Design, Spectral Characteristics, and Possibilities for Practical Application of BODIPY FL-Labeled Monoterpenoid

Galina B Guseva; Elena V Antina; Mikhail B Berezin; Roman S Pavelyev; Airat R Kayumov; Olga V Ostolopovskaya; Ilmir R Gilfanov; Larisa L Frolova; Alexander V Kutchin; Rustem F Akhverdiev; Svetlana A Lisovskaya; Elena Y Trizna; Olga A Lodochnikova; Daut R Islamov; Sergey V Efimov; Vladimir V Klochkov; Ilya A Khodov; Sergei V Boichuk; Liliya E Nikitina

doi:10.1021/acsabm.1c00550

Design, Spectral Characteristics, and Possibilities for Practical Application of BODIPY FL-Labeled Monoterpenoid

ACS Appl Bio Mater. 2021 Aug 16;4(8):6227-6235. doi: 10.1021/acsabm.1c00550. Epub 2021 Aug 4.

Authors

Galina B Guseva¹, Elena V Antina¹, Mikhail B Berezin¹, Roman S Pavelyev², Airat R Kayumov², Olga V Ostolopovskaya², Ilmir R Gilfanov³, Larisa L Frolova⁴, Alexander V Kutchin⁴, Rustem F Akhverdiev², Svetlana A Lisovskaya⁵, Elena Y Trizna², Olga A Lodochnikova^{2

6}, Daut R Islamov^{2

6}, Sergey V Efimov², Vladimir V Klochkov², Ilya A Khodov^{1

2}, Sergei V Boichuk³, Liliya E Nikitina^{2

3}

Affiliations

¹ G.A. Krestov Institute of Solution Chemistry of Russian Academy of Sciences (ISC RAS), 153045 Ivanovo, Russian Federation.
² Kazan Federal University, 420008 Kazan, Russian Federation.
³ Kazan State Medical University, 420012 Kazan, Russian Federation.
⁴ Institute of Chemistry, Federal Research Center "Komi Scientific Centre", 167000 Syktyvkar, Russian Federation.
⁵ Kazan State Medical University, Scientific Research Institute of Epidemiology and Microbiology, 420012 Kazan, Russian Federation.
⁶ Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of Russian Academy of Sciences, 420008 Kazan, Russian Federation.

PMID: 35006906
DOI: 10.1021/acsabm.1c00550

Abstract

This article describes the design and biological properties of a BODIPY FL-labeled monoterpenoid BF₂-meso-(4-((1″R)-6″,6″-dimethylbicyclo[3.1.1]hept-2″-ene-2″)yl-methoxycarbonylpropyl)-3,3',5,5'-tetramethyl-2,2'-dipyrromethene conjugate (BODIPYmyrt). The fluorophore was characterized using X-ray, NMR, MS, and UV/vis spectroscopy. The conjugate exhibits a high quantum yield (to ∼100%) in the region 515-518 nm. BODIPYmyrt effectively penetrates the membranes of the bacterial and fungal cells and therefore can be used to examine the features of a broad spectrum of Gram-positive and Gram-negative bacteria and pathogenic fungi as well. Moreover, BODIPYmyrt exhibits a moderate tropism to the subcellular structures in mammalian cells (e.g., mitochondria), thereby providing an attractive scaffold for fluorophores to examine these particular organelles.

Keywords: (+)-myrtenol; BODIPY FL-labeled monoterpenoid; biovisualization; conjugate; spectral properties; structure.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Anti-Bacterial Agents*
Boron Compounds
Fluorescent Dyes / chemistry
Gram-Negative Bacteria
Gram-Positive Bacteria
Mammals
Monoterpenes*

Substances

4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
Anti-Bacterial Agents
Boron Compounds
Fluorescent Dyes
Monoterpenes