Syntheses of novel chitosan derivative with excellent solubility, anticoagulation, and antibacterial property by chemical modification

Abstract

The soluble and antibacterial chitosan derivative was prepared on the basis of the regioselective chemical modification. The N-(2-phthaloylation) chitosan was obtained via the reaction of chitosan with phthalic anhydride in N,N-dimethylformamide (DMF) at 130 C, and O-(3,6-hydroxyethyl) chitosan was produced using chlorohydrins as grafting agent and hydrazine hydrate as reductant. The structure of hydroxyethyl chitosan (HC) was characterized by X-ray diffraction (XRD), Fourier Transform infrared spectroscopy (FTIR), and gel permeation chromatography (GPC) respectively. The solubility, anticoagulation, and antibacterial property were assessed separately. The result shows that amine I of chitosan is replaced and the amide II disappears during chemical modification, and the functional groups of C6-OH and -NH2 are also reacted. The water-solubility of the novel chitosan derivative was enhanced relatively; it could even slightly soluble in methanol. The results of platelet adhesion and the activated partial thromboplastin times (APTTs) indicate that grafting hydroxyethyl could improve anticoagulation of chitosan. The antibacterial activity of HC against Enterococcus and E. coli had been much better owing to enhancing the degree of protonation.

Antibacterial Properties of New Chitosan-Based Schiff Bases.

“…Just a brief enumeration of the fields of chitosan and its derivatives application indicates the importance of this compound (Ahmed and Ikram, 2017). Chitosan and some of its derivatives are biocompatible, have low toxicity, have bactericidal, anticoagulant, chelating (complex-forming) properties (Wang et al, 2009;Liu 2012, Subhapradha et al, 2013Gritscha et al, 2018), characterized by high radiation stability (Chmielewski, 2010), demonstrate anti-tumor properties (Wang et al, 2009;Gupta and Karar, 2012). Taking into account chelate-forming abilities of chitin/chitosan systems, efficient sorbents for bacterial cells and many heavy metals and a number of their compounds have been synthesized on their basis and studied (Guibal, 1188(Guibal, 2004Varma et al, 2004;Tariq et al,2010;Jiang et al, 2011;Kocak et al, 2012;Farag and Mohamed, 2013).…”

Synthesis of PEGylated chitosan copolymers as efficiently antimicrobial coatings for leather

“…[13][14][15][16][17] Barreiro et al developed an antimicrobial leather coating based on CS, taking advantages of CS intrinsic antimicrobial activity and film-forming capacity.…”

“…Recently, Byung‐Taek Oh's group used green‐synthesized Ag NPs to coat on the leather surface for getting rid of bad odors and bacterial infections . Chitosan (CS), the linear and partly acetylated (1‐4)‐2‐amino‐2‐deoxy‐β‐ d ‐glucan isolated from marine chitin, is being currently proposed for a wide range of applications due to antimicrobial activity, biocompatibility, nontoxicity, and biodegradability . Barreiro et al developed an antimicrobial leather coating based on CS, taking advantages of CS intrinsic antimicrobial activity and film‐forming capacity .…”

“…Despite the advantages of eco‐friendly and antimicrobial property of above leather coatings, the antimicrobial efficiency is still worth investigating. The antimicrobial mechanisms of Ag NPs or CS coatings are mainly based on destroying the microorganism cell membrane, finally leading to cell death . After a certain time, the dead microorganism on the surface will affect or shield the antimicrobial activity of these coatings, resulting in lower antimicrobial efficiency.…”

Preparation and characterization of antibacterial chitosan/Ag–montmorillonite with improved dynamic mechanic properties

“…Chitosan is a deacetylated derivative of chitin, the second abundant natural polysaccharide on earth which can be found in the exoskeletons of insects, the shells of crustaceans, and fungal cell walls. It is a polysaccharide composed of N ‐glucosamine and N ‐acetyl‐glucosamine units, in which the number of N ‐glucosamine units exceeds 50% . Because of its excellent biocompatibility, biodegradability, nontoxicity, adsorptive properties, and film‐forming ability, materials based on chitosan are widely applied in membrane separation, water treatment, tissue engineering (scaffolds), biosensors, dressing, and nanocarrier .…”