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.
Galina B Guseva  1 ,  Elena V Antina  1 ,  Mikhail B Berezin  1 ,  Roman S Pavelyev  2 ,  Airat R Kayumov  2 ,  Olga V Ostolopovskaya  2 ,  Ilmir R Gilfanov  3 ,  Larisa L Frolova  4 ,  Alexander V Kutchin  4 ,  Rustem F Akhverdiev  2 ,  Svetlana A Lisovskaya  5 ,  Elena Y Trizna  2 ,  Olga A Lodochnikova  2  6 ,  Daut R Islamov  2  6 ,  Sergey V Efimov  2 ,  Vladimir V Klochkov  2 ,  Ilya A Khodov  1  2 ,  Sergei V Boichuk  3 ,  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.
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