In this study, a new red lysosome-targeted fluorescence off–on probe has been rationally designed, synthesized and applied for the highly selective and sensitive fluorescence sensing of carboxylesterase in live cells, sera and tissues. The probe was readily synthesized by coupling N-methylated benzoindole with 4-(acetyloxy)benzaldehyd, in which the acetyl group acted as a quenching and recognizing agent and the hemicyanine skeleton worked as the fluorescent signal unit. As a consequence, the prepared spectroscopic probe displays quite a low background signal. Upon addition of carboxylesterase, the latent probe could be easily hydrolyzed to liberate the fluorophore hydroxy hemicyanine and emit the off–on spectroscopic signal, which is desirable for obtaining sensitive detection with high specificity. The newly developed probe was successfully used to monitor and image carboxylesterase activity in complex biological samples such as serum, live cells and tissues. Moreover, this probe shows great promise for biomedical studies, including obesity disease, hepatocellular carcinoma and drug screening research.

A red lysosome-targeted fluorescent probe for carboxylesterase detection and bioimaging

Near-infrared (NIR) fluorescent probes are among the most attractive chemical tools for biomedical imaging. However, their in vivo applications are hindered by albumin binding, generating unspecific fluorescence that masks the specific signal from the analyte. Here, combining experimental and docking methods, we elucidate that the reason for this problem is an acceptor (A) group-mediated capture of the dyes into hydrophobic pockets of albumin. This pocket-capturing phenomenon commonly applies to dyes designed under the twisted intramolecular charge-transfer (TICT) principle and, therefore, represents a generic but previously unidentified backdoor problem. Accordingly, we create a new A group that avoids being trapped into the albumin pockets (pocket-escaping) and thereby construct a NIR probe, BNLBN, which effectively prevents this backdoor problem with increased imaging accuracy for liver fibrosis in vivo. Overall, our study explains and overcomes a fundamental problem for the in vivo application of a broad class of bioimaging tools.

/pdf/a-pocket-escaping-design-to-prevent-the-common-interference-54zv2lxmaa.pdf

A pocket-escaping design to prevent the common interference with near-infrared fluorescent probes in vivo.

Dual-ratiometric fluorescence probe for viscosity and hypochlorite based on AIEgen with mitochondria-targeting ability.

An aggregation-induced emission (AIE)-active fluorescent chemodosimeter for selective sensing of hypochlorite in water and solid state: Endogenous detection of hypochlorite in live cells

Design of a large Stokes shift ratiometric fluorescent sensor with hypochlorite detection towards the potential application as invisible security ink.

Hypochlorous acid (HOCl/ClO−) is well-known as a pivotal member of reactive oxygen species (ROS) and acts as a vital regulator of cell activities including cell differentiation, migration, and immune response. However, overexpressed ClO− may cause tissue damage; thus, significant efforts have been devoted to ClO− sensing at the molecular level. Herein, a mitochondria-targeting fluorescent probe for ClO− was developed based on oxidation by ClO−, releasing a green emissive luminogen under physiological conditions. In particular, a “signal amplifier”, bovine serum albumin (BSA), was utilized to promote the fluorescence response, which effectively converted the probe from a “turn-off” mode to a ratiometric fluorescence system. This analytical strategy reduced the limit of detection to as low as 1.5 nM and was also applicable to live cells, accompanied by significant fluorescence change from red to green with a modified signal-to-noise ratio. Moreover, the probe exhibited good performance for targeting mitochondria and monitoring endogenous ClO−. Based on the results of this study, the well-designed probe and analytical method could be promising for intracellular ClO− detection.

Enhanced fluorescence sensing of hypochlorous acid using serum albumin as a signal amplifier.

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Enhanced fluorescence sensing of hypochlorous acid using serum albumin as a signal amplifier.