Synthesis and antioxidant action of chitosan derivatives with amino-containing groups via azide-alkyne click reaction and N-methylation

Abstract

Amino functionality has been paid growing attention in chemical modification of polysaccharides due to their potential biomedical applications. Here, the preparation of novel antioxidant materials based on chitosan derivatives bearing amino-containing groups equipped with 1,2,3-triazole and 1,2,3-triazolium by Cuprous-catalyzed azide-alkyne cycloaddition and N-methylation was described for the first time. The structural characteristics of the synthesized derivatives were examined by FTIR, H NMR, and elemental analysis. The antioxidant activities of the chitosan derivatives were assessed in vitro. The results indicated that chitosan derivatives bearing 1,2,3-triazoles displayed superior antioxidant activity over pristine chitosan, especially against superoxide anion radical. Moreover, antioxidant efficiency of chitosan derivatives further enhanced after N-methylation of 1,2,3-triazole moieties with iodomethane, which is comparative to that of ascorbic acid. Notably, of all chitosan derivatives bearing 1,2,3-triazole or 1,2,3-triazolium moieties, acylhydrazine-functionalized and amino-functionalized chitosan showed the stronger antioxidant capacity than hydroxyl-modified chitosan at the test concentration. Besides, the cytotoxicities of them were also evaluated in vitro on HaCaT cells. These results suggested that amino and acylhydrazine-functionalized chitosan derivatives with 1,2,3-triazolium could be used as novel antioxidant biomaterials.

Improved Antioxidant and Antifungal Activity of Chitosan Derivatives Bearing Urea Groups

“…However, the scavenging regularity of derivatives THUCACS, TDUCACS, MTDUCACS, and TRUCACS was not obvious. But it was still TRUCACS that had the best scavenging capacity, which was consistent with the previous conclusion that chitosan derivatives containing triazole possessed better antioxidant capacity …”

“…The superoxide‐radical scavenging ability was assessed following the previous method . The reaction mixture, involving test samples (5 mg mL −1 , 0.06, 0.12, 0.24, 0.48, and 0.96 mL), phenazine methosulfate (PMS, 30 µ m ), nitro blue tetrazolium (NBT, 72 µ m ), and nicotinamide adenine dinucleotide reduced (NADH, 338 µ m ) in Tris HCl buffer (16 m m , pH 8.0), was incubated 5 min at r.t.…”

Synthesis and Antioxidant Activity of Cationic 1,2,3-Triazole Functionalized Starch Derivatives

“…The study of the DPPH radical scavenging ability was conducted using the methods developed by Tan [33]. In brief, 1 mL of each sample at different concentrations (0.3 mg mL −1 , 0.6 mg mL −1 , 1.2 mg mL −1 , 2.4 mg mL −1 , and 4.8 mg mL −1 ) mixed with 2 mL of DPPH solution (180 µM, dissolved in ethanol), was incubated at 25 • C for 30 min.…”

“…The superoxide radical scavenging assay was performed following the methods developed by Tan [33]. Each sample (1.5 mL, 0.3 mg mL −1 , 0.6 mg mL −1 , 1.2 mg mL −1 , 2.4 mg mL −1 , and 4.8 mg mL −1 ) was seriatim added with NADH (0.5 mL, 456 µM, in Tris-HCl buffer with PH of 8.0), NBT (0.5 mL, 300 µM, in Tris-HCl buffer with PH of 8.0), and PMS (0.5 mL, 60 µM, in Tris-HCl buffer with PH of 8.0).…”

Influence of Chitosan Addition on Resorcinol–Formaldehyde Xerogel Structure

“…Therefore, it is exploited universally in various applications such as in pharmaceuticals [5], the food industry [6], and water remediation [7]. Furthermore, the surface groups, namely, hydroxyl and amino groups, contribute to the hydrophilicity and active adsorption sites of Cs [8]. Pekala introduced the polycondensation reaction of resorcinol (R) with formaldehyde (F) to form a xerogel (X), which is named hereafter as RFX [9].…”