Emissive nanoparticles from pyridinium-substituted tetraphenylethylene salts: imaging and selective cytotoxicity towards cancer cells in vitro and in vivo by varying counter anions

Huang, Yanyan; Zhang, Guanxin; Hu, Fang; Jin, Yulong; Zhao, Rui; Zhang, Deqing

doi:10.1039/c6sc02395a

Cited by 68 publications

(44 citation statements)

References 53 publications

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“…By contrast, the similar phenomenon was not observed for TPE‐IQ‐CN and TPE‐IQ‐TPA. These results hint that the cytotoxicity of TPE‐IQ‐O toward Hela cells is caused by damaged membrane of mitochondria …”

Section: Resultsmentioning

confidence: 79%

Structural Modification Orientated Multifunctional AIE Fluorescence Probes: Organelles Imaging and Effective Photosensitizer for Photodynamic Therapy

Chen

Zhang

Wang

et al. 2019

Advanced Optical Materials

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Luminogens with aggregation‐induced emission feature (AIEgens) are highly demanded because of its excellent performance in fluorescent bioprobes. In this work, three AIEgens based on tetraphenylethylene isoquinolinium (TPE‐IQ) derivatives by introducing different electron donor and sterically hindered groups to replace the phenyl ring of the isoquinolinium core are prepared in a one‐pot reaction with a high yield and characterized systematically. By the analysis of photophysical properties and theoretical calculations, the structure‐property relationships among them become clear. Although they all inherit AIE feature as expected, these similar structural AIEgens present different organelle‐targets, which is attributed to their different cellular uptake way and energy barrier to cell membrane by detailed experiments. In addition, these TPE‐IQ‐based AIEgens are potential candidates for photodynamic therapy originating from their activities of generating reactive oxygen species under visible light irradiation.

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Section: Resultsmentioning

confidence: 79%

Structural Modification Orientated Multifunctional AIE Fluorescence Probes: Organelles Imaging and Effective Photosensitizer for Photodynamic Therapy

Chen

Zhang

Wang

et al. 2019

Advanced Optical Materials

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“…Moreover, amphipathic substances comprising a specific amino acid sequence, named the mitochondria-targeting peptide, have also been used. [42][43][44][45][46] In particular, triphenylphosphonium-based nanocarriers are characterized by a mechanism of transport to the mitochondria via the endosome. [9] Furthermore, the drug release control, categorized as a core function of the nanocarrier, is mainly driven by changes in the state or structure of the reactant in response to internal or external stimuli.…”

Section: Coassembled Nanoparticles Composed Of Functionalized Mesopormentioning

confidence: 99%

Coassembled Nanoparticles Composed of Functionalized Mesoporous Silica and Pillar[5]arene‐Appended Gold Nanoparticles as Mitochondrial‐Selective Dual‐Drug Carriers

Ahn

Jin

Park

et al. 2020

Part & Part Syst Charact

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Coassembled nanoparticles composed of functionalized mesoporous silica and pillar[5]arene‐appended Au nanoparticles obtained through the formation of a host–guest complex are designed and synthesized as a mitochondrial‐selective dual‐drug delivery system. A pyridinium‐based ligand and fluorescein isothiocyanate are immobilized onto mesoporous silica to act as the mitochondria‐targeting ligand and fluorescence tracker, respectively, of a material dubbed NP‐3. Carboxylated pillar[5]arene‐capped Au nanoparticles (CP‐AuNPs) are fabricated by the templated reduction of Au3+. Interestingly, coassembled nanoparticles (NP‐1) composed of doxorubicin (DOX) loaded NP‐3 and CP‐AuNPs are then prepared via the formation of a host–guest complex between the pyridinium‐based ligand of NP‐3 and the pillar[5]arene of CP‐AuNPs. To demonstrate the effectiveness of NP‐2 and NP‐1 as mitochondrial targeting drug delivery systems, DOX and F16 are employed as model drugs. These drugs loaded onto NP‐2 and CP‐AuNPs, respectively, are selectively delivered to mitochondria, indicating the usefulness of NP‐2 and CP‐AuNPs as mitochondrial‐specific drug‐delivery carriers in cancer cells. More interestingly, the use of NP‐1 is also associated with the selective accumulation of DOX and F16 in mitochondria. The selective mitochondrial‐targeting of NP‐1 is possible by NP‐2 and F16 exposed to the cytoplasm, allowing the codelivery of the two drugs to the mitochondria.

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“…[77] Upon changing the counter anions from toluenesulfonate (TPE-Py-2O-1) to tetraphenyl borate (TPE-Py-2O-2) or tetra(4-chlorophenyl) borate (TPE-Py-2O-3) (Figure 7A), the resultant TPE-Py-2O-X mitoprobes showed red-shifted emission maximum from 560 to 605 and 620 nm, while the mitochondrial targeting ability remain inherited. [77] Upon changing the counter anions from toluenesulfonate (TPE-Py-2O-1) to tetraphenyl borate (TPE-Py-2O-2) or tetra(4-chlorophenyl) borate (TPE-Py-2O-3) (Figure 7A), the resultant TPE-Py-2O-X mitoprobes showed red-shifted emission maximum from 560 to 605 and 620 nm, while the mitochondrial targeting ability remain inherited.…”

Section: Chemotherapy With Aie Mitoprobesmentioning

confidence: 99%

Organic Mitoprobes based on Fluorogens with Aggregation‐Induced Emission

Cai

Feng

et al. 2018

Israel Journal of Chemistry

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Fluorescence imaging of mitochondria is of great interest to understand its functions and roles in various critical bioprocesses. Conventional fluorescence reagents for mitochondrial imaging and tracking suffer from various problems such as poor photostability and high cytotoxicity. The emerging of fluorogens with aggregation‐induced emission (AIE) property provides great opportunities to develop mitoprobes with high specificity, good photostability and multiple functions for mitochondrial imaging and tracking. This review summarizes the recent advance of AIE mitoprobes, including the design principle for AIE mitoprobes, the applications of AIE mitoprobes for super‐resolution mitochondrial imaging and tracking, as well as the therapeutic functions of AIE mitoprobes for cancer cell ablation.

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Emissive nanoparticles from pyridinium-substituted tetraphenylethylene salts: imaging and selective cytotoxicity towards cancer cells in vitro and in vivo by varying counter anions

Abstract: The cell selectivity, subcellular localization and cytotoxicity can be tuned by the counter anions of nanoparticles assembled from pyridinium-substituted tetraphenylethylene.

Cited by 68 publications

References 53 publications

Structural Modification Orientated Multifunctional AIE Fluorescence Probes: Organelles Imaging and Effective Photosensitizer for Photodynamic Therapy

Structural Modification Orientated Multifunctional AIE Fluorescence Probes: Organelles Imaging and Effective Photosensitizer for Photodynamic Therapy

Coassembled Nanoparticles Composed of Functionalized Mesoporous Silica and Pillar[5]arene‐Appended Gold Nanoparticles as Mitochondrial‐Selective Dual‐Drug Carriers

Organic Mitoprobes based on Fluorogens with Aggregation‐Induced Emission

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