BODIPY-17α-ethynylestradiol conjugates: Synthesis, fluorescence properties and receptor binding affinities

Osati, Samira; Ali, Hasrat; Marques, Fernanda; Paquette, Michel; Beaudoin, Simon; Guérin, Brigitte; Leyton, Jeffrey V.; Lier, Johan E. van

doi:10.1016/j.bmcl.2016.12.052

Cited by 15 publications

(17 citation statements)

References 30 publications

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“…Studies of another series of BODIPY-estradiol conjugates 77-83 (Scheme 42), carried out by Samira Osati and colleagues in [60], were aimed at modifying both steroid fragments and a carbon spacer chain. The absorption of conjugates 77-83 is characterized by a spectrum in the visible region with a maximum of the most intense long-wave S o -S 1 band in the range 502-504 nm and the emission band maximum at 519-536 nm.…”

Section: Bodipy Conjugates With Steroidsmentioning

confidence: 99%

“…In contrast, conjugate 83 also has a long spacer chain devoid of binding affinity with ERα, due to the polar nature of a triazine fragment, which can interfere with the binding process. The authors [60] note the need for further studies of conjugate 82 with high RBA values in vitro and in vivo for evaluating their potential for fluorescent visualization of ER for patient breast cancer.…”

Section: Bodipy Conjugates With Steroidsmentioning

confidence: 99%

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BODIPY Conjugates as Functional Compounds for Medical Diagnostics and Treatment

et al. 2022

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Fluorescent dyes absorbing and emitting in the visible and near-IR regions are promising for the development of fluorescent probes for labeling and bio-visualization of body cells. The ability to absorb and emit in the long-wavelength region increases the efficiency of recording the spectral signals of the probes due to the higher permeability of the skin layers. Compared to other fluorescent dyes, BODIPYs are attractive due to their excellent photophysical properties–narrow absorption and emission, intense fluorescence, simple signal modulation for the practical applications. As part of conjugates with biomolecules, BODIPY could act as a biomarker, but as therapeutic agent, which allows solving several problems at once-labeling or bioimaging and treatment based on the suppression of pathogenic microflora and cancer cells, which provides a huge potential for practical application of BODIPY conjugates in medicine. The review is devoted to the discussion of the recent, promising directions of BODIPY application in the field of conjugation with biomolecules. The first direction is associated with the development of BODIPY conjugates with drugs, including compounds of platinum, paclitaxel, chlorambucil, isoxazole, capsaicin, etc. The second direction is devoted to the labeling of vitamins, hormones, lipids, and other biomolecules to control the processes of their transport, localization in target cells, and metabolism. Within the framework of the third direction, the problem of obtaining functional optically active materials by conjugating BODIPY with other colored and fluorescent particles, in particular, phthalocyanines, is being solved.

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Section: Bodipy Conjugates With Steroidsmentioning

confidence: 99%

Section: Bodipy Conjugates With Steroidsmentioning

confidence: 99%

BODIPY Conjugates as Functional Compounds for Medical Diagnostics and Treatment

et al. 2022

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“…39 HFBI-RGD was puried by our laboratory. 1 H NMR and 13 C NMR spectra were recorded on a Bruker AV400 MHz spectrometer. HRMS results were obtained with a Bruker microTof-QII instrument.…”

Section: Materials and Instrumentsmentioning

confidence: 99%

“…Dichloromethane was removed by evaporation to obtain the crude product,which was further puried by column chromatography (silica gel) using CH 2 Cl 2 /hexane ¼ 2/1 as eluent to yield a red solid (287 mg, yield 14.4%). 1 Synthesis of 3a-3c. Compound 1 (45.9 mg, 0.12 mmol) and (29.7 mg, 0.1 mmol) 2 were dissolved in 10 mL benzene, 0.12 mL piperidine and 0.12 mL acetic acid, and this solution was then injected with a syringe.…”

Section: Synthesismentioning

confidence: 99%

The self-assembly of monosubstituted BODIPY and HFBI-RGD

et al. 2018

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“…Recently, 17α‐E2‐linked BODIPYs were reported by Osati et al . while we were working on this paper ,. Nevertheless, such conjugates are still needed to be investigated in different aspects of breast carcinogenesis due to diverse chemical modifications to improve the conjugate characteristics, such as water solubility, photophysical properties and cellular internalization behaviors.…”

Section: Introductionmentioning

confidence: 99%

Novel 17α‐Etinylestradiol‐Substituted BODIPY Dyes: Synthesis, Photophysical Properties and Fluorescence Imaging Studies in Breast Cancer Cell Lines

et al. 2018

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Novel 17a-Etinylestradiol-substituted 4,4-difluoro-4-borata-3a,4a-diaza-s-indacene (BODIPY) dyes were prepared as fluorescent imaging probes. The identities of newly synthesized dyes were fully characterized by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, and 1 H and 13 C nuclear magnetic resonance (NMR) spectroscopy. The photophysical properties (molar extinction coefficient, fluorescence lifetime and fluorescence quantum yield) of the compounds were investigated by means of absorption and fluorescence spectroscopies in dilute ethanol solutions. We were also interested in the live cell imaging studies of the 17a-etinylestradiol-linked BODIPYs, by particularly concerning their ability to monitoring breast cancer cell lines. These studies showed that one of the novel 17a-etinylestradiol-substituted BODIPY dyes was able to distinguish breast cancer subtypes. This is the first study sub-categorizing breast cancer via fluorescent-tagged estrogen analog, which is critical in terms of improving the molecular diagnostics and eliminating the drawbacks of available methods. These studies are very selective up to date for a BODIPY-based fluorescent label and define a pivotal biological importance of BODIPY as a building block in live cell imaging studies.

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BODIPY-17α-ethynylestradiol conjugates: Synthesis, fluorescence properties and receptor binding affinities

Cited by 15 publications

References 30 publications

BODIPY Conjugates as Functional Compounds for Medical Diagnostics and Treatment

BODIPY Conjugates as Functional Compounds for Medical Diagnostics and Treatment

The self-assembly of monosubstituted BODIPY and HFBI-RGD

Novel 17α‐Etinylestradiol‐Substituted BODIPY Dyes: Synthesis, Photophysical Properties and Fluorescence Imaging Studies in Breast Cancer Cell Lines

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