A Mitochondria-Specific Fluorescent Probe for Visualizing Endogenous Hydrogen Cyanide Fluctuations in Neurons

Long, Lingliang; Huang, Meiyu; Wang, Ning; Wu, Yujuan; Wang, Kun; Gong, Aihua; Zhang, Zhijian; Sessler, Jonathan L.

doi:10.1021/jacs.7b12545

Cited by 160 publications

(87 citation statements)

References 69 publications

(53 reference statements)

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“…Cyanide is one of the most hazardous chemical compounds. It causes overproduction of reactive oxygen species in the mitochondria and damages the respiratory tract by acting as an inhibitor of aerobic respiration . Extreme toxicity and increasing environmental pollution resulting from the industrial use of cyanide necessitate the development of more sensitive methods as an alternative to the current detection systems.…”

Section: Indole‐based Bodpy Systems For Sensingmentioning

confidence: 99%

Recent chemo‐/biosensor and bioimaging studies based on indole‐decorated BODIPYs

2019

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BODIPY is an important fluorophores due to its enhanced photophysical and chemical properties including outstanding thermal/photochemical stability, intense absorption/emission profiles, high photoluminescence quantum yield, and small Stokes' shifts. In addition to BODIPY, indole and its derivatives have recently gained attention because of their structural properties and particularly biological importance, therefore these molecules have been widely used in sensing and biosensing applications. Here, we focus on recent studies that reported the incorporation of indole‐based BODIPY molecules as reporter molecules in sensing systems. We highlight the rationale for developing such systems and evaluate detection limits of the developed sensing platforms. Furthermore, we also review the application of indole‐based BODIPY molecules in bioimaging studies. This article includes the evaluation of indole‐based BODIPYs from synthesis to characterization and a comparison of the advantages and disadvantages of developed reporter systems, making it instructive for researchers in various disciplines for the design and development of similar systems.

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Section: Indole‐based Bodpy Systems For Sensingmentioning

confidence: 99%

Recent chemo‐/biosensor and bioimaging studies based on indole‐decorated BODIPYs

2019

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“…This might be detrimental to brightness (see below). For example, many red and NIR dyes have been built on the well‐known fluorophore scaffolds (GFP, rhodamine, cyanine, coumarin, BODIPY featured in Figure b) to take advantage of their appealing properties such as high FQY. The push‐pull structure is usually established by incorporating the electron‐donating groups (EDGs) and electron‐withdrawing groups (EWGs) on the opposite ends of the parent backbone.…”

Section: Introductionmentioning

confidence: 99%

Devising Efficient Red‐Shifting Strategies for Bioimaging: A Generalizable Donor‐Acceptor Fluorophore Prototype

Chen

Fang

2020

Chemistry An Asian Journal

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Long emission wavelengths, high fluorescence quantum yields (FQYs), and large Stokes shifts are highly desirable features for fluorescent probes in biological imaging. However, the current development of many fluorescent probes remains largely trial-and-error and lacks efficiency. Moreover, to achieve far-red/near-infrared emission, a significant extension in the p-conjugation is usually adopted but accompanied by other drawbacks such as fluorescence loss. In this review, we discuss an effective red-shifting strategy built upon the green fluorescent protein chromophore, which enables a synergistic tuning of both the electronic ground and excited states. This approach could shorten the path toward redder emission in comparison to the conventional intramolecular charge transfer (ICT) strategy. We envision that this spectroscopy and computation-aided strategy may advance the noncanonical fluorescent protein design and be generalized to various fluorophore scaffolds for redder emission while preserving other superior properties such as high FQYs.[a] C.

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“…Mitochondria are central to cell life and death such that its dysfunction could forecast tumorigenesis and tumor progression . Great efforts have been taken on design of organelle‐specific fluorescent probes to unravel how mitochondrial damage contributes to diseases . Despite significant advances in targeting mitochondria, it is still of great challenge to address high‐fidelity trapping of mitochondrial dynamic activity in vivo.…”

Section: Introductionmentioning

confidence: 99%

High‐Fidelity Trapping of Spatial–Temporal Mitochondria with Rational Design of Aggregation‐Induced Emission Probes

Zhang

Wang

Guo

et al. 2019

Adv Funct Materials

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High-fidelity trapping of mitochondrial dynamic activity is critical to value cellular functions and forecast disease but lack of spatial-temporal probes. Given that commercial mitochondria probes suffering from low photostability, aggregation-caused quenching effect, and limited signal-to-noise ratio from fluorescence "always on" in the process of targeting mitochondria, here, the rational design strategy of a novel aggregation-induced emission (AIE) molecular motif and unique insight into the high-fidelity targeting of mitochondria is reported, thereby illustrating the relationship between tailoring molecular aggregation state and mitochondrial targeting ability. This study focuses on how to exactly modulate the hydrophilicity and the aggregated state for realizing "off-on" fluorescence, as well as matching the charge density to go across the cell membrane for mitochondrial targeting. Probe tricyano-methylene-pyridine (TCM-1) exhibits an unprecedented high-fidelity feedback on spatial-temporal mitochondrial information with several advantages such as "off-on" near-infrared characteristic, high targeting capacity, favorable biocompatibility, as well as excellent photostability. TCM-1 also produces reactive oxygen species in situ for image-guided photodynamic anticancer therapy. Through unraveling the relationship between tuning molecular aggregation behavior and organelle-specific targeting ability, for the first time, a unique guide is provided in designing AIE-active probes to explore the hydrophilicity and membrane potential for targeting subcellular organelles.

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A Mitochondria-Specific Fluorescent Probe for Visualizing Endogenous Hydrogen Cyanide Fluctuations in Neurons

Cited by 160 publications

References 69 publications

Recent chemo‐/biosensor and bioimaging studies based on indole‐decorated BODIPYs

Recent chemo‐/biosensor and bioimaging studies based on indole‐decorated BODIPYs

Devising Efficient Red‐Shifting Strategies for Bioimaging: A Generalizable Donor‐Acceptor Fluorophore Prototype

High‐Fidelity Trapping of Spatial–Temporal Mitochondria with Rational Design of Aggregation‐Induced Emission Probes

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