These results highlight that these three modified chitosan degrade at a higher temperature in comparison to unmodified chitosan and to the chitosan derivatives reported in our previous work which were also fully degraded at 625 °C . This increase in thermal stability is thus likely due to the amide bond formed via the EDC‐mediated grafting of the carboxyl‐terminated ammonium salts onto the chitosan backbone which absorbs thermal energy.…”

Section: Resultssupporting

confidence: 53%

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

Oyervides–Muñoz

Avérous

Sosa‐Santillán

et al. 2019

Macro Chemistry & Physics

Self Cite

View full text Add to dashboard Cite

The present study provides antibacterial and thermal improvements of chitosan‐based systems through chemical modification with different quaternary ammonium salts using 1‐ethyl‐3‐(3‐dimethylaminopropyl) carbodiimide (EDC) as mediator. Three different ammonium salts with a carboxylic acid end group are synthesized through a quaternization reaction between bromohexanoic acid and the respective tertiary amines (quinoline, N,N‐dimethylbenzylamine and pyridine). They are then chemically grafted along the chitosan backbone using EDC as a carboxyl activating agent for the coupling with the primary amine groups. This allows three different chitosan derivatives to be obtained: Quinolinium‐Chitosan (QA‐Cs), Benzalkonium‐Chitosan (BK‐Cs), and Pyridinium‐Chitosan (PA‐Cs), respectively. The chemical structures are characterized by 1H NMR analysis. The thermal stability is analyzed by thermogravimetric analysis. Antibacterial efficiencies of chitosan derivatives against Pseudomonas aeruginosa and Staphylococcus aureus strains are determined. All the chitosan derivatives show negligible antibacterial activity against Gram‐positive S. aureus strain. However, the antibacterial activity against Gram‐negative P. aeruginosa strain is significantly improved.

show abstract

Section: Resultssupporting

confidence: 53%

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

Oyervides–Muñoz

Avérous

Sosa‐Santillán

et al. 2019

Macro Chemistry & Physics

Self Cite

View full text Add to dashboard Cite

show abstract

“…Chemical modification is one of the most effective methods used to improve the water solubility and the bioactivity of chitosan due to the presence of primary amino groups and hydroxyl groups in chitosan [ 20 , 21 ]. Therefore, several chemically modified functional derivatives have been prepared via carboxylation, quaternization, phosphorylation, and sulfation to improve the water solubility and bioactivity of chitosan [ 22 , 23 , 24 , 25 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Antifungal Activity of Pyridine-Based Triple Quaternized Chitosan Derivatives

Wei

Chen

et al. 2018

Molecules

View full text Add to dashboard Cite

In this study, a series of triple quaternized chitosan derivatives, including 6-O-[(2-hydroxy-3-trimethylammonium)propyl]-2-N-(1-pyridylmethyl-2-ylmethyl)-N,N-dimethyl chitosan chloride (7), 6-O-[(2-hydroxy-3-trimethylammonium)propyl]-2-N-(1-pyridylmethyl-3-yl- methyl)-N,N-dimethyl chitosan chloride (8), and 6-O-[(2-hydroxy-3-trimethylammonium)propyl]- 2-N-(1-pyridylmethyl-4-ylmethyl)-N,N-dimethyl chitosan chloride (9) were successfully designed and synthesized via reacting epoxypropyl trimethylammonium chloride with the N-pyridinium double quaternized chitosan derivatives. Detailed structural characterization was carried out using FT-IR and 1H-NMR spectroscopy, and elemental analysis. Besides, the activity of the triple quaternized chitosan derivatives against three common plant pathogenic fungi, Watermelon fusarium, Fusarium oxysporum, and Phomopsis asparagi, was investigated in vitro. The results indicated that the triple quaternized chitosan derivatives had enhanced antifungal activity when compared to double quaternized chitosan derivatives and chitosan, especially at 1.0 mg/mL, which confirmed the theory that the higher density of positive charge contributed to the antifungal activity. Moreover, 8 with an almost 99% inhibitory index showed the better antifungal activity against Watermelon fusarium. Moreover, the cytotoxicity of the products was also evaluated in vitro on 3T3-L1 cells and all the triple quaternized chitosan derivatives exhibited low cytotoxicity. These results suggested that triple quaternized chitosan derivatives may be used as good antifungal biomaterials.

show abstract

“…Thus, the incorporation of organobentonite synthesized with CTAB impregnated chitosan into the blend of HDPE/chitosan can result in good interfacial adhesion between chitosan and the polymer matrix. In addition, it is established in the literature that the combination of ammonium salts with chitosan retains its properties and improves its natural antibacterial and antifungal properties [ 41 , 42 , 43 ].…”

Section: Introductionmentioning

confidence: 99%

HDPE/Chitosan Blends Modified with Organobentonite Synthesized with Quaternary Ammonium Salt Impregnated Chitosan

et al. 2018

View full text Add to dashboard Cite

In this study, blends based on a high density polyethylene (HDPE) and chitosan (CS) were successfully prepared by melt processing, in a laboratory internal mixer. The CS biopolymer content effect (up to maximum of 40%), and, the addition of bentonite clay modified with quaternary ammonium salt (CTAB) impregnated chitosan as a compatibilizing agent, on the properties of the blends was analyzed by Fourier transform-infrared spectroscopy (FT-IR), wide angle X-ray diffraction (WAXD), differential scanning calorimetry (DSC), thermogravimetric analyses (TG), tensile strength, and scanning electron microscopy (SEM). The use of clay modified with CTAB impregnated chitosan, employing a method developed here, improved the compatibility of HDPE with chitosan, and therefore the thermal and some of the mechanical properties were enhanced, making HDPE/chitosan blends suitable candidates for food packaging. It was possible to obtain products of synthetic polymer, HDPE, with natural polymer, chitosan, using a method very used industrially, with acceptable and more friendly properties to the environment, when compared to conventional synthetic polymers. In addition, due to the possibility of impregnated chitosan with quaternary ammonium salt exhibit higher antibacterial activity than neat chitosan, the HDPE/chitosan/organobentonite blends may be potentially applied in food containers to favor the preservation of food for a longer time in comparison to conventional materials.

show abstract

Original method for synthesis of chitosan-based antimicrobial agent by quaternary ammonium grafting

Cited by 68 publications

References 57 publications

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

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

Synthesis, Characterization, and Antifungal Activity of Pyridine-Based Triple Quaternized Chitosan Derivatives

HDPE/Chitosan Blends Modified with Organobentonite Synthesized with Quaternary Ammonium Salt Impregnated Chitosan

Contact Info

Product

Resources

About