Bertrand Brizet

Institut de Chimie Moléculaire de l'Université de Bourgogne

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Pierre D. Harvey

Université de Sherbrooke

Christine Goze

Université de Bourgogne

Franck Denat

Centre National de la Recherche Scientifique

Claire Bernhard

Université de Bourgogne

Yulia A. Volkova

N.D. Zelinsky Institute of Organic Chemistry

Claude P. Gros

Université de Bourgogne

Yoann Rousselin

Université de Bourgogne

Jean‐Michel Barbe

Université de Bourgogne

Victor Gonçalves

Université de Bourgogne

Adam Langlois

Université de Sherbrooke

Cooperative Institutions

Université de Bourgogne

Centre National de la Recherche Scientifique

Institut de Chimie Moléculaire de l'Université de Bourgogne

Institut de Chimie

Université Bourgogne Franche-Comté

Maison des Sciences de l’Homme de Dijon

Laboratoire Interdisciplinaire Carnot de Bourgogne

Bipar

Lomonosov Moscow State University

Université de Sherbrooke

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Boron functionalization of BODIPY by various alcohols and phenols

Organic & Biomolecular Chemistry (2013)

Bertrand Brizet Claire Bernhard Yulia A. Volkova Yoann Rousselin Pierre D. Harvey

The synthesis of new B-O BODIPY derivatives functionalized with different alkoxy or diarylalkoxy derivatives is described. These compounds were synthesized from the reaction of different B-F BODIPY precursors with various alcohols and phenols, in the presence of AlCl3. Water-soluble dyes could be synthesized as well with this method, specifically by the introduction of polyethyleneglycol (PEG) groups. A photophysical study of the different compounds was performed, and showed that the B-O BODIPY derivatives exhibit rich fluorescence properties. Finally, the conjugation of the BODIPY core has been extended using two distyryl groups, hence providing NIR emitting BODIPY derivatives, in which one or two PEG groups have been anchored, making these systems very promising for future medical imaging applications.

BODIPY

Surface Modification

10.1039/c3ob41370e

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Citations (48)

ChemInform Abstract: Boron Functionalization of BODIPY by Various Alcohols and Phenols

ChemInform (2014)

Bertrand Brizet Claire Bernhard Yu. A. Volkova Yoann Rousselin Pierre D. Harvey

Abstract preparation and photophysical study of novel BODIPY derivatives (I) (10 examples)

BODIPY

Surface Modification

10.1002/chin.201412189

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DMAP‐BODIPY Alkynes: A Convenient Tool for Labeling Biomolecules for Bimodal PET–Optical Imaging

Chemistry - A European Journal (2014)

Bertrand Brizet Victor Gonçalves Claire Bernhard Pierre D. Harvey Franck Denat

Abstract Several new boron dipyrromethene/ N , N ‐dimethylaminopyridine (BODIPY‐DMAP) assemblies were synthesized as precursors for bimodal imaging probes (optical imaging, OI/positron emission tomography, PET). The photophysical properties of the new compounds were also studied. The first proof‐of‐concept was obtained with the preparation of several new BODIPY‐labeled bombesins and evaluation of the affinity for bombesin receptors by using a competition binding assay. Fluorination reactions were investigated on DMAP‐BODIPY precursors as well as on DMAP‐BODIPY‐labeled bombesins. Chemical modifications on the BODIPY core were also performed to obtain luminescent dyes emitting in the therapeutic window (650–900 nm), suitable for in vivo imaging, making these compounds promising precursors for PET/optical dual‐modality imaging agents.

BODIPY

Imaging agent

Biomolecule

Molecular Imaging

10.1002/chem.201402379

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Citations (29)

CCDC 931678: Experimental Crystal Structure Determination

The Cambridge Structural Database (2013)

Bertrand Brizet Claire Bernhard Yulia A. Volkova Yoann Rousselin Pierre D. Harvey

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Crystal (programming language)

10.5517/cc108h4x

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BODIPY Dyes Functionalized with Pendant Cyclic and Acyclic Polyamines

European Journal of Organic Chemistry (2013)

Yulia A. Volkova Bertrand Brizet Pierre D. Harvey Alexey D. Averin Christine Goze

Abstract The synthesis and characterization of a series of BODIPY derivatives substituted with acyclic and cyclic polyamines, in particular, cyclen and homocyclen, are reported. The 19 F NMR, UV/Vis, and fluorescence spectroscopic data of these compounds are discussed. One compound was found to be very selective for Cu II ions, which makes it a very promising system for Cu II detection.

BODIPY

Cyclen

10.1002/ejoc.201300414

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Citations (28)

Origin of the temperature dependence of the rate of singlet energy transfer in a three-component truxene-bridged dyads

Journal of Porphyrins and Phthalocyanines (2013)

Adam Langlois Haijun Xu Bertrand Brizet Franck Denat Jean‐Michel Barbe

We report a truxene-based dyad built upon one donor (tri-meso-phenylzinc(II)porphyrin) and two acceptors (octa-β-alkylporphyrin free base) in which the donor exhibits free rotation around a C truxene -C meso single bond at 298 K in fluid solution but not at 77 K in a glass matrix, whereas the acceptors have very limited motion as they are blocked by β-methyl groups. This case is interesting because all the structural and spectroscopic parameters affecting the rate for singlet energy transfer according to a Förster Resonance Energy Transfer are only weakly temperature dependent, leaving only the Dexter mechanism explaining the larger variation in rate of energy transfers with the temperature hence providing a circumstantial evidence for a dual mechanism (Föster and Dexter) in truxene-based dyads (or polyads) in the S 1 excited states.

10.1142/s1088424613501150

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Citations (12)

Synthesis and study of new precursors for bimodal optic/PET or optic/SPECT imaging

HAL (Le Centre pour la Communication Scientifique Directe) (2014)

Bertrand Brizet

PET Imaging

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Synthèse et étude de nouveaux précurseurs pour une imagerie bimodale optique/TEP ou TEMP

Bertrand Brizet

Ce travail de these en cotutelle a ete realise a l’Institut de Chimie Moleculaire de l’Universite de Bourgogne (France) et au departement de chimie de l’Universite de Sherbrooke (Quebec). Ces travaux sont consacres a la conception de nouveaux derives du BODIPY en vue d'une application in vivo pour l'imagerie bimodale optique/TEP ou TEMP. Ces modifications concernent l'hydrosolubilisation des fluorophores, mais aussi le decalage des domaines d’absorption et d’emission vers la fenetre therapeutique, zone dans laquelle la lumiere est moins attenuee par les tissus biologiques. Des solutions permettant la bioconjugaison des fluorophores sur un derive de la bombesine, un peptide permettant de cibler des recepteurs membranaires surexprimes dans certains types de cellules cancereuses, sont egalement presentees. Une strategie de radiofluoration du, BODIPY, impliquant l’introduction sur l’atome de bore d’un groupe partant, est decrite.. Differents derives de BODIPY ont egalement ete utilises pour la construction d’edifices multichromophoriques a transfert d’energie. Ces travaux sont decrits dans la seconde partie de cette these. Ils comprennent notamment des etudes photophysiques permettant de mettre en evidence le transfert d’energie photo-induit donneur-accepteur entre differents chromophores. Dans les differents systemes elabores, de type BODIPY-pophyrine et BODIPY-corolle, le BODIPY est alternativement donneur, ou accepteur d’energie.

BODIPY

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High Yield S_NAr on 8‐Halogenophenyl‐BODIPY with Cyclic and Acyclic Polyamines

European Journal of Organic Chemistry (2014)

Yulia A. Volkova Bertrand Brizet Pierre D. Harvey Franck Denat Christine Goze

Abstract Selective nucleophilic aromatic substitutions with several polyamines were performed in very good yields on halogeno‐phenyl BODIPY derivatives containing an activating nitro group.

BODIPY

10.1002/ejoc.201301900

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Slow and Fast Singlet Energy Transfers in BODIPY-gallium(III)corrole Dyads Linked by Flexible Chains

Inorganic Chemistry (2014)

Bertrand Brizet Nicolas Desbois Antoine Bonnot Adam Langlois Adrien S. DuBois

Red (no styryl), green (monostyryl), and blue (distyryl) BODIPY-gallium(III) (BODIPY = boron-dipyrromethene) corrole dyads have been prepared in high yields using click chemistry, and their photophysical properties are reported. An original and efficient control of the direction of the singlet energy transfers is reported, going either from BODIPY to the gallium-corrole units or from gallium-corroles to BODIPY, depending upon the nature of the substitution on BODIPY. In one case (green), both directions are possible. The mechanism for the energy transfers is interpreted by means of through-space Förster resonance energy transfer (FRET).

BODIPY

Corrole

10.1021/ic402798f

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Citations (68)