A fluorescent molecular rotor showing vapochromism, aggregation-induced emission, and environmental sensing in living cells

Koenig, Matthias; Storti, Barbara; Bizzarri, Ranieri; Guldi, Dirk M.; Brancato, Giuseppe; Bottari, Giovanni

doi:10.1039/c5tc03541d

Cited by 42 publications

(23 citation statements)

References 52 publications

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“…Detailed information about the detection of lipid droplets will be presented in Section . Another highly sensitive intracellular viscosity probe with AIE properties, named TPAP, was reported by Bottari and co‐workers (Figure g–h) . As the solvent viscosity increased, from methanol to glycerol, the rotation of TPAP was gradually constrained and the fluorescence intensity and lifetimes were enhanced.…”

Section: Lighting Up Intracellular Microenvironmentsmentioning

confidence: 76%

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Aggregation‐Induced Emission: Lighting up Cells, Revealing Life!

Wang

Zhang

Liang

2016

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121

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Understanding metabolism and dynamic biological events in cells, as well as physiological functions and pathological changes in organisms, is the major goal of biological investigations. It will improve our capability to diagnose and treat diseases, and will enhance personalized medicine. Fluorescence imaging is a powerful tool that plays an essential role in acquiring the comprehensive knowledge necessary to help reach this goal. Fluorescent molecules are crucial factors for obtaining high quality images. In contrast to conventional fluorogens with aggregation-caused quenching (ACQ) effect, molecules that show aggregation-induced emission (AIE) effect open up new avenues for fluorescence imaging. So far, a large variety of AIE probes have been developed and applied to bioimaging because of their outstanding characteristics, such as high fluorescence efficiency, excellent photostability and high signal-to-noise ratio (SNR). In this review, recent advances in AIE-based probes for biomedical imaging of intracellular microenvironments, natural macromolecules, subcellular organelles, intracellular processes, living tissues, and diagnosis and therapeutic evaluation of diseases in vivo are summarized. It is hoped that this review generates great research enthusiasm for AIE-based bioimaging, in order to promote the development of promising AIE probes and guide us to a better understanding of the biological essence of life.

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Section: Lighting Up Intracellular Microenvironmentsmentioning

confidence: 76%

Section: Lighting Up Intracellular Microenvironmentsmentioning

confidence: 99%

Aggregation‐Induced Emission: Lighting up Cells, Revealing Life!

Wang

Zhang

Liang

2016

Small

121

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“…So far, various AIEgens have been synthesized to image bacteria, cell membranes, mitochondria, lysosomes, nuclei, tissue, blood vessels, and even tumors . In addition, different AIE probes have also been developed to monitor biological parameters within intracellular microenvironments like pH, biothiol levels, and viscosity through fluorescence, as well as lifetime imaging . Recently, AIEgens have been successfully used to light‐up cellular processes including autophagy, apoptosis, protein fibrillation, and others …”

Section: Introductionmentioning

confidence: 99%

Strategies to Overcome the Limitations of AIEgens in Biomedical Applications

Yong

Liu

2018

Small Methods

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NPs), [7][8][9][10] fluorescent proteins (FPs), [11,12] conjugated polymer NPs, [13] dye-loaded polymer NPs, [14] and lipid NPs [15] have been exploited in biomedical applications. QDs have bright fluorescence and are generally photostable under various biological conditions. To date, it is well understood that their toxicity is a major concern for translating them for clinical research. [16,17] It is also worth noting that many surfactants used currently for the synthesis of inorganic or organic NPs, e.g., sodium dodecyl sulfate and cetyltrimethylammonium bromide, [18,19] are highly toxic, and leftover surfactants deposited on these NPs may cause harmful effects to the living system. FPs are promising optical probe candidates for bioimaging due to their inherent biocompatibility and ability to be functionalized with ligands for targeted delivery. However, they require complicated transfection process in practical applications. The widely used conventional luminophores have suffered from the notorious aggregation-caused quenching (ACQ) effect, [20,21] which results in decreased or completely quenched fluorescence when they are formulated into NPs. Both dye-doped NPs and π-conjugated polymer NPs have been applied in a wide range of applications, such as fluorescence imaging and biosensing due to their distinct characteristics such as tunable emission wavelength, fast emission rate, excellent photostability, etc. However, most of these systems suffer from ACQ issue, which restricts the loading of optically active materials into the NPs. Recently, great efforts have been made to address the ACQ issue. Fluorophores are usually modified with bulky side chains to minimize the strong π-stacking. This strategy is generally associated with blueshifted fluorescence, which is undesirable for imaging applications. Recently, Klymchenko and co-workers proposed a new concept for preparing fluorescent polymer NPs. These NPs were doped with ionic-liquid-like salts of a cationic dye with a bulky hydrophobic counterion that serves as spacer for minimizing dye aggregation and self-quenching; [22] the synthesized NPs were loaded with 500 dye molecules and they were much brighter than QDs.In 2001, Tang and co-workers coined the concept of aggregation-induced emission (AIE), wherein some fluorogens have shown extremely weak emission in molecular states but highly bright emission in the aggregate or solid states. [23] Fluorogens with AIE characteristics (AIEgens) normally possess rotor-like Motivated by the demand for high-performance tools for biomedical applications, numerous new luminescent nanomaterials with advanced functionalities are synthesized in recent years. Conventional fluorophores generally suffer from the notorious aggregation-caused quenching effect that deteriorates their practical performance. The recently emerged fluorogens with aggregation-induced emission (AIE) characteristics (AIEgen) have generated a new avenue for biomedical applications due to their unique optical properties, flexible designability, and multifun...

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“…Indeed, the characteristic long lifetime of electronic excited states (from a few picoseconds to nanoseconds) makes fluorescence exquisitely sensitive to changes in the local (nano) environments. Accordingly, many fluorescent polarity and viscosity probes have been employed to image the cell environment and have contributed to the elucidation of biochemical mechanisms (8)(9)(10)(11)(12)(13)(14)(15). Most probes, however, are characterized by photophysical processes of their excited states (e.g., twisted intramolecular charge transfer) that lead to complex and intertwined responses to polarity and viscosity (16)(17)(18).…”

Section: Introductionmentioning

confidence: 99%

Simultaneous Detection of Local Polarizability and Viscosity by a Single Fluorescent Probe in Cells

Abbandonato

Polli

Viola

et al. 2018

Biophysical Journal

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Many intracellular reactions are dependent on the dielectric ("polarity") and viscosity properties of their milieu. Fluorescence imaging offers a convenient strategy to report on such environmental properties. Yet, concomitant and independent monitoring of polarity and viscosity in cells at submicron scale is currently hampered by the lack of fluorescence probes characterized by unmixed responses to both parameters. Here, the peculiar photophysics of a green fluorescent protein chromophore analog is exploited for quantifying and imaging polarity and viscosity independently in living cells. We show that the polarity and viscosity profile around a novel hybrid drug-delivery peptide changes dramatically upon cell internalization via endosomes, shedding light on the spatiotemporal features of the release mechanism. Accordingly, our fluorescent probe opens the way to monitor the environmental effects on several processes relevant to cell biochemistry and nanomedicine.

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A fluorescent molecular rotor showing vapochromism, aggregation-induced emission, and environmental sensing in living cells

Cited by 42 publications

References 52 publications

Aggregation‐Induced Emission: Lighting up Cells, Revealing Life!

Aggregation‐Induced Emission: Lighting up Cells, Revealing Life!

Strategies to Overcome the Limitations of AIEgens in Biomedical Applications

Simultaneous Detection of Local Polarizability and Viscosity by a Single Fluorescent Probe in Cells

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