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Amine-Reactive BODIPY Dye: Spectral Properties and Application for Protein Labeling

A boron-dipyrromethene (BODIPY) derivative reactive towards amino groups of proteins (NHS-Ph-BODIPY) was synthesized. Spectroscopic and photophysical properties of amine-reactive NHS-Ph-BODIPY and its non-reactive precursor (COOH-Ph-BODIPY) in a number of organic solvents were investigated. Both flu...

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Autores principales: Ksenofontova, Ksenia V., Kerner, Anastasia A., Ksenofontov, Alexander A., Shagurin, Artyom Yu., Bocharov, Pavel S., Lukanov, Michael M., Kayumov, Airat R., Zhuravleva, Darya E., Iskhakova, Zalina I., Molchanov, Evgeniy E., Merkushev, Dmitriy A., Khodov, Ilya A., Marfin, Yuriy S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9692440/
https://www.ncbi.nlm.nih.gov/pubmed/36432012
http://dx.doi.org/10.3390/molecules27227911
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author Ksenofontova, Ksenia V.
Kerner, Anastasia A.
Ksenofontov, Alexander A.
Shagurin, Artyom Yu.
Bocharov, Pavel S.
Lukanov, Michael M.
Kayumov, Airat R.
Zhuravleva, Darya E.
Iskhakova, Zalina I.
Molchanov, Evgeniy E.
Merkushev, Dmitriy A.
Khodov, Ilya A.
Marfin, Yuriy S.
author_facet Ksenofontova, Ksenia V.
Kerner, Anastasia A.
Ksenofontov, Alexander A.
Shagurin, Artyom Yu.
Bocharov, Pavel S.
Lukanov, Michael M.
Kayumov, Airat R.
Zhuravleva, Darya E.
Iskhakova, Zalina I.
Molchanov, Evgeniy E.
Merkushev, Dmitriy A.
Khodov, Ilya A.
Marfin, Yuriy S.
author_sort Ksenofontova, Ksenia V.
collection PubMed
description A boron-dipyrromethene (BODIPY) derivative reactive towards amino groups of proteins (NHS-Ph-BODIPY) was synthesized. Spectroscopic and photophysical properties of amine-reactive NHS-Ph-BODIPY and its non-reactive precursor (COOH-Ph-BODIPY) in a number of organic solvents were investigated. Both fluorescent dyes were characterized by green absorption (521–532 nm) and fluorescence (538–552 nm) and medium molar absorption coefficients (46,500–118,500 M(−1)·cm(−1)) and fluorescence quantum yields (0.32 – 0.73). Solvent polarizability and dipolarity were found to play a crucial role in solvent effects on COOH-Ph-BODIPY and NHS-Ph-BODIPY absorption and emission bands maxima. Quantum-chemical calculations were used to show why solvent polarizability and dipolarity are important as well as to understand how the nature of the substituent affects spectroscopic properties of the fluorescent dyes. NHS-Ph-BODIPY was used for fluorescent labeling of a number of proteins. Conjugation of NHS-Ph-BODIPY with bovine serum albumin (BSA) resulted in bathochromic shifts of absorption and emission bands and noticeable fluorescence quenching (about 1.5 times). It was demonstrated that the sensitivity of BSA detection with NHS-Ph-BODIPY was up to eight times higher than with Coomassie brilliant blue while the sensitivity of PII-like protein PotN (PotN) detection with NHS-Ph-BODIPY and Coomassie brilliant blue was almost the same. On the basis of the molecular docking results, the most probable binding sites of NHS-Ph-BODIPY in BSA and PotN and the corresponding binding free energies were estimated.
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spelling pubmed-96924402022-11-26 Amine-Reactive BODIPY Dye: Spectral Properties and Application for Protein Labeling Ksenofontova, Ksenia V. Kerner, Anastasia A. Ksenofontov, Alexander A. Shagurin, Artyom Yu. Bocharov, Pavel S. Lukanov, Michael M. Kayumov, Airat R. Zhuravleva, Darya E. Iskhakova, Zalina I. Molchanov, Evgeniy E. Merkushev, Dmitriy A. Khodov, Ilya A. Marfin, Yuriy S. Molecules Article A boron-dipyrromethene (BODIPY) derivative reactive towards amino groups of proteins (NHS-Ph-BODIPY) was synthesized. Spectroscopic and photophysical properties of amine-reactive NHS-Ph-BODIPY and its non-reactive precursor (COOH-Ph-BODIPY) in a number of organic solvents were investigated. Both fluorescent dyes were characterized by green absorption (521–532 nm) and fluorescence (538–552 nm) and medium molar absorption coefficients (46,500–118,500 M(−1)·cm(−1)) and fluorescence quantum yields (0.32 – 0.73). Solvent polarizability and dipolarity were found to play a crucial role in solvent effects on COOH-Ph-BODIPY and NHS-Ph-BODIPY absorption and emission bands maxima. Quantum-chemical calculations were used to show why solvent polarizability and dipolarity are important as well as to understand how the nature of the substituent affects spectroscopic properties of the fluorescent dyes. NHS-Ph-BODIPY was used for fluorescent labeling of a number of proteins. Conjugation of NHS-Ph-BODIPY with bovine serum albumin (BSA) resulted in bathochromic shifts of absorption and emission bands and noticeable fluorescence quenching (about 1.5 times). It was demonstrated that the sensitivity of BSA detection with NHS-Ph-BODIPY was up to eight times higher than with Coomassie brilliant blue while the sensitivity of PII-like protein PotN (PotN) detection with NHS-Ph-BODIPY and Coomassie brilliant blue was almost the same. On the basis of the molecular docking results, the most probable binding sites of NHS-Ph-BODIPY in BSA and PotN and the corresponding binding free energies were estimated. MDPI 2022-11-16 /pmc/articles/PMC9692440/ /pubmed/36432012 http://dx.doi.org/10.3390/molecules27227911 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
Ksenofontova, Ksenia V.
Kerner, Anastasia A.
Ksenofontov, Alexander A.
Shagurin, Artyom Yu.
Bocharov, Pavel S.
Lukanov, Michael M.
Kayumov, Airat R.
Zhuravleva, Darya E.
Iskhakova, Zalina I.
Molchanov, Evgeniy E.
Merkushev, Dmitriy A.
Khodov, Ilya A.
Marfin, Yuriy S.
Amine-Reactive BODIPY Dye: Spectral Properties and Application for Protein Labeling
title Amine-Reactive BODIPY Dye: Spectral Properties and Application for Protein Labeling
title_full Amine-Reactive BODIPY Dye: Spectral Properties and Application for Protein Labeling
title_fullStr Amine-Reactive BODIPY Dye: Spectral Properties and Application for Protein Labeling
title_full_unstemmed Amine-Reactive BODIPY Dye: Spectral Properties and Application for Protein Labeling
title_short Amine-Reactive BODIPY Dye: Spectral Properties and Application for Protein Labeling
title_sort amine-reactive bodipy dye: spectral properties and application for protein labeling
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9692440/
https://www.ncbi.nlm.nih.gov/pubmed/36432012
http://dx.doi.org/10.3390/molecules27227911
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