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Schante C.E.,University of Strasbourg | Schante C.E.,Laboratoire IDENOV | Zuber G.,University of Strasbourg | Herlin C.,Laboratoire IDENOV | Vandamme T.F.,University of Strasbourg
Carbohydrate Polymers | Year: 2012

Injection of hyaluronic acid (HA)-based hydrogels has proven to provide many therapeutic benefits. To increase the stability of HA-based products against enzymatic digestion, we modified hyaluronic acid by grafting various amino acids on its carboxylic group and then evaluated the enzymatic stability of the various conjugates in presence of a hyaluronidase. Our results showed that all amino acid-modified HA polymers were more resistant to degradation compared to the native HA albeit with variation according to the amino acids. Amino acids with carboxylate groups such as aspartic acid or with hydroxyl functions (threonine, serine or tyrosine) conferred a particularly strong resistance to HA towards enzymatic digestion. The HA-amino acid products were then cross-linked with butanediol diglycidyl ether (BDDE). The swelling properties of the formed hydrogels appeared close to native HA whereas the increased resistance towards hyaluronidase digestion remained. These results suggest that amino acid-modified HA derivatives can become promising material for viscosupplementation or drug delivery. © 2011 Elsevier Ltd. All rights reserved. Source


Schante C.,CNRS Laboratory of Design and Application of Bioactive Molecules | Schante C.,Laboratoire IDENOV | Zuber G.,CNRS Laboratory of Design and Application of Bioactive Molecules | Herlin C.,Laboratoire IDENOV | Vandamme T.F.,CNRS Laboratory of Design and Application of Bioactive Molecules
Carbohydrate Polymers | Year: 2011

In order to increase the resistance of hyaluronic acid towards enzymatic digestion, we prepared N-alanyl-hyaluronamide derivatives using different amidation methods performed either in water, water/acetonitrile mixture or anhydrous dimethylformamide. Our results indicate that amidation of hyaluronic acid in an anhydrous solvent is effective and led to a degree of substitution of the carboxylic groups up to 100%. We also demonstrated the N-alanyl- hyaluronamides present enhanced resistance towards enzymatic digestion while forming solutions with similar viscosities than solutions of hyaluronic acids of similar lengths. © 2011 Elsevier Ltd All rights reserved. Source


Schante C.E.,University of Strasbourg | Schante C.E.,Laboratoire IDENOV | Zuber G.,University of Strasbourg | Herlin C.,Laboratoire IDENOV | Vandamme T.F.,University of Strasbourg
Carbohydrate Polymers | Year: 2011

Hyaluronic acid (HA) is widely used for numerous medical applications, such as viscosupplementation, eye surgery and drug delivery. A broad range of HA-based materials have been developed and described for the enhancement, modulation and control of its therapeutic action, based on chemical modification of polysaccharides. The purpose of this paper is to review the various chemical modification methods and synthetic routes to obtain HA derivatives, encompassing all applications. © 2011 Elsevier Ltd. All rights reserved. Source

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