Thiolated chitosan-lauric acid as a new chitosan derivative: Synthesis, characterization and cytotoxicity

Kazemi, Mir Salar; Mohammadi, Zohreh; Amini, Mohsen; Yousefi, Maryam; Tarighi, Parastoo; Eftekhari, Sanaz; Tehrani, Morteza Rafiee

doi:10.1016/j.ijbiomac.2019.06.132

Cited by 45 publications

(23 citation statements)

References 20 publications

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“…Figure shows the FT‐IR spectra of chitosan and chitosan derivatives. In chitosan spectrum, the peaks observed at 3417, 2919 and 2881, and 1596 cm −1 were assigned to O─H and N─H stretching vibrations, ─CH asymmetric stretching, and vibration modes of amino group . In spectrum of CACS, there were two peaks at 1741 cm −1 and 790 cm −1 corresponding to vibrations of C═O and C─Cl .…”

Section: Resultsmentioning

confidence: 98%

Improved Antioxidant and Antifungal Activity of Chitosan Derivatives Bearing Urea Groups

Zhang

Sun

et al. 2020

Starch Stärke

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Eight novel chitosan derivatives bearing urea groups are designed and synthesized. Fourier transform infrared spectroscopy, 1 H nuclear magnetic resonance spectrometer, and elemental analysis are performed to confirm the structural characteristics of chitosan derivatives. The antioxidant activities, including superoxide radicals' scavenging activity, 1,1-diphenyl-2-picrylhydrazyl radicals' scavenging activity, and hydroxyl radical' scavenging activity, of the derivatives are explored within different concentrations in the reaction system. In vitro fungicidal activity of these compounds is further tested against Fusarium oxysporum f. sp. niveum, Phomopsis asparagus, F. oxysporum f. sp. cucumebrium Owen, and Botrytis cinerea, respectively, particularly compounds exhibit significant control effect at 1.0 mg mL −1 . The experimental results indicate that the products bearing urea groups show enhanced antifungal property and antioxidant activity compared with pristine chitosan. Meanwhile, their bioactivities follow some regularity on the whole, that is, they are related to the electron-withdrawing property of the different substituted groups of urea. Derivatives with stronger electron-withdrawing property will have higher biological activities. L929 cells are used to carry out cytotoxicity test of chitosan and chitosan derivatives by Cell Counting Kit-8 assay. The results indicate that some of the samples show low cytotoxicity. This research will be helpful to broaden the application of chitosan in materials.

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Section: Resultsmentioning

confidence: 98%

Improved Antioxidant and Antifungal Activity of Chitosan Derivatives Bearing Urea Groups

Zhang

Sun

et al. 2020

Starch Stärke

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“…[31] In other studies hydrophobic substructures were introduced in thiolated chitosan by the covalent attachment of stearic acid and lauric acid being responsible for the self-assembly of these polymers to micelles. [32,33] Other polysaccharides such as alginate were also shown to assemble to NPs by the introduction of hydrophobic groups. Chang et al formed thiolated alginate NPs applying just ultrasound to an aqueous solution of the thiolated polymer that enhanced the self-assembly process.…”

Section: Self-assemblymentioning

confidence: 99%

Thiolated Nanoparticles for Biomedical Applications: Mimicking the Workhorses of Our Body

Hock¹,

Racaniello

Aspinall

et al. 2021

Advanced Science

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Advances in nanotechnology have generated a broad range of nanoparticles (NPs) for numerous biomedical applications. Among the various properties of NPs are functionalities being related to thiol substructures. Numerous biological processes that are mediated by cysteine or cystine subunits of proteins representing the workhorses of the bodies can be transferred to NPs. This review focuses on the interface between thiol chemistry and NPs. Pros and cons of different techniques for thiolation of NPs are discussed. Furthermore, the various functionalities gained by thiolation are highlighted. These include overall bio-and mucoadhesive, cellular uptake enhancing, and permeation enhancing properties. Drugs being either covalently attached to thiolated NPs via disulfide bonds or being entrapped in thiolated polymeric NPs that are stabilized via inter-and intrachain crosslinking can be released at the diseased tissue or in target cells under reducing conditions. Moreover, drugs, targeting ligands, biological analytes, and enzymes bearing thiol substructures can be immobilized on noble metal NPs and quantum dots for therapeutic, theranostic, diagnostic, biosensing, and analytical reasons. Within this review a concise summary and analysis of the current knowledge, future directions, and potential clinical use of thiolated NPs are provided.

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“…Meanwhile, an absorption peak appeared at 1075 cm -1 that was ascribed to the stretching vibration of C-O in the secondary hydroxyl group, and an absorption peak that appeared at 1303 cm -1 was ascribed to the stretching vibration of C-N in the secondary amine structure. Hence, the hydroxypropyl groups are replaced on both hydroxyl groups and amino groups of CTS (Zhu et al 2017;Kazemi et al 2019).…”

Section: Chemical Characterizationmentioning

confidence: 99%

Synthesis and properties of dehydroabietyl glycidyl ether grafted hydroxypropyl chitosan

Guo

Cai

et al. 2020

BioRes

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A nonionic surfactant based on chitosan and rosin, i.e. dehydroabietyl glycidyl ether grafted hydroxypropyl chitosan (DAGE-g-HPCS), was synthesized for the first time through reaction between hydroxypropyl chitosan (HPCS) and dehydroabietyl glycidyl ether (DAGE). The surface activities of DAGE-g-HPCS in aqueous solution were investigated via determination of surface tension, and its emulsifying ability was evaluated according to the stability time of emulsion composed of benzene-water with DAGE-g-HPCS as emulsifier; the foam stability was evaluated using the oscillation method. Through modulating the molecular weight of HPCS and the grafting degree (DG) of DAGE-g-HPCS, the emulsion stability and foam stability were surprisingly controllable. Compared to HPCS and specific emulsifier, the stability time of emulsion composed of benzene-water with DAGE-g-HPCS showed a remarkable performance with DG of 16.5% as the emulsifier was 7320 s, and the foam retention of DAGE-g-HPCS with 2.0 g·L-1 was 91.5%. Simultaneously, the critical micelle concentration (CMC) of DAGE-g-HPCS decreased with increased DG, while the emulsifying ability and foam stability exhibited opposite trend. The CMC, emulsifying ability, and foam stability of DAGE-g-HPCS increased with decreased HPCS molecular weight. These results demonstrated that the DAGE-g-HPCS was an excellent surfactant that should be considered as a promising substitute for petrochemical nonionic surfactant.

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Thiolated chitosan-lauric acid as a new chitosan derivative: Synthesis, characterization and cytotoxicity

Cited by 45 publications

References 20 publications

Improved Antioxidant and Antifungal Activity of Chitosan Derivatives Bearing Urea Groups

Improved Antioxidant and Antifungal Activity of Chitosan Derivatives Bearing Urea Groups

Thiolated Nanoparticles for Biomedical Applications: Mimicking the Workhorses of Our Body

Synthesis and properties of dehydroabietyl glycidyl ether grafted hydroxypropyl chitosan

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