A Reduction-Sensitive Fluorous Fluorogenic Coumarin

Autor:	Ellen M. Sletten, Daniel A. Estabrook, Rachael A. Day, Margeaux A. Miller
Rok vydání:	2019
Předmět:	Fluorophore 010405 organic chemistry Reducing agent Chemistry Organic Chemistry 010402 general chemistry Coumarin 01 natural sciences Combinatorial chemistry Micelle Article 0104 chemical sciences Nanomaterials chemistry.chemical_compound Drug delivery Solubility
Zdroj:	Synlett
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-0039-1690770
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::4dc9c07382b42b620cbcca4e6aa42c79 https://doi.org/10.1055/s-0039-1690770 Zobrazit plný text záznamu