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A high-affinity fluorescence probe for copper(II) ions and its application in fluorescence lifetime correlation spectroscopy
摘要： Copper is one of the most important transition metals in many organisms where it catalyzes a manifold of different processes. As a result of copper’s redox activity, organisms have to avoid unbound ions, and a dysfunctional copper homeostasis may lead to multifarious pathological processes in cells with very severe ramifications for the affected organisms. In many neurodegenerative diseases, however, the exact role of copper ions is still not completely clarified. In this work, a high-affinity and highly selective copper probe molecule, based on the naturally occurring tetrapeptide DAHK is synthesized. The sensor (log KD = ? 12.8 ± 0.1) is tagged with a fluorescent BODIPY dye whose fluorescence lifetime distinctly decreases from 5.8 ns ± 0.2 ns to 0.4 ns ± 0.1 ns on binding to copper(II) cations. It is shown by using fluorescence lifetime correlation spectroscopy that the concentration of both probe and probe-copper complex can be simultaneously measured even at nanomolar concentration levels. This work presents a possible starting point for a new type of probe and method for future in vivo studies to further reveal the exact role of copper ions in organisms.
关键词： BODIPY,Single molecule detection,FLIM,Alzheimer,ATCUN motif,Parkinson,DAHK
更新于2025-11-21 11:24:58
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A red fluorescent BODIPY probe for iridium (III) ion and its application in living cells
摘要： A new red fluorescent probe 1 based on BODIPY skeleton has been successfully synthesized through introduction of 2-(thiophen-2-yl) quinoline moiety at meso- and 3-position, which exhibits excellent optical performance, including high fluorescence quantum yield, large pseudo Stokes’ shift as well as high selectivity and sensitivity towards iridium (III) ion in aqueous solution and in living cells.
关键词： iridium (III) ion probe,fluorescence imaging,BODIPY probe
更新于2025-11-21 11:08:12
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Visualizing Nitric Oxide in Mitochondria and Lysosomes of Living Cells with N-Nitrosation of BODIPY-based Fluorescent Probes
摘要： Nitric oxide (NO), a ubiquitous gasotransmitter which plays critical roles in cardiovascular, nervous, and immune systems related diseases, is closely related in the physiological and pathological processes of mitochondria and lysosomes. Thus, monitoring NO in mitochondria or lysosomes is very meaningful for NO related chemical biology. Herein, we rationally designed four NO probes, BDP-NO, Mito-NO-T, Mito-NO and Lyso-NO, based on BODIPY dye substituted at meso position with 5-amino-2-methoxy-phenyl scaffold. These four probes all showed fast fluorescence off-on response toward NO with excellent selectivity and high sensitivity with the detection limit of BDP-NO to reach 5.7 nM. We introduced triphenylphosphonium and morpholine moieties onto BODIPY scaffold respectively to enable organelle-targetability. MTT and flow cytometry assay demonstrated that the probes exhibited low cytotoxicity, which was beneficial to the biological application in living cells. Confocal fluorescence microscopy experiments confirmed excellent mitochondria targeting for Mito-NO and lysosome-targeting with Lyso-NO for the detection of NO in living cells.
关键词： Fluorescent probes,Mitochondria-targeted,Lysosomes-targeted,BODIPY,Nitric oxide
更新于2025-11-21 11:08:12
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A near-infrared BODIPY-based fluorescent probe for ratiometric and discriminative detection of Hg2+ and Cu2+ ions in living cells
摘要： A near-infrared distyryl boron dipyrromethene-based sensor bearing one bis(1,2,3-triazole)amino receptor has been synthesized. This probe selectively and quickly binds to Hg2+ and Cu2+ ions in CH3CN/H2O (5:1 v/v) and exhibits remarkably blue-shifted absorption and fluorescence bands due to the inhibition of the intramolecular charge transfer process. The fluorescence changes of this probe upon binding to Hg2+ or Cu2+ ion are totally different, undergoing a ratiometric fluorescence enhancement (for Hg2+) or a fluorescence quenching (for Cu2+) mechanism. The corresponding vivid color changes can be easily seen by the naked eye. This probe was further introduced into Hela cells for living cell imaging and found to discriminate Hg2+ and Cu2+ ions through two near-infrared fluorescence emission channels. These overall results indicate that this Click-derived near-infrared BODIPY-based probe is potentially useful for ratiometric and discriminative detection of Hg2+ and Cu2+ ions in solutions and living cells.
关键词： Discriminative detection,Ratiometric,Hg2+ and Cu2+ sensor,Near-infrared,BODIPY
更新于2025-11-21 11:08:12
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Magnesium tetrapyrazinoporphyrazines: tuning of the pKa of red-fluorescent pH indicators
摘要： Magnesium (II) tetrapyrazinoporphyrazines (TPyzPzs) are excellent red fluorophores (λF ~ 663 nm, ΦF ~ 0.53 in THF). In this work, a series of magnesium (II) complexes of unsymmetrical TPyzPzs bearing one or two phenol substituents was prepared. Suitable substitutions on the phenolic moiety tuned its pKa in the range of 5.5 to 13. Deprotonation of the phenolic group at higher pH induced a strong donor (phenolate) in the macrocycle that led to pH-dependent quenching of the red fluorescence of these indicators. pH sensing was proven in water solutions after incorporation of TPyzPs into two delivery systems – microemulsions and liposomes. The latter also serves as a simple model of biomembranes. Finally, a wavelength-ratiometric probe was constructed by incorporation of a TPyzPz indicator and lipophilic pH-nonsensitive BODIPY dye into liposomes. Synthetic precursors for TPyzPzs, substituted pyrazine-2,3-dicarbonitriles, also represent donor-acceptor system and the pH-dependent changes in absorption spectra may be easily visible to the naked eye.
关键词： pH indicators,microemulsions,fluorescence,BODIPY,wavelength-ratiometric probe,liposomes,tetrapyrazinoporphyrazines,magnesium complexes
更新于2025-11-20 15:33:11
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Novel BODIPY-based fluorescent probes with large Stokes shift for imaging hydrogen sulfide
摘要： Hydrogen sulfide has important biomedical significance because it plays a regulatory role in a variety of physiological processes. In our previous work, we investigated the effect of substituents on Stokes shift of BODIPY and found that methoxy groups on phenyl substituents at 3,5-positions could expand the Stokes shift of BODIPY-based probes. In this study, taking hydrogen sulfide (H2S) as analyte, we designed and synthesized 4,4-difluoro-8-{4-(2,4-dinitrophenoxy)phenyl}-3,5-bis(2,4-dimethoxyphenyl)-4-bora-3a,4a-diaza-s-indancene (DMOEPB) and 4,4-difluoro-8-(4-nitrophenyl)-3,5-bis(2,4-dimethoxyphenyl)-4-bora-3a,4a-diaza-s-indancene (DMONPB) according to the same strategy. As expected, Stokes shifts of 49 nm and 51 nm were obtained respectively, which demonstrate the feasibility of the strategy in the synthesis of other fluorescent probes for the detection of small biomolecules. DMONPB can react with H2S to form the derivative with a fluorescence quantum yield of 0.13. An excellent linear relationship was observed in the range of H2S concentrations from 0 μM to 800 μM and the detection limit was 1.3 μM. Furthermore, it can be successfully applied to imaging of H2S in cells and tissues. For DMOEPB, the presence of m-dinitrophenyl did not cause the expected fluorescence quenching, which makes it impossible to perform bioimaging. We speculate that the strong electron-withdrawing property of nitro group is obviously weaker when the two benzene rings are separated at 8-position and are not conjugated with the fluorophore. It provides experience and lessons for designing the same type of turn-on probe.
关键词： hydrogen sulfide,BODIPY,red fluorescence,bioimaging,large Stokes shift
更新于2025-11-19 16:46:39
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Enhanced In‐vivo Optical Imaging of the Inflammatory Response to Acute Liver Injury in C57Bl/6 Mice using a Highly Bright Near‐Infrared BODIPY Dye
摘要： Delving deeper is possible in whole body in vivo imaging using a super-bright membrane targeting BODIPY dye (BD). The dye was employed to monitor homing of ex vivo, fluorescently labelled neutrophils to an injured liver of dark pigmented C57BL/6 mice. In Vivo Imaging System (IVIS) data conclusively showed an enhanced signal intensity and a higher signal-to-noise ratio in mice receiving neutrophils labelled with the BD dye compared to those labelled with a gold standard dye at 2 hr post in vivo administration of fluorescently labelled cells. Fluorescence-activated cell sorting (FACS) confirmed that BD was non-toxic, and an exceptional cell labelling dye that opens up precision deep organ in vivo imaging of inflammation in mice routinely used for biomedical research. The origin of enhanced performance is identified with the molecular structure, and the distinct localisation of the dye within cells that enable remarkable changes in its optical parameters.
关键词： In-vivo imaging,Cell Sorting,Bodipy,Liver,Fluorescence
更新于2025-11-19 16:46:39
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Novel BODIPY-conjugated amino acids: Synthesis and spectral properties
摘要： Three BODIPY-based conjugates with lysine, methionine, and tryptophan bound via amino group were synthesized and characterized. Spectral properties of the compounds were studied and a number of photophysical characteristics were obtained. Bioconjugates investigated are water soluble, which makes them promising markers for various bioobjects.
关键词： conjugation,fluorescence,BODIPY,amino acids,markers
更新于2025-11-14 15:14:40
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Complementary Chromophore Decoration in NU-1000 via Solvent-Assisted Ligands Incorporation: Efficient Energy Transfer within the Metal-Organic Frameworks
摘要： BODIPY-incorporated solvent-assisted ligand incorporation metal-organic frameworks (SALI-MOFs) were designed and synthesized using NU-1000 and carboxylic acid functionalized BODIPY moieties by the solvent-assisted ligand incorporation (SALI) approach. SALI-MOFs were characterized by various technique including powder X-ray diffraction, scanning electron microscope, N2 adsorption/desorption isotherms, Fourier transform infrared spectroscopy, and nuclear magnetic resonance spectroscopy. The SALI-MOFs were found to have cooperative light-harvesting properties and shown to possess efficient singlet oxygen (1O2) generation ability.
关键词： Light-harvesting properties,Singlet oxygen,Metal-organic frameworks,Solvent-assisted ligands incorporation,Energy transfer,BODIPY
更新于2025-11-14 15:14:40
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Near-Infrared fluorescence chemosensor based on isothiocyanate-aza-BODIPY for cyanide detection in ppb level: Applications in buffer media and living cell imaging
摘要： A near-infrared chemodosimeter based on an aza-BODIPY dye was designed and synthesized. The sensor contains isothiocyanate groups for cyanide ion sensing. The sensing function was illustrated via the fluorescence changes in near-infrared frequencies as well as chromogenic change which could be easily visualized with a detection limit of 19 ppb. The sensor provides high selectivity to CN? and discriminates other anions such as CH3COO?, HPO4 2?, HSO4 ?, NO3 ?, Cl?, F?, Br?, I?, ClO3 ?, CO3 2?, SO4 2?, and phenylalanine (Phe) in 50% PBS buffer/acetonitrile at physiological pH. The potential of the sensor for CN? detection in both aqueous buffer solutions and living cells imaging were demonstrated.
关键词： selectivity,cyanide,sensors,aza-BODIPY dyes,near-infrared fluorescence
更新于2025-09-23 15:23:52