Mitochondria-targeting turn-on fluorescent probe for HClO detection and imaging in living cells

Wang, Qing-Ming; Jin, Lei; Shen, Zheyu; Sheng, Liqiang; Bai, Hui

doi:10.1016/j.saa.2019.117825

Cited by 19 publications

(6 citation statements)

References 53 publications

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“…The reaction begins from 3-acetylcoumarin (1) with bromine to produce 3-bromoacetylcoumarin (2), which is then followed by the reaction with triphenylphosphine in dichloromethane to furnish the 2H-chromen-triphenylphosphonium bromide (107) in excellent yield. [103] Both products show supreme fluorescence 'turn-on' and for exogenous and real-time imaging of mitochondrial ClO À via fluorescence microscopy, probe 107 was used for the determination of ClO À in mitochondria as a strong mitochondriatargetable fluorescence probe. [103] 3-Bromoacetylcoumarin (2) reacts with potassium cyanide to create compound 108 in reasonable yield under reflux conditions in ethanol.…”

Section: Multi-steps Synthesis Using 3-bromoacetylcoumarinmentioning

confidence: 99%

“…[103] Both products show supreme fluorescence 'turn-on' and for exogenous and real-time imaging of mitochondrial ClO À via fluorescence microscopy, probe 107 was used for the determination of ClO À in mitochondria as a strong mitochondriatargetable fluorescence probe. [103] 3-Bromoacetylcoumarin (2) reacts with potassium cyanide to create compound 108 in reasonable yield under reflux conditions in ethanol. Then it is combined with equimolar amounts of 8-hydroxy-6-sulfonaphthalene-2-diazonium chloride (109) and 8-hydroxy-3,6-disulfonaphthalene-1-diazonium chloride (111) to yield coumarin acid dyes, sodium 2-oxo-2H-chromen-hydroxynaphthalene-2-sulfonate (110) and sodium 2-oxo-2H-chromen-hydroxynaphthalene-2,7-disulfonate (112) in good yields, respectively (Scheme 31).…”

Section: Multi-steps Synthesis Using 3-bromoacetylcoumarinmentioning

confidence: 99%

“…[104] (The scheme was redrawn from literature.) [103,104] Scheme 32. Synthesis of 2H-oxazolo[3,2-a]pyridin-chroman-2-one (113 and 114).…”

Section: Multi-steps Synthesis Using 3-bromoacetylcoumarinmentioning

confidence: 99%

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3‐Bromoacetylcoumarin, a Crucial Key for Facial Synthesis of Biological Active Compounds

et al. 2022

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Compounds containing the coumarin scaffold are widely used in the pharmaceutical and medicinal industries. The biological activities of coumarin containing derivatives make the attractive for the develop new drugs. Different methods and techniques are developed to synthesize new drugs using coumarin as a starting material. This review summarized various methods, techniques and reaction conditions for synthesis of coumarins containing compounds from 3‐bromoacetylcoumarin. A total of 79 coumarin intermediates and products are reported herein. The different reactions include nucleophilic substitutions, one‐pot and multi‐step synthesis for preparation of coumarin containing compounds through different mechanisms and the outcomes achieved through such reactions are discussed. The prepared compounds showed a range of activities resulting in antifungal, antimicrobial, anti‐inflammatory, antidiabetic and cholinesterase inhibitors. The nucleophilic substitution reactions involving urea related compounds, followed by intramolecular cyclization lead to imidazole and thiazole moieties, which exhibit antibacterial activities. It is hoped that this review provides useful insight for researchers engaged in this field to expand the knowledge gained in this area.

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Section: Multi-steps Synthesis Using 3-bromoacetylcoumarinmentioning

confidence: 99%

Section: Multi-steps Synthesis Using 3-bromoacetylcoumarinmentioning

confidence: 99%

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3‐Bromoacetylcoumarin, a Crucial Key for Facial Synthesis of Biological Active Compounds

et al. 2022

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“…Wang et al synthesized triphenylphosphonium 34 via the treatment of 3-(bromoacetyl)coumarin 1 with triphenylphosphine 33 in benzene or chloroform ( Scheme 17 ). 76 …”

Section: Reactionsmentioning

confidence: 99%

3-(Bromoacetyl)coumarins: unraveling their synthesis, chemistry, and applications

et al. 2021

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“…Compared with other methods, such as colorimetric method, electrochemical analysis, , atmospheric pressure ionization mass spectrometry, liquid chromatography electrospray ionization mass spectrometry, and ion chromatography, fluorescence analysis has been widely used in the detection of HClO due to its obvious advantages such as simple, high sensitivity and easy to realize on-line detection. − In recent years, bifunctional mitochondrial fluorescent probes, which can not only locate in mitochondria but also detect various active species in mitochondria, have become a research hotspot. It is reported that some of the fluorescent probes have been reported for quantitatively detecting active oxygen species in mitochondria, such as H 2 O 2 , − O 2 •– , and • OH, , but there are few reports on the high-efficiency detection of mitochondrial HClO. − Therefore, it is urgent to design fluorescent probes that can detect the changes in HClO content in mitochondria rapidly.…”

Section: Introductionmentioning

confidence: 99%

Novel Mitochondria-Targeting and Naphthalimide-based Fluorescent Probe for Detecting HClO in Living Cells

Wang

et al. 2021

ACS Omega

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As a key reactive oxygen species (ROS), hypochlorous acid (HClO) plays an important role in many physiological and pathological processes. The mitochondria-targeting probes for the highly sensitive detection of HClO are desirable. In present work, we designed and synthesized an original mitochondria-localizing and turn-on fluorescent probe for detecting HClO. 4-Aminonaphthalimide was employed as the fluorescent section, the (2-aminoethyl)-thiourea unit was utilized as a typical sensing unit, and the quaternized pyridinium moiety was used as a mitochondria-targeted localization group. When HClO was absent, the probe showed weak fluorescence. In the existence of HClO, the probe revealed a blue fluorescence. Moreover, the turn-on fluorescent probe was able to function in a broad pH scope. There was an excellent linearity between the fluorescence emission intensity at 488 nm and the concentrations of HClO in the range of 5.0 × 10–7 to 2.5 × 10–6 mol·L–1. Additionally, the probe had almost no cell toxicity and possessed an excellent mitochondria-localizing capability. Furthermore, the probe was able to image HClO in mitochondria of living PC-12 cells. The above remarkable properties illustrated that the probe was able to determine HClO in mitochondria of living cells.

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Mitochondria-targeting turn-on fluorescent probe for HClO detection and imaging in living cells

Cited by 19 publications

References 53 publications

3‐Bromoacetylcoumarin, a Crucial Key for Facial Synthesis of Biological Active Compounds

3‐Bromoacetylcoumarin, a Crucial Key for Facial Synthesis of Biological Active Compounds

3-(Bromoacetyl)coumarins: unraveling their synthesis, chemistry, and applications

Novel Mitochondria-Targeting and Naphthalimide-based Fluorescent Probe for Detecting HClO in Living Cells

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