Ubiquinone-BODIPY nanoparticles for tumor redox-responsive fluorescence imaging and photodynamic activity

Hwang, Byung‐Hee; Kim, Tae Il; Kim, Hyun‐Jin; Jeon, Sungjin; Choi, Yongdoo; Kim, Youngmi

doi:10.1039/d0tb02529a

Cited by 12 publications

(6 citation statements)

References 79 publications

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“…To this end, Kim et al reported a GSH-activatable PDT agent (86), where a GSHsensitive moiety (a ubiquinone analogue) was covalently linked to a near-infrared PS (a meso-ester-2,6-iodinated-BODIPY) via an ester linkage (Figure 37). 325 Compound 86 is strongly hydrophobic and easily aggregates to form nanoparticles in aqueous solutions. Not only does this result in quenched photosensitivity and minimal systemic toxicity, but this also favors tumor enrichment through the EPR effect.…”

Section: Gsh Mediated Reductionmentioning

confidence: 99%

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Theranostic Fluorescent Probes

Sharma,

Verwilst,

et al. 2024

Chem. Rev.

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The ability to gain spatiotemporal information, and in some cases achieve spatiotemporal control, in the context of drug delivery makes theranostic fluorescent probes an attractive and intensely investigated research topic. This interest is reflected in the steep rise in publications on the topic that have appeared over the past decade. Theranostic fluorescent probes, in their various incarnations, generally comprise a fluorophore linked to a masked drug, in which the drug is released as the result of certain stimuli, with both intrinsic and extrinsic stimuli being reported. This release is then signaled by the emergence of a fluorescent signal. Importantly, the use of appropriate fluorophores has enabled not only this emerging fluorescence as a spatiotemporal marker for drug delivery but also has provided modalities useful in photodynamic, photothermal, and sonodynamic therapeutic applications. In this review we highlight recent work on theranostic fluorescent probes with a particular focus on probes that are activated in tumor microenvironments. We also summarize efforts to develop probes for other applications, such as neurodegenerative diseases and antibacterials. This review celebrates the diversity of designs reported to date, from discrete small-molecule systems to nanomaterials. Our aim is to provide insights into the potential clinical impact of this stillemerging research direction.

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Section: Gsh Mediated Reductionmentioning

confidence: 99%

Section: Theranostic Fluorescence Probes In Cancer Therapymentioning

confidence: 99%

Theranostic Fluorescent Probes

Sharma,

Verwilst,

et al. 2024

Chem. Rev.

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“…The reduction of ubiquinone to the hydrophilic carboxylate resulted in increased fluorescence and the generation of therapeutic singlet oxygen ( 1 O 2 ) (Table 2). 159 Recently, Chakravarty and co-workers reported the iron( iii ) catecholate of BODIPY 164 containing the dipicolylamine ligand, which shows a ligand-to-metal charge transfer (L→M CT) band at ∼800 nm (Fig. 19).…”

Section: Applications Of Bodipy Chromophoresmentioning

confidence: 99%

Design, synthesis and functionalization of BODIPY dyes: applications in dye-sensitized solar cells (DSSCs) and photodynamic therapy (PDT)

Misra

Yadav

2023

J. Mater. Chem. C

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“…It is well-known that detection methods are expanding rapidly worldwide, but the use of fluorescent techniques for the detection of analytes is always ahead of other techniques and has become a hot subject in chemical research due to its high sensitivity, selectivity, affordability, and ease of use. − Schiff-base ligands with potential fluorophores and extended conjugation are mainly used to detect Ga 3+ because of their far absorption and emission properties and the formation of the geometric cavity for chelation. − One more important factor is the selectivity, which is lacking in many chemosensors due to their multiple detection ability for many group 13 metal ions. − In group 13, the size of the Al is more than Ga due to the well-known d-contraction in Ga (poor shielding effect of the 3d-electrons). Therefore, having hard donor sites with comparatively smaller cavity sizes prefers Ga 3+ more prominently over Al 3+ .…”

Section: Introductionmentioning

confidence: 99%

Robust Optical Detection of Ga³⁺ by a Rhodamine- and Coumarin-Based Proficient Probe: Theoretical Investigations and Biological Applications

Panda,

Sahu,

Goswami

et al. 2023

ACS Appl. Bio Mater.

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The present investigation highlights a rhodamine-Band coumarin-based efficient probe that selectively detects Ga 3+ over other metal ions. The active pocket of the ligand for trapping the metal ions and the binding stoichiometry of its Ga 3+ complex were discovered by single-crystal X-ray diffraction (SC-XRD) analysis. This binding stoichiometry was further confirmed in the solution state by mass spectrometry and Job's plot. The detection limit was found to be at the nanomolar level. Pyrophosphate being a well-known quencher could easily quench the fluorescence intensity of the RC in the presence of Ga 3+ and reversibly recognize Ga 3+ in the solution. The spiro ring opening of the ligand after Ga 3+ insertion is proposed to be the principal mechanism for the turn-on fluorescence response. This ring opening was confirmed by SC-XRD data and nuclear magnetic resonance (NMR) titration experiments. Both ground-and excited-state calculations of the ligand and complex have been carried out to obtain information about their energy levels and to obtain the theoretical electronic spectra. Furthermore, the live-cell imaging of the probe only and the probe after the addition of Ga 3+ have been carried out in HaCaT cells and satisfactory responses were observed. Interestingly, with the help of this probe, Ga 3+ can be tracked inside the intracellular organelle such as lysosomes along with other regions of the cell. The article highlights a rhodamine−coumarin-based probe for the detection of Ga 3+ over other metal ions with a nanomolar level detection limit. Structural characterization of the ligand and its Ga 3+ complex was investigated by SC-XRD. Density functional theory (DFT) and time-dependent DFT (TD-DFT) studies were carried out to explore the excited-state energies and electronic spectra. The application of the probe for the detection of Ga 3+ in live cells has been explored, and positive responses were observed.

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Ubiquinone-BODIPY nanoparticles for tumor redox-responsive fluorescence imaging and photodynamic activity

Abstract: A ubiquinone-BODIPY photosensitizer self-assembles into nanoparticles (PS-Q-NPs) and undergoes selective activation within the highly reductive intracellular environment of tumors, resulting in “turn-on” fluorescence and photosensitizing activities.

Cited by 12 publications

References 79 publications

Theranostic Fluorescent Probes

Theranostic Fluorescent Probes

Design, synthesis and functionalization of BODIPY dyes: applications in dye-sensitized solar cells (DSSCs) and photodynamic therapy (PDT)

Robust Optical Detection of Ga³⁺ by a Rhodamine- and Coumarin-Based Proficient Probe: Theoretical Investigations and Biological Applications

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Ubiquinone-BODIPY nanoparticles for tumor redox-responsive fluorescence imaging and photodynamic activity

Abstract: A ubiquinone-BODIPY photosensitizer self-assembles into nanoparticles (PS-Q-NPs) and undergoes selective activation within the highly reductive intracellular environment of tumors, resulting in “turn-on” fluorescence and photosensitizing activities.

Cited by 12 publications

References 79 publications

Theranostic Fluorescent Probes

Theranostic Fluorescent Probes

Design, synthesis and functionalization of BODIPY dyes: applications in dye-sensitized solar cells (DSSCs) and photodynamic therapy (PDT)

Robust Optical Detection of Ga3+ by a Rhodamine- and Coumarin-Based Proficient Probe: Theoretical Investigations and Biological Applications

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Robust Optical Detection of Ga³⁺ by a Rhodamine- and Coumarin-Based Proficient Probe: Theoretical Investigations and Biological Applications