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Journal articles on the topic 'Quaternized chitosan'

Author: Grafiati

Published: 4 June 2021

Last updated: 11 February 2022

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1

Wongwanakul, Ratjika, Suree Jianmongkol, Pattarapond Gonil, Warayuth Sajomsang, Rawiwan Maniratanachote, and Sasitorn Aueviriyavit. "Biocompatibility study of quaternized chitosan on the proliferation and differentiation of Caco-2 cells as an in vitro model of the intestinal barrier." Journal of Bioactive and Compatible Polymers 32, no. 1 (July 28, 2016): 92–107. http://dx.doi.org/10.1177/0883911516658780.

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The development of different chitosan derivatives for medical applications has increased recently. Among these chitosan derivatives, quaternized chitosan was designed to improve the solubility of chitosan in biological fluids for oral drug delivery while retaining the cationic character for mucoadhesion. However, the biocompatibility of quaternized chitosan on the human intestine is unknown. In this study, we aimed to examine the potential biological effects of quaternized chitosan on the intestinal barrier, in terms of cell proliferation and cell differentiation, using the Caco-2 cell line as an in vitro model. The lower the degree of substitution of quaternized chitosan, the lower the cytotoxic and anti-proliferative effect on Caco-2 cells. In addition, the anti-proliferative effect of quaternized chitosan might induce a cell cycle disturbance and differentiation delay. Long-term continuous exposure (9 days) to quaternized chitosan caused a delay in differentiation of the Caco-2 cells even at non-cytotoxic quaternized chitosan doses (0.005% (w/v)), as shown by the low level of alkaline phosphatase in the quaternized chitosan–treated group compared to the control cells. In contrast, short-term discontinuous exposure to quaternized chitosan (0.005% (w/v) for 4 h/day over 9 days) that more realistically mimics the daily intestinal exposure did not inhibit the intestinal differentiation of Caco-2 cells. Thus, the use of a low degree of substitution and a low concentration of quaternized chitosan resulted in a good biocompatibility to the intestinal barrier supporting the potential usefulness of quaternized chitosan in the application of an oral drug delivery system.

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2

Freitas, Emanuelle Dantas, Celso Fidelis Moura Jr., Jonas Kerwald, and Marisa Masumi Beppu. "An Overview of Current Knowledge on the Properties, Synthesis and Applications of Quaternary Chitosan Derivatives." Polymers 12, no. 12 (November 30, 2020): 2878. http://dx.doi.org/10.3390/polym12122878.

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Chitosan, a chitin-derivative polysaccharide, known for its non-toxicity, biocompatibility and biodegradability, presents limited applications due to its low solubility in neutral or basic pH medium. Quaternization stands out as an alternative to modify this natural polymer, aiming to improve its solubility over a wide pH range and, consequently, expand its range of applications. Quaternization occurs by introducing a quaternary ammonium moiety onto or outside the chitosan backbone, via chemical reactions with primary amino and hydroxyl groups, under vast experimental conditions. The oldest and most common forms of quaternized chitosan involve N,N,N-trimethyl chitosan (TMC) and N-[(2-hydroxy-3-trimethyl ammonium) propyl] chitosan (HTCC) and, more recently, quaternized chitosan by insertion of pyridinium or phosphonium salts. By modifying chitosan through the insertion of a quaternary moiety, permanent cationic charges on the polysaccharide backbone are achieved and properties such as water solubility, antimicrobial activity, mucoadhesiveness and permeability are significantly improved, enabling the application mainly in the biomedical and pharmaceutical areas. In this review, the main quaternized chitosan compounds are addressed in terms of their structure, properties, synthesis routes and applications. In addition, other less explored compounds are also presented, involving the main findings and future prospects regarding the field of quaternized chitosans.

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Yu, Shuang, Shengnan Hao, Beini Sun, Dongying Zhao, Xingye Yan, Zheng Jin, and Kai Zhao. "Quaternized Chitosan Nanoparticles in Vaccine Applications." Current Medicinal Chemistry 27, no. 30 (September 8, 2020): 4932–44. http://dx.doi.org/10.2174/0929867326666190227192527.

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Different natural and synthetic biodegradable polymers have been used in vaccine formulations as adjuvant and delivery system but have faced various limitations. Chitosan is a new delivery system with the potential to improve development of nano vaccines and drugs. However, chitosan is only soluble in acidic solutions of low concentration inorganic acids such as dilute acetic acid and dilute hydrochloric acid and in pure organic solvents, which greatly limits its application. Chemical modification of chitosan is an important way to improve its weak solubility. Quaternized chitosan not only retains the excellent properties of chitosan, but also improves its water solubility for a wider application. Recently, quaternized chitosan nanoparticles have been widely used in biomedical field. This review focuses on some quaternized chitosan nanoparticles, and points out the advantages and research direction of quaternized chitosan nanoparticles. As shown by the applications of quaternized chitosan nanoparticles as adjuvant and delivery carrier in vaccines, quaternized chitosan nanoparticles have promising potential in application for the development of nano vaccines in the future.

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4

Wei, Lijie, Yuan Chen, Wenqiang Tan, Qing Li, Guodong Gu, Fang Dong, and Zhanyong Guo. "Synthesis, Characterization, and Antifungal Activity of Pyridine-Based Triple Quaternized Chitosan Derivatives." Molecules 23, no. 10 (October 11, 2018): 2604. http://dx.doi.org/10.3390/molecules23102604.

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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.

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5

Pathak, Kamla, Shashi Kiran Misra, Aayush Sehgal, Sukhbir Singh, Simona Bungau, Agnieszka Najda, Robert Gruszecki, and Tapan Behl. "Biomedical Applications of Quaternized Chitosan." Polymers 13, no. 15 (July 30, 2021): 2514. http://dx.doi.org/10.3390/polym13152514.

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The natural polymer chitosan is the second most abundant biopolymer on earth after chitin and has been extensively explored for preparation of versatile drug delivery systems. The presence of two distinct reactive functional groups (an amino group at C2, and a primary and secondary hydroxyl group at C3 and C6) of chitosan are involved in the transformation of expedient derivatives such as acylated, alkylated, carboxylated, quaternized and esterified chitosan. Amongst these, quaternized chitosan is preferred in pharmaceutical industries owing to its prominent features including superior water solubility, augmented antimicrobial actions, modified wound healing, pH-sensitive targeting, biocompatibility, and biodegradability. It has been explored in a large realm of pharmaceuticals, cosmeceuticals, and the biomedical arena. Immense classy drug delivery systems containing quaternized chitosan have been intended for tissue engineering, wound healing, gene, and vaccine delivery. This review article outlines synthetic techniques, basic characteristics, inherent properties, biomedical applications, and ubiquitous challenges associated to quaternized chitosan.

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6

Han, Yong Ping, and Qiang Lin. "Synthesis,Characterization, and Antibacterial Activity of Quaternized of N-Aromatic Chitosan Derivatives." Applied Mechanics and Materials 138-139 (November 2011): 1202–8. http://dx.doi.org/10.4028/www.scientific.net/amm.138-139.1202.

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The quaternized of N-aryl chitosan (CTS) derivatives containing different aromatic moieties were synthesized by two steps, N-aromatic Schiff and the quaternization. The chemical structures of all chitosan derivatives, N-vanillin Schiff’s base chitosan (NVCh), N-cinnamaldehyde Schiff’s base chitosan (NCCh), N-benzaldehyde Schiff’s base CTS (NBCh), and their quaternized of N-aromatic CTS derivatives were characterized by ATR-FTIR. The water solubility of the N-aromatic Schiff’s base CTS derivatives had very poor water solubility. But after quaternized, the water solubility of CTS derivatives was obviously improved. The antibacterial studies of these CTS derivatives were carried out by the inhibition zone diameters methods against E.coli (Gram-negative), S.aurueus and P.aeruginosa (Gram-positive) bacteria, and against V.Aspergillus niger (fungal). It was found that the quaternized NVSCTS showed higher antibacterial activity than quaternized NCCh and quaternized NVBCh at the almost same DQ and ES level. In comparison to each of the chemical structure, it was found that the phenol hydroxyl group effect on antibacterial activity was even higher than that of positive charge density of CTS.

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7

Chen, Qiyuan, Shengling Xiao, Sheldon Q. Shi, and Liping Cai. "Synthesis, characterization, and antibacterial activity of N-substituted quaternized chitosan and its cellulose-based composite film." BioResources 15, no. 1 (November 26, 2019): 415–28. http://dx.doi.org/10.15376/biores.15.1.415-428.

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A water and organic soluble N-benzyl-N,N-diethyl quaternized chitosan (NSQC) material was synthesized using chitosan, benzaldehyde, and bromoethane. Amino groups on chitosan reacted with benzaldehyde to form a Schiff base intermediate. Quaternized chitosan was obtained by reacting the Schiff base with bromoethane. The quaternized chitosan was dissolved in an organic solution with dissolved cellulose and cast to prepare quaternized chitosan/cellulose (QCC) film. The molecular structure, morphology, tensile strength, thermal stability, and antibacterial activity effects of NSQC-treated cellulose film were studied in detail. The results showed that the NSQC product exhibited superior solubility in deionized water and dimethylacetamide. The addition of NSQC as a reinforcing agent in QCC film enhanced the interlinking of fibers and slowed down the rate of cellulose pyrolysis, which improved the tensile properties and thermal stability of the cellulose film. The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values of NSQC showed that it had good antibacterial activity against Staphylococcus aureus and Escherichia coli. The QCC film also showed contact sterilization ability with regards to two kinds of bacteria, which suggested that QCC film has the potential for applications in food packaging and bacterial barriers.

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8

Khademibami, Laya, H. Michael Barnes, Dragica Jeremic, Rubin Shmulsky, Keith Bourne, and Seyed Abolghasem Fatemi. "Antifungal activity and fire resistance properties of nano-chitosan treated wood." BioResources 15, no. 3 (June 16, 2020): 5926–39. http://dx.doi.org/10.15376/biores.15.3.5926-5939.

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Fungal decay and fire resistance properties of wood treated with nano-chitosan-TPP particles were investigated. Quaternized and non-quaternized nano-chitosan particles crosslinked with a commercial fire-retardant, tripolyphosphate, were prepared from low molecular weight chitosan (with a molecular weight of 50 to 190 kDa). Different treatments were performed on southern yellow pine wood samples via a vacuum impregnation process for both quaternized and non-quaternized nano-chitosan-TPP particles with a concentration ratio of 12% to 4.8% (nano-chitosan to TPP). Both the leached and unleached treated wood samples were exposed to brown rot (Gloeophyllum trabeum) and white rot (Trametes versicolor) fungi according to AWPA standard E10-16. The flammability test was performed with a cone calorimeter according to ASTM standard E1354-15. The heat release rate and the mass loss rate were measured. The results of the fungal tests indicated that the quaternization of the nano-chitosan particles resulted in a reduced mass loss in the pine samples when exposed to Trametes versicolor under leached conditions. Additionally, without the quaternization of the nano-chitosan particles, the mass loss in the pine samples was reduced when exposed to Gloeophyllum trabeum under unleached conditions. The production of nano-chitosan-TPP particles had a significant effect on the fire-retardant activity of the treated wood samples.

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9

Xu, Qing, Tian Zhong, and Hui Li Li. "Antioxidant and Free Radical Scavenging Activities of N-Modified Chitosans." Advanced Materials Research 1002 (August 2014): 91–98. http://dx.doi.org/10.4028/www.scientific.net/amr.1002.91.

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Recently, the search for effective natural antioxidants use in food and medicinal fields to replace synthetic ones has attracted the most attention. Chitosan, a natural nontoxic biopolymer, is known to possess antioxidant property, which is attributed that NH2 and OH attached in the pyranose ring react with unstable free radicals to form stable macromolecule radicals. It has been observed that the antioxidant activity of chitosan is closely related to the form of nitrogen atom in the molecules. This review focuses on the antioxidant and free radical scavenging activities of various nitrogen atom of chitosan, including N-acylated chitosans, Schiff bases of chitosan, N-alkyl chitosan, and N-quaternized chitosan. The free radical scavenging mechanisms are summarized and the effects on free radical scavenging activity of N-modified chitosan are discussed. This work may provide more insights into the antioxidant ability of N-modified chitosans and potentially enable them to be used as natural antioxidants for application in food, agriculture, cosmetic and biomedical science. Keywords: N-modified chitosan, Sythesis, Antioxidant, Free radical scavenging

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10

Tayyem, Muna T., Mohammad B. Zughul, and Mansour H. Almatarneh. "Molecular dynamics simulation of N-octyl-N-quaternized chitosan derivatives as a drug carrier." Journal of Theoretical and Computational Chemistry 17, no. 04 (June 2018): 1850025. http://dx.doi.org/10.1142/s0219633618500256.

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The dynamic amphiphilic behavior of N-octyl-N-quaternized chitosan derivatives in aqueous solution is investigated using molecular dynamics (MD) simulations. It is found that quaternization decreases the intra-chain hydrogen bond formation which leads to reduced rigidity of the chitosan backbone. The effect of octyl substitution is much less pronounced. Analysis of hydrogen bonding reveals the presence of a hydrogen bond within the quaternized glucosamine unit, which causes the distortion of the usual chair conformation. Also, H-bond formation with the solvent water molecules was found to stabilize the intra-chain HO3-O5 hydrogen bond. Additionally, an aqueous solution containing the 10%-N-octyl-50%-N-quaternized chitosan derivative (1O5QCS) and the anti-cancer drug 10-hydroxycamptothecin (10-HCPT) was also investigated using MD simulations. It was found that van der Waals and electrostatic forces have virtually equal contributions to the nonbonded interactions responsible for complexation. Furthermore, H-bond formation between drug and drug carrier contributes to lactone ring stability and subsequent bioavailability.

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11

Cao, Zhi Ling, Wei Wei Liu, Jian Jun Xiong, Na Qu, Hong Xia Li, and Guo Wei Yao. "Synthesis and Properties of N,N-Dimethyl-O-Quaternary Ammonium Chitosan." Advanced Materials Research 152-153 (October 2010): 1337–41. http://dx.doi.org/10.4028/www.scientific.net/amr.152-153.1337.

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N,N-dimethyl-O-quaternary ammonium chitosan(NNQAC) was synthesized from chitosan by N-dimethylation then quaternized by 2,3-epoxy propyl trimethyl ammonium chloride. The structure of NNQAC was characterized by FTIR. Properties of quaternary ammonium chitosans, including solubility, antimicrobial activity, water-absorption and water-retention ability, were investigated. The results showed that NNQAC was water–soluble in neutral and basic environments. The moisture-absorption and retention abilities of NNQAC were higher than that of chitosan and equivalent to hyaluronic acid. The antibacterial activities of NNQAC were tested against Bacillus subtilis, Escherichia coli and Staphylococcus aureus. In water medium, NNQAC exhibited MIC values in the range of 10 to 2.5 μg/mL.

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12

Wei, Wei, Lian-Yan Wang, Jie Wu, and Guang-Hui Ma. "Quaternized chitosan microspheres as insulin carrier." Journal of Biotechnology 136 (October 2008): S452. http://dx.doi.org/10.1016/j.jbiotec.2008.07.1050.

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13

Song, Huanlu, Hao Wu, ShuJing Li, Huafeng Tian, YanRu Li, and JianGuo Wang. "Homogeneous Synthesis of Cationic Chitosan via New Avenue." Molecules 23, no. 8 (August 1, 2018): 1921. http://dx.doi.org/10.3390/molecules23081921.

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Using a solvent formed of alkali and urea, chitosan was successfully dissolved in a new solvent via the freezing–thawing process. Subsequently, quaternized chitosan (QC) was synthesized using 3-chloro-2-hydroxypropyl trimethyl ammonium chloride (CHPTAC) as the cationic reagent under different incubation times and temperatures in a homogeneous system. QCs cannot be synthesized at temperatures above 60 °C, as gel formation will occur. The structure and properties of the prepared QC were characterized and quaternary groups were comfirmed to be successfully incorporated onto chitosan backbones. The degree of substitution (DS) ranged from 16.5% to 46.8% and the yields ranged from 32.6% to 89.7%, which can be adjusted by changing the molar ratio of the chitosan unit to CHPTAC and the reaction time. QCs inhibits the growth of Alicyclobacillus acidoterrestris effectively. Thus, this work offers a simple and green method of functionalizing chitosan and producing quaternized chitosan with an antibacterial effect for potential applications in the food industry.

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14

Leksantikul, Lalita, Warayuth Sajomsang, Theerasak Rojanarata, Tanasait Ngawhirunpat, and Praneet Opanasopit. "Quaternized Chitosans as Gene Delivery Carriers: Effect of Degree of Quaternization." Advanced Materials Research 1060 (December 2014): 17–20. http://dx.doi.org/10.4028/www.scientific.net/amr.1060.17.

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The objective of this study was to investigate the transfection efficiency of quaternized chitosan or trimethylated chitosans (TMCs) using the plasmid DNA encoding green fluorescent protein (pEGFP-C2) on human cervical carcinoma cell line (HeLa cells). The factors affecting the transfection efficiency, e.g. degree of quaternization (DQ) and polymer/DNA weight ratio were evaluated. The results revealed that the complexes of TMC30 with DNA had the highest transfection efficiency and safety followed by the complexes of TMC60 and TMC94, respectively. Increasing the DQ of chitosan not only improve the efficiency of gene delivery, but also increase cytotoxicity. In conclusion, TMC30 showed elevated potential as a gene carrier by efficient DNA condensation and mediated the highest level of gene transfection with negligible cytotoxicity in HeLa cells.

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15

Jiang, Yao-Wen, Ge Gao, Xiaodong Zhang, Hao-Ran Jia, and Fu-Gen Wu. "Antimicrobial carbon nanospheres." Nanoscale 9, no. 41 (2017): 15786–95. http://dx.doi.org/10.1039/c7nr04679k.

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16

Ling, Yunzhi, Xiaoyun Li, Shuwei Zhou, Xiaoying Wang, and Runcang Sun. "Multifunctional cellulosic paper based on quaternized chitosan and gold nanoparticle–reduced graphene oxide via electrostatic self-assembly." Journal of Materials Chemistry A 3, no. 14 (2015): 7422–28. http://dx.doi.org/10.1039/c4ta07160c.

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17

Zhang, Jingjing, Wenqiang Tan, Lijie Wei, Fang Dong, Qing Li, and Zhanyong Guo. "Synthesis, Characterization, and Antioxidant Evaluation of Novel Pyridylurea-Functionalized Chitosan Derivatives." Polymers 11, no. 6 (June 1, 2019): 951. http://dx.doi.org/10.3390/polym11060951.

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In order to improve the bioactivity of chitosan, we synthesized a novel series of chitosan derivatives: firstly, chitosan was reacted with methylclhlorofonmate obtaining N-methoxyformylated chitosan (1), which was then converted into N-pyridylurea chitosan derivatives (2a-2c) by amine-ester exchange reaction. In addition, N-pyridylurea chitosan derivatives were conducted by reacting with iodomethane to obtain quaternized N-pyridylurea chitosan derivatives (3a-3c). The structural characteristics of as-prepared chitosan derivatives were confirmed by fourier transform infrared (FT-IR), 1H nuclear magnetic resonance (1H NMR), elemental analysis, and scanning electron microscope (SEM). Meanwhile, the antioxidant activity of the chitosan derivatives was assessed in vitro. As shown in this paper, the antioxidant activity decreased in the order: c > b > a. Moreover, after the quaternization with iodomethane, quaternized N-pyridylurea chitosan derivatives immediately exhibited enhanced antioxidant capacity compared with N-pyridylurea chitosan derivatives. For example, in 1,1-Diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, the scavenging activities of 3a-3c were 91.75%, 93.63%, and 97.63% while 2a-2c were 42.32%, 42.97%, and 43.07% at 0.4 mg/mL. L929 cells were also adopted for cytotoxicity test of chitosan and synthesized derivatives by CCK-8 assay and all samples showed decreased cytotoxicity. These results suggested that the novel pyridylurea-functionalized chitosan derivatives could be an ideal biomaterial.

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18

Wu, Jin Dan, Guo Qiang Cai, and Ji Ping Wang. "Synthesis of N-Alkyl-N,N-Dimethyl Quaternized Chitosan and its Application as Effective Absorbents towards Reactive Dye KN-R." Journal of Nano Research 43 (September 2016): 29–37. http://dx.doi.org/10.4028/www.scientific.net/jnanor.43.29.

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Several types of N-alkyl-N,N-dimethyl quaternized chitosan (QC) derivatives with different alkyl chains were prepared as effective adsorbents towards reactive dye KN-R. QC with long dodecanyl chain was insoluble in neutral solution but could self-assembled into spherical nanoparticles. The effects of degree of quaternization and alkyl chain length on the adsorption properties of KN-R onto QC were investigated. The results showed that a higher degree of quaternization of copolymers led to a higher adsorption capacity. At similar degree of quaternization, QC nanoparticles with longer alkyl chains showed better adsorption ability than soluble free QC chain with shorter alkyl chains. Positive charges were accumulated on the surface of nanoparticles, which showed higher charge density than free polymer chain. The adsorption kinetics appeared to followed a well-described by pseudo-second-order model. Meanwhile, all of the obtained quaternized chitosan samples showed a higher adsorption capacity than the commercial adsorbent polyaluminium chloride. This work showed that adsorption ability of the cationic polymer could be improved by self-assembling into nanoparticles and that synthesized quaternized chitosan could be utilized as an efficient adsorbent for dye removal.

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19

Belalia, Rachid, Stéphane Grelier, Mohammed Benaissa, and Véronique Coma. "New Bioactive Biomaterials Based on Quaternized Chitosan." Journal of Agricultural and Food Chemistry 56, no. 5 (March 2008): 1582–88. http://dx.doi.org/10.1021/jf071717+.

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20

Li, Tao, Xiao-Wen Shi, Yu-Min Du, and Yu-Feng Tang. "Quaternized chitosan/alginate nanoparticles for protein delivery." Journal of Biomedical Materials Research Part A 83A, no. 2 (2007): 383–90. http://dx.doi.org/10.1002/jbm.a.31322.

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21

Ruihua, Huang, Yang Bingchao, Dongsheng Zheng, and Bo Wang. "Preparation and characterization of a quaternized chitosan." Journal of Materials Science 47, no. 2 (August 24, 2011): 845–51. http://dx.doi.org/10.1007/s10853-011-5862-4.

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22

Khaira, Gurpreet Kaur, Rashmi Kumariya, Manmohan Chibber, and Moushumi Ghosh. "Development of a quaternized chitosan with enhanced antibacterial efficacy." Journal of Water and Health 11, no. 3 (May 15, 2013): 410–18. http://dx.doi.org/10.2166/wh.2013.029.

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The antibacterial activity of a water-soluble chitosan derivative prepared by chemical modification to quaternary ammonium compound N,N,N-trimethylchitosan (TC) was investigated against four selected waterborne pathogens: Aeromonas hydrophila ATCC 35654, Yersinia enterocolitica ATCC 9610, Listeria monocytogenes ATCC 19111 and Escherichia coli O157:H7 ATCC 32150. An inactivation of 4 log CFU/ml of all waterborne pathogens was noted for the quaternized chitosan as compared with chitosan over a short contact time (30 min) and low dosage (4.5 ppm) at ambient temperature. A marked increase in glucose level, protein content and lactate dehydrogenase (LDH) activity was observed concurrently in the cell supernatant to be a major bactericidal mechanism. The results suggest that the TC derivative may be a promising commercial substitute for acid-soluble chitosan for rapid and effective disinfection of water.

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Franconetti, Antonio, Lidia Contreras-Bernal, Rafael Prado-Gotor, and Francisca Cabrera-Escribano. "Synthesis of hyperpolarizable biomaterials at molecular level based on pyridinium–chitosan complexes." RSC Advances 5, no. 91 (2015): 74274–83. http://dx.doi.org/10.1039/c5ra09397j.

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24

Guo, Zhanyong, Ronge Xing, Song Liu, Zhimei Zhong, Xia Ji, Lin Wang, and Pengcheng Li. "Antifungal properties of Schiff bases of chitosan, N-substituted chitosan and quaternized chitosan." Carbohydrate Research 342, no. 10 (July 2007): 1329–32. http://dx.doi.org/10.1016/j.carres.2007.04.006.

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25

Wang, Lingren, Baihai Su, Chong Cheng, Lang Ma, Shuangsi Li, Shengqiang Nie, and Changsheng Zhao. "Layer by layer assembly of sulfonic poly(ether sulfone) as heparin-mimicking coatings: scalable fabrication of super-hemocompatible and antibacterial membranes." Journal of Materials Chemistry B 3, no. 7 (2015): 1391–404. http://dx.doi.org/10.1039/c4tb01865f.

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In this study, super-hemocompatible and antibacterial polymeric membranes with surface coated nanofilms were fabricated by LBL assembly of water-soluble heparin-mimicking polymer and quaternized chitosan.

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26

Guo, Zhanyong, Hongying Liu, Xiaolin Chen, Xia Ji, and Pengcheng Li. "Hydroxyl radicals scavenging activity of N-substituted chitosan and quaternized chitosan." Bioorganic & Medicinal Chemistry Letters 16, no. 24 (December 2006): 6348–50. http://dx.doi.org/10.1016/j.bmcl.2006.09.009.

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27

Nhung, Le Thi Tuyet, In Yea Kim, and Young Soo Yoon. "Quaternized Chitosan-Based Anion Exchange Membrane Composited with Quaternized Poly(vinylbenzyl chloride)/Polysulfone Blend." Polymers 12, no. 11 (November 17, 2020): 2714. http://dx.doi.org/10.3390/polym12112714.

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An efficient and effective process for the production of high-performance anion exchange membranes (AEMs) is necessary for the commercial application of fuel cells. Therefore, in this study, quaternized poly vinylbenzyl chloride (QVBC) and polysulfone were composited with glycidyltrimethylammonium-chloride-quaternized chitosan (QCS) at different ratios (viz., 1 wt %, 5 wt %, and 10 wt %). The structure and morphology of the membranes were characterized by Fourier transform infrared spectroscopy and scanning electron microscopy, respectively. Further, the water uptake, swelling ratio, and ionic conductivities of the composite membrane at different wt % of QCS were evaluated. The membrane with 5% QCS exhibited an ionic conductivity of 49.6 mS/cm and 130 mS/cm at 25 °C and 70 °C, respectively.

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Kumar, D. Gowtham, Naresh R, K. Rakesh Varma, Nagasen D, Sudheer B, and Sai Kishore V. "Modifications of Chitosan for Use in Nanoparticulate Drug Delivery Systems." International Journal of Pharmaceutical Sciences and Nanotechnology 6, no. 4 (December 31, 2013): 2210–18. http://dx.doi.org/10.37285/ijpsn.2013.6.4.3.

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Nanoparticles with naturally occurring biodegradable polymers have emerged as potential carriers of various therapeutic agents. Chitosan, a cationic polysaccharide, is one of such biodegradable polymers, which has been extensively exploited for the preparation of nanoparticles with several therapeutic agents. In recent years, the area of focus has shifted from chitosan to chitosan derivatized polymers due to its vastly improved properties such as better drug retention capability, improved permeation, enhanced mucoadhesion, and sustained release of therapeutic agents. Chitosan derivatized polymers are primarily the quaternized chitosan derivatives, chitosan cyclodextrin complexes, thiolated chitosan, pegylated chitosan, chitosan combined with sugar ligands, chitosan with cholanic acid, chitosan-linolenic acid and chitosan-DTPA. This review article covers the various modifications of chitosan, their preparation procedures and various works done with them.

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29

Wan, Ajun, Qing Xu, Yan Sun, and Huili Li. "Antioxidant Activity of High Molecular Weight Chitosan and N,O-Quaternized Chitosans." Journal of Agricultural and Food Chemistry 61, no. 28 (July 8, 2013): 6921–28. http://dx.doi.org/10.1021/jf402242e.

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30

Kalinov, Kalin N., Milena G. Ignatova, Nevena E. Manolova, Nadya D. Markova, Daniela B. Karashanova, and Iliya B. Rashkov. "Novel antibacterial electrospun materials based on polyelectrolyte complexes of a quaternized chitosan derivative." RSC Advances 5, no. 67 (2015): 54517–26. http://dx.doi.org/10.1039/c5ra08484a.

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Novel antibacterial materials based on polyelectrolyte complexes of quaternized chitosan (TMCh) and poly(2-acrylamido-2-methylpropanesulfonic acid) or poly(acrylic acid) (PAA) were prepared by electrospinning. AgNPs were loaded in TMCh/PAA fibers.

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Liao, Guan-Ming, Chun-Chen Yang, Chien-Chieh Hu, Yu-Li Pai, and Shingjiang Jessie Lue. "Novel quaternized polyvinyl alcohol/quaternized chitosan nano-composite as an effective hydroxide-conducting electrolyte." Journal of Membrane Science 485 (July 2015): 17–29. http://dx.doi.org/10.1016/j.memsci.2015.02.043.

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WANG, Xiao-Ying, Yu-Min DU, Run-Cang SUN, and Chuan-Fu LIU. "Antimicrobial Activity of Quaternized Chitosan/Organic Rectorite Nanocomposite." Journal of Inorganic Materials 24, no. 6 (November 30, 2009): 1236–42. http://dx.doi.org/10.3724/sp.j.1077.2009.01236.

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Sun, Yanming, Xiaofei Liang, Mingjie Zhu, Jungong Zhao, Yingsheng Cheng, and Yourong Duan. "Characterization and Bioactivity of Alginate-Quaternized Chitosan Microcapsules." Journal of Macromolecular Science, Part A 49, no. 6 (June 2012): 483–89. http://dx.doi.org/10.1080/10601325.2012.676908.

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Sang, Wei, Ming-Yang He, Zhe Tang, Tian-Ming Chen, and Qi Xu. "Antimicrobial Preservative Coating Prepared with Quaternized Carboxymethyl Chitosan." Asian Journal of Chemistry 27, no. 6 (2015): 2141–44. http://dx.doi.org/10.14233/ajchem.2015.17819.

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Zubareva, Anastasia A., Balzhima Ts Shagdarova, Valery P. Varlamov, and Elena V. Svirshchevskaya. "CELL BINDING AND PENETRATION OF QUATERNIZED CHITOSAN DERIVATIVES." Progress on Chemistry and Application of Chitin and its Derivatives 21 (September 30, 2016): 217–23. http://dx.doi.org/10.15259/pcacd.21.23.

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Liu, Bo, Xiaoying Wang, Xiaoyun Li, Xianjie Zeng, Runcang Sun, and John F. Kennedy. "Rapid exfoliation of rectorite in quaternized carboxymethyl chitosan." Carbohydrate Polymers 90, no. 4 (November 2012): 1826–30. http://dx.doi.org/10.1016/j.carbpol.2012.07.014.

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Bracamonte, María V., Omar E. Linárez Pérez, Manuel López Teijelo, Gustavo A. Rivas, and Nancy F. Ferreyra. "Quaternized chitosan mediated assembly of gold nanoparticles multilayers." Electrochimica Acta 146 (November 2014): 178–85. http://dx.doi.org/10.1016/j.electacta.2014.08.109.

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Cheah, Wai Yan, Pau-Loke Show, I.-Son Ng, Guan-Yu Lin, Chen-Yaw Chiu, and Yu-Kaung Chang. "Antibacterial activity of quaternized chitosan modified nanofiber membrane." International Journal of Biological Macromolecules 126 (April 2019): 569–77. http://dx.doi.org/10.1016/j.ijbiomac.2018.12.193.

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Ye, Weijie, Yi Dang, Xiaoxiang Wen, Yunzhi Ling, Houbin Li, Xiaoying Wang, and Runcang Sun. "Interface behavior of quaternized chitosan on cellulosic substrates." Fibers and Polymers 15, no. 7 (July 2014): 1450–55. http://dx.doi.org/10.1007/s12221-014-1450-y.

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Mi, Xue, K. Saagar Vijayaragavan, and Caryn L. Heldt. "Virus adsorption of water-stable quaternized chitosan nanofibers." Carbohydrate Research 387 (March 2014): 24–29. http://dx.doi.org/10.1016/j.carres.2014.01.017.

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Guo, Chuanhang, Mingyang Liu, Yuanling Xia, Xiaoqiang Fan, Yanjun Chen, and Chaocan Zhang. "Adsorption of Quaternized-chitosan-modified Reduced Graphene Oxide." Journal of Wuhan University of Technology-Mater. Sci. Ed. 33, no. 4 (July 12, 2018): 967–73. http://dx.doi.org/10.1007/s11595-018-1920-y.

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Sajomsang, Warayuth, Pattarapond Gonil, Somsak Saesoo, and Chitchamai Ovatlarnporn. "Antifungal property of quaternized chitosan and its derivatives." International Journal of Biological Macromolecules 50, no. 1 (January 2012): 263–69. http://dx.doi.org/10.1016/j.ijbiomac.2011.11.004.

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de Britto, Douglas, Rejane Celi Goy, Sergio Paulo Campana Filho, and Odilio B. G. Assis. "Quaternary Salts of Chitosan: History, Antimicrobial Features, and Prospects." International Journal of Carbohydrate Chemistry 2011 (July 26, 2011): 1–12. http://dx.doi.org/10.1155/2011/312539.

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Recently, increasing attention has been paid to water-soluble derivatives of chitosan at its applications. The chemical characteristics and the antimicrobial properties of these salts can play significant role in pharmacological and food areas mainly as carriers for drug delivery systems and as antimicrobial packaging materials. In the current paper, a historical sequence of the main preparative methods, physical chemistry aspects, and antimicrobial activity of chitosan quaternized derivatives are presented and briefly discussed. In general, the results indicated that the quaternary derivatives had better inhibitory effects than the unmodified chitosan.

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Piras, Anna Maria, Semih Esin, Arianna Benedetti, Giuseppantonio Maisetta, Angela Fabiano, Ylenia Zambito, and Giovanna Batoni. "Antibacterial, Antibiofilm, and Antiadhesive Properties of Different Quaternized Chitosan Derivatives." International Journal of Molecular Sciences 20, no. 24 (December 13, 2019): 6297. http://dx.doi.org/10.3390/ijms20246297.

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In the era of antimicrobial resistance, the identification of new antimicrobials is a research priority at the global level. In this regard, the attention towards functional antimicrobial polymers, with biomedical/pharmaceutical grade, and exerting anti-infective properties has recently grown. The aim of this study was to evaluate the antibacterial, antibiofilm, and antiadhesive properties of a number of quaternized chitosan derivatives that have displayed significant muco-adhesive properties and wound healing promotion features in previous studies. Low (QAL) and high (QAH) molecular weight quaternized chitosan derivatives were synthetized and further modified with thiol moieties or pendant cyclodextrin, and their antibacterial activity evaluated as minimal inhibitory concentrations (MIC) and minimal bactericidal concentrations (MBC). The ability of the derivatives to prevent biofilm formation was assessed by crystal violet staining. Both QAL and QAH derivatives exerted a bactericidal and/or inhibitory activity on the growth of P. aeruginosa and S. epidermidis. The same compounds also showed marked dose-dependent anti-biofilm activity. Furthermore, the high molecular weight derivative (QAH) was used to functionalize titanium plates. The successful functionalization, demonstrated by electron microscopy, was able to partially inhibit the adhesion of S. epidermidis at 6 h of incubation. The shown ability of the chitosan derivatives tested to both inhibit bacterial growth and/or biofilm formation of clinically relevant bacterial species reveals their potential as multifunctional molecules against bacterial infections.

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Gao, Kun, Yukun Qin, Song Liu, Ronge Xing, Huahua Yu, Xiaolin Chen, Kecheng Li, and Pengcheng Li. "Synthesis, Characterization, and Anti-Phytopathogen Evaluation of 6-Oxychitosan Derivatives Containing N-Quaternized Moieties in Its Backbone." International Journal of Polymer Science 2018 (August 1, 2018): 1–7. http://dx.doi.org/10.1155/2018/3970142.

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The structure modification of chitosan has great application potential. 6-Oxychitosan was prepared by specially oxidizing the C6-OH of chitosan, then 6-oxychitosan was reacted with three kinds of aldehydes to prepare N-quaternized 6-oxychitosan derivatives in this paper. The derivatives were characterized by FT-IR, NMR, and elemental analysis. The antimicrobial activity of these derivatives was tested against two common plant-threatening fungi and three plant disease bacteria. The results showed that N-quaternized 6-oxychitosan derivatives had good water-solubility and excellent antimicrobial activity. Moreover, derivative 3 which connected 8-hydroxyquinolines had the highest antimicrobial activity than the other derivatives. The inhibitory indices of derivative 3 against V. albo-atrum and P. hibernalis are 89.1% and 72.8% at 0.4 mg/ml. The MICs of 3 against X. oryzae, P. syringae, and E. rhapontici were 625, 625, and 156 mg/l, respectively. All the results indicate that derivative 3 has the potential of becoming an alternative to harmful agricultural chemicals.

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Ji, Qiu Xia, Xi Guang Chen, Qing Sheng Zhao, Cheng Sheng Liu, Xiao Jie Cheng, and Ling Chong Wang. "Injectable thermosensitive hydrogel based on chitosan and quaternized chitosan and the biomedical properties." Journal of Materials Science: Materials in Medicine 20, no. 8 (March 26, 2009): 1603–10. http://dx.doi.org/10.1007/s10856-009-3729-x.

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Peng, Zhao-Xiang, Bing Tu, Yang Shen, Lin Du, Ling Wang, Sheng-Rong Guo, and Ting-Ting Tang. "Quaternized Chitosan InhibitsicaATranscription and Biofilm Formation byStaphylococcuson a Titanium Surface." Antimicrobial Agents and Chemotherapy 55, no. 2 (December 6, 2010): 860–66. http://dx.doi.org/10.1128/aac.01005-10.

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ABSTRACTOur previous study (Z. X. Peng et al., Carbohydr. Polym.81:275-283, 2010) demonstrated that water-soluble quaternary ammonium salts, which are produced by the reaction of chitosan with glycidyl trimethylammonium chloride, provide chitosan derivatives with enhanced antibacterial ability. Because biofilm formation is believed to comprise the key step in the development of orthopedic implant-related infections, we further evaluated the efficacy of hydroxypropyltrimethyl ammonium chloride chitosan (HACC) with different degrees of substitution (DS; referred to as HACC 6%, 18%, and 44%) in preventing biofilm formation on a titanium surface. We used a tissue culture plate method to quantify the biomass ofStaphylococcus epidermidisandStaphylococcus aureusbiofilms and found that HACC, especially HACC 18% and 44%, significantly inhibited biofilm formation compared to the untreated control, even at concentrations far below their MICs (P< 0.05). Scanning electron microscopy showed that inhibition of biofilm formation on titanium increased dramatically with increased DS and HACC concentrations. Confocal laser scanning microscopy indicated that growth of a preexisting biofilm on titanium was inhibited by concentrations of HACC 18% and 44% below their minimum biofilm eradication concentrations. We also demonstrated that HACC inhibited the expression oficaA, which mediates the production of extracellular polysaccharides, both in new biofilms and in preexisting biofilms on titanium. Our results indicate that HACC may serve as a new antibacterial agent to inhibit biofilm formation and prevent orthopedic implant-related infections.

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Tang, Yang, Linlin Xie, Mingze Sai, Ningning Xu, and Derun Ding. "Preparation and antibacterial activity of quaternized chitosan with iodine." Materials Science and Engineering: C 48 (March 2015): 1–4. http://dx.doi.org/10.1016/j.msec.2014.11.019.

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Luo, Jiwen, Xiaoying Wang, Bin Xia, and Jun Wu. "Preparation and Characterization of Quaternized Chitosan Under Microwave Irradiation." Journal of Macromolecular Science, Part A 47, no. 9 (July 30, 2010): 952–56. http://dx.doi.org/10.1080/10601325.2010.501310.

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Huang, Xiujie, Changliang Xu, Yichen Li, Haibo Cheng, Xiaoying Wang, and Runcang Sun. "Quaternized chitosan-stabilized copper sulfide nanoparticles for cancer therapy." Materials Science and Engineering: C 96 (March 2019): 129–37. http://dx.doi.org/10.1016/j.msec.2018.10.062.

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