title: One-pot synthesis of α,β-unsaturated polyaldehyde of chondroitin sulfate.
abstract: Chondroitin sulfate (CS) was chemoselectively oxidized by Tempo/NaClO to C-6 aldehyde of a D-galactosamine subunit (GalNAc). The subsequent, spontaneous desulfatation of oxidized CS gave rise to α,β-unsaturated aldehyde. A new derivative of CS was fully characterized and a degree of oxidation was determined by spectroscopic analysis. The optimization of reaction conditions showed a proportional degree of oxidation to an amount of sodium hypochlorite. The utility of α,β-unsaturated aldehyde for crosslinking and conjugation was demonstrated by a seamless condensation with various N-nucleophiles. We also demonstrated pH-dependent release of biologically active agents from oxidized CS. A live-dead assay in the presence of α,β-unsaturated aldehyde revealed unaffected viability of NIH 3T3 fibroblasts, which made this precursor promising for several biomedical applications including drug delivery and tissue engineering.
authors.affiliation: Contipro Pharma, Dolní Dobrouč 401, 56102, Czech Republic. Electronic address: bobula@contipro.com.
authors.forename: Tomáš
authors.initials: T
authors.lastname: Bobula
authors.affiliation: Contipro Pharma, Dolní Dobrouč 401, 56102, Czech Republic.
authors.forename: Radovan
authors.initials: R
authors.lastname: Buffa
authors.affiliation: Contipro Pharma, Dolní Dobrouč 401, 56102, Czech Republic.
authors.forename: Pavlína
authors.initials: P
authors.lastname: Procházková
authors.affiliation: Contipro Pharma, Dolní Dobrouč 401, 56102, Czech Republic.
authors.forename: Hana
authors.initials: H
authors.lastname: Vágnerová
authors.affiliation: Contipro Pharma, Dolní Dobrouč 401, 56102, Czech Republic.
authors.forename: Veronika
authors.initials: V
authors.lastname: Moravcová
authors.affiliation: Contipro Pharma, Dolní Dobrouč 401, 56102, Czech Republic.
authors.forename: Romana
authors.initials: R
authors.lastname: Šuláková
authors.affiliation: Contipro Pharma, Dolní Dobrouč 401, 56102, Czech Republic.
authors.forename: Ondřej
authors.initials: O
authors.lastname: Židek
authors.affiliation: Contipro Pharma, Dolní Dobrouč 401, 56102, Czech Republic.
authors.forename: Vladimír
authors.initials: V
authors.lastname: Velebný
mesh_terms: D016475:3T3 Cells; D000447:Aldehydes / Q000737:chemistry; D000818:Animals; D001672:Biocompatible Materials / Q000009:adverse effects / Q000138:chemical synthesis* / Q000737:chemistry; D002470:Cell Survival; D002809:Chondroitin Sulfates / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry; D005347:Fibroblasts / Q000187:drug effects; D051379:Mice
chemical_list: D000447:Aldehydes; D001672:Biocompatible Materials; D003432:Cross-Linking Reagents; D002809:Chondroitin Sulfates
keywords: Chondroitin sulfate; Crosslinking; Hydrogel; Oxidation; Tissue engineering