AI Article Synopsis
- Chondroitin sulfate (CS) was oxidized using Tempo/NaClO, resulting in a C-6 aldehyde of the D-galactosamine subunit and the formation of a new α,β-unsaturated aldehyde derivative.
- The degree of oxidation was analyzed spectroscopically, showing that higher sodium hypochlorite levels led to a greater oxidation level.
- This new compound demonstrated potential for biomedical applications, as it allowed for the release of active agents and did not affect cell viability, suggesting its use in drug delivery and tissue engineering.
Article 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.
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| http://dx.doi.org/10.1016/j.carbpol.2015.10.005 | DOI Listing |
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