Efficient delivery of chlorin e6 into ovarian cancer cells with octalysine conjugated superparamagnetic iron oxide nanoparticles for effective photodynamic therapy

Zhao, Li; Yang, Hai; Amano, Tsukuru; Qin, Hongmei; Zheng, Luyi; Takahashi, Akimasa; Tooyama, Ikuo; Murakami, Takashi; Komatsu, Naoki

doi:10.1039/c6tb01988a

Cited by 41 publications

(32 citation statements)

References 36 publications

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“…Superparamagnetic iron oxide nanoparticle (SPION) derivatives were used for their capacity to interfere with electron transport chain (ETC) of mitochondria in cancer cells. 153–155 …”

Section: Approaches To Target Compounds To Mitochondriamentioning

confidence: 99%

Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications

Zielonka¹,

Joseph²,

et al. 2017

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Mitochondria are recognized as one of the most important targets for new drug design in cancer, cardiovascular, and neurological diseases. Currently, the most effective way to deliver drugs specifically to mitochondria is by covalent linking a lipophilic cation such as an alkyltriphenylphosphonium moiety to a pharmacophore of interest. Other delocalized lipophilic cations, such as rhodamine, natural and synthetic mitochondria-targeting peptides, and nanoparticle vehicles, have also been used for mitochondrial delivery of small molecules. Depending on the approach used, and the potentials of cell and mitochondrial membranes, more than 1000-fold higher mitochondrial concentration can be achieved. Mitochondrial targeting has been developed to study mitochondrial physiology and dysfunction and the interaction between mitochondria and other subcellular organelles and for treatment of a variety of diseases such as neurodegeneration and cancer. In this review, we discuss efforts to target small-molecule compounds to mitochondria for probing mitochondria function, as diagnostic tools and potential therapeutics. We describe the physicochemical basis for mitochondrial accumulation of lipophilic cations, synthetic chemistry strategies to target compounds to mitochondria, mitochondrial probes and sensors, and examples of mitochondrial targeting of bioactive compounds. Finally, we review published attempts to apply mitochondria-targeted agents for the treatment of cancer and neurodegenerative diseases.

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“…Superparamagnetic iron oxide nanoparticle (SPION) derivatives were used for their capacity to interfere with electron transport chain (ETC) of mitochondria in cancer cells. 153–155 …”

Section: Approaches To Target Compounds To Mitochondriamentioning

confidence: 99%

Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications

Zielonka¹,

Joseph²,

et al. 2017

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“…Nowadays, the study of iron oxide nanoparticles (IONPs) is of great interest because of their potential biomedical applications including magnetic drug delivery, tumor-specific cell targeting, biosensor, magnetic resonance imaging, hyperthermia and bioseparation [1][2][3][4][5][6][7][8]. One of the most exciting properties of IONPs is magnetism, which allows them to be guided and stimulated to a desired site of the biological system by using an external magnet.…”

Section: Introductionmentioning

confidence: 99%

A facile one-pot synthesis of poly(acrylic acid)-functionalized magnetic iron oxide nanoparticles for suppressing reactive oxygen species generation and adsorption of biocatalyst

Nahar

Rahman

Hossain

et al. 2019

Mater. Res. Express

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Functionalized iron oxide nanoparticles (IONPs) have unique physical and chemical properties, which make them potential candidates for biomedical applications. In this study, a facile one-pot method is reported for the preparation of poly(acrylic acid) (PAA) functionalized IONPsthrough in situ free radical solution polymerization of AA and subsequent coprecipitation of Fe 3+ and Fe 2+ ions. The FTIR spectroscopic and TGA results indicated the successful formation and surface functionalization of IONPs with PAA. Electron micrographs showed that the prepared particles were of nano-sized and their shape is dependent on the concentration of PAA. pH-dependent variation of average hydrodynamic diameter confirmed the pH-responsivity of PAA-functionalized IONPs. Magnetic measurement suggested that the PAA functionalized IONPs were strongly paramagnetic (53.0 emug −1 ). Fenton-like catalytic generation is carried out to measure toxicity associated with the nanoparticles. The suppression ability for reactive oxygen species (ROS) generation associated with PAA-functionalized IONPs was studied via methylene blue degradation assay to address their toxicity profile. PAA-functionalized IONPs exhibited better suppression ability than that of the bare IONPs. The adsorption behavior of trypsin was also studied at different pH levels and a maximum adsorption is occurred on PAA-functionalized IONPs at pH 5.0. Catalytic behavior study confirmed higher activity of trypsin immobilized on PAA-functionalized IONPs than that of the reference IONPs. Therefore, the functionalized IONPs can be of high interest for magnetically recyclable biocatalyst carrier.

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“…Cellular uptake of other Ce6 nanoparticles have been previously described as exemplified by Ce6-octalysine conjugated to superparamagnetic iron oxide nanoparticles being taken up by SKOV3 cells relative to free Ce6. 19 The cellular uptake of Ce6-GVs at 37°C into MCF-7 and FaDu-GFP cells was further confirmed by confocal microscopy (Fig. 5).…”

Section: Ce6-gvs Are Taken Up By Cancer Cells and Accumulate In Endosmentioning

confidence: 66%

“…4,5). This enhancement in light-activated toxicity relative to the free form of the drug has been observed in SKOV3 and MDA-MB-231 cells for other Ce6-nanoparticles such as Ce6-SPION 19 or Ce6-conjugated poly(ethylene glycol)-poly-(d,l-lactide) 21 nanoparticles, likely owing to their improved cellular uptake. In contrast, the photosensitizing efficacy and toxicity of a Ce6 conjugated human serum albumin nanoparticle was comparable to that of free Ce6 22 suggesting that all Ce6-nanoparticle formulations are not equivalent in terms of enhanced cytotoxicity.…”

Section: Gas Vesicles Dramatically Enhance the Phototoxicity Of Ce6 Tmentioning

confidence: 69%

Light-Activated Nanoscale Gas Vesicles Selectively Kill Tumor Cells

Fernando

Gariépy

2019

Preprint

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Protein-based nanobubbles such as halophilic archaeabacterial gas vesicles (GVs) represent a new class of stable, homogeneous nanoparticles with acoustic properties that allow them to be visualized by ultrasound (US) waves. To design GVs as theranostic agents, we modified them to respond to light, with a view to locally generate reactive oxygen species that can kill cancer cells. Specifically, up to 60,000 photoreactive chlorin e6 (Ce6) molecules were chemically attached to lysine ε-amino groups present on the surface of each purified Halobacterium sp. NRC-1 GV. The resulting fluorescent NRC-1 Ce6-GVs have dimensions comparable to that of native GVs and were efficiently taken up by human breast and human hypopharyngeal [FaDu-GFP] cancer cells as monitored by confocal microscopy and flow cytometry. When exposed to light, internalized Ce6-GVs were 200-fold more effective on a molar basis than free Ce6 at killing cells. These results demonstrate the potential of Ce6-GVs as novel and promising nanomaterials for image-guided photodynamic therapy.

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Efficient delivery of chlorin e6 into ovarian cancer cells with octalysine conjugated superparamagnetic iron oxide nanoparticles for effective photodynamic therapy

Abstract: Chlorin e6, loaded on the surface of SPION-PG-Lys8 through electrostatic attraction, was delivered preferentially into mitochondria of SKOV3 ovarian cancer cells, improving efficacy of photodynamic therapy significantly.

Cited by 41 publications

References 36 publications

Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications

Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications

A facile one-pot synthesis of poly(acrylic acid)-functionalized magnetic iron oxide nanoparticles for suppressing reactive oxygen species generation and adsorption of biocatalyst

Light-Activated Nanoscale Gas Vesicles Selectively Kill Tumor Cells

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