Design, Spectral Characteristics, Photostability, and Possibilities for Practical Application of BODIPY FL-Labeled Thioterpenoid

Galina B Guseva; Elena V Antina; Mikhail B Berezin; Anastassia S Smirnova; Roman S Pavelyev; Ilmir R Gilfanov; Oksana G Shevchenko; Svetlana V Pestova; Evgeny S Izmest'ev; Svetlana A Rubtsova; Olga V Ostolopovskaya; Sergey V Efimov; Vladimir V Klochkov; Ilfat Z Rakhmatullin; Ayzira F Timerova; Ilya A Khodov; Olga A Lodochnikova; Daut R Islamov; Pavel V Dorovatovskii; Liliya E Nikitina; Sergei V Boichuk

doi:10.3390/bioengineering9050210

Design, Spectral Characteristics, Photostability, and Possibilities for Practical Application of BODIPY FL-Labeled Thioterpenoid

Bioengineering (Basel). 2022 May 12;9(5):210. doi: 10.3390/bioengineering9050210.

Authors

Galina B Guseva¹, Elena V Antina¹, Mikhail B Berezin¹, Anastassia S Smirnova^{1

2}, Roman S Pavelyev³, Ilmir R Gilfanov^{3

4}, Oksana G Shevchenko⁵, Svetlana V Pestova⁶, Evgeny S Izmest'ev⁶, Svetlana A Rubtsova⁶, Olga V Ostolopovskaya^{3

7}, Sergey V Efimov³, Vladimir V Klochkov³, Ilfat Z Rakhmatullin³, Ayzira F Timerova³, Ilya A Khodov¹, Olga A Lodochnikova⁸, Daut R Islamov⁹, Pavel V Dorovatovskii¹⁰, Liliya E Nikitina^{3

7}, Sergei V Boichuk^{3

7}

Affiliations

¹ G.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, 1 Akademicheskaya Street, 153045 Ivanovo, Russia.
² Faculty of Fundamental and Applied Chemistry, Ivanovo State University of Chemistry and Technology, 7, Sheremetevskiy Avenue, 153000 Ivanovo, Russia.
³ Biologically Active Terpenoids Laboratory, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, Russia.
⁴ Varnishes and Paints Department, Kazan National Research Technological University, 68 K. Marksa Street, 420015 Kazan, Russia.
⁵ Center of Collective Usage Molecular Biology, Institute of Biology, Komi Science Centre, Ural Branch of Russian Academy of Sciences, 28 Kommunisticheskaya Street, 167982 Syktyvkar, Russia.
⁶ Medical Chemistry Laboratory, Institute of Chemistry, Komi Scientific Centre, Ural Branch of Russian Academy of Sciences, 48 Pervomaiskaya Street, 167000 Syktyvkar, Russia.
⁷ General and Organic Chemistry Department, Kazan State Medical University, 49 Butlerova Street, 420012 Kazan, Russia.
⁸ Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzova Street, 420029 Kazan, Russia.
⁹ Laboratory for Structural Analysis of Biomacromolecules, Kazan Scientific Center, Russian Academy of Sciences, 18 Kremlevskaya Street, 420008 Kazan, Russia.
¹⁰ National Research Centre "Kurchatov Institute", 1 Academician Kurchatov Street, 123098 Moscow, Russia.

Abstract

This paper presents the design and a comparative analysis of the structural and solvation factors on the spectral and biological properties of the BODIPY biomarker with a thioterpene fragment. Covalent binding of the thioterpene moiety to the butanoic acid residue of meso-substituted BODIPY was carried out to find out the membranotropic effect of conjugate to erythrocytes, and to assess the possibilities of its practical application in bioimaging. The molecular structure of the conjugate was confirmed via X-ray, UV/vis-, NMR-, and MS-spectra. It was found that dye demonstrates high photostability and high fluorescence quantum yield (to ~100%) at 514-519 nm. In addition, the marker was shown to effectively penetrate the erythrocytes membrane in the absence of erythrotoxicity. The conjugation of BODIPY with thioterpenoid is an excellent way to increase affinity dyes to biostructures, including blood components.

Keywords: BODIPY dyes; erythrocytes; fluorescent biomarker; membranotropic effect; spectral properties; thioterpenoid.

Abstract

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