Visualizing intracellular dynamics with AIE probes

Lee, Michelle M. S.; Yu, Eric Y.; Chau, Joseph Lik Hang; Lam, Jacky W. Y.; Kwok, Ryan T. K.; Wang, Dong; Tang, Benzhong

doi:10.1039/d2qm01382g

Cited by 5 publications

(2 citation statements)

References 89 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To construct a superior molecular fluorescent rotor, boron dipyrromethenes (BODIPYs) have been extensively used as excellent fluorophores, which showed strong absorptions and fluorescence emissions, with relatively high fluorescence quantum yields and tunable spectroscopic properties through simple molecular modifications. − Therefore, large numbers of BODIPY-based molecular fluorescent probes for sensing the viscosity were reported by using rotation groups of meso -CC, non- meso -CC, , CC, meso -phenyl groups, − meso -CO, , meso -CF 3 , , and meso -five-membered heterocyclic rings. , Their absorption and fluorescence properties are compared in Table S1. Among these rotors, some meso -substituted BODIPYs not only showed viscosity-responsive properties but also exhibited good aggregation-induced emission (AIE) enhancements, such as the meso -CO, meso -CF 3 , and meso -five-membered heterocyclic rings. , It is worth mentioning that AIE fluorescent probes could potentially display large Stokes shifts, excellent photostability, and low self-quenching, which have been extensively applied in bioimaging and biomedical applications. − However, most of the BODIPY-based fluorescent probes showed narrow Stokes shifts, especially for the commonly used meso -phenyl-substituted derivatives with only about 20 nm Stokes shifts, − while large Stokes shifts could reduce the crosstalk between absorptions and emissions, and improve the fluorescence signal-to-noise ratios. Meanwhile, it is also interesting to find that meso -double bond-substituted BODIPY-based fluorescent probes, including CO and CC, as shown in Figure A, have been reported to show red-shifted fluorescence at 538–570 nm with relatively large Stokes shifts in viscous glycerol; however, only the probe BK (BODIPY with ketone) has been reported to display AIE emissions at 591 nm .…”

Section: Introductionmentioning

confidence: 99%

Exploration of Novel Meso-C═N-BODIPY-Based AIE Fluorescent Rotors with Large Stokes Shifts for Organelle-Viscosity Imaging

Wan,

Anwar,

Tang

et al. 2024

Anal. Chem.

View full text Add to dashboard Cite

The research on fluorescent rotors for viscosity has attracted extensive interest to better comprehend the close relationships of microviscosity variations with related diseases. Although scientists have made great efforts, fluorescent probes for cellular viscosity with both aggregation-induced emissions (AIEs) and large Stokes shifts to improve sensing properties have rarely been reported. Herein, we first report four new meso-C�N-substituted BODIPY-based rotors with large Stokes shifts, investigate their viscosity/AIE characteristics, and perform cellular imaging of the viscosity in subcellular organelles. Interestingly, the meso-C�N-phenyl group-substituted probe 6 showed an obvious 594 nm fluorescence enhancement in glycerol and a moderate 650 nm red AIE emission in water. Further, on attaching CF 3 to the phenyl group, a similar phenomenon was observed for 7 with red-shifted emissions, attributed to the introduction of a phenyl group, which plays a key role in the red AIE emissions and large Stokes shifts. Comparatively, for phenyl-group-free probes, both the meso-C�N-trifluoroethyl group and thiazole-substituted probes (8 and 9) exhibited good viscosity-responsive properties, while no AIE was observed due to the absence of phenyl groups. For cellular experiments, 6 and 9 showed good lysosomal and mitochondrial targeting properties, respectively, and were further successfully used for imaging viscosity through the preincubation of monensin and lipopolysaccharide (LPS), indicating that C�N polar groups potentially work as rotatable moieties and organelle-targeting groups, and the targeting difference might be ascribed to increased charges of thiazole. Therefore, in this study, we investigated the structural relationships of four meso-C�N BODIPY-based rotors with respect to their viscosity/AIE characteristics, subcellular-targeting ability, and cellular imaging for viscosity, potentially serving as AIE fluorescent probes with large Stokes shifts for subcellular viscosity imaging.

show abstract

Section: Introductionmentioning

confidence: 99%

Exploration of Novel Meso-C═N-BODIPY-Based AIE Fluorescent Rotors with Large Stokes Shifts for Organelle-Viscosity Imaging

Wan,

Anwar,

Tang

et al. 2024

Anal. Chem.

View full text Add to dashboard Cite

show abstract

“…1–4 Due to their high sensitivity and selectivity, AIE-based luminogens (AIEgens) have gained considerable attention in applications such as detection and biological imaging. 5–20 Recently, several types of AIEgens, mainly including siloles, 21 pyroles, 22 tetraphenylethylenes, 23–25 pyrazines, 26 triphenylamines, 27 naphthalenes, 28 and tetraphenyl-1,3-butadiene, 29 have been successfully developed. Experimental studies and theoretical calculations consistently indicate that the restriction of intramolecular motion (RIM) serves as the primary mechanism underlying the AIE effect.…”

Section: Introductionmentioning

confidence: 99%

Tetrasubstituted imidazole derivatives and their imidazolium: photophysical properties in the aggregate state and application for adenosine detection

Zhao,

Dong

2024

Mater. Chem. Front.

View full text Add to dashboard Cite

show abstract

Reviewing the evolutive ACQ‐to‐AIE transformation of photosensitizers for phototheranostics

Zhu,

Huang,

et al. 2023

Luminescence

View full text Add to dashboard Cite

Photodynamic therapy (PDT) represents an emerging noninvasive treatment technique for cancers and various nonmalignant diseases, including infections. During the process of PDT, the physical and chemical properties of photosensitizers (PSs) critically determine the effectiveness of PDT. Traditional PSs have made great progress in clinical applications. One of the challenges is that traditional PSs suffer from aggregation‐caused quenching (ACQ) due to their discotic structures. Recently, aggregation‐induced emission PSs (AIE‐PSs) with a twisted propeller‐shaped conformation have been widely concerned because of high reactive oxygen species (ROS) generation efficiency, strong fluorescence efficiency, and resistance to photobleaching. However, AIE‐PSs also have some disadvantages, such as short absorption wavelengths and insufficient molar absorption coefficient. When the advantages and disadvantages of AIE‐PSs and ACQ‐PSs are complementary, combining ACQ‐PSs and AIE‐PSs is a “win‐to‐win” strategy. As far as we know, the conversion of traditional representative ACQ‐PSs to AIE‐PSs for phototheranostics has not been reviewed. In the review, we summarize the recent progress on the ACQ‐to‐AIE transformation of PSs and the strategies to achieve desirable theranostic applications. The review would be helpful to design more efficient ACQ‐AIE‐PSs in the future and to accelerate the development and clinical application of PDT.

show abstract

Visualizing intracellular dynamics with AIE probes

Abstract: As a sensitive, selective, and non-invasive method, fluorescence bioimaging stands out in biological and pathological studies to visualize biological processes on a microscale. However, the initial photophysical property of conventional...

Cited by 5 publications

References 89 publications

Exploration of Novel Meso-C═N-BODIPY-Based AIE Fluorescent Rotors with Large Stokes Shifts for Organelle-Viscosity Imaging

Exploration of Novel Meso-C═N-BODIPY-Based AIE Fluorescent Rotors with Large Stokes Shifts for Organelle-Viscosity Imaging

Tetrasubstituted imidazole derivatives and their imidazolium: photophysical properties in the aggregate state and application for adenosine detection

Reviewing the evolutive ACQ‐to‐AIE transformation of photosensitizers for phototheranostics

Contact Info

Product

Resources

About