Physicochemical characterization of water-soluble chitosan derivatives with singlet oxygen quenching and antibacterial capabilities

Abstract

New water-soluble chitosan derivatives (WSCh) were obtained by Maillard reaction (MR) between glucosamine (GA) with both low and medium molecular weight chitosans (Ch). The WSCh showed larger solubility than the respective Ch, while their deacetylation degree (DD) decreased by approximately 12%. Infrared spectroscopy experiments of WSCh confirmed the formation of imine bonds after MR with intensified pyranose structure, and sugar molecules as polymer branches. However, a 6-times reduction of the molecular weight of WSCh was measured, indicating the breakdown of the polysaccharide chain during the MR. The polysaccharides quenched singlet molecular oxygen (O), with rate quenching constants correlating with the DD value of the samples, suggesting the important role of amino groups (-NH) in the deactivation of O. Additionally, all polysaccharides presented antimicrobial activity against pathogenic bacteria, e.g. Staphylococcus aureus, Escherichia coli, Salmonella sp., Enterococcus faecalis and Listeria ivanovii, as tested by their minimum inhibitory concentration (MIC). This way we obtained new water-soluble polysaccharides, with similar functional properties to those presented by native Ch, enhancing its potential application as carrier material for bioactive compounds.

Design, Characterization, and Biopharmaceutical Behavior of Nanoparticles Loaded with an HIV-1 Fusion Inhibitor Peptide

“…Chitosan has attracted a lot of attention as a biomedical material for in addition to the advantages described throughout this manuscript; this biopolymer has immune-stimulating biological, anti-tumor and anti-microbial activities, among others. However, the pharmaceutical applications related to Chitosan are limited by the compound's insolubility at neutral or high pH values 48 . With the aim of overcoming the insolubility problems associated with a natural polymer, GC was used.…”

Pembuatan Kitosan Termodifikasi Melalui Reaksi Maillard

“…Kitosan merupakan produk deasetilasi kitin yang merupakan komponen penyusun eksokeleton dari crustacean, jamur, dan serangga. Kitosan memiliki sifat tidak beracun, bio kompatibel, dan biasanya digunakan sebagai anti mikroba (Qin et al 2006;Vanden Braber et al 2017;Kosaraju, Weerakkody, and Augustin 2010) antioksidan (Kosaraju, Weerakkody, and Augustin 2010; Phisut and Jiraporn 2013; Mahae, Chalat, and Muhamud 2011) dan sebagai bahan enkapsulasi dalam aplikasi makanan dan farmasi (Estevinho et al 2013;Alborzi 2012). Namun kitosan memiliki hambatan dalam aplikasinya seperti sifat sukar larut pada pH netral dan tinggi (Chung, Kuo, and Chen 2005).…”

Soy genistein administered in soluble chitosan microcapsules maintains antioxidant activity and limits intestinal inflammation

“…Specifically, for oral delivery of antiinflammatory drugs, nanocarriers of functionalized mesoporous silica or multilaminated metal hydroxide have been designed [18,19]. Herein, to preserve the antioxidant potential of Ge, we prepared microcapsules (MCs) with glucosamine watersoluble Chitosan derivative (WSChitosan) [20] by spray drying, a technique widely used due to its low cost that offer the possibility of continuous production of tailormade particles for specific functions and needs of food industry [21]. Our findings show that microencapsulated Ge maintained its antioxidant properties in vitro.…”

“…Herein, we microencapsulated soy Ge using WSChitosan obtained by Maillard reaction as wall material, as we found previously that Chitosan derivatives kept functional properties of native polymer [20,22]. Microencapsulation was performed by spray drying, an efficient and economical method [34] that has been successfully used with…”

“…4D). Interestingly, mice treated with empty MCs showed a mild protective effect on days 6-8, possibly related to the antioxidant and antiinflammatory bioactivities of WSChitosan derivatives [20,22] and Chitosan itself [49].…”