Comparison of the acylation of chitosan with succinic anhydride in aqueous suspension and in solution

Golyshev, Anton A.; Moskalenko, Yu. E.; Skorik, Yury А.

doi:10.1007/s11172-015-0994-3

Cited by 11 publications

(4 citation statements)

References 23 publications

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“…Herein, the sharper peak exhibited at 3420 cm −1 is attributed to the additional, due to the modification, hydroxyl groups of the derivative, while peak shifting in comparison to the acrylic monomer ( Figure S1 ) is attributed to the hydrogen bonds formed between the amino and hydroxyl groups of CS and the ester groups of HEA units [ 35 ]. Finally, as for the CS-g-PAA derivative, the bands observed at 1646 and 1573 cm −1 correspond to amide I and II, respectively, while a new shoulder detected at 1719 cm −1 reveals the evolved interactions taking place between the amino groups of neat CS with the carbonyl groups of the acrylic acid [ 47 ]. For a further confirmation of the successful preparation of the four CS derivatives, the samples were subjected to nuclear magnetic resonance (NMR) spectra.…”

Section: Resultsmentioning

confidence: 99%

Microencapsulation of Fluticasone Propionate and Salmeterol Xinafoate in Modified Chitosan Microparticles for Release Optimization

et al. 2020

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Chitosan (CS) is a natural polysaccharide, widely studied in the past due to its unique properties such as biocompatibility, biodegradability and non-toxicity. Chemical modification of CS is an effective pathway to prepare new matrices with additional functional groups and improved properties, such as increment of hydrophilicity and swelling rate, for drug delivery purposes. In the present study, four derivatives of CS with trans-aconitic acid (t-Acon), succinic anhydride (Succ), 2-hydroxyethyl acrylate (2-HEA) and acrylic acid (AA) were prepared, and their successful grafting was confirmed by FTIR and 1H-NMR spectroscopies. Neat chitosan and its grafted derivatives were fabricated for the encapsulation of fluticasone propionate (FLU) and salmeterol xinafoate (SX) drugs, used for chronic obstructive pulmonary disease (COPD), via the ionotropic gelation technique. Scanning electron microscopy (SEM) micrographs demonstrated that round-shaped microparticles (MPs) were effectively prepared with average sizes ranging between 0.4 and 2.2 μm, as were measured by dynamic light scattering (DLS), while zeta potential verified in all cases their positive charged surface. FTIR spectroscopy showed that some interactions take place between the drugs and the polymeric matrices, while X-ray diffraction (XRD) patterns exhibited that both drugs were encapsulated in MPs’ interior with a lower degree of crystallinity than the neat drugs. In vitro release studies of FLU and SX exposed a great amelioration in the drugs’ dissolution profile from all modified CS’s MPs, in comparison to those of neat drugs. The latter fact is attributed to the reduction in crystallinity of the active substances in the MPs’ interior.

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Section: Resultsmentioning

confidence: 99%

Microencapsulation of Fluticasone Propionate and Salmeterol Xinafoate in Modified Chitosan Microparticles for Release Optimization

et al. 2020

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“…The solution was filtered using a Buchner funnel, washed using distilled water to pH 7, rinsed with ethanol, and dried in an oven. The synthesized powder was characterized using a Genesys 10S UV-Vis spectrophotometer and Perkin Elmer's Fourier Transform InfraRed (FTIR) Frontier Type 14 .…”

Section: Synthesis Of Maleoyl Chitosan Amide (Mca) With Variation Of ...mentioning

confidence: 99%

Synthesis of Carboxylated Chitosan Amide Using Some Cyclic Anhydride and Their Activities as Antifungal

Ismiyarto,

Mumtazati,

Pandelaki

et al. 2023

Valensi

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Chitosan is a natural polymer that has antifungal activity. It is necessary to modify chitosan into its derivatives to increase its activity. One modification of chitosan that has the potential to be developed as an antifungal is carboxylated chitosan amide because this chitosan derivative contains a carboxylic group and is more hydrophilic. This research aims to synthesize chitosan amide carboxylate using several cyclic anhydride compounds and test its antifungal activity against Aspergillus flavus. The cyclic anhydrides used in this research are maleic anhydride and phthalic anhydride. In the initial stage of chitosan amide carboxylate synthesis, reaction optimization was carried out at varying temperatures of 25, 50, and 72oC for 7 hours. Compound characterization was carried out using FTIR and UV-Vis spectrophotometry. The disc diffusion method tested the chitosan amide carboxylate product for its antifungal activity against Aspergillus flavus. The optimal MCA (Maleoyl Chitosan Amide) product is (MCA_50), synthesized at a reaction temperature of 50oC. Under these optimal reaction conditions, PCA_50 (Pthaloyl Chitosan Amide) was successfully synthesized to produce a brownish-yellow solid with a yield of 46.1% (w/w) and a degree of substitution (DS) of 41.93%. The diameter of the inhibition zone against Aspergillus flavus for PCA_50 was 30 mm at the 12th hour of observation. The product (PCA_50) has better antifungal activity than chitosan and MCA_50.

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“…The existence of chemically active hydroxyl and amino groups results in an easy modification of CH to improve intrinsic properties or give some new features. CH can form N-derivatives by reactions with amino groups and O-derivatives by reactions with hydroxyl groups and sometimes both N, O-derivatives [23]. Tein et al synthesized N-acylated CH to increase hydrophobicity by reacting CH with fatty acid chlorides for drug release application [24].…”

Section: Introductionmentioning

confidence: 99%

Carbamoylated chitosan hydrogels with improved viscoelastic properties and stability for potential 3D cell culture applications

et al. 2021

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We demonstrate a benign and straightforward method to modify the chitosan (CH) by carbamoylation. The free amines on CH are converted into carbamyl functionalities by reacting with potassium cyanate (KCNO). One wt% CH solution, when reacted with KCNO ⩾ 0.1 M, leads to the sol–gel transition of CH through the hydrogen bonding to form carbamoylated chitosan (CCH) hydrogel. Gelation time of CCH decreases with an increase in the KCNO concentration and an interconnected porous network is formed as observed under SEM. Rheological studies show that while one wt% CH solution is a viscous liquid, the CCH hydrogel with 0.5 M KCNO has a storage modulus (G') of 104 Pa. The CCH hydrogel is proved to be non-cytotoxic and promotes the attachment and growth of the small lung cancer model A549, and the neuroblastoma SH-SY5Y cell lines. CCH hydrogel also promotes the differentiation of SH-SY5Y cells into neuronal cells, as supported by immunostaining and thus demonstrating its utility as a versatile scaffold for three-dimensional cell-culture systems.

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Comparison of the acylation of chitosan with succinic anhydride in aqueous suspension and in solution

Cited by 11 publications

References 23 publications

Microencapsulation of Fluticasone Propionate and Salmeterol Xinafoate in Modified Chitosan Microparticles for Release Optimization

Microencapsulation of Fluticasone Propionate and Salmeterol Xinafoate in Modified Chitosan Microparticles for Release Optimization

Synthesis of Carboxylated Chitosan Amide Using Some Cyclic Anhydride and Their Activities as Antifungal

Carbamoylated chitosan hydrogels with improved viscoelastic properties and stability for potential 3D cell culture applications

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