N‐Heterocyclic Carbene Boranes as Reactive Oxygen Species‐Responsive Materials: Application to the Two‐Photon Imaging of Hypochlorous Acid in Living Cells and Tissues

Pak, Yen Leng; Park, Sang Jun; Wu, Di; Cheon, Bo Hyun; Kim, Hwan Myung; Bouffard, Jean; Yoon, Juyoung

doi:10.1002/anie.201711188

Cited by 138 publications

(68 citation statements)

References 57 publications

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“…Moreover, Yoon and co‐workers developed a diverse range of fluorescent probes for the imaging‐guided detection of HClO or ClO − in living cells. For example, a sulfur‐substituted fluorescein with borate ester group as the ROS recognition site was synthesized .…”

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

confidence: 99%

“…Then, a modified N‑heterocyclic carbene borane probe with the thione group replaced by a boron‐carbon linkage C‐BH 3 − , was shown to be cleaved and removed with HClO, was synthesized to achieve two‐photon HClO imaging in RAW 264.7 cells . Furthermore, two‐photon pyrene‐based fluorescent probes with imidazoline‐2‐thione or C‐BH 3 − as the ClO − recognition site were developed.…”

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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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%

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

et al. 2019

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“…In 2018, the Juyoung Yoon research group developed a probe for the selective detection of HOCl based on ap revious reported by their group in 2015. [142] In this study,t he Juyoung Yoon group replaced N-Heterocyclic carbene(NHC)borane moiety with imidazoline-2-thione( Scheme123). [140] The probe, upon reaction with HOCl undergoes ah ipsochromic shift from 462 nm (excimer formation) to 378 nm (monomer formation).…”

Section: Scheme118mentioning

confidence: 99%

“…Juyoung Yoon research group, in 2018, developed aH OCl probe based on the oxidation of BÀHb onds. [142] The probe consists of N-Heterocyclic carbene(NHC) boranes as aH OCl receptor/reactive positiona nd pyrene as fluorophore (Scheme 124). In this study,c onversion of NHC boranes to imidazolium salt due to the reaction with HOCl;c onsequently,t he emission of the probe change because of monomer formation (see Scheme 123).…”

Section: Scheme118mentioning

confidence: 99%

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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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Carbenes and Nitrenes

Gras

Chassaing

2021

Organic Reaction Mechanisms Series

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N‐Heterocyclic Carbene Boranes as Reactive Oxygen Species‐Responsive Materials: Application to the Two‐Photon Imaging of Hypochlorous Acid in Living Cells and Tissues

Cited by 138 publications

References 57 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

Carbenes and Nitrenes

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