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Crosstalk between the lysosome and the endoplasmic reticulum (ER) is essential for maintaining intracellular homeostasis and normal physiological activities. However, simultaneously visualizing the lysosome and ER by using a single fluorescent probe is of considerable significance and challenge. In this work, we developed a near-infrared (NIR) pH probe (F–CCOH) by introducing 7-hydroxycoumarin into the curcumin difluoroboron skeleton. The F–CCOH probe presented strong red emission (630 nm) under acidic conditions and NIR emission (755 nm) under basic conditions, which was attributed to the deprotonation of the hydroxyl group on coumarin. Moreover, by monitoring changes in the fluorescent intensity of F–CCOH in two channels, the pH variety of the lysosomes and ER in living cells can be visualized simultaneously. The experimental results showed that pH changes in the lysosome and ER were opposite during dexamethasone-induced apoptosis. This finding is extremely valuable for revealing the crosstalk between lysosome and ER in physiological activities. • F–CCOH exhibits red emission (630 nm) and near-infrared emission (755 nm) under different pH. • F–CCOH can simultaneously target lysosome and endoplasmic reticulum (ER) in living cells. • The pH changes in the lysosome and ER were opposite during dexamethasone-induced apoptosis. [ABSTRACT FROM AUTHOR]

SO 2 and its derivatives (HSO 3 −, SO 3 2−) play a significant important role in many industries and organisms. Based on coumarin and benzopyranose, a promising NIR ratiometric fluorescent probe BAOA (11-oxo-2,2′,3,3′,6,7,7′,8′-octahydro -1H,1′H,5H,6′H,11H- [10,12′-bipyrano [2,3-f] pyrido [3,2,1-ij] quinolin]-13′-ium perchlorate) was designed and developed to detect HSO 3 − rapidly and sensitively. The sensing mechanism was Michael addition reaction, in which, strongly nucleophilic HSO 3 − attacked carbon-carbon double bonds and BAOA-HSO 3 was formed. A superior linear calibration curve between the fluorescence ratio I 490 /I 722 and concentrations of HSO 3 − was obtained in the range of 1.25–8.75 μmol/L and the LOD was figured out as 63.0 nmol/L. Cell experiments showed that BAOA could not only locate mitochondria, lysosomes, ER and Golgi but also detect exogenous HSO 3 − in living cells. A promising NIR ratiometric fluorescent probe for HSO 3 − was designed, which sensing mechanism was nucleophilic HSO 3 − attacking carbon-carbon double bonds resulting from Michael addition reaction. [Display omitted] [ABSTRACT FROM AUTHOR]

Two asymmetrical benzoxanthene dyes (BP-1 and BP-2) were designed and synthesized by a convenient one-step procedure from naphthaldehyde and m -aminophenol precursors. These dyes showed long-wavelength absorption, near-infrared emission (>650 nm), and large Stokes shifts (>90 nm) because of the asymmetrical introduction of the benzene ring into the xanthene structure. BP-1 exhibited high fluorescence quantum yield in organic solvents, whereas BP-2 showed very weak fluorescence due to the photoinduced electron transfer of 9-substituted groups. Cell experiments indicated that BP-1 with crescent-shape structure showed lower cytotoxicity and higher photostability than BP-2 and could rapidly stain RNA in nucleoli at low concentration. [Display omitted] • Two asymmetrical benzoxanthene dyes were synthesized by a convenient one-step procedure. • The dyes showed long-wavelength absorption, near-infrared emission and large Stokes shifts. • BP-1 could stained RNA in nucleoli rapidly with low cytotoxicity and good photostability. • BP-2 showed a very weak fluorescence and cytotoxicity due to 9-substituted groups. [ABSTRACT FROM AUTHOR]

Solvents exhibit different color reactions via regulation of the structure, kinetics, and charge distribution of organic compound molecules. In recent years, solvatochromic probes have good application prospects in the fields of chemistry and biology. In this work, we synthesized three fluorescent probes (PBIC–C, PAIC-C, PPIC-C) sensitive to solvent polarity. We have studied the photophysical properties (spectra, quantum yield, and fluorescence lifetime under different solvents) of these probes. The isomerization nature was verified by nuclear magnetic titration. In order to further confirm our guess, we also performed theoretical calculations, and the results were roughly the same as the experimental results. In addition, cell imaging tests revealed that the designed probes could be used as dual intracellular mitochondria/lysosome-targeting fluorescent probes for biological applications. [Display omitted] • The probes exhibit sharp color changes in different polar solvents. • The probes show relatively high fluorescence quantum yields. • The probes achieve dual targeting of mitochondrials and lysosomes. [ABSTRACT FROM AUTHOR]