Reversible Reaction‐Based Fluorescent Probes for Dynamic Sensing and Bioimaging

Abstract

Diverse chemical species such as ions and molecules exist within living cells and organisms undergoing dynamic changes in their local environment by a web of continuously interacting reactions. Reaction‐based fluorescent probes with a highly sought reversible feature can provide a real‐time monitor of the concentration dynamics (increases and decreases) of such chemical species, thus ideally suited to understand the physiological function, and pathogenic mechanisms of corresponding bio‐species in the regulation of cellular function and disease progression. This review summarizes the current methods for constructing reversible reaction‐based fluorescent probes. The sensing mechanisms and biological applications of these probes are also discussed. The representative examples reported recently are categorized according to the type of reversible chemical reactions utilized: nucleophilic additions (Michael additions, chromophore reactions), nucleophilic addition‐condensation reactions, and redox reactions. Finally, we present the potential challenges and suggestions for developing probes based on dynamic and reversible covalent bond formation reactions.

Dynamic Covalent Synthesis Applied to Optoelectronic and Energy Materials: Design, Applications and Limitations

“…[95] The Michael addition reaction has found a myriad of bio-applications, [96] especially with fluorescent probes as Michael acceptors. [97] Indeed, the Michael addition to these probes can affect their luminescence properties leading to the design of numerous stimuli-responsive live cell imaging probes and sensors. [98] We believe that the use of this dynamic covalent reaction can open up many opportunities for the design of stimuli responsive emissive organic electronic materials.…”

Recent Progress in the Rational Design of Biothiol-Responsive Fluorescent Probes

“…Real-time monitoring of dynamic changes in biothiols is of great significance to reveal their physiological and pathological functions and provide a foundation for early treatment and diagnosis of diseases. To this end, many reversible fluorescent probes have been reported to monitor the dynamics of GSH in living specimens recently, and these reversible fluorescent probes are frequently designed on the basis of the reversible Michael addition reactions (Scheme 14) [80,81]. The Bhuniya group reported a reversible ratiometric fluorescent probe 35 (GS cp ) for imaging GSH in living cells (Schemes 14 and 15) [82].…”

“Covalent‐Disassembly”‐Based Approaches For Sensing Applications

“…Activity‐based sensing (ABS) [15] is a complementary sensing approach that relies upon chemical reactivity of bond formation and bond breakage reactions. ABS has been excellently reviewed in 2020 by Chang and coworkers as well as by other groups [15–18] . One powerful strategy of ABS represents the “covalent‐assembly“ approach, in which a profluorophore is converted rapidly and selectively by an analyte into a fluorophore, and through a tandem reaction [19] .…”

“…ABS has been excellently reviewed in 2020 by Chang and coworkers as well as by other groups. [15][16][17][18] One powerful strategy of ABS represents the "covalentassembly" approach, in which a profluorophore is converted rapidly and selectively by an analyte into a fluorophore, and through a tandem reaction. [19] The "covalent-disassembly" concept represents the conceptually reverse approach and has so far been little explored for analyte detection.…”