Assessment of chemically and enzymatically modified chitosan with eugenol as a coating for viscose functionalization for potential medical use

Abstract

The present work deals with the preparation of chemically and enzymatically eugenol-modified chitosan and its application as a green coating on viscose for the potential production of medical textiles. The elemental composition of chemically and enzymatically eugenol-modified chitosan was determined by attenuated total reflection Fourier transform infrared (ATR FT-IR) and proton nuclear magnetic resonance (1H NMR) spectroscopy. Moreover, potentiometric titration was used to estimate the number of accessible amino groups. The chitosan–eugenol formulation possesses a high antioxidant capacity level, as shown by the high content of phenolic compounds analyzed by the following methods: (a) Folin–Ciocalteu; (b) reduction of Fe3+ ions; and (c) α, α-diphenyl-β-picrylhydrazyl (DPPH•). Viscose coated with chitosan–eugenol formulations was evaluated by ATR FT-IR spectroscopy and Acid Orange VII spectrophotometric methods, the results of which demonstrated the successful deposition of these formulations on the fibers. Scanning electron microscopy showed the presence of the functional coating on the viscose. Finally, antimicrobial testing was performed to determine inhibition of selected pathogenic micro-organisms using the ASTM E 2149-01 standard. The antioxidant activity of the functionalized viscose was investigated spectrophotometrically by the DPPH• method. It was found that the coatings of eugenol-modified chitosan impart antimicrobial activity to the viscose against Gram-positive and Gram-negative bacteria as well as fungi, and cause inhibition of free radicals by introducing an antioxidant character. The chemical and enzymatic modification of chitosan offers many opportunities for the incorporation of many natural active ingredients into the chitosan system, which provides a good basis for further work related to the functionalization of chitosan for sanitary and medical use.

Cellulose–Chitosan Functional Biocomposites

“…Further studies have been conducted to improve and extend the antimicrobial activity of chitosan, while its disadvantage is that it is more active against Gram-positive pathogenic bacteria and less so against negative Gram-pathogenic bacteria. Moreover, chitosan is a poor antioxidant; thus, antioxidative properties have been achieved by binding or encapsulating some other substances such as flavonoids, curcumin, iodine, and eugenol [ 123 , 124 , 125 , 126 ]. Ristić et al showed that quaternary chitosan is more effective than primary chitosan as a cellulose coating because it contains quaternary amino groups that are not protonated pH-dependent [ 127 ].…”

DEAE/Catechol–Chitosan Conjugates as Bioactive Polymers: Synthesis, Characterization, and Potential Applications

“…Consequently, polyphenols are considered candidates to produce water-soluble Cs derivatives. Various polyphenols such as gallic acid, 24 ferulic acid, 25 catechin, 26 epigallocatechin gallate, 27 eugenol, 28 quercetin, 29 caffeic, 30 and hydrocaffeic acid 31 have already been introduced into the Cs structure by using several methods that include free radicalinduced grafting reaction, activated ester-mediated modification, and an enzyme-mediated method. 32 Recently, Huerta-Madronãl et al in 2021 synthesized a water-soluble conjugate based on Cs and rosmarinic acid, which has shown a threefold increase in radical scavenger activity (RSA) against the 2,2diphenyl-1-picrylhydrazyl (DPPH) free radical and improved antimicrobial properties over free polyphenol and unmodified Cs.…”

Modified Chitosan Based on Optimized Design in the Treatment of Microbial Leaching Wastewater

“…The eugenol-modified chitosan coating was found to impart antibacterial activity to the viscose against Gram-positive and Gram-negative bacteria and fungi, and to inhibit free radicals by introducing antioxidant properties. The chemical and enzymatic modification of chitosan offers many opportunities to incorporate many natural active ingredients into chitosan systems, which provide a good basis for further studies on the functionalization of chitosan for hygiene and medical use [3] ]. Shahraki Z M examined whether the accumulation of nitrogen in and around leaching ponds used for on-site wastewater treatment (carryover nitrogen) could be a source of groundwater nitrogen contamination as the pond inflow volume and/or composition changes.…”