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

Abstract

This article describes the design and biological properties of a BODIPY FL-labeled monoterpenoid BF 2 -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.

Remodeling of the Enterococcal Cell Envelope during Surface Penetration Promotes Intrinsic Resistance to Stress

“…To visualize putative N- acetylglucosamine-containing polymers and residues that constitute the peptidoglycan layer of the cell wall ( 29 ), samples were incubated with 5 μg/mL of the lectin wheat germ agglutinin (WGA) directly conjugated to Texas Red (Thermo Fisher Scientific) and analyzed as previously described in reference 21 . The intracellular lipid content was evaluated with either the anionic lipid-specific FM 5-95 ( N -3-trimethylammoniumpropyl-4-6-4-diethylaminophenyl-hexatrienyl pyridinium dibromide; Thermo Fisher Scientific) or the neutral lipid-specific BODIPY (boron-dipyrromethene 4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indacene 493/503; Life Technologies) as reported ( 107 , 108 ). Briefly, enterococcal cells were fixed with 4% paraformaldehyde-DPBS (BioWorld) for 15 min, pelleted down, and treated with either BODIPY (4 μg/mL) or FM 5-95 (16 μg/mL) in DPBS, followed by incubation for 60 min in the dark at room temperature or 37°C, respectively.…”

“…Samples of nonpenetrating and agar-penetrating cells were diluted down until an absorbance of 0.8 OD 600 in DPBS and stained with BODIPY at 4 μg/mL ( 108 ) or FM 4-64FX ( N -3-triethylammoniumpropyl-4-p-diethylaminophenyl-hexatrienyl pyridinium dibromide; Thermo Fisher Scientific) at 20 μg/mL ( 60 ) for 60 min in the dark at room temperature and 37°C, respectively. Samples were washed twice with DPBS and subsequently fixed with 4% paraformaldehyde-DPBS (BioWorld) overnight at 4°C.…”

BODIPY Conjugates as Functional Compounds for Medical Diagnostics and Treatment

“…Among the studied compounds, only the 3-O-acetyl-betulinic acid-derived BODIPY FL conjugate 34 (Scheme 22) holding an ethylendiamine spacer was cytotoxic for human breast adenocarcinoma cells MCF7 but not cytotoxic for all other cell lines. Recently, the authors [40] presented the results of spectral and biological studies of the BODIPY phosphor with myrtenol 35 (Scheme 23). Studies have shown that the conjugate efficiently absorbs (ε ~10 5 mol•L −1 ) and fluoresces (from ~75 to ~100%) regardless of the medium properties in the region at 500-518 nm (Figure 9).…”

On the Use of Polymer-Based Composites for the Creation of Optical Sensors: A Review

“…Another approach to the development of a targeted measurement system is the chemical modification of an indicator molecule in order to give it the ability to bind to a specific target or to penetrate the lipid membrane in a biological sample under study. For example, meso-substituted BODIPY with the butanoic acid residue was covalently binded to the thioterpene moiety was performed to examine the membranotropic effect to erythrocytes and to evaluate the practical application of the conjugate in bioimaging [ 237 ]. The obtained dye exhibited high fluorescence quantum yield at 514–519 nm and high photostability.…”