title: α,β-Unsaturated aldehyde of hyaluronan--Synthesis, analysis and applications.
abstract: Hyaluronic acid (HA) modified with an aldehyde group (HA-CHO or HA-aldehyde) has been extensively used for various biomedical applications. The main advantage of the aldehyde moieties is the ability to react with a wide range of amino compounds under physiological conditions. Reactions of aldehydes with primary amines in water are reversible and equilibrium is thoroughly shifted towards starting aldehyde and amine. This work presents an unique modification of HA: α,β-unsaturated aldehyde of HA (4,5-anhydro-6(GlcNAc)-oxo HA or ΔHA-CHO), which allows the primary amines to be attached to HA more effectively in comparison to the saturated HA-CHO. Higher hydrolytic stability is caused by the conjugation of imine with an adjacent --C=C-- double bond. Two strategies for the preparation of unsaturated HA-aldehyde were developed and chemical structures were studied in details. Cross-linked materials prepared from this precursor are biocompatible and suitable for applications in drug delivery and regenerative medicine.
authors.affiliation: Contipro Pharma, Ltd., Dolní Dobrouč 401, 56102, Czech Republic. Electronic address: buffa@contipro.com.
authors.forename: Radovan
authors.initials: R
authors.lastname: Buffa
authors.affiliation: Contipro Pharma, Ltd., Dolní Dobrouč 401, 56102, Czech Republic.
authors.forename: Petra
authors.initials: P
authors.lastname: Šedová
authors.affiliation: Contipro Pharma, Ltd., Dolní Dobrouč 401, 56102, Czech Republic.
authors.forename: Ivana
authors.initials: I
authors.lastname: Basarabová
authors.affiliation: Contipro Pharma, Ltd., Dolní Dobrouč 401, 56102, Czech Republic.
authors.forename: Martina
authors.initials: M
authors.lastname: Moravcová
authors.affiliation: Contipro Pharma, Ltd., Dolní Dobrouč 401, 56102, Czech Republic.
authors.forename: Lucie
authors.initials: L
authors.lastname: Wolfová
authors.affiliation: Contipro Pharma, Ltd., Dolní Dobrouč 401, 56102, Czech Republic.
authors.forename: Tomáš
authors.initials: T
authors.lastname: Bobula
authors.affiliation: Contipro Pharma, Ltd., Dolní Dobrouč 401, 56102, Czech Republic.
authors.forename: Vladimír
authors.initials: V
authors.lastname: Velebný
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D001672:Biocompatible Materials / Q000138:chemical synthesis / Q000737:chemistry*; D016503:Drug Delivery Systems; D006820:Hyaluronic Acid / Q000138:chemical synthesis / Q000737:chemistry*; D020100:Hydrogels / Q000138:chemical synthesis / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000475:Alkenes; D001672:Biocompatible Materials; D020100:Hydrogels; D007097:Imines; D006820:Hyaluronic Acid
keywords: Aldehyde; Hyaluronan; Hydrogel; Imine conjugate; Oxidation