Dihydroxanthene-Based Near-infrared Fluorescent Probes for Monitoring Mitochondrial Viscosity in Living Cells and Mice

Wu, Xue; Fu, Guanyu; Li, Ying; Li, Sijin; Zhao, Qiuyue; Kong, Fanming; Li, Lü; Tang, Bo

doi:10.1021/acs.analchem.2c05713

Cited by 30 publications

(16 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The dihydroxanthene fluorophores (denoted as DHX ) are the most commonly utilized NIR dyes due to their long wavelength emission, good water solubility, and biocompatibility. , As shown in Scheme a, a rigid dihydroxanthene fluorophore was selected as part of the core structure, a pH-insensitive methoxy group was selected as the electron donor, and pyridinium units served as the electron-accepting and mitochondria-targeting group. Mitochondria-immobilized probes have been developed based on fixed groups, such as benzyl chloride, − aldehyde, − 1,3-cyclohexanedione, maleimide, and alkyne . The reactive fixed groups react with nucleophiles, such as the reactive thiol groups present in mitochondrial polypeptides and proteins, and form covalent bonds to immobilize the probes within mitochondria, even if the MMP decreases or dissipates.…”

Section: Resultsmentioning

confidence: 99%

Rational Design of MMP-Independent Near-Infrared Fluorescent Probes for Accurately Monitoring Mitochondrial Viscosity

Zhang

et al. 2023

Anal. Chem.

Self Cite

View full text Add to dashboard Cite

Mitochondrial viscosity affects metabolite diffusion and mitochondrial metabolism and is associated with many diseases. However, the accuracy of mitochondria-targeting fluorescent probes in measuring viscosity is unsatisfactory because these probes can diffuse from mitochondria during mitophagy with a decreased mitochondrial membrane potential (MMP). To avoid this problem, by incorporating different alkyl side chains into dihydroxanthene fluorophores (denoted as DHX), we developed six near-infrared (NIR) probes for the accurate detection of mitochondrial viscosity, and the sensitivity to viscosity and the mitochondrial targeting and anchoring capability of these probes increased by increasing the alkyl chain length. Among them, DHX-V-C 12 had a highly selective response to viscosity variations with minimum interference from polarity, pH, and other biologically relevant species. Furthermore, DHX-V-C 12 was used to monitor the mitochondrial viscosity changes of HeLa cells treated by ionophores (nystatin, monensin) or under starvation conditions. We hope that this mitochondrial targeting and anchoring strategy based on increasing the alkyl chain length will be a general strategy for the accurate detection of mitochondrial analytes, enabling the accurate study of mitochondrial functions.

show abstract

Section: Resultsmentioning

confidence: 99%

Rational Design of MMP-Independent Near-Infrared Fluorescent Probes for Accurately Monitoring Mitochondrial Viscosity

Zhang

et al. 2023

Anal. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…The improved viscosity sensing ability of molecule 76 is further employed to detect viscosity in cells and mice. 62 Inducing the viscosity by adding Nystatin and LPS yields a 10 times higher enhanced fluorescence intensity. While cat-ionic derivatives are known and show possible localization within mitochondria, neutral pyridine derivatives show localization within the lipid droplets.…”

Section: Account Synlettmentioning

confidence: 99%

“…(E) Effect of starvation (media devoid of FBS) on fluorescence intensity of 76 in cells. (F) Recognition of cellular viscosity induced during inflammation (LPS treatment) and Nystatin 62.…”

mentioning

confidence: 99%

Functional α-Cyanostilbenes: Sensing to Imaging

Dahiwadkar

Kaloo

Kanvah³

2023

Synlett

View full text Add to dashboard Cite

In recent years, there has been considerable interest in cyanostilbenes due to their unique photophysical properties. The compounds emit light when aggregating, commonly called aggregation-induced emission (AIE). This remarkable feature makes cyanostilbenes ideal for various sensing applications, especially in aqueous environments. The detection of various analytes, such as metal ions and nitroaromatic compounds, has been accomplished using these compounds through various sensing mechanisms from chelation-enhanced fluorescence to fluorescence quenching. Furthermore, cyanostilbenes have shown great promise in biological imaging applications and have been employed for intracellular imaging, tracking, and targeting of sub-cellular organelles. The development and utilization of cyanostilbenes can significantly impact advancing sensing and imaging technologies in both analytical and biological fields. This potential stems from the unique properties of cyanostilbenes, such as their AIE characteristic, which sets them apart from other compounds and makes them highly useful for various applications. Further exploration and development of cyanostilbenes could lead to the creation of novel sensing and imaging technologies with wide-ranging applications in both academic and industrial settings

show abstract

“…The increased mitochondrial viscosity is related with cellular malignancy, atherosclerosis, and many other diseases and dysfunctions. − In addition, abnormal lysosomal viscosity is associated with many diseases, such as lysosomal storage diseases, cardiovascular diseases, inflammation, and neurodegenerative diseases. − Therefore, monitoring the slight viscosity changes in cells and especially subcellular organelles is important to better understand the cellular functions and mechanisms of related diseases. Recently, fluorescent probes have been developed and become a powerful method for tracing slight viscosity changes in biological systems. − Subcellular viscosity fluorescent probes are now singly detecting one organelle, such as mitochondria or lysosomes mainly using specific targeting groups, for example, ammonium or phosphonium salts for mitochondria and morpholine ring for lysosomes; − however, dual-organelle fluorescent probes with one targeting group remain rare, which could simultaneously target two organelles, helping monitor the slight changes of two organelles at the same times by using only one molecule and potentially understand the interaction of two organelles. Therefore, development of novel fluorescent probes for dual-organelle viscosity imaging is meaningful and urgent to better understand the close relationships of organelle viscosity and related diseases.…”

Section: Introductionmentioning

confidence: 99%

Development of meso-Five-Membered Heterocycle BODIPY-Based AIE Fluorescent Probes for Dual-Organelle Viscosity Imaging

et al. 2023

View full text Add to dashboard Cite

Fluorescent rotors with aggregation-induced emission (AIE) and organelle-targeting properties have attracted great attention for sensing subcellular viscosity changes, which could help understand the relationships of abnormal fluctuations with many associated diseases. Despite the numerous efforts spent, it remains rare and urgent to explore the dualorganelle targeting probes and their structural relationships with viscosityresponsive and AIE properties. Therefore, in this work, we reported four meso-five-membered heterocycle-substituted BODIPY-based fluorescent probes, explored their viscosity-responsive and AIE properties, and further investigated their subcellular localization and viscosity-sensing applications in living cells. Interestingly, the meso-thiazole probe 1 showed both good viscosity-responsive and AIE (in pure water) properties and could successfully target both mitochondria and lysosomes, further imaging cellular viscosity changes by treating lipopolysaccharide and nystatin, attributing to the free rotation and potential dual-organelle targeting ability of the meso-thiazole group. The meso-benzothiophene probe 3 with a saturated sulfur only showed good viscosityresponsive properties in living cells with the aggregation-caused quenching effect and no subcellular localization. The meso-imidazole probe 2 showed the AIE phenomenon without an obvious viscosity-responsive property with a C�N bond, while the mesobenzopyrrole probe 4 displayed fluorescence quenching in polar solvents. Therefore, for the first time, we investigated the structure− property relationships of four meso-five-membered heterocycle-substituted BODIPY-based fluorescent rotors with viscosityresponsive and AIE properties, and among these, 1 with a C�N bond and a saturated sulfur on the meso-thiazole, potentially contributing to their corresponding AIE and viscosity-responsive properties, served as a sensitive AIE fluorescent rotor for imaging dual-organelle viscosity in both mitochondria and lysosomes.

show abstract

Dihydroxanthene-Based Near-infrared Fluorescent Probes for Monitoring Mitochondrial Viscosity in Living Cells and Mice

Cited by 30 publications

References 40 publications

Rational Design of MMP-Independent Near-Infrared Fluorescent Probes for Accurately Monitoring Mitochondrial Viscosity

Rational Design of MMP-Independent Near-Infrared Fluorescent Probes for Accurately Monitoring Mitochondrial Viscosity

Functional α-Cyanostilbenes: Sensing to Imaging

Development of meso-Five-Membered Heterocycle BODIPY-Based AIE Fluorescent Probes for Dual-Organelle Viscosity Imaging

Contact Info

Product

Resources

About