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

Гусева, Г. Б.; Антина, Е. В.; Березин, М. Б.; Pavelyev, Roman S.; Kayumov, Airat R.; Sharafutdinov, Irshad; Lisovskaya, Svetlana А.; Лодочникова, О. А.; Islamov, Daut R.; Usachev, Konstantin S.; Boichuk, Sergei; Никитина, Л. Е.

doi:10.1016/j.jphotochem.2020.112783

Cited by 21 publications

(19 citation statements)

References 44 publications

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“…The molar absorption coefficient logarithm (log ε) of the first intensive band of compound 3 is relatively high, and it is in the range of 4.63–4.78 (Table ). It is comparable to the log ε values of the structural analogues. , …”

Section: Results and Discussionsupporting

confidence: 66%

“…BF 2 complex with ms -methoxycarbonylpropyl-substituted dipyrromethene 1 was synthesized according to the procedure previously reported. − …”

Section: Methodsmentioning

confidence: 99%

“…In our recent studies, we described the biomarkers based on the BODIPYs with an ester group ((−(CH 2 ) n COOCH 3 ), n = 3 or 4) into dipyrromethene meso -spacer ( [BF 2 dpm] ). , The meso-substituted BODIPYs preferentially stained Gram-positive bacteria and were suggested to be useful in distinguishing between Gram-positive bacteria and Gram-negative bacteria in mixed cultures . We showed that these luminophores accumulate in the cytoplasm of mammalian cells and exhibit a polar micro-speckled staining pattern that is more intensive in tumor cells compared to the nontransformed fibroblasts. , Moreover, [BF 2 dpm] can be used as a fluorescent marker when assessing the features and structural changes of cellular membranes of mammalian and fungal cells.…”

Section: Introductionmentioning

confidence: 99%

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

Гусева

Антина

Березин

et al. 2021

ACS Appl. Bio Mater.

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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.

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Section: Results and Discussionsupporting

confidence: 66%

“…BF 2 complex with ms -methoxycarbonylpropyl-substituted dipyrromethene 1 was synthesized according to the procedure previously reported. − …”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Гусева

Антина

Березин

et al. 2021

ACS Appl. Bio Mater.

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“…The stability of luminophores under the influence of UV irradiation is an important indicator for their practical use, including as fluorescent biomarkers. Our previous studies [ 21 , 22 ] showed that the photochemical degradation of open-chain oligopyrroles complexes occur due to redox processes involving oxygen, pyrrole and meso -substituents and heteroatoms. The nature of the medium had a significant effect on the efficiency of the photodegradation processes.…”

Section: Resultsmentioning

confidence: 99%

Spectroscopic and In Vitro Investigations of Boron(III) Complex with Meso-4-Methoxycarbonylpropylsubstituted Dipyrromethene for Fluorescence Bioimaging Applications

et al. 2020

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This study focuses on the behavior of a new fluorescent marker for labeling individual biomolecules and staining cell organelles developed on a meso-substituted BODIPY platform. Boron(III) complex with meso-4-methoxycarbonylpropylsubstituted 3,3’,5,5’-tetramethyl-2,2′-dipyrromethene has been synthesized and identified via visible, UV-, NMR- and MS-spectra X-ray. The behavior of fluorophore in solutions has been studied with various experimental techniques. It has been found that luminophore exhibits a high quantum yield (almost ~100–75%) in the blue-green region (513–520 nm) and has high photostability. In addition, biological analysis indicates that the fluorophore exhibits a tendency to effectively penetrate into cell membranes. On the other hand, the proposed BODIPY can be used to study the significant differences among a large number of pathogens of mycotic infections, as well as to visualize structural changes in the plasma membrane, which is necessary for the clearance of mammalian cells undergoing apoptotic cell death.

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“…Fluorescence bioimaging allows for the acquisition of images of whole cells or cell compartments in a quick and simple way [1]. For a long time it relied on luminescent molecules that can be tailor-made to target specific organelles, membranes [2,3], or bio macromolecules (e.g., DNA, proteins) [4][5][6][7]. However, only a few of these chromophores are approved for use in the human body because of their potential toxicity [8].…”

Section: Introductionmentioning

confidence: 99%

FRET-mediated quenching of BODIPY fluorescent nanoparticles by methylene blue and its application to bacterial imaging

Grazon

Clavier

et al. 2022

Photochem Photobiol Sci

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High resolution and a good signal to noise ratio are a requirement in cell imaging. However, after labelling with fluorescent entities, and after several washing steps, there is often an unwanted fluorescent background that reduces the images resolution. For this purpose, we developed an approach to remove the signal from extra-cellular fluorescent nanoparticles (FNPs) during bacteria imaging, without the need for any washing steps. Our idea is to use methylene blue to quench > 90% of the emission of BODIPY-based fluorescent polymer nanoparticle by a FRET process. This "Hide-and-Seek Game" approach offers a novel strategy to apply fluorescence quenching in bioimaging to improve image accuracy.

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

Cited by 21 publications

References 44 publications

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

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

Spectroscopic and In Vitro Investigations of Boron(III) Complex with Meso-4-Methoxycarbonylpropylsubstituted Dipyrromethene for Fluorescence Bioimaging Applications

FRET-mediated quenching of BODIPY fluorescent nanoparticles by methylene blue and its application to bacterial imaging

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