Design, Spectral Characteristics, Photostability, and Possibilities for Practical Application of BODIPY FL-Labeled Thioterpenoid
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 <i>meso</i>-substitu...
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MDPI AG
2022-05-01
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| Series: | Bioengineering |
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| Online Access: | https://www.mdpi.com/2306-5354/9/5/210 |
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| author | 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 |
| author_facet | 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 |
| author_sort | Galina B. Guseva |
| collection | DOAJ |
| description | 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 <i>meso</i>-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 <i>X</i>-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. |
| first_indexed | 2024-03-10T03:19:38Z |
| format | Article |
| id | doaj.art-9a292a6347e244fcbe2ef01ffad795ff |
| institution | Directory Open Access Journal |
| issn | 2306-5354 |
| language | English |
| last_indexed | 2024-03-10T03:19:38Z |
| publishDate | 2022-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Bioengineering |
| spelling | doaj.art-9a292a6347e244fcbe2ef01ffad795ff2023-11-23T10:05:47ZengMDPI AGBioengineering2306-53542022-05-019521010.3390/bioengineering9050210Design, Spectral Characteristics, Photostability, and Possibilities for Practical Application of BODIPY FL-Labeled ThioterpenoidGalina B. Guseva0Elena V. Antina1Mikhail B. Berezin2Anastassia S. Smirnova3Roman S. Pavelyev4Ilmir R. Gilfanov5Oksana G. Shevchenko6Svetlana V. Pestova7Evgeny S. Izmest’ev8Svetlana A. Rubtsova9Olga V. Ostolopovskaya10Sergey V. Efimov11Vladimir V. Klochkov12Ilfat Z. Rakhmatullin13Ayzira F. Timerova14Ilya A. Khodov15Olga A. Lodochnikova16Daut R. Islamov17Pavel V. Dorovatovskii18Liliya E. Nikitina19Sergei V. Boichuk20G.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, 1 Akademicheskaya Street, 153045 Ivanovo, RussiaG.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, 1 Akademicheskaya Street, 153045 Ivanovo, RussiaG.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, 1 Akademicheskaya Street, 153045 Ivanovo, RussiaG.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, 1 Akademicheskaya Street, 153045 Ivanovo, RussiaBiologically Active Terpenoids Laboratory, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, RussiaBiologically Active Terpenoids Laboratory, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, RussiaCenter of Collective Usage Molecular Biology, Institute of Biology, Komi Science Centre, Ural Branch of Russian Academy of Sciences, 28 Kommunisticheskaya Street, 167982 Syktyvkar, RussiaMedical Chemistry Laboratory, Institute of Chemistry, Komi Scientific Centre, Ural Branch of Russian Academy of Sciences, 48 Pervomaiskaya Street, 167000 Syktyvkar, RussiaMedical Chemistry Laboratory, Institute of Chemistry, Komi Scientific Centre, Ural Branch of Russian Academy of Sciences, 48 Pervomaiskaya Street, 167000 Syktyvkar, RussiaMedical Chemistry Laboratory, Institute of Chemistry, Komi Scientific Centre, Ural Branch of Russian Academy of Sciences, 48 Pervomaiskaya Street, 167000 Syktyvkar, RussiaBiologically Active Terpenoids Laboratory, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, RussiaBiologically Active Terpenoids Laboratory, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, RussiaBiologically Active Terpenoids Laboratory, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, RussiaBiologically Active Terpenoids Laboratory, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, RussiaBiologically Active Terpenoids Laboratory, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, RussiaG.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, 1 Akademicheskaya Street, 153045 Ivanovo, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzova Street, 420029 Kazan, RussiaLaboratory for Structural Analysis of Biomacromolecules, Kazan Scientific Center, Russian Academy of Sciences, 18 Kremlevskaya Street, 420008 Kazan, RussiaNational Research Centre “Kurchatov Institute”, 1 Academician Kurchatov Street, 123098 Moscow, RussiaBiologically Active Terpenoids Laboratory, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, RussiaBiologically Active Terpenoids Laboratory, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, RussiaThis 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 <i>meso</i>-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 <i>X</i>-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.https://www.mdpi.com/2306-5354/9/5/210fluorescent biomarkerBODIPY dyesthioterpenoiderythrocytesspectral propertiesmembranotropic effect |
| spellingShingle | 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 Design, Spectral Characteristics, Photostability, and Possibilities for Practical Application of BODIPY FL-Labeled Thioterpenoid Bioengineering fluorescent biomarker BODIPY dyes thioterpenoid erythrocytes spectral properties membranotropic effect |
| title | Design, Spectral Characteristics, Photostability, and Possibilities for Practical Application of BODIPY FL-Labeled Thioterpenoid |
| title_full | Design, Spectral Characteristics, Photostability, and Possibilities for Practical Application of BODIPY FL-Labeled Thioterpenoid |
| title_fullStr | Design, Spectral Characteristics, Photostability, and Possibilities for Practical Application of BODIPY FL-Labeled Thioterpenoid |
| title_full_unstemmed | Design, Spectral Characteristics, Photostability, and Possibilities for Practical Application of BODIPY FL-Labeled Thioterpenoid |
| title_short | Design, Spectral Characteristics, Photostability, and Possibilities for Practical Application of BODIPY FL-Labeled Thioterpenoid |
| title_sort | design spectral characteristics photostability and possibilities for practical application of bodipy fl labeled thioterpenoid |
| topic | fluorescent biomarker BODIPY dyes thioterpenoid erythrocytes spectral properties membranotropic effect |
| url | https://www.mdpi.com/2306-5354/9/5/210 |
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