A colorimetric and ratiometric fluorescent probe for ClO<sup>−</sup>targeting in mitochondria and its application in vivo

Xiao, Haiyan; Li, Jianhui; Zhao, Jinhui; Yin, Geping; Quan, Yiwu; Wang, Jie; Wang, Ruiyong

doi:10.1039/c4tb02003k

Cited by 146 publications

(36 citation statements)

References 32 publications

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“…[70] As imilar concept was later adopted by Kim and coworkers to develop am itochondria-targetable ratiometric two-photon probe (SHP-Mito (17), Scheme 4) to measure H 2 O 2 . [75] Although HClO is endogenously produced as both as ignaling molecule and an oxidative cell defender,i ts real production site is still under debate.T oa ddress this issue, Yuan et al designed two fluorescent probes with the same mechanism for sensing hypochlorous acid, but different organelle-targeting moieties (20 and 21,S cheme 6). SHP-Mito showed ar atiometric shift in the emission wavelength from blue to yellow in response to H 2 O 2 as well as selective localization of the mitochondria over other organelles in Raw 264.7 cells.T he two-photon feature allowed SHP-Mito to detect changes in mitochondrial H 2 O 2 levels in live cells and live tissues at adepth of 90-190 mm.…”

Section: Mitafps For Ros/rns and Redox Balancementioning

confidence: 99%

“…19 b and 19 c, Scheme 5). [75] Although HClO is endogenously produced as both as ignaling molecule and an oxidative cell defender,i ts real production site is still under debate.T oa ddress this issue, Yuan et al designed two fluorescent probes with the same mechanism for sensing hypochlorous acid, but different organelle-targeting moieties (20 and 21,S cheme 6). [76] By capping the Acedan fluorophore with am ecaptoethanol protecting group,they masked its emission, which could later be recovered upon reaction with HClO.T he mitochondriaand lysosome-targeting moieties were readily attached to the other end of the fluorophore,t hus representing as imple design strategy for OTAFPs.B yu tilizing these probes,t he authors managed to detect HClO traces within both organelles of the stimulated macrophage cells ( Figure 6).…”

Section: Mitafps For Ros/rns and Redox Balancementioning

confidence: 99%

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Discerning the Chemistry in Individual Organelles with Small‐Molecule Fluorescent Probes

et al. 2016

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Principle has it that even the most advanced super-resolution microscope would be futile in providing biological insight into subcellular matrices without well-designed fluorescent tags/probes. Developments in biology have increasingly been boosted by advances of chemistry, with one prominent example being small-molecule fluorescent probes that not only allow cellular-level imaging, but also subcellular imaging. A majority, if not all, of the chemical/biological events take place inside cellular organelles, and researchers have been shifting their attention towards these substructures with the help of fluorescence techniques. This Review summarizes the existing fluorescent probes that target chemical/biological events within a single organelle. More importantly, organelle-anchoring strategies are described and emphasized to inspire the design of new generations of fluorescent probes, before concluding with future prospects on the possible further development of chemical biology.

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Section: Mitafps For Ros/rns and Redox Balancementioning

confidence: 99%

Section: Mitafps For Ros/rns and Redox Balancementioning

confidence: 99%

Discerning the Chemistry in Individual Organelles with Small‐Molecule Fluorescent Probes

et al. 2016

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“…[128] In 2015, RuiyongW ang research group developed ar atiometricf luorescent probe for imaging mitochondrial HOCl (Scheme 53). [135] The probe can selectively detect HOCl upon other ROS/RNS;t he limit of detection of the probe was determined to be 0.43 mm.T he probe performed well in detecting in exogenous and endogenous HOCl in the living RAW264.7 macrophage cells.…”

Section: Oxime/imine-basedrecognitionmentioning

confidence: 99%

“…In 2015, Ruiyong Wang research group developed a ratiometric fluorescent probe for imaging mitochondrial HOCl (Scheme ) . The probe can selectively detect HOCl upon other ROS/RNS; the limit of detection of the probe was determined to be 0.43 μ m .…”

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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“…The uorescence method also meets the requirement of a fast response and real-time detection, which is appropriate for the investigation of HClO in complicated and living systems. [11][12][13][14] Therefore, many uorescent probes have been designed and developed in recent years. Wang et al 15 developed an effective method for the imaging of lysosomal HClO to better understand its role in HClO-related diseases.…”

Section: Introductionmentioning

confidence: 99%

A novel ratiometric fluorescent probe for the selective determination of HClO based on the ESIPT mechanism and its application in real samples

Gong

Shi

et al. 2019

RSC Adv.

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A colorimetric and ratiometric fluorescent probe for ClO⁻targeting in mitochondria and its application in vivo

Abstract: A colorimetric and ratiometric fluorescent probe PMN–TPP for imaging mitochondrial ClO− was prepared. The probe performed well in detecting ClO− in the mitochondria of living RAW264.7 macrophage cells and a living nude mouse.

Cited by 146 publications

References 32 publications

Discerning the Chemistry in Individual Organelles with Small‐Molecule Fluorescent Probes

Discerning the Chemistry in Individual Organelles with Small‐Molecule Fluorescent Probes

Imaging of Hypochlorous Acid by Fluorescence and Applications in Biological Systems

A novel ratiometric fluorescent probe for the selective determination of HClO based on the ESIPT mechanism and its application in real samples

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A colorimetric and ratiometric fluorescent probe for ClO−targeting in mitochondria and its application in vivo

Abstract: A colorimetric and ratiometric fluorescent probe PMN–TPP for imaging mitochondrial ClO− was prepared. The probe performed well in detecting ClO− in the mitochondria of living RAW264.7 macrophage cells and a living nude mouse.

Cited by 146 publications

References 32 publications

Discerning the Chemistry in Individual Organelles with Small‐Molecule Fluorescent Probes

Discerning the Chemistry in Individual Organelles with Small‐Molecule Fluorescent Probes

Imaging of Hypochlorous Acid by Fluorescence and Applications in Biological Systems

A novel ratiometric fluorescent probe for the selective determination of HClO based on the ESIPT mechanism and its application in real samples

Contact Info

Product

Resources

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A colorimetric and ratiometric fluorescent probe for ClO⁻targeting in mitochondria and its application in vivo