High-Quantum-Yield Mitochondria-Targeting Near-Infrared Fluorescent Probe for Imaging Native Hypobromous Acid in Living Cells and in Vivo

Liu, Xiaojun; Zheng, Aishan; Luan, Dongrui; Wang, Xiaoting; Kong, Fanming; Tong, Lili; Xu, Kehua; Tang, Bo

doi:10.1021/acs.analchem.6b04094

Cited by 62 publications

(23 citation statements)

References 31 publications

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“…Due to the different nucleophilicities of the three biothiols, selective identification of biothiols can be achieved via their different addition reaction rates and cyclization cleavage processes [41][42][43]. To date, it is still a challenge to distinguish three biothiols completely with fluorescent probes [44][45][46]. Therefore, a new strategy for the design and development of fluorescent probes for selectively detecting Cys is highly desirable.…”

Section: Introductionmentioning

confidence: 99%

A novel and simple imidazo[1,2-a]pyridin fluorescent probe for the sensitive and selective imaging of cysteine in living cells and zebrafish

Zhu

Wang

et al. 2019

Analytica Chimica Acta

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Cysteine (Cys), homocysteine (Hcy) and glutathione (GSH) play many crucial physiological roles in organisms. Their abnormal levels can cause and indicate various diseases. In the present study, a small-molecule fluorescent probe 2-(imidazo[1,2-a]pyridin-2-yl)phenyl acrylate (IPPA) was designed, synthesized and characterized by NMR, FT-IR and HRMS. IPPA can selectively detect Cys over other analytes because of an approximately 76 times enhancement in fluorescence intensity. The limit of detection of IPPA for Cys was 0.33 μM. The pseudo-first-order rate constant of the reaction between IPPA and Cys was approximately 10 times that of the reaction between IPPA and Hcy (K Cys 3.18 × 10 −3 S −1 vs K Hcy 4.92 × 10 −4 S −1), indicating that Cys can be distinguished from Hcy. In addition, IPPA exhibits strong anti-interference ability, small molecular weight, high efficiency, low toxicity and good cell permeability. It was successfully used in imaging HepG2 cells and zebrafish. The fluorescence response of IPPA for calf serum are powerful proofs for practical application. Therefore, IPPA has high potential for bioassay applications.

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Section: Introductionmentioning

confidence: 99%

A novel and simple imidazo[1,2-a]pyridin fluorescent probe for the sensitive and selective imaging of cysteine in living cells and zebrafish

Zhu

Wang

et al. 2019

Analytica Chimica Acta

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“…The preparation of NaOBr solution was carried out according to Liu et al . 32 NaOH (11.7 g, 0.30 mol) was dissolved in water (100 ml). The solution was cooled in an ice bath to −5 °C.…”

Section: Methodsmentioning

confidence: 99%

“…A significant drawback of these approaches is that they do not monitor real-time dynamics within live cells. Therefore, over the past few years, the market has seen a large number of fluorescent dyes for measuring HOCl [25][26][27][28][29][30][31] , and some selective synthetic indicators for HOBr detection 32 . Despite all the advantages of these dyes, they have several shortcomings compared to genetically encoded biosensors based on fluorescent proteins, which are able to follow their analyte in living systems of any level of complexity.…”

mentioning

confidence: 99%

Hypocrates is a genetically encoded fluorescent biosensor for (pseudo)hypohalous acids and their derivatives

et al. 2022

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The lack of tools to monitor the dynamics of (pseudo)hypohalous acids in live cells and tissues hinders a better understanding of inflammatory processes. Here we present a fluorescent genetically encoded biosensor, Hypocrates, for the visualization of (pseudo)hypohalous acids and their derivatives. Hypocrates consists of a circularly permuted yellow fluorescent protein integrated into the structure of the transcription repressor NemR from Escherichia coli. We show that Hypocrates is ratiometric, reversible, and responds to its analytes in the 106 M−1s−1 range. Solving the Hypocrates X-ray structure provided insights into its sensing mechanism, allowing determination of the spatial organization in this circularly permuted fluorescent protein-based redox probe. We exemplify its applicability by imaging hypohalous stress in bacteria phagocytosed by primary neutrophils. Finally, we demonstrate that Hypocrates can be utilized in combination with HyPerRed for the simultaneous visualization of (pseudo)hypohalous acids and hydrogen peroxide dynamics in a zebrafish tail fin injury model.

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“…The fluorescent D‐π‐A compounds with ‐COOH group are important for NIR probes in the detection of living cell and in vivo imaging, flow cytometry, and reactive oxygen species sensors,, They are used in bio‐conjugation with affinity proteins and antibodies,, tagging quantum dots (QD) for resonance energy transfer, and carbon quantum dots for DNA sensing . Rhodanine‐3‐acetic acid (RAA) is a widely used acceptor in DSSCs ,.…”

Section: Introductionmentioning

confidence: 99%

Extensive Study of Rhodanine‐Arylamine‐Based Chromophores: Consolidated Optical, DFT/TD‐DFT and Non‐Linear Optical Properties

et al. 2019

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Three push-pull rhodanine-arylamine based D-π-A dyes (2a-2c) are prepared to study the effect of donor on electronic, linear and nonlinear optical properties. The dyes, 2a,2b and 2c have a vinyl spacer conjugated with triphenylamine, julolidine, and carbazole donors respectively, with a methoxy group and rhodanine-3-acetic acid. The dyes exhibited solvent dependent absorption-emission up to the red region with large Stokes shifts (2a = 77-130 nm). This dyes possess charge transfer characteristics as established by transition dipole moment (μ eg ), dipole moment ratio (μ e /μ g ), Generalised Mulliken-Hush analysis, and electron distribution (DFT). The non-linear optical study revealed that quadratic hyperpolarizability (μβ CT ) are 1098.9 (2a), 515.0 (2b) and 339.6 x 10 -48 e.s.u. (2c) depending on donor strength. The intrinsic hyperpolarizabilities fall below b int 0 ¼ 10 À 3=2 limit i.e. less than unity. Solvatochromic two-level model is used to study the trends in two photon cross-section (σ2PA). Solvatochromic two-level model is used to study the trends in two photon absorption cross-section (σ2PA). The dye 2a exhibited high σ2PA, 216 GM (λ max 485 nm and 564 nm). The dyes 2a and 2c with analogue dye 3a show reverse saturable absorption (RSA) therefore, show positive third order nonlinear absorption coefficient, β and reasonable values of third order nonlinear susceptibility and high laser damage threshold. The Re χ (3) factors are responsible for the high values of χ (3) in the range of 0.77 to 8.09 x 10-12 e.s.u. Therefore, this material would serve as good candidate in the photonic application.

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High-Quantum-Yield Mitochondria-Targeting Near-Infrared Fluorescent Probe for Imaging Native Hypobromous Acid in Living Cells and in Vivo

Cited by 62 publications

References 31 publications

A novel and simple imidazo[1,2-a]pyridin fluorescent probe for the sensitive and selective imaging of cysteine in living cells and zebrafish

A novel and simple imidazo[1,2-a]pyridin fluorescent probe for the sensitive and selective imaging of cysteine in living cells and zebrafish

Hypocrates is a genetically encoded fluorescent biosensor for (pseudo)hypohalous acids and their derivatives

Extensive Study of Rhodanine‐Arylamine‐Based Chromophores: Consolidated Optical, DFT/TD‐DFT and Non‐Linear Optical Properties

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