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A highly selective copper ions fluorescent probe based on the coumarin-type Schiff base derivative 1 (probe) was produced by condensation reaction between coumarin carbohydrazide and 1H-indazole-3-carbaldehyde. The UV–vis spectroscopy showed that the maximum absorption peak of compound 1 appeared at 439 nm. In the presence of Cu 2 + ions, the maximum peak decreased remarkably compared with other physiological important metal ions and a new absorption peak at 500 nm appeared. The job's plot experiments showed that complexes of 1:2 binding mode were formed in CH 3 CN:HEPES (3:2, v/v) solution. Compound 1 exhibited a strong blue fluorescence. Upon addition of copper ions, the fluorescence gradually decreased and reached a plateau with the fluorescence quenching rate up to 98.73%. The detection limit for Cu 2 + ions was estimated to 0.384 ppm. Fluorescent microscopy experiments demonstrated that probe 1 had potential to be used to investigate biological processes involving Cu 2 + ions within living cells. [ABSTRACT FROM AUTHOR]

[Display omitted] • Based on dicyanoisophorone skeleton a near-infrared fluorescent probe was prepared and used to detect CO with high selectivity. • Two emission channels ratiometric fluorescence changes can be observed through adjusting the ICT effect of probe by CO. • The design of the probe enables it to be used for detecting CO in lysosomal subcellular organelles and further validated through cell co-localization imaging experiments. • The probe can be used to detect the endogenous and exogenous CO in Hela cells and could be used in living mice. • The probe is capable of detecting endogenous and exogenous CO through cell imaging experiments and has been successfully used in living mice. Carbon monoxide (CO) as an endogenous gas signaling molecule possesses important physiological functions and is of great significance in the treatment of various diseases. Real-time tracking of CO in living organisms has become a research hotspot in recent years. This article presents a lysosomal targeted near-infrared ratio fluorescence probe (TBM-CO) for selective detection of CO based on the dicyanoisophorone skeleton and morpholine fragment. The probe TBM-CO with weak ICT effect can be transformed to precursor TBM-NH 2 with strong ICT effect by the traditional Tsuji-Trost reaction procession in the presence of Pd2+ ions. The mechanism was proved by DFT calculation or the MS and HPLC results respectively. In the near-infrared region an obvious ratio fluorescence intensity change (F 686 / F 616) is observed in vitro spectral experiments. The concentration titration experiments indicate that there is a good liner relationship between the ratio fluorescence intensity and the concentration in the range of 0 to 50 μM (R2 = 0.996) and the detection limit is calculated as 0.38 μM. The cell fluorescence imaging and co-localization experiments further demonstrate that TBM-CO is able to detect the exogenous and endogenous CO in lysosomal subcellular organelle. Finally, it was used to detect the changes of CO concentration in living mice successfully. In short, a probe with three advantages of near-infrared emission, ratiometric fluorescence and organelle targeting was reported and used to detect CO successfully in cells and in living mice. [ABSTRACT FROM AUTHOR]

[Display omitted] • A simple flavone-based chemosensor was synthesized based on ESIPT process for ratiometric detection of hydrogen polysulfides. • The probe displayed high selective and sensitive for hydrogen polysulfides (detection limit is 0.63 μM). • The probe was successfully applied to exogenous H 2 S n detection and imaging by dual emission channels in living Hela cells. Hydrogen polysulfides (H 2 S n) as an important member of reactive sulfur species is closely relevant to many physiological functions in redox homeostasis and metabolism. Dual-channel monitor the changes of H 2 S n level in vivo is highly desired. Herein we design a simple ratiometric fluorescent probe based on flavone skeleton for highly selective detection of H 2 S n. The probe HF-NA-MC bearing 2-fluoro-5-nitrobenzoic acid group inhibited the intramolecular ESIPT process, which show the blue fluorescence of adjacent naphthalene unit. In the presence of H 2 S n , the enol form of probe is converted to conjugated keto form, resulted in a 90 nm red-shift of fluorescence emission from 450 nm to 540 nm. The ratiometric intensity (I 540 /I 450) of the probe exhibits a good linear relationship toward H 2 S n in the range of 0–120 μM, and the detection limit is estimated to be 0.63 μM. The ratiometric fluorescent probe shows high specificity and anti-interference ability for H 2 S n over other related reactive sulfur species. The probe HF-NA-MC shows promising outlook and could be applied to the confocal imaging of H 2 S n by dual emission channels in Hela cells. [ABSTRACT FROM AUTHOR]

A specific Cu2+ sensor, 2-amino-3-(BODIPYmethyleneamino)maleonitrile (BDM), was established by a simple dehydration between BODIPY and diaminomaleonitrile. Cu2+ could be recognized by BDM over other competing metal ions in acetonitrile with distinct fluorescence emission signal response. Upon the addition of Cu2+ to BDM in acetonitrile, the maximum absorption at approximately 530 nm on the longer wavelength side was quenched, and the emission at 530 nm was ignited simultaneously. The fluorescence intensity enhancement could reach a maximum of 204 times the intensity of the BDM blank solution. The fluorescence "off-on" effect is established according to the Cu2+-induced fast intramolecular oxidative cyclization reaction, which could be deduced from the formation of an imidazole ring appended to the cyclization product (2-BODIPY-1 H -imidazole-4,5-dicarbonitrile, BMC). Single-crystal structure analysis of the sensor BDM and cyclization product BMC further demonstrated this oxidative cyclization. Finally, the Cu2+ recognition property of BDM was validated in SiHa cells and living zebrafish. Additionally, the blood-brain barrier of the zebrafish can be penetrated by the BDM dye and the neuron cells in the brain were stained. Unlabelled Image • Intramolecular oxidative cyclization reaction based sensor was established. • Single crystal structure analysis was also demonstrated. • Sensing property was validated in Siha cells and living vertebrate model, zebrafish. [ABSTRACT FROM AUTHOR]