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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 meso-substituted BODIPY was carr...

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Autores principales: Guseva, Galina B., Antina, Elena V., Berezin, Mikhail B., Smirnova, Anastassia S., Pavelyev, Roman S., Gilfanov, Ilmir R., Shevchenko, Oksana G., Pestova, Svetlana V., Izmest’ev, Evgeny S., Rubtsova, Svetlana A., Ostolopovskaya, Olga V., Efimov, Sergey V., Klochkov, Vladimir V., Rakhmatullin, Ilfat Z., Timerova, Ayzira F., Khodov, Ilya A., Lodochnikova, Olga A., Islamov, Daut R., Dorovatovskii, Pavel V., Nikitina, Liliya E., Boichuk, Sergei V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9138141/
https://www.ncbi.nlm.nih.gov/pubmed/35621488
http://dx.doi.org/10.3390/bioengineering9050210
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author Guseva, Galina B.
Antina, Elena V.
Berezin, Mikhail B.
Smirnova, Anastassia S.
Pavelyev, Roman S.
Gilfanov, Ilmir R.
Shevchenko, Oksana G.
Pestova, Svetlana V.
Izmest’ev, Evgeny S.
Rubtsova, Svetlana A.
Ostolopovskaya, Olga V.
Efimov, Sergey V.
Klochkov, Vladimir V.
Rakhmatullin, Ilfat Z.
Timerova, Ayzira F.
Khodov, Ilya A.
Lodochnikova, Olga A.
Islamov, Daut R.
Dorovatovskii, Pavel V.
Nikitina, Liliya E.
Boichuk, Sergei V.
author_facet Guseva, Galina B.
Antina, Elena V.
Berezin, Mikhail B.
Smirnova, Anastassia S.
Pavelyev, Roman S.
Gilfanov, Ilmir R.
Shevchenko, Oksana G.
Pestova, Svetlana V.
Izmest’ev, Evgeny S.
Rubtsova, Svetlana A.
Ostolopovskaya, Olga V.
Efimov, Sergey V.
Klochkov, Vladimir V.
Rakhmatullin, Ilfat Z.
Timerova, Ayzira F.
Khodov, Ilya A.
Lodochnikova, Olga A.
Islamov, Daut R.
Dorovatovskii, Pavel V.
Nikitina, Liliya E.
Boichuk, Sergei V.
author_sort Guseva, Galina B.
collection PubMed
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 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.
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spelling pubmed-91381412022-05-28 Design, Spectral Characteristics, Photostability, and Possibilities for Practical Application of BODIPY FL-Labeled Thioterpenoid Guseva, Galina B. Antina, Elena V. Berezin, Mikhail B. Smirnova, Anastassia S. Pavelyev, Roman S. Gilfanov, Ilmir R. Shevchenko, Oksana G. Pestova, Svetlana V. Izmest’ev, Evgeny S. Rubtsova, Svetlana A. Ostolopovskaya, Olga V. Efimov, Sergey V. Klochkov, Vladimir V. Rakhmatullin, Ilfat Z. Timerova, Ayzira F. Khodov, Ilya A. Lodochnikova, Olga A. Islamov, Daut R. Dorovatovskii, Pavel V. Nikitina, Liliya E. Boichuk, Sergei V. Bioengineering (Basel) Article 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. MDPI 2022-05-12 /pmc/articles/PMC9138141/ /pubmed/35621488 http://dx.doi.org/10.3390/bioengineering9050210 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Guseva, Galina B.
Antina, Elena V.
Berezin, Mikhail B.
Smirnova, Anastassia S.
Pavelyev, Roman S.
Gilfanov, Ilmir R.
Shevchenko, Oksana G.
Pestova, Svetlana V.
Izmest’ev, Evgeny S.
Rubtsova, Svetlana A.
Ostolopovskaya, Olga V.
Efimov, Sergey V.
Klochkov, Vladimir V.
Rakhmatullin, Ilfat Z.
Timerova, Ayzira F.
Khodov, Ilya A.
Lodochnikova, Olga A.
Islamov, Daut R.
Dorovatovskii, Pavel V.
Nikitina, Liliya E.
Boichuk, Sergei V.
Design, Spectral Characteristics, Photostability, and Possibilities for Practical Application of BODIPY FL-Labeled Thioterpenoid
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 Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9138141/
https://www.ncbi.nlm.nih.gov/pubmed/35621488
http://dx.doi.org/10.3390/bioengineering9050210
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