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Molecules, том 27, издание 22, номер публикации: 7911

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

Kerner Anastasia A.
Shagurin Artyom Yu.
Lukanov Michael M.
Molchanov Evgeniy E.
Merkushev Dmitriy A.
Marfin Yuriy S.
Тип документаJournal Article
Дата публикации2022-11-16
ИздательMultidisciplinary Digital Publishing Institute (MDPI)
Название журналаMolecules
Квартиль по SCImagoQ1
Квартиль по Web of ScienceQ2
Импакт-фактор 20214.93
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Краткое описание

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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1. Ksenofontova K. V. и др. Amine-Reactive BODIPY Dye: Spectral Properties and Application for Protein Labeling // Molecules. 2022. Т. 27. № 22. С. 7911.


DO - 10.3390/molecules27227911

UR -

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

T2 - Molecules

AU - Ksenofontova, Ksenia V.

AU - Kerner, Anastasia A.

AU - Ksenofontov, Alexander A.

AU - Shagurin, Artyom Yu.

AU - Bocharov, Pavel S.

AU - Lukanov, Michael M.

AU - Kayumov, Airat R.

AU - Zhuravleva, Darya E.

AU - Iskhakova, Zalina I.

AU - Molchanov, Evgeniy E.

AU - Merkushev, Dmitriy A.

AU - Khodov, Ilya A.

AU - Marfin, Yuriy S.

PY - 2022

DA - 2022/11/16


SP - 7911

IS - 22

VL - 27

SN - 1420-3049

ER -

BibTex |


doi = {10.3390/molecules27227911},

url = {},

year = 2022,

month = {nov},

publisher = {{MDPI} {AG}},

volume = {27},

number = {22},

pages = {7911},

author = {Ksenia V. Ksenofontova and Anastasia A. Kerner and Alexander A. Ksenofontov and Artyom Yu. Shagurin and Pavel S. Bocharov and Michael M. Lukanov and Airat R. Kayumov and Darya E. Zhuravleva and Zalina I. Iskhakova and Evgeniy E. Molchanov and Dmitriy A. Merkushev and Ilya A. Khodov and Yuriy S. Marfin},

title = {Amine-Reactive {BODIPY} Dye: Spectral Properties and Application for Protein Labeling},

journal = {Molecules}


Ksenofontova, Ksenia V., et al. “Amine-Reactive BODIPY Dye: Spectral Properties and Application for Protein Labeling.” Molecules, vol. 27, no. 22, Nov. 2022, p. 7911. Crossref,