Meta-CF3-Substituted Analogues of the GFP Chromophore with Remarkable Solvatochromism

Author:

Perfilov Maxim1ORCID,Zaitseva Elvira1,Baleeva Nadezhda12,Kublitski Vadim1,Smirnov Alexander123ORCID,Bogdanova Yulia1ORCID,Krasnova Svetlana1,Myasnyanko Ivan12,Mishin Alexander1ORCID,Baranov Mikhail12ORCID

Affiliation:

1. Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, Moscow 117997, Russia

2. Laboratory of Medicinal Substances Chemistry, Institute of Translational Medicine, Pirogov Russian National Research Medical University, Ostrovitianov 1, Moscow 117997, Russia

3. Center of Molecular and Cellular Biology, Skolkovo Institute of Science and Technology, Bolshoi Blvd. 30, Bld. 1, Moscow 121205, Russia

Abstract

In this work, we have shown that the introduction of a trifluoromethyl group into the me-ta-position of arylidene imidazolones (GFP chromophore core) leads to a dramatic increase in their fluorescence in nonpolar and aprotic media. The presence of a pronounced solvent-dependent gradation of fluorescence intensity makes it possible to use these substances as fluorescent polarity sensors. In particular, we showed that one of the created compounds could be used for selective labeling of the endoplasmic reticulum of living cells.

Funder

Ministry of Science and Higher Education of the Russian Federation

Publisher

MDPI AG

Subject

Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Computer Science Applications,Spectroscopy,Molecular Biology,General Medicine,Catalysis

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