Meso-substituted-BODIPY based fluorescent biomarker: Spectral characteristics, photostability and possibilities for practical application

© 2020 Elsevier B.V. A fluorescent biomarker based on the boron(III) complex with meso-4-methoxycarbonylbutyl-substituted 3,3′,5,5′-tetramethyl-2,2′-dipyrromethene (BODIPY) was synthesized. The BODIPY exhibits a large extinction coefficient (lgε ∼4.82–5.00) at 496–501 nm and high fluorescence quantum yield (∼77–100 %) in the blue-green region of the spectrum (509–518 nm). The maximal fluorescence quantum yield (φ) is observed in non-polar media (∼100 %) while φ slightly decreases to ∼90 % in alcohols (with the exception of octanol-1) and to ∼77 % in electron-donating dimethyl sulfoxide (DMSO). The BODIPY fluorophore demonstrates high photostability with the half-life of 41.4 and 91 h in toluene and cyclohexane, respectively. The proposed luminophore preferentially stains gram-positive bacteria and can be used for differential staining of gram-positive and gram-negative bacteria in mixed cultures. BODIPY also accumulates in the cytoplasm of the mammalian cells giving polar micro-speckled staining pattern which is more intensive in the tumor cells when compared to the fibroblasts. The pronounced affinity of BODIPY to mitochondria of eukaryotic cells could be used for specific staining of these organelles

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

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