Highly Water-Soluble BODIPY-Based Fluorescent Probe for Sensitive and Selective Detection of Nitric Oxide in Living Cells

Vegesna, Giri K.; Sripathi, Srinivas R.; Zhang, Jingtuo; Zhu, Shilei; He, Weilue; Luo, Fen; Jahng, Wan Jin; Frost, Megan C.; Liu, Haiying

doi:10.1021/am303247s

Cited by 75 publications

(48 citation statements)

References 43 publications

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“…The first possibility is excluded due to the observation that the fluorescent BDP dyes with branched tri(ethylene glycol) arms still show a strong fluorescence intensity in cells 14. 21 BDP‐G0 is likely to stay in the endocytotic vesicles and to show enhanced fluorescence intensity in this confined environments 9a…”

Section: Resultsmentioning

confidence: 99%

BODIPY‐Based Oligo(ethylene glycol) Dendrons as Fluorescence Thermometers: When Thermoresponsiveness Meets Intramolecular Electron/Charge Transfer

Wang

Fan

et al. 2014

Chemistry A European J

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The temperature-dependent photophysical properties of a series of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) derivatives with different oligo(ethylene glycol) (OEG) dendrons were investigated. Weak fluorescence emission was observed for these BODIPY derivatives in dilute solution with low viscosity. BDP-G0 and BDP-G1-TEG exhibit a high quantum yield in viscous glycerol solutions, contrary to the moderate and little fluorescence enhancement for BDP-G1 and BDP-G2 under the same conditions. The photoinduced electron transfer (PET) may have quenched the fluorescence, as supported by calculation. Interestingly, the thermoresponsive BODIPY derivatives show heat-induced luminescence enhancement with a high signal-to-noise ratio and their emission maxima are dependent on the structures of branched tri(ethylene glycol) moieties. Finally, preliminary studies on the BODIPY derivatives as intracellular fluorescence indicators in living HeLa cells were carried out.

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Section: Resultsmentioning

confidence: 99%

BODIPY‐Based Oligo(ethylene glycol) Dendrons as Fluorescence Thermometers: When Thermoresponsiveness Meets Intramolecular Electron/Charge Transfer

Wang

Fan

et al. 2014

Chemistry A European J

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“…47 The desired dyads were obtained in moderate yields (46–56%). The target dyads were easily isolated by column chromatography.…”

Section: Resultsmentioning

confidence: 99%

BODIPY–Bacteriochlorin Energy Transfer Arrays: Toward Near-IR Emitters with Broadly Tunable, Multiple Absorption Bands

2017

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A series of energy transfer arrays, comprising of a near-IR absorbing and emitting bacteriochlorin, and BODIPY derivatives with different absorption bands in the visible region (503 – 668 nm) have been synthesized. Absorption band of BODIPY was tuned by installation of 0, 1, or 2 styryl substituents [2-(2,4,6-trimethoxyphenyl)ethenyl], which leads to derivatives with absorption maxima at 503 nm, 587 nm, and 668 nm, respectively Efficient energy transfer (>0.90) is observed for each dyad, which is manifested by nearly exclusive emission from bacteriochlorin moiety upon BODIPY excitation. Fluorescence quantum yield of each dyad in non-polar solvent (toluene) is comparable with that observed for corresponding bacteriochlorin monomer, and is significantly reduced in solvent of high dielectric constants (DMF), most likely by photoinduced electron transfer. Given the availability of diverse BODIPY derivatives, with absorption in 500–700 nm, BODIPY-bacteriochlorin arrays should allow for construction of near-IR emitting agents with multiple and broadly tunable absorption bands. Solvent-dielectric constants dependence of Φf in dyads gives an opportunity to construct environmentally-sensitive fluorophores and probes.

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“…The vast majority of the reported nitric oxide probes were prepared from the corresponding nitrobenzyl compounds, with the final products being obtained by reduction; 11,15 however, the method was not effective in this case since the dibenzoxanthenium will be reduced to colorless solutions. The synthetic route used for the construction of the dibenzoxanthenium compounds evaluated in this study is shown in Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

Near-infrared emission of dibenzoxanthenium and its application in the design of nitric oxide probes

et al. 2015

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Two dibenzoxanthenium derivatives bearing a 3,4-diaminophenyl group, compounds 1a and 1b, have been prepared and evaluated as near-infrared probes for the detection of nitric oxide. Compound 1a gave a 3-fold emission enhancement towards nitric oxide at 681 nm, whereas compound 1b exhibited OFF-ON emission behavior towards nitric oxide, resulting in a 35-fold increase in the fluorescence intensity with an emission maximum of 750 nm being approved through (TD)DFT calculations. Probe 1b showed independent emission in the presence of common cations, amino acids, reactive oxygen and nitrogen species; furthermore, it can be used for the in cellulo imaging of nitric oxide under acidic and neutral conditions.

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Highly Water-Soluble BODIPY-Based Fluorescent Probe for Sensitive and Selective Detection of Nitric Oxide in Living Cells

Cited by 75 publications

References 43 publications

BODIPY‐Based Oligo(ethylene glycol) Dendrons as Fluorescence Thermometers: When Thermoresponsiveness Meets Intramolecular Electron/Charge Transfer

BODIPY‐Based Oligo(ethylene glycol) Dendrons as Fluorescence Thermometers: When Thermoresponsiveness Meets Intramolecular Electron/Charge Transfer

BODIPY–Bacteriochlorin Energy Transfer Arrays: Toward Near-IR Emitters with Broadly Tunable, Multiple Absorption Bands

Near-infrared emission of dibenzoxanthenium and its application in the design of nitric oxide probes

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