One-pot synthesis of α,β-unsaturated polyaldehyde of chondroitin sulfate
Language English Country Great Britain, England Media print-electronic
Document type Journal Article
PubMed
26572440
DOI
10.1016/j.carbpol.2015.10.005
PII: S0144-8617(15)00984-4
Knihovny.cz E-resources
- Keywords
- Chondroitin sulfate, Crosslinking, Hydrogel, Oxidation, Tissue engineering,
- MeSH
- Aldehydes chemistry MeSH
- Biocompatible Materials adverse effects chemical synthesis chemistry MeSH
- 3T3 Cells MeSH
- Chondroitin Sulfates chemistry MeSH
- Fibroblasts drug effects MeSH
- Mice MeSH
- Cross-Linking Reagents chemistry MeSH
- Cell Survival MeSH
- Animals MeSH
- Check Tag
- Mice MeSH
- Animals MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Aldehydes MeSH
- Biocompatible Materials MeSH
- Chondroitin Sulfates MeSH
- Cross-Linking Reagents MeSH
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.
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