HOCl can appear in the mitochondria of macrophages during bacterial infection as revealed by a sensitive mitochondrial-targeting fluorescent probe

Zhou, Jin; Li, Lihong; Shi, Wen; Gao, Xinjie; Li, Xiaohua; Ma, Huimin

doi:10.1039/c5sc01562f

Cited by 227 publications

(89 citation statements)

References 37 publications

(34 reference statements)

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“…[70] Reaction with H 2 O 2 resulted in the ring of the rhodol dye opening with formation of afluorescent product 16' ',thereby resulting in at urn-on response.T he co-localization of MitoPY1 with MitoTracker Red indicated that MitoPY1 specifically localized in the mitochondria of av ariety of mammalian cell types,i ncluding HeLa ( Figure 5), HEK293, Cos-7, and CHO.K1. [74] Upon reaction, ring opening of the spiro-rhodamine triggered substantial and sensitive fluorescence enhancement, which was used to monitor HClO formation within macrophage cells during bacterial infection. [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 .…”

Section: Mitafps For Ros/rns and Redox Balancementioning

confidence: 99%

“…Confocal imaging experiments confirmed that the probe enabled the assessment of both endogenous production and changes in H 2 O 2 levels within the mitochondria of live cells. [74] Several more examples that incorporate charged pyridine groups or TPP as the mitochondria-targeting motif have also been reported as HClO probes (e.g. [71] This probe utilizes 6-(benzo[d]thiazol-20-yl)-2-(N,Ndimethylamino)naphthalene as at wo-photon fluorophore, ab oronate group as the H 2 O 2 -reactive site and fluorophore masking moiety,a nd with TPP as the mitochondria vector.…”

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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“…The Ma group et al developed am itochondria targeting fluorescent probe to detect for HOCl (Scheme 65). [74] This small molecule-based probe shows important properties such as mitochondrial-targeting ability (positivelyc harged) species, af ast response and highs electivity and sensitivity.I np articular,t he limit of detection was found to be 9nm.T his molecular recognition mode showing af luorescent "turn-on" response is due to the spiroring-opening of the rhodamine thiolactoneo ft he probe.T od emonstrate the ability of mitochondrial-targeting, confocal microscopy imaging was exploited. Thep robe was incubated to RAW2 64.7 macrophage cells;t he confocal imaging data shows that the probe can be used to detect endogenous HOCl.…”

Section: Scheme59mentioning

confidence: 99%

“…The Ma group et al. developed a mitochondria targeting fluorescent probe to detect for HOCl (Scheme ) . This small molecule‐based probe shows important properties such as mitochondrial‐targeting ability (positively charged) species, a fast response and high selectivity and sensitivity.…”

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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“…Toward this end, there have a number of fluorescent probes for HOCl been developed and used in living systems. But most of them are based on changes of the intensity, [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24] which are limited to the quantification of HOCl due to the fluorescence intensity may be influenced by some external factors such as the concentration of probe, test temperature and instrument performance. Some small molecular based ratiometric HOCl probes have been constructed successfully.…”

Section: Introductionmentioning

confidence: 99%

A lysosome-targeted and ratiometric fluorescent probe for imaging exogenous and endogenous hypochlorous acid in living cells

et al. 2016

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Hypochorous acid plays important roles in many physiological and pathological processes. At the cell organelles level, the abnormal concentration of hypochorous acid in the lysosomes causes redox imbalance and the loss of function of the lysosomes. Herein, the first small molecule based, lysosomal-targeted ratiometric fluorescent HOCl probe (Lyso-HA) was synthesized through reasonable design. The new probe was highly selective toward HOCl over other reactive oxygen species and exhibits a large variation (up to 97-fold) in its fluorescence ratio (I585/I450) with good signal resolution. The probe Lyso-HA was membrane-permeable and suitable for ratiometric visualization of exogenous and endogenous HOCl at lysosomes in living cells.

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HOCl can appear in the mitochondria of macrophages during bacterial infection as revealed by a sensitive mitochondrial-targeting fluorescent probe

Abstract: HOCl can appear in the mitochondria of macrophages during bacterial infection as revealed by a new sensitive mitochondrial-targeting fluorescent probe.

Cited by 227 publications

References 37 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 lysosome-targeted and ratiometric fluorescent probe for imaging exogenous and endogenous hypochlorous acid in living cells

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