A Promising Family of Fluorescent Water-Soluble aza-BODIPY Dyes for <i>in Vivo</i> Molecular Imaging

Pliquett, Jacques; DuBois, Adrien S.; Racoeur, Cindy; Mabrouk, Nesrine; Amor, Souheila; Lescure, Robin; Bettaı̈eb, Ali; Collin, Bertrand; Bernhard, Claire; Denat, Franck; Bellaye, Pierre‐Simon; Paul, Catherine; Bodio, Ewen; Goze, Christine

doi:10.1021/acs.bioconjchem.8b00795

Cited by 55 publications

(56 citation statements)

References 20 publications

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“…28 A commercially available boron-dipyrromethene (BODIPY) fluorophore was selected as the source of the read-out signal, based on the well-documented ability of BODIPY fluorophores to display high quantum yield and robust performance under a variety of experimental conditions. 29…”

Section: Resultsmentioning

confidence: 99%

Identification of 15 Phthalate Esters in Commercial Cheese Powder via Cyclodextrin-Promoted Fluorescence Detection

et al. 2019

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A challenge for detecting phthalates in commercial products such as cheese powders is that the composition of the products is highly complex, and current methods for detection rely on gas chromatography–mass spectrometry, which is not portable and cannot be used by individual consumers at a time and place of their choosing. Herein, we report the development of a new method for phthalate detection in cheese powder using cyclodextrin-promoted fluorescence detection, in which the presence of the phthalate analytes leads to highly analyte-specific changes in the fluorescence emission signal of a fluorophore bound in a cyclodextrin cavity. This method relies on subtle changes in the analyte affinity for the fluorophore and the cyclodextrin cavity and provides for markedly more straightforward sample preparation procedures and an extremely rapid read-out signal, with potential for the development of portable fluorescence sensors. Using this method, we were able to detect 15 phthalate esters with highly analyte-specific responses and at concentrations as low as 0.12 μM, which is well below regulatory levels of concern. Computational investigations strongly support the observed experimental trends.

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Section: Resultsmentioning

confidence: 99%

Identification of 15 Phthalate Esters in Commercial Cheese Powder via Cyclodextrin-Promoted Fluorescence Detection

et al. 2019

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“…Detailed syntheses and analyses-NMR, mass-analyses (the calculations are based on the mass of the most abundant isotopologue, unless otherwise specified), and HPLC-MS-can be found in ESI and previously reported studies [29,48]. ( 1 H, 11 B, 13 C, 19 F)-NMR spectra were recorded at 300 K on Bruker 500 Avance III or 600 Avance III spectrometers.…”

Section: Synthesis and Characterization Of Compoundsmentioning

confidence: 99%

“…To bridge this gap, we decided to tether a 10 B-BSH on a NIR-emitting BODIPY derivative named aza-BODIPY ( Figure 1b), thereby creating a theranostic system gathering the advantages of both aza-BODIPY and 10 B-BSH components. media (i.e., water, PBS, or serum), by substituting the fluorine atoms on the boron by alkyne ammonium groups [34,35,48]. Very recently, we used this strategy on a particular Donor-Acceptor-Donor' aza-BODIPY structure, which emits in the SWIR region, yielding a water-soluble derivative SWIR-WAZABY-01 (See the ESI and Reference [29]; WAZABY for Water-Soluble aza-BODIPY).…”

Section: Introductionmentioning

confidence: 99%

Aza-BODIPY: A New Vector for Enhanced Theranostic Boron Neutron Capture Therapy Applications

Kalot

Godard

Busser

et al. 2020

Cells

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Boron neutron capture therapy (BNCT) is a radiotherapeutic modality based on the nuclear capture of slow neutrons by stable 10B atoms followed by charged particle emission that inducing extensive damage on a very localized level (<10 μm). To be efficient, a sufficient amount of 10B should accumulate in the tumor area while being almost cleared from the normal surroundings. A water-soluble aza-boron-dipyrromethene dyes (BODIPY) fluorophore was reported to strongly accumulate in the tumor area with high and BNCT compatible Tumor/Healthy Tissue ratios. The clinically used 10B-BSH (sodium borocaptate) was coupled to the water-soluble aza-BODIPY platform for enhanced 10B-BSH tumor vectorization. We demonstrated a strong uptake of the compound in tumor cells and determined its biodistribution in mice-bearing tumors. A model of chorioallantoic membrane-bearing glioblastoma xenograft was developed to evidence the BNCT potential of such compound, by subjecting it to slow neutrons. We demonstrated the tumor accumulation of the compound in real-time using optical imaging and ex vivo using elemental imaging based on laser-induced breakdown spectroscopy. The tumor growth was significantly reduced as compared to BNCT with 10B-BSH. Altogether, the fluorescent aza-BODIPY/10B-BSH compound is able to vectorize and image the 10B-BSH in the tumor area, increasing its theranostic potential for efficient approach of BNCT.

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“…30,33,34 Very recently, some of us succeeded in designing fully water-soluble aza-BODIPY derivatives, called Wazaby (for watersoluble aza-BODIPY), thanks to the introduction of ammonium groups via boron functionalization (functionalizing boron induced aza-BODIPY faces hindrance, which prevented aggregation) ( Figure 1). 27 These probes were bioconjugated onto antibodies, were very stable in physiological media, and presented better in vivo optical properties than the Cy5, used as a control.…”

Section: Figure 1: Structure Of Some Optical Imaging Clinically Used mentioning

confidence: 99%

Aza-BODIPY Platform: Toward an Efficient Water-Soluble Bimodal Imaging Probe for MRI and Near-Infrared Fluorescence

et al. 2020

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In this study, an original aza-BODIPY system comprising two Gd 3+ complexes has been designed and synthesized for magnetic resonance imaging/optical imaging application, by functionalization of the boron center. This strategy enabled to obtain a positively-charged bimodal probe, which displays an increased water-solubility, optimized photophysical properties in the near-infrared region, and very promising relaxometric properties. The absorption and emission wavelengths are 705 and 741 nm respectively, with a quantum yield of around 10 % in aqueous media. Moreover, the system does not produce singlet oxygen upon excitation, which would be toxic for tissues. The relaxivity obtained is high at intermediate fields (16.1 mM-1 .s-1 at 20 MHz and 310 K) and competes with that of bigger or more rigid systems. A full relaxometric and 17 O NMR study and fitting of the data using the Lipari-Szabo approach showed that this high relaxivity can be explained by the size of the system and the presence of some small aggregates. These optimized photophysical and relaxometric properties highlight the potential use of such systems for future bimodal imaging studies.

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A Promising Family of Fluorescent Water-Soluble aza-BODIPY Dyes for in Vivo Molecular Imaging

Cited by 55 publications

References 20 publications

Identification of 15 Phthalate Esters in Commercial Cheese Powder via Cyclodextrin-Promoted Fluorescence Detection

Identification of 15 Phthalate Esters in Commercial Cheese Powder via Cyclodextrin-Promoted Fluorescence Detection

Aza-BODIPY: A New Vector for Enhanced Theranostic Boron Neutron Capture Therapy Applications

Aza-BODIPY Platform: Toward an Efficient Water-Soluble Bimodal Imaging Probe for MRI and Near-Infrared Fluorescence

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