Preparation of succinylated cellulose membranes for functionalization purposes

Abstract

The anhydroglucose chains of cellulose possess hydroxyls that facilitate different chemical modification strategies to expand on, or provide new applications for membranes produced by the bacteria Gluconacetobacter xylinus. Conjugation with biomolecules such as proteins, especially by the amine groups, is of great value and interest for the production of biomaterial derivatives from bacterial cellulose. To assist in these modifications, cellulose was succinylated in order to prevent steric hindrance and to create an attachment point for conjugation. Bacterial cellulose membranes were first treated in dichloromethane and reacted with succinic anhydride through a series of conditions. The membrane structure remained intact after these first processes and the product was confirmed by Infra-Red spectroscopy and solid state nuclear magnetic resonance and characterized by X-ray diffraction, thermogravimetry and atomic force microscopy. Hydrolyzed collagen was used as a model protein of interest to be conjugated to these membranes, which furnished a biomaterial functionalized over its surface.

Enhancement of fibroblast growing on the mannosylated surface of cellulose membranes

“…This derivative was prepared in a three steps synthetical route from per-O-acetyl mannose (1), according to Hoshino et al [29] Using a soft condition (succinic anhydride, pyridine in dichloromethane in reflux) which was used to append a protein to cellulose in previous work [26], we were able to prepare a suitable and intact succinylated membrane (BC-Sc). This cellulose derivative exposes carboxylic acid of Initial attempts to couple the mannoside 4 were performed using EDC/DMAP or EDC/NHS as carboxylic acid activator in anhydrous DMF or water, respectively, as solvent.…”

“…Our group has been pursuing chemical methodologies to modify and bond biological relevant molecules to the surface of bacterial cellulose in parallel to understand the structural changes that it could bring. As a sequence of the methodology presented by Ribeiro-Viana [26], we have used a mix of homogeneous and heterogeneous chemical synthesis to insert an aryl mannoside over a surface of a succinylated bacterial cellulose membrane and fully chemically (NMR, IR and UV-vis) and topologically (TGA and AFM) characterize it. Besides, this new material showed good compatibility with growing of fibroblast, demonstrating its potential in the tissue engineer field.…”

“…Bacterial cellulose membranes were prepared as described previously [26]. Briefly, before the reactions, the membranes were prepared by solvent exchange in order to eliminate the excess water.…”

Cellulose Biomaterials for Tissue Engineering

“…At the nanoscale, different crystallinities can be obtained; moreover, the chemical structure of the cellulose can be modified to include specific functional groups to elicit particular cellular responses (He et al, 2014; Shao et al, 2017; Courtenay et al, 2018a,b; Stumpf et al, 2018). For example, collagen can be chemically attached to the cellulose scaffold via linker molecules such as succinic acid (Ribeiro-Viana et al, 2016). At the microscale, the porosities of the materials can be tuned to suit the intended application.…”

Latest Advances on Bacterial Cellulose‐Based Materials for Wound Healing, Delivery Systems, and Tissue Engineering

“…Therefore, there have been several attempts to change the surface chemistry of BC, taking advantage of this specific property. Oxidation mediated by (2,2,6,6‐tetramethylpiperidin‐1‐yl)oxyl (TEMPO), phosphorylation, and succinylation are examples of this type of modifications . Usually, BC nanofibers are randomly orientated; however, there have been several attempts to align the BC nanofibers, namely using microfluidic channels, a scaffolding of nematic ordered cellulose with aligned cellulose fibers or external electromagnetic fields to direct the bacteria motion and achieve fiber alignment.…”