Mitochondria-targeting self-assembled nanoparticles derived from triphenylphosphonium-conjugated cyanostilbene enable site-specific imaging and anticancer drug delivery

Kim, Ka Young; Jin, Hanyong; Park, Jae Won; Jung, Sung Ho; Lee, Ji Ha; Park, Hyesong; Kim, Sung Kuk; Bae, Jang–Ho; Jung, Jong Hwa

doi:10.1007/s12274-017-1728-7

Cited by 46 publications

(23 citation statements)

References 79 publications

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“…Since TPP-appended dicyanostilbene derivatives often demonstrate amphiphilic properties [26]. we observed the self-assembling behaviors in aqueous solution.…”

Section: Resultsmentioning

confidence: 95%

Self-Assembled Triphenylphosphonium-Conjugated Dicyanostilbene Nanoparticles and Their Fluorescence Probes for Reactive Oxygen Species

et al. 2018

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We report self-assembled novel triphenylphosphonium-conjugated dicyanostilbene-based as selective fluorescence turn-on probes for 1O2 and ClO−. Mono- or di-triphenylphosphonium-conjugated dicyanostilbene derivatives 1 and 2 formed spherical structures with diameters of ca. 27 and 56.5 nm, respectively, through π-π interaction between dicyanostilbene groups. Self-assembled 1 showed strong fluorescent emission upon the addition of 1O2 and ClO− compared to other ROS (O2−, •OH, NO, TBHP, H2O2, GSH), metal ions (K+, Na+), and amino acids (cysteine and histidine). Upon addition of 1O2 and ClO−, the spherical structure of 1 changed to a fiber structure (8-nm wide; 300-nm long). Upon addition of 1O2 and ClO−, the chemical structural conversion of 1 was determined by FAB-Mass, NMR, IR and Zeta potential analysis, and the strong emission of the self-assembled 1 was due to an aggregation-induced emission enhancement. This self-assembled material was the first for selective ROS as a fluorescence turn-on probe. Thus, a nanostructure change-derived turn-on sensing strategy for 1O2 or ClO− may offer a new approach to developing methods for specific guest molecules in biological and environmental subjects.

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“…Since TPP-appended dicyanostilbene derivatives often demonstrate amphiphilic properties [26]. we observed the self-assembling behaviors in aqueous solution.…”

Section: Resultsmentioning

confidence: 95%

Self-Assembled Triphenylphosphonium-Conjugated Dicyanostilbene Nanoparticles and Their Fluorescence Probes for Reactive Oxygen Species

et al. 2018

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Section: Fluorescent Nanomaterials For Mitochondriamentioning

confidence: 99%

“…A theragnostic approach for tumor targeting, imaging, and drug delivery with mitochondria-targeting nanoparticles was reported [ 62 ]. In this study, the author employed the AIE approach to display playing multiple roles in selective drug delivery, anticancer activity, and mitochondria targeting, showing potential ability for theragnostic tools in cancer therapy [ 62 ]. A self-assembled nanoparticle with cyanostilbene and a long alkyl chain was designed for targeting mitochondria by incorporation of a TPP moiety and revealed the accumulation in mitochondria by AIE phenomena [ 62 ].…”

Section: Fluorescent Nanomaterials For Mitochondriamentioning

confidence: 99%

“…In this study, the author employed the AIE approach to display playing multiple roles in selective drug delivery, anticancer activity, and mitochondria targeting, showing potential ability for theragnostic tools in cancer therapy [ 62 ]. A self-assembled nanoparticle with cyanostilbene and a long alkyl chain was designed for targeting mitochondria by incorporation of a TPP moiety and revealed the accumulation in mitochondria by AIE phenomena [ 62 ]. Moreover, encapsulation of doxorubicin was successfully delivered to mitochondria and induced anti-cancer activity in both cell-based and in vivo systems [ 62 ].…”

Section: Fluorescent Nanomaterials For Mitochondriamentioning

confidence: 99%

“…A self-assembled nanoparticle with cyanostilbene and a long alkyl chain was designed for targeting mitochondria by incorporation of a TPP moiety and revealed the accumulation in mitochondria by AIE phenomena [ 62 ]. Moreover, encapsulation of doxorubicin was successfully delivered to mitochondria and induced anti-cancer activity in both cell-based and in vivo systems [ 62 ]. Furthermore, photothermal properties of hydrophilic nanoparticles are expected to be a theragnostic approach based on photothermal therapy and photothermal/photoacoustic imaging [ 64 ].…”

Section: Fluorescent Nanomaterials For Mitochondriamentioning

confidence: 99%

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Fluorescent Materials for Monitoring Mitochondrial Biology

et al. 2021

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Mitochondria play important roles in diverse cellular processes such as energy production, cellular metabolism, and apoptosis to promote cell death. To investigate mitochondria-associated biological processes such as structure, dynamics, morphological change, metabolism, and mitophagy, there exists a continuous demand for visualizing and monitoring techniques elucidating mitochondrial biology and disease-relevancy. Due to the advantages of high sensitivity and practicality, fluorescence phenomena have been most widely used as scientific techniques for the visualization of biological phenomena and systems. In this review, we briefly overview the different types of fluorescent materials such as chemical probes, peptide- or protein-based probes, and nanomaterials for monitoring mitochondrial biology.

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Molecular Design of a Diketopyrrolopyrrole Conjugated Oligoelectrolyte Capable of Imaging Intracellular Vesicle Membrane Dynamics

Chan,

Zhu,

Yip

et al. 2024

Advanced Materials

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Conjugated oligoelectrolytes (COEs) are lipid bilayer spanning optical reporters that hold promise for delineating spatiotemporal changes in subcellular compartments. However, their ability to probe a broader range of biological processes remains restricted due to the lack of environmentally‐responsive chemical functionalities. Herein, the study reports a novel COE, namely COE‐KP, for monitoring spatiotemporal changes in the endolysosomal vesicles. COE‐KP features a central diketopyrrolopyrrole functional group in the optically active conjugated core that confers photophysical properties suitable for bioimaging, in particular responding to the presence of hydrogen bonding functionalities within the hydrophobic domain of the lipid bilayer. COE‐KP can thus discriminate cells in different growth states through two‐photon fluorescence lifetime imaging microscopy (FLIM) with excitation in the NIR‐II range. These changes in lifetime most reasonably reflect the degree of water permeability through the membrane and are not linked to notable differences in membrane tension or solvent polarity. Furthermore, using stimulated emission depletion (STED) nanoscopy, it is possible to directly visualize membrane‐bound COEs within cellular vesicles. These results illustrate further opportunities for applying COE‐based reporters for super‐resolution microscopy of organelle membranes, visualization of subcellular membrane morphologies, and imaging long‐term changes in membrane properties.

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Mitochondria-targeting self-assembled nanoparticles derived from triphenylphosphonium-conjugated cyanostilbene enable site-specific imaging and anticancer drug delivery

Cited by 46 publications

References 79 publications

Self-Assembled Triphenylphosphonium-Conjugated Dicyanostilbene Nanoparticles and Their Fluorescence Probes for Reactive Oxygen Species

Self-Assembled Triphenylphosphonium-Conjugated Dicyanostilbene Nanoparticles and Their Fluorescence Probes for Reactive Oxygen Species

Fluorescent Materials for Monitoring Mitochondrial Biology

Molecular Design of a Diketopyrrolopyrrole Conjugated Oligoelectrolyte Capable of Imaging Intracellular Vesicle Membrane Dynamics

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