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![Modification scheme of N-acylated chitosan: (A) The synthetic route of O-acylated CSNFs. Adapted with permission from [50], Copyright © 2017 Elsevier. (B) the synthetic route of NSC and its structural characterization. Adapted with permission from [51], Copyright © 2016, Elsevier.](publication/362844211/figure/fig2/AS:11431281080190005@1661176811946/Modification-scheme-of-N-acylated-chitosan-A-The-synthetic-route-of-O-acylated-CSNFs.png)
Modification scheme of N-acylated chitosan: (A) The synthetic route of O-acylated CSNFs. Adapted with permission from [50], Copyright © 2017 Elsevier. (B) the synthetic route of NSC and its structural characterization. Adapted with permission from [51], Copyright © 2016, Elsevier.
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![Figure 7. APANCS synthetic route [84].](publication/362844211/figure/fig5/AS:11431281080201854@1661176812377/APANCS-synthetic-route-84_Q320.jpg)
Chitosan, which is derived from chitin, is the only known natural alkaline cationic polymer. Chitosan is a biological material that can significantly improve the living standard of the country. It has excellent properties such as good biodegradability, biocompatibility, and cell affinity, and has excellent biological activities such as antibacteria...
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... O-acylated chitosan is relatively difficult to prepare, it is usually necessary to add trifluoroacetic acid or methanesulfonic acid to protect C 2 -NH 2 prior to the acylation reaction; then, the protective group must be removed after the reaction is complete. Zhang et al. [50] used pyridine as a catalyst, short-chain and long-chain fatty acid anhydrides as acylating agents, and chitosan nanofibers (CSNFs) as modifiers, and they synthesized O-acylated CSNFs under the presence of trifluoroacetate; its synthetic route is shown in Figure 3A. X-ray diffraction analysis revealed that O-acylation modification altered the crystal structure of CSNFs. ...
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... CSNFs under the presence of trifluoroacetate; its synthetic route is shown in Fig- ure 3A. X-ray diffraction analysis revealed that O-acylation modification altered the crystal structure of CSNFs. ...
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... modification of chitosan with acid anhydride can result in NSC with good solubility. For example, Tang et al. [51] synthesized NSC via acylation modification of chitosan using succinic anhydride, hydrochloric acid, and alkaline chitosan as raw materials; its structure was characterized by Fourier transform infrared spectroscopy, and hydrogen nuclear magnetic resonance spectroscopy was then used to investigate its solubility and toxicity, antibacterial properties, and ability to promote wound healing; its synthetic route and structural characterization are shown in Figure 3B. The results revealed that compared with chitosan, NSC had significantly higher solubility and better antibacterial activity. ...
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... prepared amphiphilic chitosan Acylation modification of chitosan with acid anhydride can result in NSC with good solubility. For example, Tang et al. [51] synthesized NSC via acylation modification of chitosan using succinic anhydride, hydrochloric acid, and alkaline chitosan as raw materials; its structure was characterized by Fourier transform infrared spectroscopy, and hydrogen nuclear magnetic resonance spectroscopy was then used to investigate its solubility and toxicity, antibacterial properties, and ability to promote wound healing; its synthetic route and structural characterization are shown in Figure 3B. The results revealed that compared with chitosan, NSC had significantly higher solubility and better antibacterial activity. ...
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Using environmentally friendly biomaterials in different aspects of human life has been considered extensively. In this respect, different biomaterials have been identified and different applications have been found for them. Currently, chitosan, the well-known derivative of the second most abundant polysaccharide in the nature (i.e., chitin), has...
Citations
... There are a variety of reactive functional groups in chitosan; thus, a variety of chemical transformations can be performed on this polymer, notably imination, carboxylation, alkylation, acylation, sulfonation, and cross-linking [10]. These modifications aim to improve the physical and chemical properties of the polymer for specific applications [11][12][13]. ...
Chitosan is a biopolymer that can be subjected to a variety of chemical modifications to generate new materials. The properties of modified chitosan are affected by its degree of deacetylation (DDA), which corresponds to the percentage of D-glucosamine monomers in its polymeric structure. Potentiometric titration is amongst the simplest, most readily available, and most cost-effective methods of determining the DDA. However, this method often suffers from a lack of precision, especially for modified chitosan resins. This is in large part because the equation used to calculate the DDA does not consider the molecular weight of the chemically modified monomeric units. In this paper, we introduce a new equation that is especially suited for modified chitosan bearing three different types of monomers. To test this equation, we prepared naphthalene–chitosan resins and subjected them to potentiometric titration. Our results show that our new equation, which is truer to the real structure of the polymeric chains, gives higher DDA values than those of the routinely used equations. These results show that the traditional equations underestimate the DDA of modified chitosan resins.
... The large volume of research and practical interest in chitin and chitosan are driven by their unique structures, which, due to the presence of both hydroxyl and amine groups, lead to a variety of functional features. Moreover, Cht is characterized as a biocompatible, low-toxic, biodegradable polymer possessing a high sorption capacity for a multitude of compounds [1][2][3][4][5]. ...
Chitosan takes second place of the most abundant polysaccharides naturally produced by living organisms. Due to its abundance and unique properties, such as its polycationic nature, ability to form strong elastic porous films, and antibacterial potential, it is widely used in the food industry and biomedicine. However, its low solubility in both water and organic solvents makes its application difficult. We have developed an environmentally friendly method for producing water-soluble graft copolymers of chitosan and poly (N-vinylpyrrolidone) with high grafting efficiency and a low yield of by-products. By using AFM, SEM, TGA, DSC, and XRD, it has been demonstrated that the products obtained have changed properties compared to the initial chitosan. They possess a smoother surface and lower thermal stability but are sufficient for practical use. The resulting copolymers have a higher viscosity than the original chitosan, making them a promising thickener and stabilizer for food gels. Moreover, the copolymers exhibit an antibacterial effect, suggesting their potential use as a component in smart food packaging.
... The solubility profile has been improved in aqueous media by different chemical pathways like deacetylation, depolymerisation and quaternisation. The parent structure of chitosan can be modified through acylation, alkylation, esterification, and other processes to produce modified chitosan derivatives with desirable physical, chemical, and biological properties making them an ideal drug and vaccine carriers owing to the possession of ridiculous functional groups, specifically the amino group, primary hydroxyl group, and secondary hydroxyl group at C-2, C-3, and C-6 positions, respectively (Chen et al., 2022;Pellis et al., 2022). Although, C3-OH (secondary hydroxyl) exhibit steric hindrance hence does not rotate freely and creates issues in chemical reactions. ...
... 60 However, the utilization of chitosan's release profile varies significantly depending on polymer chain modifications, which can be easily performed. 61 On the other hand, alginate not only exhibits pH-dependent release capabilities but also boasts high mucoadhesive properties. 62 This additional advantage enables efficient drug adhesion in topical applications on mucosal surfaces, further enhancing drug delivery efficacy. ...
Nanoparticle systems integrating alginate and chitosan emerge as a promising avenue to tackle challenges in leveraging the potency of pharmacological active agents. Owing to their intrinsic properties as polysaccharides, alginate and chitosan, exhibit remarkable biocompatibility, rendering them conducive to bodily integration. By downsizing drug particles to the nano-scale, the system enhances drug solubility in aqueous environments by augmenting surface area. Additionally, the system orchestrates extended drug release kinetics, aligning well with the exigencies of chronic drug release requisite for antibacterial therapeutics. A thorough scrutiny of existing literature underscores a wealth of evidence supporting the utilization of the alginate-chitosan nanoparticle system for antibacterial agent delivery. Literature reviews present abundant evidence of the utilization of nanoparticle systems based on a combination of alginate and chitosan for antibacterial agent delivery. Various experiments demonstrate enhanced antibacterial efficacy, including an increase in the inhibitory zone diameter, improvement in the minimum inhibitory concentration, and an enhancement in the bacterial reduction rate. This enhancement in efficacy occurs due to mechanisms involving increased solubility resulting from particle size reduction, prolonged release effects, and enhanced selectivity towards bacterial cell walls, stemming from ionic interactions between positively charged particles and teichoic acid on bacterial cell walls. However, clinical studies remain limited, and there are currently no marketed antibacterial drugs utilizing this system. Hence, expediting clinical efficacy validation is crucial to maximize its benefits promptly.
... Bone tissue engineering. [49,52] Increases the solubility and extends the release of drugs. ...
... Drug carrier. [47][48][49] Azidated chitosan Enhancement of mechanical stability. Thiolated chitosan Thiolated chitosan offers various advantages over native chitosan, including increased solubility at low degrees of substitution and mucoadhesive and cellular penetration capabilities. ...
... Bone tissue engineering. [49,52] Enhanced mechanical strength, prolonged drug release kinetics, and targeted delivery. ...
Chitosan, a versatile biopolymer derived from chitin, has garnered significant attention in various biomedical applications due to its unique properties, such as biocompatibility, biodegradability, and mucoadhesiveness. This review provides an overview of the diverse applications of chitosan and its derivatives in the antibacterial, anticancer, wound healing, and tissue engineering fields. In antibacterial applications, chitosan exhibits potent antimicrobial properties by disrupting microbial membranes and DNA, making it a promising natural preservative and agent against bacterial infections. Its role in cancer therapy involves the development of chitosan-based nanocarriers for targeted drug delivery, enhancing therapeutic efficacy while minimising side effects. Chitosan also plays a crucial role in wound healing by promoting cell proliferation, angiogenesis, and regulating inflammatory responses. Additionally, chitosan serves as a multifunctional scaffold in tissue engineering, facilitating the regeneration of diverse tissues such as cartilage, bone, and neural tissue by promoting cell adhesion and proliferation. The extensive range of applications for chitosan in pharmaceutical and biomedical sciences is not only highlighted by the comprehensive scope of this review, but it also establishes it as a fundamental component for forthcoming research in biomedicine.
... Malignant cells having more negative charges compared to their normal cell counterparts, which make them a selective target for positively charged modified chitosan, which interferes with metabolic and growth processes and induces apoptosis in cancer cells. Additionally, chitosan can improve the immune response, boost the activity of phagocytic cells, and prevent the spread and infiltration of cancer into adjacent tissues by disrupting the formation of vascular endothelial cells 34,68 . ...
Chitosan (CH) exhibits low antimicrobial activity. This study addresses this issue by modifying the chitosan with a sulfonamide derivative, 3-(4-(N,N-dimethylsulfonyl)phenyl)acrylic acid. The structure of the sulfonamide-chitosan derivative (DMS-CH) was confirmed using Fourier transform infrared spectroscopy and Nuclear magnetic resonance. The results of scanning electron microscopy, thermal gravimetric analysis, and X-ray diffraction indicated that the morphology changed to a porous nature, the thermal stability decreased, and the crystallinity increased in the DMS-CH derivative compared to chitosan, respectively. The degree of substitution was calculated from the elemental analysis data and was found to be moderate (42%). The modified chitosan exhibited enhanced antimicrobial properties at low concentrations, with a minimum inhibitory concentration (MIC) of 50 µg/mL observed for B. subtilis and P. aeruginosa, and a value of 25 µg/mL for S. aureus, E. coli, and C. albicans. In the case of native chitosan, the MIC values doubled or more, with 50 µg/mL recorded for E. coli and C. albicans and 100 μg/mL recorded for B. subtilis, S. aureus, and P. aeruginosa. Furthermore, toxicological examinations conducted on MCF-7 (breast adenocarcinoma) cell lines demonstrated that DMS-CH exhibited greater toxicity (IC50 = 225.47 μg/mL) than pure CH, while still maintaining significant safety limits against normal lung fibroblasts (WI-38). Collectively, these results suggest the potential use of the newly modified chitosan in biomedical applications.
... The reaction using halogenated alkanes and Schiff's base are two common methods used to synthesize N-alkylated chitosan. 22 The reaction using halogenated alkanes is performed by introducing an alkyl to chitosan. The solubility depends on the length of the alkyl group introduced to chitosan; the lower the length of the alkyl group, the higher the solubility of alkylated chitosan. ...
Chitosan is a functional polymer in the pharmaceutical field, including for nanoparticle drug delivery systems. Chitosan-based nanoparticles are a promising carrier for a wide range of therapeutic agents and can be administered in various routes. Solubility is the main problem for its production and utilization in large-scale industries. Chitosan modifications have been employed to enhance its solubility, including chemical modification. Many reviews have reported the chemical modification but have not focused on the specific characteristics obtained. This review focused on the modification to improve chitosan solubility. Additionally, this review also focused on the application of chitosan derivatives in nanoparticle drug delivery systems since very few similar reviews have been reported. The specific method for chitosan derivative-based nanoparticles was also reported and the latest report of chitosan, chitosan derivative, and chitosan toxicity were also described.
... Common methods for graft copolymerization methods include oxidative coupling copolymerization, radiation grafting, radical graft copolymerization, enzyme graft copolymerization, etc. Chemical methods of graft copolymerization typically use initiators such as potassium persulfate, ammonium persulfate, iron sulfate, etc. [61,64,65]. This grafting copolymerization modification not only enhances the antibacterial, anticancer, and antioxidant abilities of chitosan polymers but also improves their solubility and biocompatibility [64]. ...
... Chemical methods of graft copolymerization typically use initiators such as potassium persulfate, ammonium persulfate, iron sulfate, etc. [61,64,65]. This grafting copolymerization modification not only enhances the antibacterial, anticancer, and antioxidant abilities of chitosan polymers but also improves their solubility and biocompatibility [64]. ...
... In addition to the reactions mentioned above, commonly used chemical modifications of chitosan include glycosylation, sulfation, etherification, thiolation, etc. [62][63][64][65]. Research has shown that a chitosan Schiff base containing thiophene, indole, and pyrazole groups and CS was transformed into nanoparticles with high inhibitory activity on tumor cells [66]. ...
The management of wound healing represents a significant clinical challenge due to the complicated processes involved. Chitosan has remarkable properties that effectively prevent certain microorganisms from entering the body and positively influence both red blood cell aggregation and platelet adhesion and aggregation in the bloodstream, resulting in a favorable hemostatic outcome. In recent years, chitosan-based hydrogels have been widely used as wound dressings due to their biodegradability, biocompatibility, safety, non-toxicity, bioadhesiveness, and soft texture resembling the extracellular matrix. This article first summarizes an overview of the main chemical modifications of chitosan for wound dressings and then reviews the desired properties of chitosan-based hydrogel dressings. The applications of chitosan-based hydrogels in wound healing, including burn wounds, surgical wounds, infected wounds, and diabetic wounds are then discussed. Finally, future prospects for chitosan-based hydrogels as wound dressings are discussed. It is anticipated that this review will form a basis for the development of a range of chitosan-based hydrogel dressings for clinical treatment.
... In the realm of pesticide formulation, CMCS is frequently employed as a novel formulation to enhance the water solubility of fat-soluble pesticide compounds. This, in turn, reduces the need for large quantities of organic solvents and lowers the ecological impact (Chen et al., 2022). Wang et al. synthesized CMCS-grafted daphnetin (DA) NPs and evaluated the antimicrobial its antibacterial efficacy against bacterial wiltcausing phytopathogen Ralstonia solanacearum . ...
Chitosan, an economically viable and versatile biopolymer, exhibits a wide array of advantageous physicochemical and biological properties. Chitosan nanocomposites, formed by the amalgamation of chitosan or chitosan nanoparticles with other nanoparticles or materials, have garnered extensive attention across agricultural, pharmaceutical, and biomedical domains. These nanocomposites have been rigorously investigated due to their diverse applications, notably in combatting plant pathogens. Their remarkable efficacy against phytopathogens has positioned them as a promising alternative to conventional chemical-based methods in phytopathogen control, thus exploring interest in sustainable agricultural practices with reduced reliance on chemical interventions. This review aims to highlight the anti-phytopathogenic activity of chitosan nanocomposites, emphasizing their potential in mitigating plant diseases. Additionally, it explores various synthesis methods for chitosan nanoparticles to enhance readers' understanding. Furthermore, the analysis delves into elucidating the intricate mechanisms governing the antimicrobial effectiveness of these composites against bacterial and fungal phytopathogens.
... Chemical modification of chitosan can occur at one of the active sites or equally at both sites to form N-, O-, or N, O-modified chitosan derivatives, and this can be achieved by a variety of chemical reactions (Figure 3). Chen et al. (2022) discuss the latest advances in chitosan chemical modification methods and review the uses of chitosan and its derivatives in several fields. The choice of modification depends on the desired properties and the intended use of the modified chitosan. ...
For many years, chitosan has been widely regarded as a promising eco-friendly polymer thanks to its renewability, biocompatibility, biodegradability, non-toxicity, and ease of modification, giving it enormous potential for future development. As a cationic polysaccharide, chitosan exhibits specific physicochemical, biological, and mechanical properties that depend on factors such as its molecular weight and degree of deacetylation. Recently, there has been renewed interest surrounding chitosan derivatives and chitosan-based nanocomposites. This heightened attention is driven by the pursuit of enhancing efficiency and expanding the spectrum of chitosan applications. Chitosan’s adaptability and unique properties make it a game-changer, promising significant contributions to industries ranging from healthcare to environmental remediation. This review presents an up-to-date overview of chitosan production sources and extraction methods, focusing on chitosan’s physicochemical properties, including molecular weight, degree of deacetylation and solubility, as well as its antibacterial, antifungal and antioxidant activities. In addition, we highlight the advantages of chitosan derivatives and biopolymer modification methods, with recent advances in the preparation of chitosan-based nanocomposites. Finally, the versatile applications of chitosan, whether in its native state, derived or incorporated into nanocomposites in various fields, such as the food industry, agriculture, the cosmetics industry, the pharmaceutical industry, medicine, and wastewater treatment, were discussed.
