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Evaluation of HOCl-generating anticancer agents by an ultrasensitive dual-mode fluorescent probe.

ABSTRACT: Hypochlorous acid (HOCl), a reactive oxygen species (ROS), plays a crucial role in the process of pathogenic oxidative stress. Some powerful anticancer agents, such as elesclomol, specifically induce cancer cell apoptosis by increasing HOCl levels. However, sensitive tools to monitor subtle changes of biological HOCl in vivo are limited. To achieve this, we herein present rationally designed probes C1-C7 through introducing a bioorthogonal dimethylthiocarbamate receptor. All the probes were shown to sensitively and rapidly detect HOCl in the nanomolar/biologically relevant concentration range with fluorescence turn-on observed in their respective optical regions, resulting in a blue-to-red "fluorescence rainbow" and providing a broad selection of colors for imaging HOCl in vivo. Remarkably, probe C7 exhibited both a turn-on signal at biologically relevant concentrations (LOD₁ = 18 nM) and a ratiometric response at the high risk pathogenic concentrations (LOD₂ = 0.47 ?M), which gives a higher reliability compared to a single signal and avoids cross-talk caused by the combined use of several probes. C7 was used to monitor the oxidative stress process induced by elesclomol in live cancer cells, and using this probe it was further discovered that an evodiamine derivative was capable of generating cancer-cell HOCl.

SUBMITTER: Shi D

PROVIDER: S-EPMC6457194 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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Evaluation of HOCl-generating anticancer agents by an ultrasensitive dual-mode fluorescent probe.

Shi Donglei D Chen Shuqiang S Dong Biao B Zhang Yanhui Y Sheng Chunquan C James Tony D TD Guo Yuan Y

Chemical science 20190304 13

Hypochlorous acid (HOCl), a reactive oxygen species (ROS), plays a crucial role in the process of pathogenic oxidative stress. Some powerful anticancer agents, such as elesclomol, specifically induce cancer cell apoptosis by increasing HOCl levels. However, sensitive tools to monitor subtle changes of biological HOCl <i>in vivo</i> are limited. To achieve this, we herein present rationally designed probes <b>C1-C7</b> through introducing a bioorthogonal dimethylthiocarbamate receptor. All the pr ...[more]

PMID: 31015915

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Project description:The outbreak and spread of Corona Virus Disease 2019 (COVID-19) has led to a significant increase in the consumption of sodium hypochlorite (NaOCl) disinfectants. NaOCl hydrolyzes to produce hypochlorous acid (HOCl) to kill viruses, which is a relatively efficient chlorine-based disinfectant commonly used in public disinfection. While people enjoy the convenience of NaOCl disinfection, excessive and indiscriminate use of it will affect the water environment and threaten human health. Importantly, HOCl is an indispensable reactive oxygen species (ROS) in human body. Whether its concentration is normal or not is closely related to human health. Excessive production of HOCl in the body contributes to some inflammatory diseases and even cancer. Also, we noticed that the concentration of ROS in cancer cells is about 10 times higher than that in normal cells. Herein, we developed a HOCl-activatable biotinylated dual-function fluorescent probe BTH. For this probe, we introduced biotin on the naphthalimide fluorophore, which increased the water solubility and enabled the probe to aggregate in cancer cells by targeting specific receptor overexpressed on the surface of cancer cell membrane. After reacting to HOCl, the p-aminophenylether moiety of this probe was oxidatively removed and the fluorescence of the probe was recovered. As expected, in the PBS solution with pH of 7.4, BTH could give full play to the performance of detecting HOCl, and it has made achievements in detecting the concentration of HOCl in actual water samples. Besides that, BTH had effectively distinguished between cancer cells and normal cells through a dual-function discrimination strategy, which used biotin to enrich the probe in cancer cells and reacted with overexpressed HOCl in cancer cells. Importantly, this dual-function discrimination strategy could obtain the precision detection of cancer cells, thereby offering assistance for improving the accuracy of early cancer diagnosis.

Dataset Information

Evaluation of HOCl-generating anticancer agents by an ultrasensitive dual-mode fluorescent probe.

Publications

Evaluation of HOCl-generating anticancer agents by an ultrasensitive dual-mode fluorescent probe.

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