Sulfated xanthan: synthesis, characterization and biological evaluation
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Sulfated xanthan: synthesis, characterization and biological evaluation Sayyid Mahdi Rafigh1 · Atrin Rahimpour Soleymani2 · Amir Heydarinasab1 Received: 8 February 2020 / Revised: 8 February 2020 / Accepted: 14 August 2020 © Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract In this study, sulfated derivatives of xanthan gum (XG) were synthesized and then characterized using FTIR, 1H NMR, 13C NMR, GPC, DSC, TGA, SEM, HPLC, Zeta (ζ) potential and elemental analysis. The degrees of substitution (DS) was 0.51 (SXG-1) and 1.23 (SXG-2). From the NMR spectrum and methylation analysis by GC–MS, it was concluded that the sulfate groups had completely introduced into the C-6 hydroxyl groups. The native XG and SXGs were further evaluated for their anticoagulant, antithrombotic and cytotoxic activities. The results suggest that the SXG-2 could be used as a promising anticoagulant and antithrombotic agent for clinical applications. Keywords Xanthan gum · Sulfate modification · Anticoagulant activity · Antithrombotic activity · Cytotoxicity
Introduction Xanthan gum is a natural extracellular hetero-polysaccharide produced by fermentation from Xanthomonas campestris [1, 2]. Primary structure of XG contains a glucose molecule connected by β-1,4 glycosidic links and it also possesses acetate and pyruvate groups on inner and terminal mannoses of the side chain respectively [3–6]. XG is biodegradable, nontoxic toward humans and the environment, edible and it has been approved by the FDA in 1969 [7, 8]. XG is the Electronic supplementary material The online version of this article (https://doi.org/10.1007/s0028 9-020-03344-8) contains supplementary material, which is available to authorized users. * Sayyid Mahdi Rafigh [email protected] 1
Department of Chemical Engineering, Faculty of Petroleum and Chemical Engineering, Science and Research Branch, Islamic Azad University, Tehran, Iran
2
Department of Organic Chemistry, Faculty of Pharmaceutical Chemistry, Tehran Medical Sciences, Islamic Azad University, Tehran, Iran
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first polysaccharide produced by bacterial fermentation on an industrial scale [4, 7, 9]. XG is highly soluble and viscous even at low concentration and because of it’s resistance to thermal degradation, excellent suspending and safety properties, has the growing capacity in the food and pharmaceutical applications [3, 9–11]. The total global consumption of xanthan gum reached 248,578 tons in 2016 [12]. The chemical structure of XG and its sulfated derivatives were depicted in Scheme 1 [7, 8]. Sulfated polysaccharides as highly negatively charged biomacromolecules are achievable or chemically synthesized, and exhibit specific biological capacities [13–15]. In recent years, more attention has been paid to sulfate modification of polysaccharides for improving their properties for applications in the medicine, food, cosmetic and pharmaceutical industries [16–18]. Sulfated polysaccharides display a huge number of different biological properties s
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