Synthesis of N-succinyl- and N-glutaryl-chitosan derivatives and their antioxidant, antiplatelet, and anticoagulant activity

Skorik, Yury А.; Kritchenkov, Andreii S.; Moskalenko, Yulia E.; Golyshev, Anton A.; Raik, Sergei V.; Whaley, A. K.; Васина, Л. В.; Sonin, Dmitry

doi:10.1016/j.carbpol.2017.02.097

Cited by 47 publications

(20 citation statements)

References 37 publications

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“…Compared with that of CS, the signal for H 2 was shifted to a higher chemical shift due to less chemical shielding. There were distinctive signals at 2.47 ppm and 2.45 ppm, which were attributed to the protons of methylene groups in succinyl [ 14 , 22 , 23 ]. The 1 H NMR result confirms the FTIR result.…”

Section: Resultsmentioning

confidence: 99%

Study on TEMPO-Mediated Oxidation of N-Succinyl Chitosan and the Water Retention Property

Xue

Ye³

et al. 2020

Molecules

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C-6 oxidized chitosan is of great interest in obtaining a new moisture retention polymer like hyaluronic acid. The direct C-6 specific oxidation of chitosan mediated by the TEMPO/NaClO/NaBr system has proven to be difficult because of the high crystalline and high C-2 amino group content. In this work, the pre-modification of chitosan by N-succinylation was investigated and followed by the TEMPO-mediated C-6 specific oxidation under homogeneous conditions. The desired 6-oxidized N-succinyl chitosan product was obtained within 15 min with a yield of about 92%. The structure of these chitosan derivatives was confirmed by FTIR and NMR spectroscopy. Moreover, it was observed that the selective oxidation led to a great improvement in water solubility and moisture retention ability. These results present a wide range of possibilities for expanding the utilization of chitosan resources.

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Section: Resultsmentioning

confidence: 99%

Study on TEMPO-Mediated Oxidation of N-Succinyl Chitosan and the Water Retention Property

Xue

Ye³

et al. 2020

Molecules

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“…The anticoagulant properties of a dispersed CNP solution were evaluated by its ability to lengthen the clotting time (compared to controls) when added to platelet-poor plasma. Measurements included the activated partial thromboplastin time (APTT), prothrombin time (PT), and thrombin time (TT) [34].…”

Section: Assessment Of Anticoagulant Activitymentioning

confidence: 99%

Biological Safety and Biodistribution of Chitosan Nanoparticles

et al. 2020

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The effect of unmodified chitosan nanoparticles with a size of ~100 nm and a weakly positive charge on blood coagulation, metabolic activity of cultured cardiomyocytes, general toxicity, biodistribution, and reactive changes in rat organs in response to their single intravenous administration at doses of 1, 2, and 4 mg/kg was studied. Chitosan nanoparticles (CNPs) have a small cytotoxic effect and have a weak antiplatelet and anticoagulant effect. Intravenous administration of CNPs does not cause significant hemodynamic changes, and 30 min after the CNPs administration, they mainly accumulate in the liver and lungs, without causing hemolysis and leukocytosis. The toxicity of chitosan nanoparticles was manifested in a dose-dependent short-term delay in weight gain with subsequent recovery, while in the 2-week observation period no signs of pain and distress were observed in rats. Granulomas found in the lungs and liver indicate slow biodegradation of chitosan nanoparticles. In general, the obtained results indicate a good tolerance of intravenous administration of an unmodified chitosan suspension in the studied dose range.

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“…The synthesis of CS-Succ was set up as reported by Skorik et al [75]. In brief, 2 g of chitosan were dissolved in 100 mL of aqueous acetic acid solution (1% v/v), followed by the addition of 0.3 g of succinic anhydride, diluted in a small volume of acetone.…”

Section: Chitosan Modified With Succinic Anhydride (Cs-succ)mentioning

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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Synthesis of N-succinyl- and N-glutaryl-chitosan derivatives and their antioxidant, antiplatelet, and anticoagulant activity

Cited by 47 publications

References 37 publications

Study on TEMPO-Mediated Oxidation of N-Succinyl Chitosan and the Water Retention Property

Study on TEMPO-Mediated Oxidation of N-Succinyl Chitosan and the Water Retention Property

Biological Safety and Biodistribution of Chitosan Nanoparticles

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

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