Preparation of a two-photon fluorescent probe with a large turn-on signal for imaging hypochlorous acid in living tissues

Zhou, Kai; Ren, Mingguang; Wang, Li; Li, Zihong; Lin, Weiying

doi:10.1039/c8ay00607e

Cited by 12 publications

(8 citation statements)

References 33 publications

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“…A benzoylhydrazine luciferin scaffold was developed by Liang and co‐workers to realize the imaging of HClO in living MDA‐MB‐231 cells as well as in tumors in vivo. Lin and co‐workers described a two‐photon fluorescent probe TP‐HA, which has a significant “turn‐on” signal due to cleavage for the imaging of HClO in HeLa cells, RAW264.7 cells and living tissue. The probe displayed an enhanced fluorescence intensity with HClO under two‐photon excitation ( Figure ).…”

Section: Fluorescent Imaging Agents For Diagnosis Of Ros‐relevant Dismentioning

confidence: 99%

“…Structure of a two‐photon HClO probe TP‐HA (above) and fluorescence images in the rat liver slice with different probe concentrations (below). Reproduced with permission . Copyright 2018, The Royal Society of Chemistry.…”

Section: Fluorescent Imaging Agents For Diagnosis Of Ros‐relevant Dismentioning

confidence: 99%

Section: Fluorescent Imaging Agents For Peroxynitritementioning

confidence: 99%

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Sensors, Imaging Agents, and Theranostics to Help Understand and Treat Reactive Oxygen Species Related Diseases

et al. 2019

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Reactive oxygen species (ROS) consist of a diverse range of oxidative small molecular ions and free radicals that are produced throughout the body during certain biological processes. Due to their high reactivity, these molecules result in the damage of tissues and cells. Therefore, ROS have been implicated in an array of diseases including cancer, inflammation, and neurodegenerative diseases such as Parkinson's disease and Alzheimer's disease. Owing to the simplicity, sensitivity, and selectivity of fluorescence‐based strategies, many small‐molecular sensors or imaging agents have been developed to sense and visualize ROS both in vitro and in vivo. Likewise, activatable drug delivery and prodrug systems that can be triggered by ROS for disease theranostics (diagnostic and therapeutic combined) have been developed. Herein, recently developed fluorescence‐based sensing and imaging agents for the detection of ROS both intracellularly and in vivo are summarized. In addition, drug delivery, which require activation by ROS to achieve disease theranostics is also discussed.

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Section: Fluorescent Imaging Agents For Diagnosis Of Ros‐relevant Dismentioning

confidence: 99%

Section: Fluorescent Imaging Agents For Diagnosis Of Ros‐relevant Dismentioning

confidence: 99%

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Sensors, Imaging Agents, and Theranostics to Help Understand and Treat Reactive Oxygen Species Related Diseases

et al. 2019

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“…The Lin group reported a probe that displayed a fluorescence enhancement (≈16‐fold) in response to HOCl with high sensitivity and selectivity. The new probe was membrane‐permeable and suitable for visualization of the changes of HOCl in living cells and tissues (Scheme ) …”

Section: Introductionmentioning

confidence: 99%

Imaging of Hypochlorous Acid by Fluorescence and Applications in Biological Systems

Yudhistira

Mulay

Kim

et al. 2019

Chemistry An Asian Journal

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In recent decades, HOCl research has attracted a lot of scientists from around the world. This chemical species is well known as an important player in the biological systems of eukaryotic organisms including humans. In the human body, HOCl is produced by the myeloperoxidase enzyme from superoxide in very low concentrations (20 to 400 μm); this species is secreted by neutrophils and monocytes to help fight pathogens. However, in the condition called “oxidative stress”, HOCl has the capability to attack many important biomolecules such as amino acids, proteins, nucleotides, nucleic acids, carbohydrates, and lipids; these reactions could ultimately contribute to a number of diseases such as neurodegenerative diseases (AD, PD, and ALS), cardiovascular diseases, and diabetes. In this review, we discuss recent efforts by scientists to synthesize various fluorophores which are attached to receptors to detect HOCl such as: chalcogen‐based oxidation, oxidation of 4‐methoxyphenol, oxime/imine, lactone ring opening, and hydrazine. These synthetic molecules, involving rational synthetic pathways, allow us to chemoselectively target HOCl and to study the level of HOCl selectivity through emission responses. Virtually all the reports here deal with well‐defined and small synthetic molecular systems. A large number of published compounds have been reported over the past years; this growing field has given scientists new insights regarding the design of the chemosensors. Reversibility, for example is considered important from the stand point of chemosensor reuse within the biological system; facile regenerability using secondary analytes to obtain the initial probe is a very promising avenue. Another aspect which is also important is the energy of the emission wavelength of the sensor; near‐infrared (NIR) emission is favorable to prevent autofluorescence and harmful irradiation of tissue; thus, extended applicability of such sensors can be made to the mouse model or animal model to help image internal organs. In this review, we describe several well‐known types of receptors that are covalently attached to the fluorophore to detect HOCl. We also discuss the common fluorophores which are used by chemist to detect HOCl, Apart from the chemical aspects, we also discuss the capabilities of the compounds to detect HOCl in living cells as measured through confocal imaging. The growing insight from HOCl probing suggests that there is still much room for improvement regarding the available molecular designs, knowledge of interplay between analytes, biological applicability, biological targeting, and chemical switching, which can also serve to further sensor and theurapeutic agent development alike.

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“…It is endogenously generated in living organisms from hydrogen peroxide and chloride ions under the catalysis of heme-enzyme myeloperoxidase in order to kill invading bacterial pathogens. , However, excessive production of HOCL will lead to the oxidation of biomolecules, resulting in various diseases such as arthritis, atherosclerosis, and cancer. − For real-time monitoring the distribution and level of endogenous HOCL, many OPEF probes for HOCL detection have been developed in the last years, but they are not suitable for tissue imaging in vivo due to short excitation wavelengths. − In 2015, Chang et al first reported the TPEF probe (TP-HOCL1) for HOCL based on the oxidative deprotection of an oxathiolane group introduced onto the acedan fluorophore . Then, some TPEF probes for HOCL gradually appeared, but most of them possess the “turn-on” mechanism, which are easily interfered and unsuitable for quantitative analysis. − Recently, several ratiometric fluorescence probes have been researched, which can provide two separate signals for probe and reaction product molecules avoiding the influence of environmental factors on detection. − Ahn and co-workers reported a radiometric benzocoumarin probe (rTP-HOCL1) also based on the oxathiolane recognition group. Although the limit of detection is very low (34.8 nM), the emission separation (35 nm) is not large enough, which may cause spectral overlap and decrease spectral resolution .…”

Section: Introductionmentioning

confidence: 99%

Design Strategies for High-Efficiency Ratiometric Two-Photon-Excited Fluorescent and Room-Temperature Phosphorescent Probes for Hypochlorous Acid

Hao

Guo

et al. 2019

J. Phys. Chem. C

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Hypochlorous acid (HOCL) plays a critical role in the natural defense system, but excessive production of HOCL leads to many diseases. It is very essential to monitor the distribution and level of endogenous HOCL. However, the applicable two-photon-excited fluorescent (TPEF) and phosphorescent probes for biological imaging and quantitative detection is rare due to low efficiency and vague mechanism. Therefore, we thoroughly researched the electron structures and luminous mechanisms of turn-on and ratiometric TPEF probe compounds and provide design strategies for high-efficient ratiometric TPEF probes. The designed ratiometric TPEF probe benza1-COCL and product benza1-CO have quite large two-photon absorption (TPA) cross sections (143 GM/898 nm, 168 GM/988 nm), high fluorescence efficiencies (0.15, 0.28), and spectral resolution, contributing to the real-time monitoring level of HOCL in vivo. Besides, a long-lived two-photon-excited room-temperature phosphorescent probe benza2-COCL is provided first, which possesses a large TPA cross section (144 GM/838 nm) and time-resolved biological imaging (1.09 ms).

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Preparation of a two-photon fluorescent probe with a large turn-on signal for imaging hypochlorous acid in living tissues

Abstract: We have developed a new two-photon fluorescent HOCl probe (TP-HA). Fluorescence imaging shows that TP-HA is suitable for visualization of the changes of HOCl in living cells and tissues.

Cited by 12 publications

References 33 publications

Sensors, Imaging Agents, and Theranostics to Help Understand and Treat Reactive Oxygen Species Related Diseases

Sensors, Imaging Agents, and Theranostics to Help Understand and Treat Reactive Oxygen Species Related Diseases

Imaging of Hypochlorous Acid by Fluorescence and Applications in Biological Systems

Design Strategies for High-Efficiency Ratiometric Two-Photon-Excited Fluorescent and Room-Temperature Phosphorescent Probes for Hypochlorous Acid

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