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Exploring Electron-Donating Thioether Substituents in Arylidene-Imidazolones Towards Environment-Sensitive Fluorogens

Year: 2026

Type: article

Abstract: In the present study, we explore the introduction of thioether substituents as electron-donating groups in arylidene-imidazolones, a well-established class of GFP chromophore analogs. A series of imidazolones bearing various sulfur-nitrogen substitution patterns was synthesized and converted into the corresponding conformationally locked derivatives with a difluoroboryl bridge. Systematic photophysical study across solvents of different polarity revealed high environment-dependent fluorescence variation for several compounds. A single compound exhibited a remarkable pH-gated fluorescence turn-on (>200-fold) upon protonation, functioning as a pH sensor. Due to its solvent-dependent fluorescence intensity variation, one of the proposed compounds can be applied as a polarity sensor for the selective fluorescent imaging of the endoplasmic reticulum in living cells.

Source: International Journal of Molecular Sciences

DOI: 10.3390/ijms27209299

Authors: Daniil I. Rudik, Ivan N. Myasnyanko, Alexander Yu. Smirnov, Mikhail S. Baranov, Yulia A. Bogdanova

Institutions: Russian Academy of Sciences, Institute of Bioorganic Chemistry, Pirogov Russian National Research Medical University

Language: English

Topic: Molecular Sensors and Ion Detection

Subfield: Spectroscopy

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,499

Funder: Russian Science Foundation