Rational Design and Synthesis of Large Stokes Shift 2,6-Sulphur-Disubstituted BODIPYs for Cell Imaging

Reese, Abigail E.; Lochenie, Charles; Geddis, Ailsa; Machado, Luana A.; Souza, Marcos C. de; Marques, Flávia Ferreira de Carvalho; Simone, C. A. De; Gouvêa, Marcos Martins; Pedrosa, Leandro F.; Júnior, Eufrânio N. da Silva; Vendrell, Marc

doi:10.3390/chemosensors10010019

Cited by 3 publications

(2 citation statements)

References 69 publications

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“…Grignard reaction with MeMgBr was also performed with 3a , which very efficiently produced the methyl-substituted BODIPY at the boron center ( 5a ) in 84% yield. Finally, N -chlorosuccinamide (NCS)-mediated thiolation was performed easily at C2 and C6 with 4-methyl benzothiol to furnish 5b in excellent yield (81%) . All of these reactions confirmed that the meso -morpholino BODIPYs can undergo various types of reactions to produce a library of functionalized BODIPYs with a variety of optoelectronic properties.…”

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confidence: 79%

meso-Methyl Amination of BODIPYs by Regiospecific Cross Dehydrogenative Coupling via Direct C(sp³)–N(sp³) Bond Formation

Dutta,

Wadawale,

Mula

2024

Org. Lett.

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Herein, we report a direct meso-methyl amination of BODIPY dyes by C(sp 3 )−N(sp 3 ) bond formation using PIDA as an oxidant with a wide range of aliphatic secondary amines. This metal free cross dehydrogenative coupling reaction is regiospecific at the meso-methyl position of BODIPY in the presence of C1, C3, C5, and C7 methyl groups. Detailed nuclear magnetic resonance spectroscopy, high-resolution mass spectrometry, and X-ray crystallographic studies were performed to establish the reaction mechanism and the regiospecificity of the reaction. Finally, the photophysical and electrochemical properties of the newly synthesized dyes were evaluated and rationalized.

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confidence: 79%

meso-Methyl Amination of BODIPYs by Regiospecific Cross Dehydrogenative Coupling via Direct C(sp³)–N(sp³) Bond Formation

Dutta,

Wadawale,

Mula

2024

Org. Lett.

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“…A BODIPY core structure in molecular rotors grants large molar extinction coefficients, photostability and chemical inertness [ 17 , 18 , 19 ]. Furthermore, BODIPY-based probes can be easily functionalized at the appropriate positions to tune their sensitivity to micro-environment viscosity, polarity or temperature; increase the emission wavelength or Stokes shift; or direct the molecules to specific cells or organelles [ 20 , 21 , 22 , 23 , 24 , 25 ]. Recently, we demonstrated that the functionalization of meso -phenyl BODIPY (BDP-H) ( Figure 1 ) with a heavy-electron withdrawing –NO 2 group results in a viscosity-sensor with an extremely wide viscosity-sensitivity range (0.5–50,000 cP) [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

Exploring BODIPY-Based Sensor for Imaging of Intracellular Microviscosity in Human Breast Cancer Cells

Jurgutis

Jarockytė

Poderys

et al. 2022

IJMS

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BODIPY-based molecular rotors are highly attractive imaging tools for imaging intracellular microviscosity in living cells. In our study, we investigated the ability to detect the microviscosity of biological objects by using BDP-NO2 and BDP-H molecular rotors. We describe in detail the optical properties of BDP-NO2 and BDP-H molecular rotors in aqueous media with and without proteins, together with their accumulation dynamics and localization in live and fixed human breast cancer cells. Furthermore, we investigate the applicability of these molecules to monitor microviscosity in the organelles of human breast cancer cells by fluorescence lifetime imaging microscopy (FLIM). We demonstrate that the BDP-NO2 molecular rotor aggregates in aqueous media and is incompatible with live cell imaging. The opposite effect is observed with BDP-H which preserves its stability in aqueous media, diffuses through the plasma membrane and accumulates in lipid droplets (LDs) and the cytosol of both live and fixed MCF-7 and MDA-MB-231 cancer cells. Finally, by utilizing BDP-H we demonstrate that LD microviscosity is significantly elevated in more malignant MDA-MB-231 human breast cancer cells, as compared to MCF-7 breast cancer cells. Our findings demonstrate that BDP-H is a water-compatible probe that can be successfully applied to measure microviscosity in the LDs of living cells.

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BODIPYs as Fluorogenic Probes for Live-cell Imaging of Lipid Droplets: Photophysical and Computational Studies

Machado,

Pereira,

de Souza

et al. 2025

COS

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Introduction: Lipid droplets (LDs) serve as primary storage sites for neutral lipids within cells and are crucial for lipid metabolism. Disorders affecting LDs can contribute to the pathogenesis of common metabolic diseases such as obesity and can-cer, highlighting the importance of comprehending LD biology in health and disease contexts. background: Several synthetic methods for the preparation of BODIPYs are reported in the literature, yet the exploration of the different applications of this exciting class of fluorescent compounds is less studied and, therefore, a wide avenue of possibilities remains to be discovered. Methods: Fluorescence assays are commonly used for the detection and quantification of lipids in biological samples or lipid-rich environments. In this study, BODIPYs were synthesized and analyzed for structural confirmation. objective: synthesis of BODIPYs and evaluation of their affinity for intracellular lipid droplets Results: These compounds were subsequently evaluated for photophysical, electro-chemical (cyclic voltammetry) and theoretical analysis, followed by live-cell imaging studies to confirm their affinity for intracellular lipid droplets. method: In this study, BODIPYs were synthesized and analyzed for structural confirmation. These compounds were subsequently evaluated for photophysical, electrochemical (cyclic voltammetry) and theoretical analysis followed by live-cell imaging studies to confirm their affinity for intracellular lipid droplets. Conclusion: BODIPYs have been identified as fluorogenic probes for live-cell imag-ing studies and found to serve as efficient and selective fluorescent compounds for intracellular lipid droplets. result: BODIPYs have been identified as fluorogenic probes for live-cell imaging studies and found to serve as efficient and selective fluorescent compounds for intracellular lipid droplets.

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Rational Design and Synthesis of Large Stokes Shift 2,6-Sulphur-Disubstituted BODIPYs for Cell Imaging

Cited by 3 publications

References 69 publications

meso-Methyl Amination of BODIPYs by Regiospecific Cross Dehydrogenative Coupling via Direct C(sp³)–N(sp³) Bond Formation

meso-Methyl Amination of BODIPYs by Regiospecific Cross Dehydrogenative Coupling via Direct C(sp³)–N(sp³) Bond Formation

Exploring BODIPY-Based Sensor for Imaging of Intracellular Microviscosity in Human Breast Cancer Cells

BODIPYs as Fluorogenic Probes for Live-cell Imaging of Lipid Droplets: Photophysical and Computational Studies

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Rational Design and Synthesis of Large Stokes Shift 2,6-Sulphur-Disubstituted BODIPYs for Cell Imaging

Cited by 3 publications

References 69 publications

meso-Methyl Amination of BODIPYs by Regiospecific Cross Dehydrogenative Coupling via Direct C(sp3)–N(sp3) Bond Formation

meso-Methyl Amination of BODIPYs by Regiospecific Cross Dehydrogenative Coupling via Direct C(sp3)–N(sp3) Bond Formation

Exploring BODIPY-Based Sensor for Imaging of Intracellular Microviscosity in Human Breast Cancer Cells

BODIPYs as Fluorogenic Probes for Live-cell Imaging of Lipid Droplets: Photophysical and Computational Studies

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meso-Methyl Amination of BODIPYs by Regiospecific Cross Dehydrogenative Coupling via Direct C(sp³)–N(sp³) Bond Formation

meso-Methyl Amination of BODIPYs by Regiospecific Cross Dehydrogenative Coupling via Direct C(sp³)–N(sp³) Bond Formation