ArticleBioconjugate chemistry2026
Glutathione-Responsive Fragmentation of Heteronorbornadiene-Based Thiovinyl Sulfones in Glioma Cells.
Article in Bioconjugate chemistry, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
We report the synthesis and fluorescent properties of dansylated heteronorbornadienes (HNDs) featuring a thiovinyl sulfone moiety as a thiol-reactive trigger. These systems undergo thiol addition which promotes fragmentation via a thioketal intermediate, leading to the release of fluorescent heterocycles (furan or pyrrole) and ketene S,S-acetals. Distinct fluorescence signatures enable real-time monitoring of the fragmentation process. We also report cellular studies to demonstrate that HND-thiovinyl sulfones are membrane-permeable and undergo glutathione (GSH)-mediated activation in glioma cells, resulting in intracellular release of fluorescent products. These findings establish HND-based architectures as promising platforms for the design of cleavable linkers in controlled release applications, particularly in targeted drug delivery and theranostics where stimuli-responsive behavior is essential.
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