Open AccessA Reduction-Sensitive Fluorous Fluorogenic Coumarin
Author(s) -
Margeaux A. Miller,
Rachael A. Day,
Daniel A. Estabrook,
Ellen M. Sletten
Publication year - 2019
Publication title -
synlett
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.712
H-Index - 133
eISSN - 1437-2096
pISSN - 0936-5214
DOI - 10.1055/s-0039-1690770
Subject(s) - chemistry , fluorophore , coumarin , nanomaterials , micelle , combinatorial chemistry , glutathione , nanotechnology , drug delivery , solubility , fluorescence , organic chemistry , aqueous solution , physics , materials science , quantum mechanics , enzyme
Fluorophores that are sensitive to their environment are useful tools for sensing chemical changes and probing biological systems. Here, we extend responsive fluorophores to the fluorous phase with the synthesis of a reduction-sensitive fluorous-soluble fluorogenic coumarin. We demonstrate that this fluorophore responds to various reducing agents, most notably glutathione, a key biological reductant. The fluorous solubility of this probe allows for its encapsulation into two different fluorous nanomaterials: perfluorocarbon nanoemulsions and fluorous core-shell micelles. The fluorogenic coumarin allows us to study how efficiently these vehicles protect the contents of their interior from the external environment. In the presence of glutathione, we observe different degrees of release for micelles and emulsions. This understanding will help guide future applications of fluorous nanomaterials as drug delivery vehicles.