Lysosome-targeting ratiometric fluorescent pH probes based on long-wavelength BODIPY

Abstract

BODIPY-based ratiometric fluorescent probes show remarkable sensitivity under acidic conditions via a protonation-modulated ICT mechanism for monitoring lysosomal pH in living cells.

A “weak acid and weak base” type fluorescent probe for sensing pH: mechanism and application in living cells

“…[12][13][14][15] An optical probe, especially a uorescent probe, is one of the most powerful tools for detecting pH in cells for its advantages of simple operation, high sensitivity, and temporal resolution. [16][17][18] Many pH uorescent probes have been designed. There are two classes of synthetic pH probesone for acidic organelles (such as, lysosomes) functioning in the pH range of 4.00-6.00, and another for cytosol that works in the pH range 6.80-7.40.…”

Two-Photon Excited FRET Dyads for Lysosome-Targeted Imaging and Photodynamic Therapy

“…2-Acetyl-6-dimethylaminonaphthalene (AceDAN), 29 as a typical TPE chromophore, was selected to pair up with a metal-free or zinc porphyrin (H 2 Por or ZnPor) to formulate the FRET dyads. A morpholine (MPL) moiety was also incorporated into the TPE-FRET system for lysosome-targeted cell imaging 30 and to improve the PDT efficiency by lysosomal photodamage induced cell death. 31 The introduction of 3,5-di-tert-butylphenyl groups at the remaining meso-sites was expected to suppress the tendency of aggregation; thus it could increase the solubility and be beneficial for the fluorescent emission and singlet oxygen generation.…”

Recent Advances in Small Molecule‐Based Intracellular pH Probes

“…The ratiometric BODIPY probes 24 and 25 were synthesized to target the lysosomal pH (Figure 16). [55] In acidic pH, the protonation of the dimethylamino group takes place resulted in suppression of the ICT process, leading to a blue shift and substantial enhancement in fluorescence. Both the probes exhibit low toxicity and strong lysosomal localization ability in living cells.…”