Synthesis and Characterization of Conjugated Hyaluronic Acids. Application to Stability Studies of Chitosan-Hyaluronic Acid Nanogels Based on Fluorescence Resonance Energy Transfer
Volodymyr Malytskyi,
Juliette Moreau,
Maité Callewaert,
Céline Henoumont,
Cyril Cadiou,
Cécile Feuillie,
Sophie Laurent,
Michael Molinari,
Françoise Chuburu
Affiliations
Volodymyr Malytskyi
Institut de Chimie Moléculaire de Reims, University of Reims Champagne Ardenne, CNRS, ICMR UMR 7312, 51097 Reims, France
Juliette Moreau
Institut de Chimie Moléculaire de Reims, University of Reims Champagne Ardenne, CNRS, ICMR UMR 7312, 51097 Reims, France
Maité Callewaert
Institut de Chimie Moléculaire de Reims, University of Reims Champagne Ardenne, CNRS, ICMR UMR 7312, 51097 Reims, France
Céline Henoumont
NMR and Molecular Imaging Laboratory, University of Mons UMons, B-7000 Mons, Belgium
Cyril Cadiou
Institut de Chimie Moléculaire de Reims, University of Reims Champagne Ardenne, CNRS, ICMR UMR 7312, 51097 Reims, France
Cécile Feuillie
Center for Microscopy and Molecular Imaging, Rue Adrienne Bolland 8, B-6041 Charleroi, Belgium
Sophie Laurent
NMR and Molecular Imaging Laboratory, University of Mons UMons, B-7000 Mons, Belgium
Michael Molinari
Center for Microscopy and Molecular Imaging, Rue Adrienne Bolland 8, B-6041 Charleroi, Belgium
Françoise Chuburu
Institut de Chimie Moléculaire de Reims, University of Reims Champagne Ardenne, CNRS, ICMR UMR 7312, 51097 Reims, France
Hyaluronic acid (HA) was functionalized with a series of amino synthons (octylamine, polyethylene glycol amine, trifluoropropyl amine, rhodamine). Sodium hyaluronate (HAs) was first converted into its protonated form (HAp) and the reaction was conducted in DMSO by varying the initial ratio (−NH2 (synthon)/COOH (HAp)). HA derivatives were characterized by a combination of techniques (FTIR, 1H NMR, 1D diffusion-filtered 19F NMR, DOSY experiments), and degrees of substitution (DSHA) varying from 0.3% to 47% were determined, according to the grafted synthon. Nanohydrogels were then obtained by ionic gelation between functionalized hyaluronic acids and chitosan (CS) and tripolyphosphate (TPP) as a cross-linker. Nanohydrogels for which HA and CS were respectively labeled by rhodamine and fluorescein which are a fluorescent donor-acceptor pair were subjected to FRET experiments to evaluate the stability of these nano-assemblies.
