BODIPY‐Based Fluorescent Probes for Biothiols

Abstract

Fluorescent probes for biothiols have aroused increasing interest owing to their potential to enable better understanding of the diverse physiological and pathological processes related to the biothiol species. BODIPY fluorophores exhibit excellent optical properties, which can be readily tailored by introducing diverse functional units at various positions of the BODIPY core. In the present review, the development of fluorescent probes based on BODIPYs for the detection of biothiols are systematically summarized, with emphasis on the preferable detection of individual biothiols, as well as simultaneous discrimination among cysteine (Cys), homocysteine (Hcy), reduced glutathione (GSH). In addition, organelle‐targeting probes for biothiols are also highlighted. The general design principles, various recognition mechanisms, and biological applications are elaboratively discussed, which could provide a useful reference to researchers worldwide interested in this area.

The chronological evolution of small organic molecular fluorescent probes for thiols

“…Recently, several excellent reviews have summarized the recent development of uorescent probes for the detection of thiols. [20][21][22][23][24] In this minireview, we will discuss the chronological evolution of application-oriented small molecular uorescent probes for the detection of thiols over the last 60 years. We will also examine the present challenges and hope to inspire the design of future uorescent probes to move from approaches that utilize trial and error to those that use designbased molecular engineering.…”

BODIPY- and Porphyrin-Based Sensors for Recognition of Amino Acids and Their Derivatives

“…The detection of other natural derivatives based on amino acids, such as G-proteins [ 19 ], neurofibrillary tangles [ 20 ] and bio-thiols [ 21 ], are strongly related with many cellular functions and pathologies and are also mentioned in this work.…”

Detecting Cysteine in Bioimaging with a Near‐Infrared Probe Based on a Novel Fluorescence Quenching Mechanism

“…Over the last dozen years, many fluorescent probes for Cys sensing have been developed with highly sensitive, distinct fluorescence changes, real-time detection and noninvasiveness, as well as simplicity of operation. [13][14][15][16][17][18] However, most of them are limited by insufficient selectivity to discriminate Cys from other biothiols, in particular Hcy and GSH. Geometrically speaking, Hcy has a minor difference from Cys: an extra methylene unit in the side chain.…”

“…[15,16,[19][20][21][22][23][24][25][26][27] Despite significant advances, a great number of these fluorescent probes exhibited absorption and emission in the ultraviolet or visible-light range, which may be strongly interfered by biological autofluorescence. [13][14][15][16][17][18] On the other hand, near-infrared region (650-900 nm) fluorescent probes emissive have been developed for biothiols in favour of the advantages of minimal damage, less light scattering, deep tissue penetration, and low background interference. The most popular strategy for the development of Cysselective fluorescent probes is using Michael addition/intramolecular cyclizations of acrylic ester pioneered by Strongin's group to differentiate Cys between Hcy.…”