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Author: search.filters.author.Nootem, JukkritSubject: search.filters.subject.BODIPY

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    BODIPY-Based Fluorescent Probes for Selective Visualization of Endogenous Hypochlorous Acid in Living Cells via Triazolopyridine Formation
    (2022-11-01)
    Hiranmartsuwan, Peraya
    ;
    Wangngae, Sirilak
    ;
    Nootem, Jukkrit
    ;
    Kamkaew, Anyanee
    ;
    Daengngern, Rathawat
    In this work, the two pyridylhydrazone-tethered BODIPY compounds (2 and 3) were synthesized. These compounds aimed to detect hypochlorous acid (HOCl) species via cyclic triazolopyridine formation. The open forms and the resulting cyclic forms of BODIPYs (2, 3, 4, and 5) were fully characterized by nuclear magnetic resonance, mass spectrometry, infrared spectroscopy, and single-crystal X-ray diffraction. These two probes can selectively detect HOCl through a fluorescence turn-on mechanism with the limit of detections of 0.21 µM and 0.77 µM for compounds 2 and 3, respectively. This fluorescence enhancement phenomenon could be the effect from C = N isomerization inhibition due to HOCl-triggered triazolopyridine formation. In cell imaging experiments, these compounds showed excellent biocompatibility toward RAW 264.7 murine live macrophage cells and greatly visualized endogenous HOCl in living cells stimulated with lipopolysaccharide.
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    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.