Synthesis and spectral properties of estrogen- and androgen-BODIPY conjugates

Osati, Samira; Ali, Hasrat; Guérin, Brigitte; Lier, Johan E. van

doi:10.1016/j.steroids.2017.04.007

Cited by 14 publications

(9 citation statements)

References 47 publications

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“…The most potent with an IC50 value of 9 μM was the protected cytidine conjugate and the thymidine conjugate presented a considerable 17μ-HSD1 inhibitory activity (IC50 = 19 μM). Van Liera et al 33 described the synthesis of estrogen, testosterone-and 19-nortestosterone conjugates linked to BODIPY (4,4-difluoro-4-bora-3α,4α-diaza-s-indacene) or aza-BODIPY to obtain receptor-based fluorescence ligands for imaging breast and prostate cancer. Their synthesis is based on coupling of iodo derivatives of differently substituted BODIPY and aza-BODIPY analogs and steroid alkynes using the click reaction conditions.…”

Section: Synthesis Of Steroids Using the Cuaac "Click" Reactionmentioning

confidence: 99%

Recent syntheses of steroid derivatives using the CuAAC “click” reaction

Ibrahim‐Ouali¹,

Dumur²

2021

Arkivoc

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The introduction of heterocycles into steroids is often at the origin of a modification of their physiological activity and thus allows the formation of new biologically interesting molecules. Recent advances in the field of steroid synthesis using the copper-catalyzed azide-alkyne cycloaddition (CuAAC) are presented here. Compounds exhibiting known biological activities are also reported in this review. This approach holds great promise and allows us to consider preparing new, highly functionalized complex molecules using the CuAAC "click" reaction.

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Section: Synthesis Of Steroids Using the Cuaac "Click" Reactionmentioning

confidence: 99%

Recent syntheses of steroid derivatives using the CuAAC “click” reaction

Ibrahim‐Ouali¹,

Dumur²

2021

Arkivoc

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“…Recently, it has been shown that among a series of E2-BODIPY conjugates, the highest receptor binding affinity (RBA) for ERα was observed in conjugate 1 , featuring a linear eight-carbon spacer chain ( Scheme 1 ), whereas the parent conjugate lacking the spacer chain showed little affinity for the ER [ 62 ]. A series of estrogen-, 19-nortestosterone-, and testosterone-BODIPY conjugates were subsequently prepared, providing a platform of potential receptor-based fluorescence ligands for imaging breast and prostate cancer [ 63 ]. The 11β-OMeE2 conjugate 2 is of particular interest, since it has been reported that the 11β-OMe substitution of estradiol facilitates in vivo localization in receptor-rich tissues [ 51 , 61 ].…”

Section: Introductionmentioning

confidence: 99%

Cell Uptake of Steroid-BODIPY Conjugates and Their Internalization Mechanisms: Cancer Theranostic Dyes

Amendoeira

Luz

Valente

et al. 2023

IJMS

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Estradiol-BODIPY linked via an 8-carbon spacer chain and 19-nortestosterone- and testosterone-BODIPY linked via an ethynyl spacer group were evaluated for cell uptake in the breast cancer cell lines MCF-7 and MDA-MB-231 and prostate cancer cell lines PC-3 and LNCaP, as well as in normal dermal fibroblasts, using fluorescence microscopy. The highest level of internalization was observed with 11β-OMe-estradiol-BODIPY 2 and 7α-Me-19-nortestosterone-BODIPY 4 towards cells expressing their specific receptors. Blocking experiments showed changes in non-specific cell uptake in the cancer and normal cells, which likely reflect differences in the lipophilicity of the conjugates. The internalization of the conjugates was shown to be an energy-dependent process that is likely mediated by clathrin- and caveolae-endocytosis. Studies using 2D co-cultures of cancer cells and normal fibroblasts showed that the conjugates are more selective towards cancer cells. Cell viability assays showed that the conjugates are non-toxic for cancer and/or normal cells. Visible light irradiation of cells incubated with estradiol-BODIPYs 1 and 2 and 7α-Me-19-nortestosterone-BODIPY 4 induced cell death, suggesting their potential for use as PDT agents.

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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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Synthesis and spectral properties of estrogen- and androgen-BODIPY conjugates

Cited by 14 publications

References 47 publications

Recent syntheses of steroid derivatives using the CuAAC “click” reaction

Recent syntheses of steroid derivatives using the CuAAC “click” reaction

Cell Uptake of Steroid-BODIPY Conjugates and Their Internalization Mechanisms: Cancer Theranostic Dyes

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

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