Synthesis and Characterization of Conjugated Hyaluronic Acids. Application to Stability Studies of Chitosan-Hyaluronic Acid Nanogels Based on Fluorescence Resonance Energy Transfer
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 (−NH<s...
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MDPI AG
2022-03-01
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| author | Volodymyr Malytskyi Juliette Moreau Maité Callewaert Céline Henoumont Cyril Cadiou Cécile Feuillie Sophie Laurent Michael Molinari Françoise Chuburu |
| author_facet | Volodymyr Malytskyi Juliette Moreau Maité Callewaert Céline Henoumont Cyril Cadiou Cécile Feuillie Sophie Laurent Michael Molinari Françoise Chuburu |
| author_sort | Volodymyr Malytskyi |
| collection | DOAJ |
| description | 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 (−NH<sub>2</sub> (synthon)/COOH (HAp)). HA derivatives were characterized by a combination of techniques (FTIR, <sup>1</sup>H NMR, 1D diffusion-filtered <sup>19</sup>F NMR, DOSY experiments), and degrees of substitution (DS<sub>HA</sub>) 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. |
| first_indexed | 2024-03-09T19:48:02Z |
| format | Article |
| id | doaj.art-22fa250717c344f7aa17d15d03ba167c |
| institution | Directory Open Access Journal |
| issn | 2310-2861 |
| language | English |
| last_indexed | 2024-03-09T19:48:02Z |
| publishDate | 2022-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Gels |
| spelling | doaj.art-22fa250717c344f7aa17d15d03ba167c2023-11-24T01:16:54ZengMDPI AGGels2310-28612022-03-018318210.3390/gels8030182Synthesis and Characterization of Conjugated Hyaluronic Acids. Application to Stability Studies of Chitosan-Hyaluronic Acid Nanogels Based on Fluorescence Resonance Energy TransferVolodymyr Malytskyi0Juliette Moreau1Maité Callewaert2Céline Henoumont3Cyril Cadiou4Cécile Feuillie5Sophie Laurent6Michael Molinari7Françoise Chuburu8Institut de Chimie Moléculaire de Reims, University of Reims Champagne Ardenne, CNRS, ICMR UMR 7312, 51097 Reims, FranceInstitut de Chimie Moléculaire de Reims, University of Reims Champagne Ardenne, CNRS, ICMR UMR 7312, 51097 Reims, FranceInstitut de Chimie Moléculaire de Reims, University of Reims Champagne Ardenne, CNRS, ICMR UMR 7312, 51097 Reims, FranceNMR and Molecular Imaging Laboratory, University of Mons UMons, B-7000 Mons, BelgiumInstitut de Chimie Moléculaire de Reims, University of Reims Champagne Ardenne, CNRS, ICMR UMR 7312, 51097 Reims, FranceCenter for Microscopy and Molecular Imaging, Rue Adrienne Bolland 8, B-6041 Charleroi, BelgiumNMR and Molecular Imaging Laboratory, University of Mons UMons, B-7000 Mons, BelgiumCenter for Microscopy and Molecular Imaging, Rue Adrienne Bolland 8, B-6041 Charleroi, BelgiumInstitut de Chimie Moléculaire de Reims, University of Reims Champagne Ardenne, CNRS, ICMR UMR 7312, 51097 Reims, FranceHyaluronic 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 (−NH<sub>2</sub> (synthon)/COOH (HAp)). HA derivatives were characterized by a combination of techniques (FTIR, <sup>1</sup>H NMR, 1D diffusion-filtered <sup>19</sup>F NMR, DOSY experiments), and degrees of substitution (DS<sub>HA</sub>) 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.https://www.mdpi.com/2310-2861/8/3/182nanohydrogels–hyaluronic acid–HA-mPEG<sub>2000</sub>fluorinated and fluorescent HA conjugates–hyaluronic acid degree of substitution–diffusion ordered spectroscopy (DOSY)–1D diffusion-filtered <sup>19</sup>F NMR–atomic force microscopy–FRET experiments–hyaluronidase–nanohydrogel stability |
| spellingShingle | Volodymyr Malytskyi Juliette Moreau Maité Callewaert Céline Henoumont Cyril Cadiou Cécile Feuillie Sophie Laurent Michael Molinari Françoise Chuburu Synthesis and Characterization of Conjugated Hyaluronic Acids. Application to Stability Studies of Chitosan-Hyaluronic Acid Nanogels Based on Fluorescence Resonance Energy Transfer Gels nanohydrogels–hyaluronic acid–HA-mPEG<sub>2000</sub> fluorinated and fluorescent HA conjugates–hyaluronic acid degree of substitution–diffusion ordered spectroscopy (DOSY)–1D diffusion-filtered <sup>19</sup>F NMR–atomic force microscopy–FRET experiments–hyaluronidase–nanohydrogel stability |
| title | Synthesis and Characterization of Conjugated Hyaluronic Acids. Application to Stability Studies of Chitosan-Hyaluronic Acid Nanogels Based on Fluorescence Resonance Energy Transfer |
| title_full | Synthesis and Characterization of Conjugated Hyaluronic Acids. Application to Stability Studies of Chitosan-Hyaluronic Acid Nanogels Based on Fluorescence Resonance Energy Transfer |
| title_fullStr | Synthesis and Characterization of Conjugated Hyaluronic Acids. Application to Stability Studies of Chitosan-Hyaluronic Acid Nanogels Based on Fluorescence Resonance Energy Transfer |
| title_full_unstemmed | Synthesis and Characterization of Conjugated Hyaluronic Acids. Application to Stability Studies of Chitosan-Hyaluronic Acid Nanogels Based on Fluorescence Resonance Energy Transfer |
| title_short | Synthesis and Characterization of Conjugated Hyaluronic Acids. Application to Stability Studies of Chitosan-Hyaluronic Acid Nanogels Based on Fluorescence Resonance Energy Transfer |
| title_sort | synthesis and characterization of conjugated hyaluronic acids application to stability studies of chitosan hyaluronic acid nanogels based on fluorescence resonance energy transfer |
| topic | nanohydrogels–hyaluronic acid–HA-mPEG<sub>2000</sub> fluorinated and fluorescent HA conjugates–hyaluronic acid degree of substitution–diffusion ordered spectroscopy (DOSY)–1D diffusion-filtered <sup>19</sup>F NMR–atomic force microscopy–FRET experiments–hyaluronidase–nanohydrogel stability |
| url | https://www.mdpi.com/2310-2861/8/3/182 |
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