Synthesis and Biological Evaluation of a Novel Glycidyl Metharcylate/Phaytic Acid-Based on Bagasse Xylan Composite Derivative.

Mingkun Li,Chaoyu Xie,Zhiming Zou,Hongli Liu,Heping Li

doi:10.3390/polym13132084

Abstract

The development of natural biomass materials with excellent properties is an attractive way to improve the application range of natural polysaccharides. Bagasse Xylan (BX) is a natural polysaccharide with various biological activities, such as antitumor, antioxidant, etc. Its physic-chemical and biological properties can be improved by functionalization. For this purpose, a novel glycidyl metharcylate/phytic acid based on a BX composite derivative was synthesized by a free radical polymerization technique with glycidyl metharcylate (GMA; GMABX) and further esterification with phytic acid (PA; GMABX-PA) in ionic liquid. The effects of the reaction conditions (i.e., temperature, time, initiator concentration, catalyst concentration, GMA concentration, PA concentration, mass of ionic liquid) on grafting rate(G), conversion rate(C) and degree of substitution(DS) are discussed. The structure of the composite material structure was confirmed by FTIR, 1H NMR and XRD. SEM confirmed the particle morphology of the composite derivative. The thermal stability of GMABX-PA was determined by TG-DTG. Molecular docking was further performed to study the combination mode of the GMABX-PA into the active site of two lung cancer proteins (5XNV, 2EB2) and a blood cancer protein (2M6N). In addition, tumor cell proliferation inhibition assays for BX, GMABX-PA were carried out using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetraz -olium bromide (MTT) method. The results showed that various reaction conditions exhibited favorable gradient curves, and that a maximum G of 56% for the graft copolymerization and a maximum DS of 0.267 can be achieved. The thermal stability was significantly improved, as demonstrated by the fact that there was still 60% residual at 800 °C. The molecular docking software generated satisfactory results with regard to the evaluated binding energy and combining sites. The inhibition ratio of GMABX-PA on NCI-H460 (lung cancer cells) reached 29.68% ± 4.45%, which is five times higher than that of BX. Therefore, the material was shown to be a potential candidate for biomedical applications as well as for use as a heat resistant material.

Highlights

Natural polysaccharides have been proposed as materials from which to produce functional materials and alternatives to petroleum-based materials
Glycidyl methacrylate (GMA) Bagasse Xylan (BX) copolymer was synthesized by a free radical polymerization technique, resulting in a G and C of 56% and 29%, respectively
Fourier Transform Infrared (FTIR), 1 H NMR, and X-ray Diffraction (XRD) showed that epoxy groups and phosphate groups had been introduced into the BX

Summary

Introduction

Natural polysaccharides have been proposed as materials from which to produce functional materials and alternatives to petroleum-based materials. The use of polysaccharides has been proposed for drug carriers with slow release function [1,2,3], complex films with antibacterial properties [4,5], etc. The anticancer activity of xylan has been demonstrated; for example, xylan extracted from corn cobs by Cao et al [6] was shown to possess biological activity against cervical and lung cancer. Some modification methods, such as grafting, esterification and etherification, have been reported, and their properties have been improved to a certain extent. Some grafted monomers, such as polyhexa-methylene guanidine hydrochloride [7]

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