Anthracene-isatoic anhydride hybrids for bioconjugation: chromophores with nucleophile dependent response
Document Type
Article
Publication Date
2025
Department/School
Chemistry
Publication Title
Organic & Biomolecular Chemistry
Abstract
The use of activated esters to label nucleophilic sites in biomolecules is a well established platform in bioconjugate chemistry. Here, we report the synthesis of a pair of anthracene–isatoic anhydride hybrid molecules that exhibit a characteristic spectroscopic response depending on the identity of the reacting nucleophile. A survey of substrates shows that primary amines, alcohols, and thiols can produce the corresponding acyl derivatives in good isolated yield. Spectroscopic studies show a strong donor–acceptor absorbance at >500 nm along with fluorescence into the near IR. Finally, we demonstrate the anthracene anhydride's potential as a bioconjugate reagent in the labeling of a lysine-containing 11-residue peptide. Owing to our novel platform's unique response against a range of nucleophiles, it is possible to determine the fate and target of the labeling reaction.
Link to Published Version
Recommended Citation
Fordyce, C. D., Robinson, C. J., & Rudebusch, G. E. (2025). Anthracene-isatoic anhydride hybrids for bioconjugation: Chromophores with nucleophile dependent response. Organic & Biomolecular Chemistry, 23(39), 8937–8947. https://doi.org/10.1039/D5OB01187F
Comments
G. E. Rudebusch is a faculty member in EMU's Department of Chemistry.
*C. D. Fordyc and C. J. Robinson are EMU students.