A BODIPY fluorescent probe with selective response for hypochlorous acid and its application in cell imaging

Gai, Lizhi; Mack, John; Liu, Hui; Xu, Zheng; Lü, Hua; Li, Zhifang

doi:10.1016/j.snb.2013.02.106

Cited by 52 publications

(19 citation statements)

References 46 publications

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“…The fluorescence intensity of structurally modified BODIPY dyes can be quenched in polar solvents due to an enhancement of the rate of nonradiative decay via what are often referred to as intramolecular charge transfer (ICT) states. [84][85][86][87] ICT states are derived from the S 1 state of the fluorophore and are caused by a separation of charge on different portions of the structure upon electronic excitation. The rate of nonradiative decay is believed to be enhanced by the formation of 10 conical intersections between this low-lying non-emissive S 1 state and the ground state.…”

Section: Optical Properties Of Bodipymentioning

confidence: 99%

Structural modification strategies for the rational design of red/NIR region BODIPYs

et al. 2014

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This review focuses on classifying different types of long wavelength absorbing BODIPY dyes based on the wide range of structural modification methods that have been adopted, and on tabulating their spectral and photophysical properties. The structure-property relationships are analyzed in depth with reference to molecular modeling calculations, so that the effectiveness of the different structural modification strategies for shifting the main BODIPY spectral bands to longer wavelengths can be readily compared, along with their effects on the fluorescence quantum yield (ΦF) values. This should facilitate the future rational design of red/NIR region BODIPY dyes for a wide range of different applications.

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Section: Optical Properties Of Bodipymentioning

confidence: 99%

Structural modification strategies for the rational design of red/NIR region BODIPYs

et al. 2014

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“…With this reaction, Gai et al prepared a BODIPY dye-based probe, 2 (Fig. 6), for the detection of HOCl [127].…”

Section: "On-off" Fluorescence Probesmentioning

confidence: 99%

Bioanalytical methods for hypochlorous acid detection: Recent advances and challenges

Zhang

Song

Yuan

2018

TrAC Trends in Analytical Chemistry

214

115

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Hypochlorous acid (HOCl), a well-known universal disinfectant in clinical practice, plays important roles in immune systems of animal and human bodies. For understanding the roles of HOCl in living systems, a number of approaches, including chemiluminescence, colorimetric, electrochemical and chromatographic methods have been explored. For the detection of HOCl in live organisms, cuttingedge techniques, such as fluorescence/phosphorescence molecular probes, responsive nanoprobes, Raman and activatable photoacoustic sensors, have also been developed recently. In this review, the recent advances in the development of bioanalytical methods for detection of HOCl in environmental and biological specimens were summarized. More specifically, traditional techniques for assay of HOCl in bulk solution were initially discussed, and then fluorescence molecular probes, phosphorescence probes, responsive nanoprobes and other methods for HOCl detection were reviewed, which gives an overview of the developments and applications in bioanalytical methods for HOCl detection.

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“…Another class of chromophores with growing importance are 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐ s ‐indacenes, also known as boron‐centered dipyrrins or BODIPYs (Figure 1), which were reported for the first time by Treibs and Kreuzer in 1968 8. Favorable properties such as high fluorescence quantum yields, high molar absorption coefficients, low intersystem crossing rates, a long lifetime after excitation, and a high photostability are reasons why BODIPYs are excellent dyes for a variety of applications in fields such as organic‐based photonics,9 biological labeling,10 OLED‐technology,11 fluorescent probes for cell imaging,12 and artificial photosynthetic systems 13. From the photophysical aspect, BODIPYs exhibit sharp absorption and emission in the visible light spectrum around 500 nm.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Functionalized BODIPYs, BODIPY‐Corrole, and BODIPY‐Porphyrin Arrays with 1,2,3‐Triazole Linkers Using the 4‐Azido(tetrafluorophenyl)‐BODIPY Building Block

et al. 2015

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The copper(I)‐catalyzed 1,3‐dipolar cycloaddition of 4‐azido(tetrafluorophenyl)boron‐dipyrrin (azido‐BODIPY) with diverse terminal alkynes, varying from simple alkyl‐substituted derivatives to alkynes with functional groups and carbohydrates, was successfully employed to obtain meso‐functionalized BODIPY derivatives through the 1,2,3‐triazole linkage. The scope of this reaction was extended to the preparation of di‐ and trivalent BODIPY systems through the use of appropriate alkynyl linkers. Moreover, the synthesis of hydroxyl‐ and pentafluorothio‐(SF5)‐substituted, 1,2,3‐triazole‐linked array systems consisting of porphyrins and corroles as the central scaffold, in combination with a BODIPY, was investigated. These covalently connected tetrapyrrole‐BODIPY arrays exemplify a versatile approach to the construction of multichromophore systems: the combination of 1,3‐dipolar cycloaddition and nucleophilic substitution on pentafluorophenyl‐substituted porphyrinoids. The systems designed herein could serve in various light‐harvesting applications and electron‐transfer studies.

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A BODIPY fluorescent probe with selective response for hypochlorous acid and its application in cell imaging

Cited by 52 publications

References 46 publications

Structural modification strategies for the rational design of red/NIR region BODIPYs

Structural modification strategies for the rational design of red/NIR region BODIPYs

Bioanalytical methods for hypochlorous acid detection: Recent advances and challenges

Synthesis of Functionalized BODIPYs, BODIPY‐Corrole, and BODIPY‐Porphyrin Arrays with 1,2,3‐Triazole Linkers Using the 4‐Azido(tetrafluorophenyl)‐BODIPY Building Block

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