A novel dithiourea-appended naphthalimide "on-off" fluorescent probe for detecting Hg2+ and Ag+ and its application in cell imaging

Abstract

An effective dithiourea-appended 1,8-naphthalimide fluorescent probe was designed and synthesized. This probe could recognize Hg²⁺ and Ag⁺ sensitively and selectively in neutral and alkaline conditions. Moreover, the probe detected Hg²⁺ alone at pH between 2 and 6. The sensing ability of the probe was explored by UV-vis, fluorescence, FTIR and ¹H NMR spectroscopy. The probe was quenched by Hg²⁺ and Ag⁺ with 1:1 binding ratios in MeCN/H₂O (4/1, v/v) mixed solution with binding constants of 3.76 × 10⁴ L mol^-1 and 2.47 × 10⁴ L mol^-1, respectively. The linear concentration ranges for Hg²⁺ and Ag⁺ were 0-17 μmol L^-1 and 0-24 μmol L^-1 with detection limits of 0.83 μmol L^-1 and 1.20 μmol L^-1, respectively, which allowed for the quantitative determination of Hg²⁺ and Ag⁺. The new probe, 3a, was successfully applied to the fluorescence imaging of Hg²⁺ and Ag⁺ in HepG2 cells, demonstrating its potential application in biological science. Moreover, 3a was used to measure Hg²⁺ and Ag⁺ in tap water, drinking water and ultrapure water samples. The recoveries of Hg²⁺ and Ag⁺ in water samples were 96-99% and 98-103%, respectively. Therefore, the proposed method showed promising perspectives for its application, aimed at detecting Hg²⁺ and Ag⁺ in fluorescence imaging and real water samples.

Keywords: Bioimaging N,N′-(((2-((2-(4-methoxyphenyl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)amino)ethyl)azanediyl)bis(carbonothioyl))dibenzamide (3a); Fluorescence probe; Hg(2+) and Ag(+); Naphthalimide; Thiourea.