Conjugate of meso-carboxysubstituted-BODIPY with thioterpenoid as an effective fluorescent probe: Synthesis, structure, spectral characteristics, and molecular docking

Galina B Guseva; Elena V Antina; Mikhail B Berezin; Alexander A Ksenofontov; Pavel S Bocharov; Anastassia S Smirnova; Roman S Pavelyev; Ilmir R Gilfanov; Svetlana V Pestova; Evgeny S Izmest'ev; Svetlana A Rubtsova; Airat R Kayumov; Sergei V Kiselev; Zulfiya R Azizova; Olga V Ostolopovskaya; Sergey V Efimov; Vladimir V Klochkov; Ilya A Khodov; Liliya E Nikitina

doi:10.1016/j.saa.2021.120638

Conjugate of meso-carboxysubstituted-BODIPY with thioterpenoid as an effective fluorescent probe: Synthesis, structure, spectral characteristics, and molecular docking

Spectrochim Acta A Mol Biomol Spectrosc. 2022 Mar 5:268:120638. doi: 10.1016/j.saa.2021.120638. Epub 2021 Nov 18.

Authors

Galina B Guseva¹, Elena V Antina², Mikhail B Berezin², Alexander A Ksenofontov², Pavel S Bocharov³, Anastassia S Smirnova³, Roman S Pavelyev⁴, Ilmir R Gilfanov⁵, Svetlana V Pestova⁶, Evgeny S Izmest'ev⁶, Svetlana A Rubtsova⁶, Airat R Kayumov⁴, Sergei V Kiselev⁵, Zulfiya R Azizova⁵, Olga V Ostolopovskaya⁴, Sergey V Efimov⁴, Vladimir V Klochkov⁴, Ilya A Khodov², Liliya E Nikitina⁷

Affiliations

¹ G.A. Krestov Institute of Solution Chemistry of Russian Academy of Sciences, 1 Akademicheskaya st., 153045 Ivanovo, Russia. Electronic address: gbg@isc-ras.ru.
² G.A. Krestov Institute of Solution Chemistry of Russian Academy of Sciences, 1 Akademicheskaya st., 153045 Ivanovo, Russia.
³ G.A. Krestov Institute of Solution Chemistry of Russian Academy of Sciences, 1 Akademicheskaya st., 153045 Ivanovo, Russia; Ivanovo State University of Chemistry and Technology, 7, Sheremetevskiy Avenue, 153000 Ivanovo, Russia.
⁴ Kazan Federal University, 18 Kremlevskaya st., 420008 Kazan, Russia.
⁵ Kazan State Medical University, 49 Butlerova st., 420012 Kazan, Russia.
⁶ Institute of Chemistry, Federal Research Center "Komi Scientific Centre", Ural Branch, Russian Academy of Sciences, ul. Pervomaiskaya 48, 167000 Syktyvkar, Russia.
⁷ Kazan State Medical University, 49 Butlerova st., 420012 Kazan, Russia; Kazan Federal University, 18 Kremlevskaya st., 420008 Kazan, Russia.

PMID: 34840052
DOI: 10.1016/j.saa.2021.120638

Abstract

This paper is devoted to the design of a fluorescent probe based on meso-carboxysubstituted-BODIPY with a thioterpene fragment. The functional replacement of the methoxy group in the BODIPY molecule on a thioterpene fragment was carried out in order to find out the antiplatelet and anticoagulant action mechanisms of thioterpenoids and to assess the membrane and receptor factors contributions. The molecular structure of the conjugate was confirmed via UV/vis-, NMR- and MS-spectra. It is found that the probe is a high fluorescence quantum yield (to ∼ 100%) in the blue-green region at 509-516 nm. Molecular docking of all studied molecules showed that the BODIPY with terpenoid conjugation is an excellent way to increase their affinity to platelet receptor P2Y₁₂.

Keywords: BODIPY; Conjugate; Molecular docking; Spectral properties; Structure; Thioterpenoid.

MeSH terms

Boron Compounds*
Fluorescent Dyes*
Molecular Docking Simulation
Molecular Structure

Substances

4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
Boron Compounds
Fluorescent Dyes