Discerning the Chemistry in Individual Organelles with Small‐Molecule Fluorescent Probes

Wang, Xu; Zeng, Zebing; Jiang, Jian‐Hui; Chang, Young‐Tae; Yuan, Lin

doi:10.1002/anie.201510721

Cited by 668 publications

(395 citation statements)

References 407 publications

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“…Triphenylphosphonium-based modification of molecules facilitating mitochondria targeting is not a totally new concept as abundant literature already exists with regard to the potent biological effects exhibited by small molecules containing TPP + 28,32,33,40–44 . Alkylated triphenylphosphonium cations initially were used as probes to study the mechanism of coupling of the mitochondrial membrane potential with oxidative phosphorylation (OXPHOS) and subsequently were used to determine mitochondrial membrane potential.…”

Section: Approaches To Target Compounds To Mitochondriamentioning

confidence: 99%

Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications

Zielonka¹,

Joseph²,

et al. 2017

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Mitochondria are recognized as one of the most important targets for new drug design in cancer, cardiovascular, and neurological diseases. Currently, the most effective way to deliver drugs specifically to mitochondria is by covalent linking a lipophilic cation such as an alkyltriphenylphosphonium moiety to a pharmacophore of interest. Other delocalized lipophilic cations, such as rhodamine, natural and synthetic mitochondria-targeting peptides, and nanoparticle vehicles, have also been used for mitochondrial delivery of small molecules. Depending on the approach used, and the potentials of cell and mitochondrial membranes, more than 1000-fold higher mitochondrial concentration can be achieved. Mitochondrial targeting has been developed to study mitochondrial physiology and dysfunction and the interaction between mitochondria and other subcellular organelles and for treatment of a variety of diseases such as neurodegeneration and cancer. In this review, we discuss efforts to target small-molecule compounds to mitochondria for probing mitochondria function, as diagnostic tools and potential therapeutics. We describe the physicochemical basis for mitochondrial accumulation of lipophilic cations, synthetic chemistry strategies to target compounds to mitochondria, mitochondrial probes and sensors, and examples of mitochondrial targeting of bioactive compounds. Finally, we review published attempts to apply mitochondria-targeted agents for the treatment of cancer and neurodegenerative diseases.

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Section: Approaches To Target Compounds To Mitochondriamentioning

confidence: 99%

Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications

Zielonka¹,

Joseph²,

et al. 2017

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“…Many fluorescent organelle probes have been developed by covalently incorporating an organelle-anchoring motif. 63, 64 However, the cytotoxicity, cell membrane permeability, non-specific interaction and photo-stability are the major issues in fluorescent organelle imaging.…”

Section: Organelle Imagingmentioning

confidence: 99%

Applications of vibrational tags in biological imaging by Raman microscopy

Zhao

Shen

et al. 2017

Analyst

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As a superb tool to visualize and study the spatial-temporal distribution of chemicals, Raman microscopy has made big impacts to many disciplines of science. While the label-free imaging has been the prevailing strategy in Raman microscopy, recent development and applications of vibrational/Raman tags, particularly when coupled with stimulated Raman Scattering (SRS) microscopy, have generated intense excitement in biomedical imaging. SRS imaging of vibrational tags has enabled researchers to study a wide range of small biomolecules with high specificity, sensitivity and multiplex capability, at single live cell level, tissue level or even in vivo. As reviewed in the article, this platform has facilitated imaging distribution and dynamics of small molecules such as glucose, lipids, amino acids, nucleic acids, and drugs that are otherwise difficult to do with other means. As both the vibrational tags and Raman instrumental development progress rapidly and synergistically, we anticipate that the technique will shed light onto an even broader spectrum of biomedical problems.

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“…Finally, possibly the biggest opportunity for future expansion of the fluorescent nucleobase field may be their biological and biomedical applications 125–128 . There are numerous possible uses of such compounds in biological imaging, and this has only just begun to be explored.…”

Section: Concluding Remarks and Future Prospectsmentioning

confidence: 99%

Fluorescent nucleobases as tools for studying DNA and RNA

2017

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Understanding the diversity of dynamic structures and functions of DNA and RNA in biology requires tools that can selectively and intimately probe these biomolecules. Synthetic fluorescent nucleobases that can be incorporated into nucleic acids alongside their natural counterparts have emerged as a powerful class of molecular reporters of location and environment. They are enabling new basic insights into DNA and RNA, and are facilitating a broad range of new technologies with chemical, biological and biomedical applications. In this Review, we will present a brief history of the development of fluorescent nucleobases and explore their utility as tools for addressing questions in biophysics, biochemistry and biology of nucleic acids. We provide chemical insights into the two main classes of these compounds: canonical and non-canonical nucleobases. A point-by-point discussion of the advantages and disadvantages of both types of fluorescent nucleobases is made, along with a perspective into the future challenges and outlook for this burgeoning field.

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Discerning the Chemistry in Individual Organelles with Small‐Molecule Fluorescent Probes

Cited by 668 publications

References 407 publications

Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications

Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications

Applications of vibrational tags in biological imaging by Raman microscopy

Fluorescent nucleobases as tools for studying DNA and RNA

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