Abstract
Acid-base balance in cells is vital to maintain the normal biological processes, and its disorders could lead to various diseases. It is significant to develop a reliable and portable method for tracing intracellular pH changes. Herein, a novel colorimetric and fluormetric dual-modal probe 2-(((6,6-dimethylbicyclo [3.1.1]hept-2-en-2-yl)methylene)hydrazono)-3-ethyl-5-(2-hydroxybenzylidene)thiazolidine-4-one (MTHB) was constructed for sensitive and rapid detection of alkaline pH changes by employing myrtenal as a starting material. MTHB showed a significantly enhanced yellow fluorescence upon increasing pH from 7.45 to 12.89, and the pKa was determined as 9.84. The probe MTHB was featured with large Stokes shift, high selectivity, good reversibility, and excellent photostability. The sensing mechanism of MTHB for alkaline pH was verified by HRMS, 1H NMR titration, and theoretical calculations. Additionally, in view of its low toxicity and good biocompatibility, MTHB was successfully utilized to visualize the pH variations in living HeLa cells and zebrafish.
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