Abstract
Carbohydrates and derivatives (such as glycolipids, glycoproteins) are of critical importance for cell structure, metabolism and functions. The effects of carbohydrate and lipid metabolic imbalances most often cause health disorders and diseases. In this study, new carbohydrate-based nanobioconjugates were designed and synthesized at room temperature using a single-step aqueous route combining chitosan and acyl-modified chitosan with fluorescent inorganic nanoparticles. N-palmitoyl chitosan (C-Pal) was prepared aiming at altering the lipophilic behavior of chitosan (CHI), but also retaining its reasonable water solubility for potential biomedical applications. CHI and C-Pal were used for producing biofunctionalized CdS quantum dots (QDs) as colloidal water dispersions. Fourier transform infrared spectroscopy (FTIR), thermal analysis (TG/DSC), surface contact angle (SCA), and degree of swelling (DS) in phosphate buffer were used to characterize the carbohydrates. Additionally, UV-Visible spectroscopy (UV-Vis), photoluminescence spectroscopy (PL), dynamic light scattering (DLS), scanning and transmission electron microscopy (SEM/TEM) were used to evaluate the precursors and nanobioconjugates produced. The FTIR spectra associated with the thermal analysis results have undoubtedly indicated the presence of N-palmitoyl groups “grafted” to the chitosan chain (C-Pal) which significantly altered its behavior towards water swelling and surface contact angle as compared to the unmodified chitosan. Furthermore, the results have evidenced that both CHI and C-Pal performed as capping ligands on nucleating and stabilizing colloidal CdS QDs with estimated average size below 3.5 nm and fluorescent activity in the visible range of the spectra. Therefore, an innovative “one-step” process was developed via room temperature aqueous colloidal chemistry for producing biofunctionalized quantum dots using water soluble carbohydrates tailored with amphiphilic behavior offering potential applications as fluorescent biomarkers in the investigation of glycoconjugates for the nutrition, biology, pharmaceutical, and medicine fields.
Highlights
Glycoconjugates such as glycoproteins and glycolipids have structures in which proteins or lipids are conjugated with saccharide moieties, and are crucial components of biological organisms, including cells, tissues of animals and plants
The degree of deacetylation (DD) of chitosan was calculated from Fourier transform infrared spectroscopy (FTIR) spectrum using Equation (2) [29]: A1320/A1420 = 0.3822+ 0.03133 × (100-DD)
Where A1320 and A1420 are the absorbance associated with amide III C-N bonds and C-H symmetrical deformation vibrations, respectively
Summary
Glycoconjugates such as glycoproteins and glycolipids have structures in which proteins or lipids are conjugated with saccharide moieties, and are crucial components of biological organisms, including cells, tissues of animals and plants. Pure chitosan exhibits biodegradability and biocompatibility, but low solubility in aqueous media at physiological pH, leading to the formation of brittle films with unsuitable mechanical properties. For that reason, it has been blended with other polymers [11,12], crosslinked or grafted with chemical functionalities offering countless alternatives for developing new materials with a set of characteristics tailored for specific biomedical application
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