4 years ago

Azo-Based Fluorogenic Probes for Biosensing and Bioimaging: Recent Advances and Upcoming Challenges

Azo-Based Fluorogenic Probes for Biosensing and Bioimaging: Recent Advances and Upcoming Challenges
Arnaud Chevalier, Pierre-Yves Renard, Anthony Romieu
The use of nonfluorescent azo dyes as dark quenchers in activatable optical bioprobes based on the Förster resonance energy transfer (FRET) mechanism and designed to target a wide range of enzymes has been established for over two decades. The key value of the azo moiety (−N=N−) to act as an efficient “ON–OFF” switch of fluorescence once introduced within the core structure of conventional organic-based fluorophores (mainly fluorescent aniline derivatives) has recently been exploited in the development of alternative reaction-based small-molecule probes based on the “profluorescence” concept. These unprecedented “azobenzene-caged” fluorophores are valuable tools for the detection of a wide range of reactive (bio)analytes. This review highlights the most recent and relevant advances made in the design and biosensing/bioimaging applications of azo-based fluorogenic probes. Emphasis is also placed on relevant achievements in the synthesis of bioconjugatable/biocompatible azo dyes used as starting building blocks in the rational and rapid construction of these fluorescent chemodosimeters. Finally, a brief glimpse of possible future biomedical applications (theranostics) of these “smart” azobenzene-based molecular systems is presented. Small but strong! The unique photophysical properties and sensitivity of the azo bridge to bioreductive metabolism make it a key component in the rational design of a wide range of reaction-based fluorescent probes suitable for applications in biosensing/bioimaging (see figure). Advances in this field since the early 2000s are summarized in this review.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/asia.201700682

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