Modulation of Aggregation-Induced Emission by Excitation Energy Transfer: Design and Application

Dong, Lei; Peng, Hui‐Qing; Niu, Li‐Ya; Yang, Qing‐Zheng

doi:10.1007/s41061-021-00330-0

“…S1 † ). 39 Demethylation of 7 with BBr 3 in CH 2 Cl 2 afforded the bis-phenolic 8 (Scheme S1 † ). Subsequently, glycosylation under phase transfer conditions with bromo tetra- O -acetyl- d -galactose afforded the desired bis-glycosylated derivative 9.…”

Section: Resultsmentioning

confidence: 99%

A general strategy to the intracellular sensing of glycosidases using AIE-based glycoclusters

Dong

¹

,

Zhang

²

,

Han

³

et al. 2022

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“…S1), which is characteristic of AIE. 52 With TD-Gal2 in hand, we tested its fluorescence response to β-Gal (derived from E.…”

Section: Resultsmentioning

confidence: 99%

“…The known TPE-aldehyde 548 was coupled to DCM 651 through aldolization/crotonization. The resultant conjugate 7 with a red fluorescence emission showed a gradual fluorescence enhancement with increasing water fraction in THF (Fig.S1), which is characteristic of AIE 52. Demethylation of 7 with BBr3 in CH2Cl2 afforded the bisphenolic 8.…”

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confidence: 95%

A General Strategy to the Intracellular Sensing of Glycosidases using AIE-Based Glycoclusters

Dong

¹

,

Zhang

²

,

Han

³

et al. 2021

Preprint

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0

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Glycosidases, which are the enzymes responsible for removal of residual monosaccharides from glycoconjugates, are implicated in a myriad of biological and pathological events. The ability to detect sensitively the activity and spatiotemporal distribution of glycosidases in cells may facilitate the study of glycobiology, and add useful diagnostic tools. However, the currently developed fluorogenic probes for glycosidases are generally based on glycosylation of a phenol group of a donor-acceptor type fluorogen. This general molecular scaffold has potential drawbacks in terms of substrate scope, sensitivity because of aggregation-caused quenching (ACQ), and the inability for long-term cell tracking. Here, we developed glycoclusters characterized by aggregation-induced emission (AIE) properties as a general platform for the sensing of a variety of glycosidases. To overcome the low chemical reactivity during phenol glycosylation, we synthesized an AIE-based dye composed of tetraphenylethylene conjugated with dicyanomethylene-4H-pyran (TPE-DCM) with a red fluorescence emission. Subsequently, a pair of dendritic linkages was introduced to both sides of the fluorophore, to which six copies of different monosaccharides (D-glucose, D-galactose and L-fucose) were conjugated through azide-alkyne click chemistry. The resulting AIE-active glycoclusters were shown to be capable of (1) fluorogenic sensing of a diverse range of glycosidases including β-D-galactosidase, β-D-glucosidase and α-L-fucosidase through the AIE mechanism, (2) fluorescence imaging of the endogenous glycosidase activities in healthy and cancer cells, and during cell senescence, and (3) glycosidase-activated, long-term imaging of cells. The present study provides a general strategy to the functional imaging of glycosidase activities through the multivalent display of sugar epitopes of interest onto AIE-active dyes.

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“…S1 †). 39 of 7 with BBr 3 in CH 2 Cl 2 afforded the bis-phenolic 8 (Scheme S1 †). Subsequently, glycosylation under phase transfer conditions with bromo tetra-O-acetyl-D-galactose afforded the desired bis-glycosylated derivative 9.…”

Section: Synthesis and Structure-activity Relationship Of Tpe-dcmbased Glycoclustersmentioning

confidence: 99%

A General Strategy to the Intracellular Sensing of Glycosidases using AIE-Based Glycoclusters

Liu

¹

,

Zhang

²

,

Han

³

et al. 2021

Preprint

Self Cite

0

View full text Add to dashboard Cite

Glycosidases, which are the enzymes responsible for removal of residual monosaccharides from glycoconjugates, are implicated in a myriad of biological and pathological events. The ability to detect sensitively the activity and spatiotemporal distribution of glycosidases in cells may facilitate the study of glycobiology, and add useful diagnostic tools. However, the currently developed fluorogenic probes for glycosidases are generally based on glycosylation of a phenol group of a donor-acceptor type fluorogen. This general molecular scaffold has potential drawbacks in terms of substrate scope, sensitivity because of aggregation-caused quenching (ACQ), and the inability for long-term cell tracking. Here, we developed glycoclusters characterized by aggregation-induced emission (AIE) properties as a general platform for the sensing of a variety of glycosidases. To overcome the low chemical reactivity during phenol glycosylation, we synthesized an AIE-based dye composed of tetraphenylethylene conjugated with dicyanomethylene-4H-pyran (TPE-DCM) with a red fluorescence emission. Subsequently, a pair of dendritic linkages was introduced to both sides of the fluorophore, to which six copies of different monosaccharides (D-glucose, D-galactose and L-fucose) were conjugated through azide-alkyne click chemistry. The resulting AIE-active glycoclusters were shown to be capable of (1) fluorogenic sensing of a diverse range of glycosidases including β-D-galactosidase, β-D-glucosidase and α-L-fucosidase through the AIE mechanism, (2) fluorescence imaging of the endogenous glycosidase activities in healthy and cancer cells, and during cell senescence, and (3) glycosidase-activated, long-term imaging of cells. The present study provides a general strategy to the functional imaging of glycosidase activities through the multivalent display of sugar epitopes of interest onto AIE-active dyes.

show abstract

Modulation of Aggregation-Induced Emission by Excitation Energy Transfer: Design and Application

Cited by 9 publications

References 133 publications

A general strategy to the intracellular sensing of glycosidases using AIE-based glycoclusters

A general strategy to the intracellular sensing of glycosidases using AIE-based glycoclusters

A General Strategy to the Intracellular Sensing of Glycosidases using AIE-Based Glycoclusters

A General Strategy to the Intracellular Sensing of Glycosidases using AIE-Based Glycoclusters

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