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    Synthesis and properties of AIE-active Triazaborolopyridiniums toward fluorescent nanoparticles for cellular imaging and their biodistribution in vivo and ex vivo
    (2022-12-01)
    Hiranmartsuwan, P.
    ;
    Ma, X.
    ;
    Nootem, J.
    ;
    Daengngern, R.
    ;
    Kamkaew, A.
    Three new aggregation-induced emission (AIE) molecules have been prepared by incorporation of the tetraphenylethylene (TPE) unit to the triazaborolopyridinium (TBP). The compounds exhibit broad absorption from 470 to 510 nm and emission from 530 to 600 nm in various solvents. The TPE-linked TBP, TT-1, and the compound with a phenylene bridge, TT-2, demonstrated high fluorescence quantum yields and solvent-sensitive behaviors due to twisted intramolecular charge transfer (TICT). In contrast, the derivative with a thiophene bridge, TT-3, showed less solvent dependence and low fluorescence quantum yield. The presence of a thiophene moiety led to redshift in the absorption and emission spectra due to a lower energy gap, confirmed by cyclic voltammetry (CV) and density functional theory (DFT) calculations. All derivatives displayed AIE in THF-water mixtures at water contents higher than 80% v/v. TT-1 was encapsulated within phospholipid-connected polyethylene glycol (DSPE-PEG) by nanoprecipitation, yielding fluorescent nanoparticles with the average sizes of 80.7–83.7 nm. In cell imaging experiments, the resulting TT-1@DSPE-PEG nanoparticles (NPs) showed no toxicity to H1299 lung carcinoma cells at concentrations up to 50 μM and were successfully internalized by the cells after 2 h incubation. Finally, the biodistribution of TT-1@DSPE-PEG NPs was studied in a bladder cancer murine model. In vivo and ex vivo images indicated that the NPs were highly localized in the stomach of the mouse after 2 h post-injection and showed a small uptake by the tumor after 4 h post-injection.
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    Item type:Publication,
    Bodipy-pyridylhydrazone probe for fluorescence turn-on detection of fe3+ and its bioimaging application
    (2021-07-01)
    Nootem, Jukkrit
    ;
    Sattayanon, Chanchai
    ;
    Daengngern, Rathawat
    ;
    Kamkaew, Anyanee
    ;
    Wattanathana, Worawat
    A novel pyridylhydrazone-tethered BODIPY (BODIPY-PH) was synthesized, fully characterized via nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopic (FTIR), and single-crystal X-ray diffraction (SC-XRD) techniques, and developed for the selective detection of Fe<sup>3+</sup> through fluorescent enhancement process. This derivative showed 1:1 binding with Fe<sup>3+</sup> in an acetonitrile-water mixture (1:9 v/v) with the binding constant (K) of 5.4 × 10<sup>4</sup> M<sup>−1</sup> and the limit of detection of 0.58 µM. The Fe<sup>3+</sup> complexation reaction has been proved to be a reversible process and could be effectively repeated up to three cycles. The electronic properties of BODIPY-PH and its Fe<sup>3+</sup> complex modeled by the density functional theory (DFT) method suggested the presence of chelation-enhanced fluorescence (CHEF) effect in the Fe<sup>3+</sup> binding reaction. The X-ray absorption spectroscopy (XAS) probed at Fe K-edge confirmed the complex formation between BODIPY-PH and the Fe<sup>3+</sup> in an octahedral geometry. Finally, bioimaging against human embryonic kidney (Hek293) cell, through confocal fluorescence microscopic technique indicated that the BODIPY-PH displayed good permeability and low toxicity toward the tested cell lines and showed enhanced fluorescent signal in the cells incubated with Fe<sup>3+</sup> proving its capability for Fe<sup>3+</sup> analysis in cellular matrix.