ABSTRACT
A deep-red emission and lipid droplets-targeted fluorescence probe (named ZFPy) for effective bioimaging of bisulfite was developed from flavone moiety and benzoindole derivative based on intramolecular charge transfer (ICT) and Förster resonance energy transfer (FRET) platform. ZFPy displayed promising fluorescence parameters including bright deep red fluorescence (615 nm), large Stokes shift (205 nm), extended emission window gap (140 nm), high absolute fluorescence quantum yield (4.1%) and stable emission signal output. In addition, ZFPy realized ratiometric fluorescence monitoring for SO2 derivatives with low detection limit (30 nM), preferable linearity, high sensitivity and selectivity. Interestingly, dual fluorophores (i.e. the donor moiety and 1,1,2,3-tetra-substituent-1H-benzo[e]indol-3-ium iodide moiety) released the same emission band about 475 nm to enhance the emission signal when ZFPy reacted with SO2 derivatives, to the best of our knowledge, this is the first synergetic FRET/ICT platform for fluorescence probe, which might effectively offer ZFPy a high sensitivity and low detection limit in the detection of SO2 derivatives. More importantly, ZFPy could image exogenous and endogenous SO2 derivatives in living HeLa, HepG2 and L-O2 cells with good biocompatibility and photostability. ZFPy also preferred to load on lipid droplets with high Pearson's coefficient (0.95).
Subject(s)
Fluorescence Resonance Energy Transfer , Lipid Droplets , Fluorescent Dyes , Humans , SulfitesABSTRACT
A unique fluorescent probe (ZACA) for the monitoring of SO2 derivatives was developed from coumarin and benzoindoles based on FRET and ICT. ZACA exhibited an active emission signal, large Stokes shift, wide emission window distance, and high photostability. It also possessed many advantages in the ratiometric detection of HSO3-/SO32- including low detection limit and high selectivity and sensitivity. Importantly, ZACA was successfully applied in the ratiometric detection of endogenous HSO3-/SO32- in living cells with excellent cellular imaging capability (1 µM) and mitochondria-targeting ability (co-localization coefficient: 0.91).
Subject(s)
Fluorescent Dyes/chemistry , Mitochondria/metabolism , Sulfites/analysis , Cell Line, Tumor , Coumarins/chemical synthesis , Coumarins/chemistry , Fluorescent Dyes/chemical synthesis , Humans , Indoles/chemical synthesis , Indoles/chemistry , Limit of Detection , Microscopy, FluorescenceABSTRACT
A promising near-infrared emissive and mitochondria-targeted fluorescence probe (SNB) for the ratiometric detection of sulfur dioxide derivatives with a novel reaction mechanism was developed on the basis of FRET and the ICT platform. Probe SNB showed favorable fluorescence properties, including an active NIR emission signal (671 nm), ultra-large Stokes shift (251 nm) and an ultra-broad emission band gap (193 nm). Furthermore, SNB was applied to detect sulfur dioxide derivatives with a low detection limit (17 nM), excellent sensitivity and exceptional selectivity. Of greater significance, SNB also successfully implemented the real-time and ratiometric surveillance for exogenous or endogenous sulfur dioxide derivatives in living HeLa, L-O2 and HepG2 cells. Interestingly, SNB possessed a subcellular organelle targeting ability with a preferred co-localization coefficient of 0.91 for mitochondria, which revealed its promising potential in the detection of subcellular sulfur dioxide derivatives.
Subject(s)
Fluorescent Dyes/chemistry , Mitochondria/metabolism , Sulfites/analysis , Cell Line, Tumor , Cell Survival/drug effects , Fluorescent Dyes/toxicity , Humans , Limit of Detection , Microscopy, Fluorescence/methodsABSTRACT
A novel ratiometric fluorescence probe for hypochlorous acid was constructed by coumarin and pyridinium fluorophore based on the Forster resonance energy transfer (FRET) and intramolecular charge transfer (ICT) platform. In this ICT/FRET system, the energy transfer efficiency is high to 94.3%. Moreover, the probe could respond to hypochlorous acid with high selectivity and sensitivity, and exhibited a large Stokes shift. It was interesting to find that the probe could recognize hypochlorous acid via a new mechanism, in which the α-position of carbonyl group was oxidized to form a diketone derivative. More importantly, the probe was successfully applied to the ratiometric imaging of both exogenous and endogenous hypochlorous acid in living RAW 264.7â¯cells, with low toxicity and high photo-stability.
Subject(s)
Coumarins/chemistry , Fluorescent Dyes/chemistry , Hypochlorous Acid/analysis , Hypochlorous Acid/metabolism , Pyridinium Compounds/chemistry , Animals , Coumarins/chemical synthesis , Coumarins/radiation effects , Drug Design , Fluorescence , Fluorescence Resonance Energy Transfer/methods , Fluorescent Dyes/chemical synthesis , Fluorescent Dyes/radiation effects , Hydrogen-Ion Concentration , Light , Limit of Detection , Mice , Optical Imaging/methods , Pyridinium Compounds/chemical synthesis , Pyridinium Compounds/radiation effects , RAW 264.7 CellsABSTRACT
A ratiometric fluorescence probe (named ZOC) for the fast detection of HClO/ClO- was constructed by coumarin (donor) and pyridinium (acceptor) based on Forster resonance energy transfer (FRET) and intramolecular charge transfer (ICT) platform. ZOC possessed red emission signal (610â¯nm), large Stocks shift (190â¯nm), high energy transfer efficiency (95.3%), high selectivity and sensitivity, low detection limit (25â¯nM), wider detection range (from 25â¯nM to 30⯵M), rapid response (within 13â¯S), and good biocompatibility. It was very interesting that the recognition mechanism involved a new organic reaction in which olefin double bond reacted first with HClO/ClO- regioselectively, followed by cyclization. ZOC was successfully used to the real time detection of endogenous HClO/ClO- in RAW 264.7â¯cells.
