BODIPY-Pyridylhydrazone Probe for Fluorescence Turn-On Detection of Fe3+ and Its Bioimaging Application

Abstract

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 Fe3+ through fluorescent enhancement process. This derivative showed 1:1 binding with Fe3+ in an acetonitrile-water mixture (1:9 v/v) with the binding constant (K) of 5.4 × 104 M−1 and the limit of detection of 0.58 µM. The Fe3+ 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 Fe3+ complex modeled by the density functional theory (DFT) method suggested the presence of chelation-enhanced fluorescence (CHEF) effect in the Fe3+ binding reaction. The X-ray absorption spectroscopy (XAS) probed at Fe K-edge confirmed the complex formation between BODIPY-PH and the Fe3+ 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 Fe3+ proving its capability for Fe3+ analysis in cellular matrix.

BODIPY-Based Fluorescent Probes for Selective Visualization of Endogenous Hypochlorous Acid in Living Cells via Triazolopyridine Formation

“…Compounds 1 and 2 were synthesized according to the reports in the literature [ 48 , 49 , 50 ]. 2-Hydrazinopyridine, 2-hydrazino-5-iodopyridine, Dess–Martin periodinane, 2,3-dichloro-5,6-dicyanoquinone (DDQ), 2,4-dimethylpyrrole, sodium hypochlorite, and glacial acetic acid were purchased from Tokyo Chemical Industry (TCI), Tokyo, Japan; boron trifluoride diethyl etherate purified by redistillation, and 4-(hydroxymethyl)benzaldehyde dimethyl acetal were purchased from Sigma-Aldrich, St. Louis, MO, USA; organic solvents, including dichloromethane (DCM), tetrahydrofuran (THF), and ethanol (ACS grade) were purchased from Honeywell, Charlotte, NC, USA.…”

Synthesis and bioimaging of a BODIPY-based fluorescence quenching probe for Fe3+

“…The detection limit and response time of BODIPY-CL are tabulated and compared with previous literature (Table 1). [65][66][67][68][69]…”

A Water-Soluble Naphthalimide-Based Fluorescent Probe for Specific Sensing of Fe3+ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$

“…[12,[14][15] Excessive Fe 3 ＋ ion in the body may lead to the risk of osteoporosis, hemochromatosis, diabetes, depression, hepatitis, organ failure, respiratory problems, convulsions, cardiac arrest, ucleic acid and protein damage, gastrointestinal diseases and other diseases. [5][6]8,11,13,[18][19] At the same time, insufficient Fe 3 ＋ ion in the human body will induce Parkinsonʼs disease, Huntingtonʼs disease, Alzheimerʼs disease, anemia, insomnia and hair loss. [1,9,17,20] It is well known that chromium is a heavy metal element, and its two oxidation states (Cr 3 ＋ and Cr 6 ＋ ) dominate in water and soil.…”

“…[8,17,26,35] In contrast, fluorescent probe detection has the characteristics of high selectivity, high sensitivity, low cost, rapid response, visualization and biological imaging, which can make up for the shortcomings of traditional analytical methods. [11,[15][16]24,37] At present, there are many reports on fluorescence sensing for the detection of Fe 3 ＋ , including organic small molecules, [4][5][6][11][12]16,18,20,26] metal organic frameworks [2,[7][8]10,38,[40][41][42] , quantum dots and so on. [9,[13][14][15]39,43] However, when considering the practical application ability of the probe in selectivity, sensitivity, competitiveness and applicable conditions, researchers believe that there is still a need for development and progress for Fe 3 ＋ fluorescent sensors.…”