A Reduction-Sensitive Fluorous Fluorogenic Coumarin

^◊ These authors contributed equally to this work

Published as part of the Special Section 11th EuCheMS Organic Division Young Investigator Workshop

Abstract

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.

Key words

fluorous - fluorogenic - fluorofluorophore - perfluorocarbon nanoemulsions - fluorous micelles - glutathione responsive - coumarin

• References and Notes

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