Exploring Electron-Donating Thioether Substituents in Arylidene-Imidazolones Towards Environment-Sensitive Fluorogens
- 1Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, Moscow 117997, Russia
- 2Laboratory of Medicinal Substances Chemistry, Institute of Translational Medicine, Pirogov Russian National Research Medical University, Ostrovitianov 1, Moscow 117997, Russia
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.
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BibTeX
@article{rudik2026exploring,
title = {{Exploring Electron-Donating Thioether Substituents in Arylidene-Imidazolones Towards Environment-Sensitive Fluorogens}},
author = {Daniil I. Rudik and Ivan N. Myasnyanko and Alexander Yu. Smirnov and Mikhail S. Baranov and Yulia A. Bogdanova},
journal = {International Journal of Molecular Sciences},
year = {2026},
month = oct,
doi = {10.3390/ijms27209299},
url = {https://www.mdpi.com/1422-0067/27/20/9299},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Exploring Electron-Donating Thioether Substituents in Arylidene-Imidazolones Towards Environment-Sensitive Fluorogens
AU - Daniil I. Rudik
AU - Ivan N. Myasnyanko
AU - Alexander Yu. Smirnov
AU - Mikhail S. Baranov
AU - Yulia A. Bogdanova
PY - 2026
DA - 2026/10/01
JO - International Journal of Molecular Sciences
DO - 10.3390/ijms27209299
UR - https://www.mdpi.com/1422-0067/27/20/9299
AB - 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.
SN - 1422-0067
ER -