Molecular design and synthesis of a pH independent and cell permeant fluorescent dye and its applications

Abstract

Fluorescent dyes have played crucial roles in the field of molecular imaging as fluorescent fluorophores. In this work, a novel water-soluble and pH-independent fluorescent xanthene dye, a hydroxyl regioisomeric 3′,4′-benzorhodol, has been designed and synthesized. Compared with those of rhodol dyes, the absorption (ca. 570 nm) and maximum emission (ca. 620 nm) of the dye are largely red-shifted. Due to its ring-opened zwitterion structure in water media, the dye showed good membrane permeability and distributed in the whole cell cytoplasm upon incubation with live cells. Meanwhile, the dye could be easily modified to probes. The hydrazide derivative of the dye exhibited an excellent Hg²⁺ selectivity over other relevant metal ions with a detection limit down to 3 nM. Thus, the excellent fluorescence properties and chemical properties of the dye allow it to be designed as a fluorescent chemosensor and biomarker for biological applications.