High Yield SNAr on 8-Halogenophenyl-BODIPY with Cyclic and Acyclic Polyamines

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

Towards the elaboration of new gold-based optical theranostics.

Four new red BODIPY–gold(I) theranostic compounds were synthesized. Some of them were vectorized by tethering a biovector (glucose or bombesin derivatives) to the metallic center. Their photophysical properties were studied. Additionally, their cytotoxicity was examined on different cancer cell lines and on a normal cell line, they were tracked in vitro by fluorescence detection, and their uptake was evaluated by ICP-MS measurements.

Boron functionalization of BODIPY by various alcohols and phenols.

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 on…

Optical method for predicting the composition of self-assembled monolayers of mixed thiols on surfaces coated with silver nanoparticles.

With a simple optical method, based on UV-vis absorption spectra on glass slides, it is possible to predict the composition of self-assembled monolayers of mixed thiols, grafted on monolayers of silver nanoparticles. Glass slides are modified with the layer-by-layer technique, first forming a monolayer of mercaptopropyltrimethoxysilane, then grafting a monolayer of silver nanoparticles on it. These surfaces are further coated by single or mixed thiol monolayers, by dipping the slides in toluene solutions of the chosen thiols. Exchange constants are calculated for the competitive deposition between the colorless 1-dodecanethiol or PEG5000 thiol and BDP-SH, with the latter being a thiol-beari…

BODIPYS and aza-BODIPY derivatives as promising fluorophores for in vivo molecular imaging and theranostic applications

Since their discovery in 1968, the BODIPYs dyes (4,4-difluoro-4-bora-3a, 4a diaza-s-indacene) have found an exponentially increasing number of applications in a large variety of scientific fields. In particular, studies reporting bioapplications of BODIPYs have increased dramatically. However, most of the time, only in vitro investigations have been reported. The in vivo potential of BODIPYs and aza-BODIPYs is more recent, but considering the number of in vivo studies with BODIPY and aza-BODIPY which have been reported in the last five years, we can now affirm that this family of fluorophores can be considered important as cyanine dyes for future in vivo and even clinical applications. Thi…

Dual Labeling of Lipopolysaccharides for SPECT-CT Imaging and Fluorescence Microscopy.

International audience; : Lipopolysaccharides (LPS) or endotoxins are amphipathic, pro-inflammatory components of the outer membrane of Gram-negative bacteria. In the host, LPS can trigger a systemic inflammatory response syndrome. To bring insight into in vivo tissue distribution and cellular uptake of LPS, dual labeling was performed with a bimodal molecular probe designed for fluorescence and nuclear imaging. LPS were labeled with DOTA-Bodipy-NCS, and pro-inflammatory properties were controlled after each labeling step. LPS were then radiolabeled with (111)In and subsequently injected intravenously into wild-type, C57B16 mice, and their in vivo behavior was followed by single photon emis…

Efficient Synthesis of Multifunctional Chelating Agents Based on Tetraazacycloalkanes

An efficient route has been developed for the synthesis of multifunctional tetraazacycloalkanes (in particular 1,4,7,10-tetraazacyclotridecane) incorporating an aminomethyl pendant arm on the carbon skeleton. Starting from the appropriate C-functionalized bisaminal-protected intermediate, the target macrocycles were easily obtained by means of a step-by-step introduction of the desired functional groups onto the free primary amine group, followed by deprotection of the bisaminal intermediates. This straightforward and versatile synthetic approach paves the way for the design of a new family of multifunctional chelators.

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

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 (&lt

Near-infrared emitting fluorescent homobimetallic gold(I) complexes displaying promising in vitro and in vivo therapeutic properties

International audience; Boron neutron capture therapy (BNCT) has the potential to specifically destroy tumor cells without damaging the tissues infiltrated by the tumor. BNCT is a binary treatment method based on the combination of two agents that have no effect when applied individually: 10B and thermal neutrons. Exclusively, the combination of both produces an effect, whose extent depends on the amount of 10B in the tumor but also on the organs at risk. It is not yet possible to determine the 10B concentration in a specific tissue using non-invasive methods. At present, it is only possible to measure the 10B concentration in blood and to estimate the boron concentration in tissues based o…

Proton and metal binding by cyclen-based highly rigid cryptands.

The basicity properties of the two cryptands L1 and L2, featuring, respectively, a dibenzofuran or a diphenyl ether moiety bridging the 1,7 positions of a 1,4,7,10-tetraazacyclododecane macrocycle (cyclen) have been studied by means of potentiometric, UV-vis and fluorescence emission measurements. Both ligands show a high basicity in the first protonation step, the first basicity constant of L1 being too high to be measured in aqueous solution. The crystal structure of {[HL1]L1}(+) shows that the NH(2)(+) group is involved in an intramolecular hydrogen bonding network, which justifies the observed high basicity in solution. (1)H, (13)C NMR, UV-vis and fluorescence emission measurements show…

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

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 (6…

Copper radiopharmaceuticals for theranostic applications

The growing advancement in nuclear medicine challenges researchers from several different fields to integrate imaging and therapeutic modalities in a theranostic radiopharmaceutical, which can be defined as a molecular entity with readily replaceable radioisotope to provide easy switch between diagnostic and therapeutic applications for efficient and patient-friendly treatment of diseases. For such a reason, the diagnostic and therapeutic potential of all five medical radionuclides of copper have thoroughly been investigated as they boost the hope for development of successful radiotheranostics. To facilitate the mutual understanding between all different specialists working on this multidi…

Remarkable Inertness of Copper(II) Chelates of Cyclen-Based Macrobicycles with Two trans-N-Acetate Arms

Two cross-bridged cyclen-based macrocycles with two trans-N-acetic acid arms, one having a dibenzofuran (DBF) moiety as the bridge, H2L1, and the other a diphenyl ether (DPE) one, H2L2, were synthesized. Both compounds behave as "proton sponges." The thermodynamic stability constants for the Cu(2+), Zn(2+), Al(3+), and Ga(3+) complexes of both compounds were determined. They exhibit an excellent thermodynamic selectivity for copper(II), ensuring that metal ions largely present in the human body do not interfere with the copper(II) chelates. All complexes are very slow to form, and [CuL2] and [CuL1] are extremely inert to demetallate, especially [CuL2]. The acid-assisted dissociation of [CuL…

BODIPY atropisomer interconversion, face discrimination, and superstructure appending

International audience; A strategy was developed to append sterically hindered apical pickets on both faces of the BODIPY platform to prevent stacking and aggregation. Ortho-substitution of both the meso-phenyl ring and the boron-bound catechol affords the right directionality to append pickets, achieve face discrimination, featuring two inter-convertible atropisomers, and is reminiscent of the picket-fence strategy in porphyrins.

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

A new family of water-soluble and bioconjugatable aza-BODIPY fluorophores was designed and synthesized using a boron- functionalization strategy. These dissymmetric bis-ammonium aza-BODIPY dyes present optimal properties for a fluorescent probe; i.e., they are highly water-soluble, very stable in physiological medium; they do not aggregate in PBS, possess high quantum yield; and finally, they can be easily bioconjugated to antibodies. Preliminary in vitro and in vivo studies were performed for one of these fluorophores to image PD-L1 (Programmed Death-Ligand 1), highlighting the high potential of these new probes for future in vivo optical imaging studies.

B,B-Diporphyrinbenzyloxy-BODIPY dyes: synthesis and antenna effect.

B,B-Diporphyrinbenzyloxy-BODIPY derivatives have been prepared in high yields, and the photophysical properties are reported. Singlet energy transfers from BODIPY to the porphyrin units have been analyzed.

MANOTA: a promising bifunctional chelating agent for copper-64 immunoPET

International audience; Improved bifunctional chelating agents (BFC) are required for copper-64 radiolabelling of monoclonal antibodies (mAbs) under mild conditions to yield stable, target-specific imaging agents. Four different bifunctional chelating agents (BFC) were evaluated for Fab (Fragment antigen binding) conjugation and radiolabelling with copper-64. Two DOTA- (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) and two NOTA- (1,4,7-triazacyclononane-1,4,7-triacetic acid) derivatives bearing a p-benzyl-isothiocyanate group were conjugated to Fab-trastuzumab - which targets the HER2/neu receptor - and the average number of chelators attached ranged from 2.4 to 4.3 macrocycles …

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

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 on…

Synthesis and Photodynamics of Fluorescent Blue BODIPY-Porphyrin Tweezers Linked by Triazole Rings

Novel zinc porphyrin tweezers in which two zinc porphyrins were connected with π-conjugated boron dipyrromethenes (BDP meso-Por(2) and BDP β-Por(2)) through triazole rings were synthesized to investigate the photoinduced energy transfer and electron transfer. The UV-vis spectrum of BDP β-Por(2) which has less bulky substituents than BDP meso-Por(2) exhibits splitting of the Soret band as a result of the interaction between porphyrins of BDP β-Por(2) in the excited state. Such interaction between porphyrins of both BDP β-Por(2) and BDP meso-Por(2) is dominant at room temperature, while the coordination of the nitrogen atoms of the triazole rings to the zinc ions of the porphyrins occurs at l…

Selectively Functionalized Constrained Polyazamacrocycles: Building Blocks for Multifunctional Chelating Agents

A new class of cross-bridged and side-bridged 1,4,7,10-tetraazacyclotridecanes (homocyclens) bearing an aminomethyl pendant arm on the carbon skeleton has been prepared. The regioselectivity of the quaternization of the bis-aminal intermediates is discussed on the basis of X-ray diffraction and NMR experiments. These new polyazamacrocycles are valuable precursors of bifunctional chelating agents for applications in nuclear medicine.

Efficient Synthesis of 1,4,7-Triazacyclononane and 1,4,7-Triazacyclononane-Based Bifunctional Chelators for Bioconjugation (Eur. J. Org. Chem. 35/2014)

First bodipy–DOTA derivatives as probes for bimodal imaging

The synthesis and the photophysical studies of the first bodipy-DOTA and its In(III), Ga(III) and Cu(II) complexes are reported. The introduction of an isothiocyanate handle generates a new bimodal imaging agent capable of both optical and nuclear imaging.

Water-Soluble Aza-BODIPYs: Biocompatible Organic Dyes for High Contrast In Vivo NIR-II Imaging

International audience; A simple NIR-II emitting water-soluble system has been developed and applied in vitro and in vivo. In vitro, the fluorophore quickly accumulated in 2D and 3D cell cultures and rapidly reached the tumor in rodents, showing high NIR-II contrast for up to 1 week. This very efficient probe possesses all the qualities necessary for translation to the clinic as well as for the development of NIR-II emitting materials.

Design of a multifunctionalizable BODIPY platform for the facile elaboration of a large series of gold(i)-based optical theranostics.

A simple trifunctional BODIPY platform was designed. The high potential of this platform was validated via the elaboration of twelve optical theranostics. More specifically, we reported on the synthesis, the characterization, the photophysical properties, and the evaluation of the hydrophilicity properties of the different BODIPY derivatives, as well as a theoretical rationalization of the intriguing chemical behavior of some of them. The antiproliferative evaluation and confocal imaging of the different compounds in three human and murine cancer cell lines were performed and analysed, along with the measurement of gold(I) uptake in one cancer cell line via ICP-MS.

BODIPY Dyes Functionalized with Pendant Cyclic and Acyclic Polyamines

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

Development of Trackable Anticancer Agents Based on Metal Complexes

Abstract The design of trackable anticancer agents is of major interest for the future development of therapeutics based on nonplatinum metal complexes such as Ru(II), Os(II), or Au(I) derivatives, and more particularly for the understanding of the mechanism of action of these metal-based drugs. This review reports the synthesis and the first biological studies of original trackable complexes, in which the metal complex was coupled to an imaging probe, such as a fluorophore (coumarin, borodipyrromethene derivative (BODIPY), porphyrin), or a chelating agent (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA)) for radioisotopic imaging PET (positron emission tomography) or SPECT …

Coumarin-Phosphine-Based Smart Probes for Tracking Biologically Relevant Metal Complexes: From Theoretical to Biological Investigations

International audience; Ten metal-based complexes and associated ligands have been synthesized and characterized. One of the metal ligands is a coumarin-phosphine derivative, which displays tunable fluorescence properties. The fluorescence is quenched in the case of the free ligand and ruthenium and osmium complexes, whereas it is strong for the gold complexes and phosphonium derivatives. These trends were rationalized by theoretical calculations, which revealed non-radiative channels involving a dark state for the free ligands that is lower in energy than the emissive state and is responsible for the quenching of fluorescence. For the Ru-II and Os-II complexes, other non-radiative channels…

Reinforced cyclam derivatives functionalized on the bridging unit

International audience; A new synthetic method has been developed for the preparation of reinforced cyclams (1,4,8,11-tetraazacyclotetradecane) C-functionalized on the bridging unit, by using a "one pot" reaction starting from the appropriate bis-aminal cyclam intermediate. The high reactivity of quaternized aminal moiety toward nucleophilic agent has been used to elaborate a new class of cross-bridged and side-bridged cyclam derivatives containing cyanide group on the ethylene bridge. Several chelators and corresponding copper(II) complexes have been prepared and characterized by X-ray diffraction. These new constrained polyazamacrocycles are valuable precursors of bifunctional chelating a…

Efficient Synthesis of 1,4,7-Triazacyclononane and 1,4,7-Triazacyclononane-Based Bifunctional Chelators for Bioconjugation

The reaction of diethylenetriamine with chloroacetaldehyde yielded a bicyclic aminal intermediate for the synthesis of 1,4,7-triazacyclononane (TACN), a macrocyclic polyamine the derivatives of which find applications as catalysts, bleaching agents, and chelators for medical imaging. This new synthetic protocol outperforms the synthetic methods described so far because it does not involve any cyclization step. Moreover, this aminal intermediate allowed access to a new family of TACN derivatives functionalized on the carbon skeleton, for example, C-aminomethyl-TACN. This novel compound is a precursor of valuable bifunctional chelating agents for nuclear medicine, in particular, for the prepa…

AMD3100: A Versatile Platform for CXCR4 Targeting 68 Ga-Based Radiopharmaceuticals

International audience; CXCR4 is a G protein-coupled receptor (GPCR), which is overexpressed in numerous diseases, particularly in multiple cancers. Therefore, this receptor represents a valuable target for imaging and therapeutic purposes. Among the different approaches, which were developed for CXCR4 imaging, a CXCR4 antagonist biscyclam system (AMD3100, also called Mozobil), currently used in the clinic for the mobilization of hematopoietic stem cells, was radiolabeled with different radiometals such as 62Zn, 64Cu, 67Ga, or 99mTc. However, cyclam is not an ideal chelator for most of these radiometals, and could lead to the release of the radionuclide in vivo. In the current study, a new …

Development of trackable metal-based drugs: new generation of therapeutic agents

International audience; In medicinal chemistry, the aim is not only to conceive ever more efficient molecules, but also to understand their mechanism of action. In very recent years, a new promising strategy was developed to tackle this issue: the conception of trackable therapeutic agents. Metal-based drugs are ideal to exploit this expanding area of research.

Development of an Easily Bioconjugatable Water-Soluble Single-Photon Emission-Computed Tomography/Optical Imaging Bimodal Imaging Probe Based on the aza-BODIPY Fluorophore

A water-soluble fluorescent aza-BODIPY platform (Wazaby) was prepared and functionalized by a polyazamacrocycle agent and a bioconjugable arm. The resulting fluorescent derivative was characterized and bioconjugated onto a trastuzumab monoclonal antibody as a vector. After bioconjugation, the imaging agent appeared to be stable in serum (>72 h at 37 °C) and specifically labeled HER-2-positive breast tumors slices. The bioconjugate was radiolabeled with [111In] indium and studied in vivo. The developed monomolecular multimodal imaging probe (MOMIP) is water-soluble and chemically and photochemically stable, emits in the near infrared (NIR) region (734 nm in aqueous media), and displays a goo…

DOTAGA-anhydride: a valuable building block for the preparation of DOTA-like chelating agents.

International audience; A DOTA derivative that contains an anhydride group was readily synthesized by reacting DOTAGA with acetic anhydride and its reactivity was investigated. Opening the anhydride with propylamine led to the selective formation of one of two possible regioisomers. The structure of the obtained isomer was unambiguously determined by 1D and 2D NMR experiments, including COSY, HMBC, and NOESY techniques. This bifunctional chelating agent offers a convenient and attractive approach for labeling biomolecules and, more generally, for the synthesis of a large range of DOTA derivatives. The scope of the reaction was extended to prepare DOTA-like compounds that contained various f…

Cellular imaging using BODIPY-, pyrene- and phthalocyanine-based conjugates

International audience; Fluorescent Probes aimed at absorbing in the blue/green region of the spectrum and emitting in the green/red have been synthesized (as the form of dyads-pentads), studied by spectrofluorimetry, and used for cellular imaging. The synthesis of phthalocyanine-pyrene 1 was achieved by cyclotetramerization of pyrenyldicyanobenzene, whereas phthalocyanine-BODIPY 2c was synthesized by Sonogashira coupling between tetraiodophthalocyanine and meso-alkynylBODIPY. The standard four-steps BODIPY synthesis was applied to the BODIPY-pyrene dyad 3 starting from pyrenecarbaldehyde and dimethylpyrrole. H-1, C-13, F-19, (BNMR)-B-11, ICP, MS, and UV/Vis spectroscopic analyses demonstra…

BODIPY-phosphane as a versatile tool for easy access to new metal-based theranostics

A new BODIPY-phosphane was synthesized and proved to be a versatile tool for imaging organometallic complexes. It also led to easy access to a new family of theranostics, featuring gold, ruthenium and osmium complexes. The compounds' cytotoxicity was tested on cancer cells, and their cell uptake was followed by fluorescence microscopy in vitro.

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

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).

Synthesis of a Linear Assembly Consisting of a Central Ru(Phen)32+ Derivative and Two Peripheral Porphyrins

A ruthenium(II) precursor complex containing a bis-phenanthroline ligand, leading to a controlled helical structure around the metal centre, and a third phenanthroline-type ligand has been prepared. The spatial arrangement of the system is such that two chemical groups are disposed trans to one another on an axis running through the Ru centre. By appropriate functional group transformation, these two groups can be attached to monosubstituted zinc(II) porphyrins (PZn) to afford a linear array consisting of a central ruthenium(II) complex and two peripheral PZn motifs. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

Anticancer Agents: Does a Phosphonium Behave Like a Gold(I) Phosphine Complex? Let a “Smart” Probe Answer!

Gold phosphine complexes, such as auranofin, have been recognized for decades as antirheumatic agents. Clinical trials are now underway to validate their use in anticancer or anti-HIV treatments. However, their mechanisms of action remain unclear. A challenging question is whether the gold phosphine complex is a prodrug that is administered in an inactive precursor form or rather that the gold atom remains attached to the phosphine ligand during treatment. In this study, we present two novel gold complexes, which we compared to auranofin and to their phosphonium analogue. The chosen ligand is a phosphine-based smart probe, whose strong fluorescence depends on the presence of the gold atom. …

Gold( i )–BODIPY–imidazole bimetallic complexes as new potential anti-inflammatory and anticancer trackable agents

International audience; Two new gold(I)–BODIPY–imidazole based trackable therapeutic bimetallic complexes have been synthesized and fully characterized. They display strong antiproliferative properties on several types of cancers including colon, breast, and prostate and one of them presents a significant anti-inflammatory effect. Additionally, the two compounds could be visualised in vitro by confocal microscopy in the submicromolar range.

CCDC 1439080: Experimental Crystal Structure Determination

Related Article: Nicolas Sok, Isabelle Baglin, Yoann Rousselin, Frederic Boschetti, Claire Bernhard, Christine Goze, Franck Denat|2016|New J.Chem.|40|5829|doi:10.1039/C5NJ03488D

CCDC 1583210: Experimental Crystal Structure Determination

Related Article: Nicolas Sok, Claire Bernhard, Pauline Désogère, Christine Goze, Yoann Rousselin, Frédéric Boschetti, Isabelle Baglin, Franck Denat|2018|Eur.J.Org.Chem.|2018|4762|doi:10.1002/ejoc.201800801

CCDC 1439078: Experimental Crystal Structure Determination

Related Article: Nicolas Sok, Isabelle Baglin, Yoann Rousselin, Frederic Boschetti, Claire Bernhard, Christine Goze, Franck Denat|2016|New J.Chem.|40|5829|doi:10.1039/C5NJ03488D

CCDC 1439081: Experimental Crystal Structure Determination

Related Article: Nicolas Sok, Isabelle Baglin, Yoann Rousselin, Frederic Boschetti, Claire Bernhard, Christine Goze, Franck Denat|2016|New J.Chem.|40|5829|doi:10.1039/C5NJ03488D

CCDC 1439077: Experimental Crystal Structure Determination

Related Article: Nicolas Sok, Isabelle Baglin, Yoann Rousselin, Frederic Boschetti, Claire Bernhard, Christine Goze, Franck Denat|2016|New J.Chem.|40|5829|doi:10.1039/C5NJ03488D

CCDC 1583212: Experimental Crystal Structure Determination

Related Article: Nicolas Sok, Claire Bernhard, Pauline Désogère, Christine Goze, Yoann Rousselin, Frédéric Boschetti, Isabelle Baglin, Franck Denat|2018|Eur.J.Org.Chem.|2018|4762|doi:10.1002/ejoc.201800801

CCDC 1825949: Experimental Crystal Structure Determination

Related Article: Jacques Pliquett, Souheila Amor, Miguel Ponce-Vargas, Myriam Laly, Cindy Racoeur, Yoann Rousselin, Franck Denat, Ali Bettaïeb, Paul Fleurat-Lessard, Catherine Paul, Christine Goze, Ewen Bodio|2018|Dalton Trans.|47|11203|doi:10.1039/C8DT02364F

CCDC 1583211: Experimental Crystal Structure Determination

Related Article: Nicolas Sok, Claire Bernhard, Pauline Désogère, Christine Goze, Yoann Rousselin, Frédéric Boschetti, Isabelle Baglin, Franck Denat|2018|Eur.J.Org.Chem.|2018|4762|doi:10.1002/ejoc.201800801

CCDC 1583209: Experimental Crystal Structure Determination

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CCDC 924316: Experimental Crystal Structure Determination

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CCDC 1439082: Experimental Crystal Structure Determination

Related Article: Nicolas Sok, Isabelle Baglin, Yoann Rousselin, Frederic Boschetti, Claire Bernhard, Christine Goze, Franck Denat|2016|New J.Chem.|40|5829|doi:10.1039/C5NJ03488D

CCDC 1825950: Experimental Crystal Structure Determination

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CCDC 1476682: Experimental Crystal Structure Determination

Related Article: Nicolas Sok, Isabelle Baglin, Christelle Basset, Fatima Fakkor, Evelyne Kohli, Yoann Rousselin, Claire Bernhard, Frédéric Boschetti, Christine Goze, Franck Denat|2017|RSC Advances|7|28291|doi:10.1039/C7RA04218C

CCDC 1583208: Experimental Crystal Structure Determination

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CCDC 1420553: Experimental Crystal Structure Determination

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CCDC 1014822: Experimental Crystal Structure Determination

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CCDC 1439079: Experimental Crystal Structure Determination

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CCDC 984188: Experimental Crystal Structure Determination

Related Article: Bertrand Brizet, Victor Goncalves, Claire Bernhard, Pierre D. Harvey, Franck Denat and Christine Goze|2014|Chem.-Eur.J.|20|12933|doi:10.1002/chem.201402379

CCDC 1538131: Experimental Crystal Structure Determination

Related Article: Audrey Trommenschlager, Florian Chotard, Benoît Bertrand, Souheila Amor, Lucile Dondaine, Michel Picquet, Philippe Richard, Ali Bettaïeb, Pierre Le Gendre, Catherine Paul, Christine Goze, Ewen Bodio|2017|Dalton Trans.|46|8051|doi:10.1039/C7DT01377A

CCDC 907927: Experimental Crystal Structure Determination

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CCDC 931678: Experimental Crystal Structure Determination

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CCDC 960361: Experimental Crystal Structure Determination

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CCDC 1476683: Experimental Crystal Structure Determination

Related Article: Nicolas Sok, Isabelle Baglin, Christelle Basset, Fatima Fakkor, Evelyne Kohli, Yoann Rousselin, Claire Bernhard, Frédéric Boschetti, Christine Goze, Franck Denat|2017|RSC Advances|7|28291|doi:10.1039/C7RA04218C

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