Synthesis of fluorescent polycarbonates with highly twisted <i>N</i>,<i>N</i>-bis(dialkylamino)anthracene AIE luminogens in the main chain

Sairi, Amir Sharidan; Kuwahara, Kohei; Sasaki, Shunsuke; Suzuki, Satoshi; Igawa, Kazunobu; Tokita, Masatoshi; Ando, Shinji; Morokuma, Keiji; Suenobu, Tomoyoshi; Konishi, Gen Ichi

doi:10.1039/c9ra03701b

Cited by 12 publications

(7 citation statements)

References 123 publications

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“…Fluorescent probes, on the other hand, are more stable and sensitive, allowing for more accurate and rapid monitoring, and are easy to use. Small-molecule fluorescent probes, in particular, are simple in structure, easy to design/modify, and good in biocompatibility and have attracted increasing attention for monitoring the mitophagy process. − These probes offer a more effective way for monitoring changes that occur during mitophagy compared with other probes.…”

Section: Introductionmentioning

confidence: 99%

Advances in Small-Molecule Fluorescent pH Probes for Monitoring Mitophagy

Liu

Zhang

et al. 2023

Chemical & Biomedical Imaging

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Mitochondria play a crucial role in regulating cellular energy homeostasis and cell death, making them essential organelles. Maintaining proper cellular functions relies on the removal of damaged mitochondria through a process called mitophagy. Mitophagy is associated with changes in the pH value and has implications for numerous diseases. To effectively monitor mitophagy, fluorescent probes that exhibit high selectivity and sensitivity based on pH detection have emerged as powerful tools. In this review, we present recent advancements in the monitoring of mitophagy using small-molecule fluorescence pH probes. We focus on various sensing mechanisms employed by these probes, including intramolecular charge transfer (ICT), fluorescence resonance energy transfer (FRET), through bond energy transfer (TBET), and photoelectron transfer (PET). Additionally, we discuss disease models used for studying mitophagy and summarize the design requirements for small-molecule fluorescent pH probes suitable for monitoring the mitophagy process. Lastly, we highlight the remaining challenges in this field and propose potential directions for the future development of mitophagy probes.

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Section: Introductionmentioning

confidence: 99%

Advances in Small-Molecule Fluorescent pH Probes for Monitoring Mitophagy

Liu

Zhang

et al. 2023

Chemical & Biomedical Imaging

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“…To demonstrate the application of this strategy for developing viscosity-responsive fluorescent probes that can work in cellular systems, we chose 9,10-bis(N,N-dialkylamino)anthracene, reported by Konishi and co-workers. 41,[43][44][45][46] They showed by theoretical study that this molecule adopts a Dewar-benzene-like non-flat structure at the MECI due to a large structural change from the planar geometry at the Frank-Condon state, together with experimentally confirmed viscosity-responsiveness of this molecule. 41 Herein we selected acidic organelles as targets for visualizing the intracellular viscous environment, since the most viscous organelle in the cell is lysosome, 19,34 which is also known as the most acidic.…”

Section: Introductionmentioning

confidence: 99%

Dense and Acidic Organelle-Targeted Visualization in Living Cells: Application of Viscosity-Responsive Fluorescence Utilizing Restricted Access to Minimum Energy Conical Intersection

Adachi

Oda

Fukushima

et al. 2023

Preprint

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Cell-imaging methods with functional fluorescent probes are an indispensable technique to evaluate physical parameters in cellular mi-croenvironments. In particular, molecular rotors, which take advantage of the twisted intramolecular charge transfer (TICT) process, have helped evaluate microviscosity. However, the involvement of charge-separated species in the fluorescence process potentially limits the quantitative evaluation of viscosity. Herein we developed viscosity-responsive fluorescent probes for cell imaging that are not depend-ent on the TICT process. We synthesized AnP2-H and AnP2-OEG, both of which contain 9,10-di(piperazinyl)anthracene, based on 9,10-bis(N,N-dialkylamino)anthracene that adopt a non-flat geometry at minimum energy conical intersection. AnP2-H and AnP2-OEG exhibited enhanced fluorescence as the viscosity increased, with sensitivities comparable to those of conventional molecular rotors. In living cell systems, AnP2-OEG showed low cytotoxicity and, reflecting its viscosity-responsive property, allowed specific visualization of dense and acidic organelles such as lysosomes, secretory granules and melanosomes under washout-free conditions. These results provide a new direction for developing functional fluorescent probes targeting dense organelles.

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“…17,18 and chemical probes in biosensing and bioimaging. [19][20][21] Tetraphenylethylenes, 22 siloles, 23 anthracene derivatives, 24,25 organoboron complexes, 26,27 and other organic phosphors have all been reported to exhibit AIE behavior. The crystals of 1,1,2,3,4,5-hexaphenyl-1H-silole (HPS) have been fabricated and the differences in their AIE behavior in solutions, films, and crystals investigated.…”

Section: Introductionmentioning

confidence: 99%

Novel class of organic crystal scintillators based on aggregation-induced emission

Satô

Koshimizu

Fujimoto

et al. 2022

Mater. Chem. Front.

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Synthesis of fluorescent polycarbonates with highly twisted N,N-bis(dialkylamino)anthracene AIE luminogens in the main chain

Abstract: Fluorescent polycarbonates were synthesized by embedding AIE-active diol monomers with simple structures in the polymer chain.

Cited by 12 publications

References 123 publications

Advances in Small-Molecule Fluorescent pH Probes for Monitoring Mitophagy

Advances in Small-Molecule Fluorescent pH Probes for Monitoring Mitophagy

Dense and Acidic Organelle-Targeted Visualization in Living Cells: Application of Viscosity-Responsive Fluorescence Utilizing Restricted Access to Minimum Energy Conical Intersection

Novel class of organic crystal scintillators based on aggregation-induced emission

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