Conjugate of meso-carboxysubstituted-BODIPY with thioterpenoid as an effective fluorescent probe: Synthesis, structure, spectral characteristics, and molecular docking

Гусева, Г. Б.; Антина, Е. В.; Березин, М. Б.; Ksenofontov, Alexander A.; Bocharov, Pavel S.; Smirnova, Anastassia S.; Pavelyev, Roman S.; Gilfanov, Ilmir R.; Пестова, С. В.; Изместьев, Е. С.; Рубцова, С. А.; Kayumov, Airat R.; Киселев, С. В.; Azizova, Zulfiya R.; Ostolopovskaya, Olga V.; Ефимов, С. В.; Клочков, В. В.; Khodov, Ilya A.; Никитина, Л. Е.

doi:10.1016/j.saa.2021.120638

Cited by 8 publications

(7 citation statements)

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“…Synthesis, purification and identification of 29 BODIPYs are described in ref. 28–38. 11 B NMR spectra of these compounds were obtained only in chloroform-d1 solvent.…”

Section: Methodsmentioning

confidence: 99%

Accurate prediction of ¹¹B NMR chemical shift of BODIPYs via machine learning

Ksenofontov

Isaev

Lukanov

et al. 2023

Phys. Chem. Chem. Phys.

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“…Synthesis, purification and identification of 29 BODIPYs are described in ref. 28–38. 11 B NMR spectra of these compounds were obtained only in chloroform-d1 solvent.…”

Section: Methodsmentioning

confidence: 99%

Accurate prediction of ¹¹B NMR chemical shift of BODIPYs via machine learning

Ksenofontov

Isaev

Lukanov

et al. 2023

Phys. Chem. Chem. Phys.

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“…This property ensures nontoxic staining of erythrocytes. 25 Furthermore, thioterpene−BODIPY 5 exhibits considerable antiplatelet and anticoagulant activities. Molecular docking revealed that conjugating BODIPY with thioterpenoids enhanced dye affinity for the platelet receptor P2Y12.…”

Section: ■ Monoterpenes and Monoterpenoidsmentioning

confidence: 99%

“…They are commonly found in various plants, including fruits, herbs, and essential oils, where they play important roles in defense mechanisms against herbivores and pathogens and aid in attracting pollinators. Several applications of monoterpenes conjugated with meso -modified BODIPYs were reported by Guseva et al (Figure A). − Changes in the BODIPY structure have been suggested to improve the properties of the dye, such as photostability and affinity of the molecule to targets. The meso -substituted BODIPY stains Gram-positive bacteria and can thus be used for the differential staining of Gram-positive and -negative bacteria in mixed cultures .…”

Section: Monoterpenes and Monoterpenoidsmentioning

confidence: 99%

“…The tested myrtenol–BODIPY 2 was localized in fungal cells (Figure B) and was also able to stain bacteria. A thioterpene moiety was introduced at the meso -position of BODIPY in subsequent studies. , The thioterpene–BODIPY conjugate 4 actively penetrates erythrocytes and is poorly removed, even after washing with phosphate-buffered saline. This property ensures nontoxic staining of erythrocytes .…”

Section: Monoterpenes and Monoterpenoidsmentioning

confidence: 99%

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Terpenes and Terpenoids Conjugated with BODIPYs: An Overview of Biological and Chemical Properties

Stanková,

Jurášek,

Hajdúch

et al. 2024

J. Nat. Prod.

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Advancements in small-molecule research have created the need for sensitive techniques to accurately study biological processes in living systems. Fluorescent-labeled probes have become indispensable tools, particularly those that use boron−dipyrromethene (BODIPY) dyes. Terpenes and terpenoids are organic compounds found in nature that offer diverse biological activities, and BODIPY-based probes play a crucial role in studying these compounds. Monoterpene−BODIPY conjugates have exhibited potential for staining bacterial and fungal cells. Sesquiterpene−BODIPY derivatives have been used to study sarcoplasmic/endoplasmic reticulum calcium ATPase (SERCA), indicating their potential for drug development. Owing to their unique properties, diterpenes have been investigated using BODIPY conjugates to evaluate their mechanisms of action. Triterpene−BODIPY conjugates have been synthesized for biological studies, with different spacers affecting their cytotoxicity. Fluorescent probes, inspired by terpenoid-containing vitamins, have also been developed. Derivatives of tocopherol, coenzyme Q10, and vitamin K1 can provide insights into their oxidation−reduction abilities. All these probes have diverse applications, including the study of cell membranes to investigate immune responses and antioxidant properties. Further research in this field can help better understand and use terpenes and terpenoids in various biological contexts.

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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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Conjugate of meso-carboxysubstituted-BODIPY with thioterpenoid as an effective fluorescent probe: Synthesis, structure, spectral characteristics, and molecular docking

Cited by 8 publications

References 50 publications

Accurate prediction of ¹¹B NMR chemical shift of BODIPYs via machine learning

Accurate prediction of ¹¹B NMR chemical shift of BODIPYs via machine learning

Terpenes and Terpenoids Conjugated with BODIPYs: An Overview of Biological and Chemical Properties

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

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Conjugate of meso-carboxysubstituted-BODIPY with thioterpenoid as an effective fluorescent probe: Synthesis, structure, spectral characteristics, and molecular docking

Cited by 8 publications

References 50 publications

Accurate prediction of 11B NMR chemical shift of BODIPYs via machine learning

Accurate prediction of 11B NMR chemical shift of BODIPYs via machine learning

Terpenes and Terpenoids Conjugated with BODIPYs: An Overview of Biological and Chemical Properties

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

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Product

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Accurate prediction of ¹¹B NMR chemical shift of BODIPYs via machine learning

Accurate prediction of ¹¹B NMR chemical shift of BODIPYs via machine learning