Microwave-Assisted Synthesis of Modified Glycidyl Methacrylate-Ethyl Methacrylate Oligomers, Their Physico-Chemical and Biological Characteristics.

Adam Chyzy,Marta E Plonska-Brzezinska,Joanna Breczko,Michael Bratychak,Agata Przekora,Olena Astakhova,Damian Pawelski,Pawel Drozdzal,Vladyslav Vivcharenko

doi:10.3390/molecules27020337

Abstract

In this study, well-known oligomers containing ethyl methacrylate (EMA) and glycidyl methacrylate (GMA) components for the synthesis of the oligomeric network [P(EMA)-co-(GMA)] were used. In order to change the hydrophobic character of the [P(EMA)-co-(GMA)] to a more hydrophilic one, the oligomeric chain was functionalized with ethanolamine, xylitol (Xyl), and L-ornithine. The oligomeric materials were characterized by nuclear magnetic resonance and Fourier transform infrared spectroscopy, scanning electron microscopy, and differential thermogravimetric analysis. In the final stage, thanks to the large amount of -OH groups, it was possible to obtain a three-dimensional hydrogel (HG) network. The HGs were used as a matrix for the immobilization of methylene blue, which was chosen as a model compound of active substances, the release of which from the matrix was examined using spectrophotometric detection. The cytotoxic test was performed using fluid extracts of the HGs and human skin fibroblasts. The cell culture experiment showed that only [P(EMA)-co-(GMA)] and [P(EMA)-co-(GMA)]-Xyl have the potential to be used in biomedical applications. The studies revealed that the obtained HGs were porous and non-cytotoxic, which gives them the opportunity to possess great potential for use as an oligomeric network for drug reservoirs in in vitro application.

Highlights

IntroductionSince 1960, when Wichterle and Lim published pioneering work on hydrogels (HGs) [1], interest in this group of hydrophilic polymers/oligomers has continued to grow, mainly in widely understood biomedicine, pharmacy, and bioengineering [2,3,4,5,6,7,8,9,10]
Synthesis of the [P(EMA)-co-(GMA)] and their further modification with moieties containing –OH and –NH2 groups (Xyl, ETA or Orn) allow us to obtain the products in the form of white or slightly yellow solid powders (Scheme 2)
The synthesis of the oligomeric network [P(EMA)-co-(GMA)] was performed, which was used as a matrix for further functionalization

Summary

Introduction

Since 1960, when Wichterle and Lim published pioneering work on hydrogels (HGs) [1], interest in this group of hydrophilic polymers/oligomers has continued to grow, mainly in widely understood biomedicine, pharmacy, and bioengineering [2,3,4,5,6,7,8,9,10] Properties such as the hydrophilic nature of the three-dimensional (3D) network, the ability to expand its volume by 10–20% after water absorption, and biocompatibility make these polymeric materials successfully used as matrices in tissue engineering [11,12,13,14], transdermal therapy [15], angiogenesis [16], antifungal therapy [17], chemotherapy [18], drug delivery [3,5,6,19], etc. The possibility of the controlled chemical and physical modification of polymeric chains gives the opportunity to design the 3D HGs matrix with targeted physico-chemical and biological properties [14], which enable the design of a biomaterial with a specific application [8,9,14]

Methods

Results

Conclusion