Interactions between quaternized chitosan and surfactant studied by diffusion NMR and conductivity

Senra, Tonimar D.A.; Khoukh, Abdel; Desbrières, Jacques

doi:10.1016/j.carbpol.2016.09.025

Cited by 35 publications

(21 citation statements)

References 71 publications

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“…Quaternization generally involves reaction of chitosan with methyl iodide, although it may involve chemicals other than methyl iodide [34,35,36]. The derivatives are synthesized by chitosan and quaternary epoxides; it is possible to prepare cationized derivatives (quaternary ammonium chitosan) with diverse hydrophobicity/hydrophilicity through the various alkyl chains on quaternary epoxides [37].…”

Section: Chitosan Derivativesmentioning

confidence: 99%

Biomedical Applications of Chitosan and Its Derivative Nanoparticles

et al. 2018

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Chitosan is a biodegradable natural polymer with many advantages such as nontoxicity, biocompatibility, and biodegradability. It can be applied in many fields, especially in medicine. As a delivery carrier, it has great potential and cannot be compared with other polymers. Chitosan is extremely difficult to solubilize in water, but it can be solubilized in acidic solution. Its insolubility in water is a major limitation for its use in medical applications. Chitosan derivatives can be obtained by chemical modification using such techniques as acylation, alkylation, sulfation, hydroxylation, quaternization, esterification, graft copolymerization, and etherification. Modified chitosan has chemical properties superior to unmodified chitosan. For example, nanoparticles produced from chitosan derivatives can be used to deliver drugs due to their stability and biocompatibility. This review mainly focuses on the properties of chitosan, chitosan derivatives, and the origin of chitosan-based nanoparticles. In addition, applications of chitosan-based nanoparticles in drug delivery, vaccine delivery, antimicrobial applications, and callus and tissue regeneration are also presented. In summary, nanoparticles based on chitosan have great potential for research and development of new nano vaccines and nano drugs in the future.

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Section: Chitosan Derivativesmentioning

confidence: 99%

Biomedical Applications of Chitosan and Its Derivative Nanoparticles

et al. 2018

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“…49,50 Since the translational diffusion coefficients (D) of molecular species reflect their effective sizes and shapes, DOSY NMR allows both the identification and separation of the chemical entities in multicomponent systems, and provides information on their intermolecular interactions as well as on the dynamics of the system. 49,51,52 In other words, a small molecule diffuses faster than a large one and the binding of a freely diffusing molecule to another species leads to a decrease of D. Indeed, in the fast exchange limit, the observed diffusion coefficient of the guest is the mole fraction weighted average of the diffusion coefficient of the free and bound states. This means that, in the presence of a complex, the diffusion of the encapsulated molecule will be slower than that measured for the free compound.…”

Section: Sementioning

confidence: 99%

Do Cyclodextrins Encapsulate Volatiles in Deep Eutectic Systems?

Pietro

Dugoni

Ferro

et al. 2019

ACS Sustainable Chem. Eng.

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Efficient renewable and non-toxic absorbents can now be designed to eliminate air pollutants such as volatile organic compounds (VOCs) from confined atmospheres. New hybrid materials result from the combination of Deep Eutectic Systems (DES) with well-known VOCs capture agents like β-cyclodextrin (βCD). Yet, a question arises: does βCD retain its encapsulation ability in DES? Multiple NMR techniques are used here to demonstrate the formation of inclusion complexes of βCD with two VOCs, aniline and toluene, in the pure DES reline and in reline/water mixtures. Complexation-induced chemical shift changes and intermolecular hostguest NOEs in the rotating frame give evidence of a genuine encapsulation in the βCD cavity, and complementary information on the dynamics of the VOC is gathered via relaxation and diffusion experiments. This work shows how different NMR techniques can contribute to the design of task-specific sustainable materials for absorption/extraction processes.

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“…The proton assignments in chitosan spectrum are assigned at 4.75 ppm (D 2 O overlaps H-1), 3.44-3.93 ppm (H-3,4,5,6), 3.13 ppm (H-2), and 1.99 ppm (acetic acid overlaps NHCOCH 3 ) [30]. In the spectrum of cationic chitosan derivative 2, the new signal at 3.39 ppm (a in the spectrum) corresponds to the methyl protons (-N + (CH 3 ) 3 ) of the quaternary ammonium group [31], and the new signals at 4.33 and 2.70 ppm (b and c in the spectrum) belong to the protons on the methylene and terminal alkynyl of propargyl group (\ \CH 2 C`CH) [32]. Changes in the chemical structure of chitosan after the CuAAC reaction are detected by 1 H NMR spectroscopy.…”

Section: H Nmr Analysismentioning

confidence: 98%

“…Moreover, in comparison with the spectrum of cationic chitosan derivative 2, the increasing intensity of signals at 3.21 ppm (a and g in the spectrum) indicates that N,N,N-trimethyl moiety has been grafted onto chitosan backbones. Besides, the additional signals at 5.07 and 4.03 ppm (e and f in the spectrum) are assigned to the protons of methylene groups (NCH 2 CH 2 N + (-CH 3 ) 3 ) of chitosan derivative 3 [31].…”

Section: H Nmr Analysismentioning

confidence: 99%

Synthesis, characterization, and evaluation of antifungal and antioxidant properties of cationic chitosan derivative via azide-alkyne click reaction

Zhang

Dong

et al. 2018

International Journal of Biological Macromolecules

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In this work, quaternary ammonium group was introduced into chitosan backbone by cuprous-catalyzed azide-alkyne cycloaddition (CuAAC) to synthesize the cationic chitosan derivative bearing 1,2,3-triazole. The products were identified structurally by FTIR, H NMR spectroscopy, XRD, and elemental analysis. The water solubility of chitosan derivatives at different pH values was determined by a turbidity measurement. The antifungal properties of cationic chitosan derivatives against Botryis cinerea, Phomopsis asparagi, Fusarium oxysporum f. sp. niveum, and Fusarium oxysporum f. sp. cucumerium were evaluated using the radial growth assay. Besides, the antioxidant activities of them were also tested by superoxide-radical scavenging and reducing power assays. Compared to chitosan, cationic chitosan derivative bearing 1,2,3-triazole showed the good water solubility especially at alkaline condition, excellent antifungal action with over 70% inhibitory indices against tested fungi at 1.0 mg/mL, and enhanced antioxidant activity with complete scavenging efficiency against superoxide-radical at 1.6 mg/mL because of the introduction of 1,2,3-triazole and quaternary ammonium moieties. These excellent biological properties present a promising prospect for this chitosan derivative in antifungal and antioxidant biomaterials.

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Interactions between quaternized chitosan and surfactant studied by diffusion NMR and conductivity

Cited by 35 publications

References 71 publications

Biomedical Applications of Chitosan and Its Derivative Nanoparticles

Biomedical Applications of Chitosan and Its Derivative Nanoparticles

Do Cyclodextrins Encapsulate Volatiles in Deep Eutectic Systems?

Synthesis, characterization, and evaluation of antifungal and antioxidant properties of cationic chitosan derivative via azide-alkyne click reaction

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