Substituent Effects in BODIPY in Live Cell Imaging

Mulay, Sandip V.; Yudhistira, Tesla; Choi, Minsuk; Kim, Young-Sam; Kim, Jinjoo; Jang, Yoon Jeong; Jon, Sangyong; Churchill, David G.

doi:10.1002/asia.201601400

Cited by 46 publications

(32 citation statements)

References 94 publications

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“…Confocal fluorescence microscopy imaging demonstrated that the probe could be utilized to evaluate the important roles of HClO/GSH in biological systems. By employing the oxidation and reduction of selenium/tellurium, Churchill and co‐workers described three probes ( 88 , 89 , and 90 ) for monitoring of the ROS/biothiols redox cycle (Figure ) …”

Section: Bodipy‐based Probes For Biothiolsmentioning

confidence: 99%

“…[115,116] In this section, we only highlight BODIPYbased reversible probesfor ROS/biothiols. [117][118][119][120][121][122][123] By exploitingt he oxidation and reduction of selenium, Han's group developed probe 85 by installation of ad iphenyl selenium moiety via the para position into the meso of BODIP for the detection of the HClO/H 2 Sr edox cycle (Scheme 10). [117] When the probe was oxidized by HClO, ab right green fluorescence (510 nm) increment was observed.…”

Section: Reversible Probes For Ros/biothiolsmentioning

confidence: 99%

“…By employing the oxidation and reduction of selenium/tellurium, Churchill and co-workers described three probes (88, 89,a nd 90)f or monitoring of the ROS/biothiols redox cycle( Figure 21). [120][121][122] The oxidation and reduction of pyrocatecholisanother strategy to design probes for tracing the ROS/biothiols redox cycle. Zhang, Tana nd co-workers reported ar ed-emitting twophoton fluorescent probe 91 for detection of the superoxide anion/GSH redox cycle (Scheme 11).…”

Section: Reversible Probes For Ros/biothiolsmentioning

confidence: 99%

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BODIPY‐Based Fluorescent Probes for Biothiols

Zhang

Wang

et al. 2020

Chemistry A European J

190

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Fluorescent probes for biothiols have aroused increasing interest owing to their potential to enable better understanding of the diverse physiological and pathological processes related to the biothiol species. BODIPY fluorophores exhibit excellent optical properties, which can be readily tailored by introducing diverse functional units at various positions of the BODIPY core. In the present review, the development of fluorescent probes based on BODIPYs for the detection of biothiols are systematically summarized, with emphasis on the preferable detection of individual biothiols, as well as simultaneous discrimination among cysteine (Cys), homocysteine (Hcy), reduced glutathione (GSH). In addition, organelle‐targeting probes for biothiols are also highlighted. The general design principles, various recognition mechanisms, and biological applications are elaboratively discussed, which could provide a useful reference to researchers worldwide interested in this area.

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Section: Bodipy‐based Probes For Biothiolsmentioning

confidence: 99%

Section: Reversible Probes For Ros/biothiolsmentioning

confidence: 99%

Section: Reversible Probes For Ros/biothiolsmentioning

confidence: 99%

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BODIPY‐Based Fluorescent Probes for Biothiols

Zhang

Wang

et al. 2020

Chemistry A European J

190

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“…We show now that BODIPYs( Scheme1)a re able to generate the T 1 state based on ad ifferent mechanism.B ODIPY and its derivatives are well-known highlyf luorescent materials for various applications, [13][14][15][16][17] but these dyes lack the ability to produce the T 1 state upon photo excitation. [12,18,19] Unsubstituted BODIPY,f or example, shows fluorescencee fficiency near unity (0.97 AE 0.03) and al ong fluorescence lifetime of 6.89 ns in methanol, [20] which leaves it little space to form the T 1 state.…”

Section: Introductionmentioning

confidence: 99%

Photoinduced Electron Transfer‐based Halogen‐free Photosensitizers: Covalent meso‐Aryl (Phenyl, Naphthyl, Anthryl, and Pyrenyl) as Electron Donors to Effectively Induce the Formation of the Excited Triplet State and Singlet Oxygen for BODIPY Compounds

Zhang

Feng

2017

Chemistry An Asian Journal

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Pristine BODIPY compounds have negligible efficiency to generate the excited triplet state and singlet oxygen. In this report, we show that attaching a good electron donor to the BODIPY core can lead to singlet oxygen formation with up to 58 % quantum efficiency. For this purpose, BODIPYs with meso-aryl groups (phenyl, naphthyl, anthryl, and pyrenyl) were synthesized and characterized. The fluorescence, excited triplet state, and singlet oxygen formation properties for these compounds were measured in various solvents by UV/Vis absorption, steady-state and time-resolved fluorescence methods, as well as laser flash photolysis technique. In particular, the presence of anthryl and pyrenyl showed substantial enhancement on the singlet oxygen formation ability of BODIPY with up to 58 % and 34 % quantum efficiency, respectively, owing to their stronger electron-donating ability. Upon the increase in singlet oxygen formation, the fluorescence quantum yield and lifetime values of the aryl-BODIPY showed a concomitant decrease. The increase in solvent polarity enhances the singlet oxygen generation but decreases the fluorescence quantum yield. The results are explained by the presence of intramolecular photoinduced electron transfer from the aryl moiety to BODIPY core. This method of promoting T formation is very different from the traditional heavy atom effect by I, Br, or transition metal atoms. This type of novel photosensitizers may find important applications in organic oxygenation reactions and photodynamic therapy of tumors.

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“…In the same year, the Churchill group incorporated the BODIPY system with a single mesityl moiety (C 6 Me 3 H 3 ) at the so‐called meso position of the fluorophore; it turns out to play a significant part in the detection of ROS for in vitro and live cell imaging studies (Scheme ) . The addition of 2‐chloro and 6‐phenyl selenium groups within the BODIPY periphery served to quench the fluorescence due to a photoinduced electron transfer (PET) effect (Figure ); the probe shows high selectivity with NaOCl among other ROS/RNS; a maximum fluorescence intensity is achieved within 1 min and involved a low detection limit (19.6 n m ) and a 110‐fold fluorescence enhancement, compared to the signals generated upon the addition of other ROS/RNS.…”

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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Substituent Effects in BODIPY in Live Cell Imaging

Cited by 46 publications

References 94 publications

BODIPY‐Based Fluorescent Probes for Biothiols

BODIPY‐Based Fluorescent Probes for Biothiols

Photoinduced Electron Transfer‐based Halogen‐free Photosensitizers: Covalent meso‐Aryl (Phenyl, Naphthyl, Anthryl, and Pyrenyl) as Electron Donors to Effectively Induce the Formation of the Excited Triplet State and Singlet Oxygen for BODIPY Compounds

Imaging of Hypochlorous Acid by Fluorescence and Applications in Biological Systems

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