DOTAGA-Trastuzumab. A New Antibody Conjugate Targeting HER2/Neu Antigen for Diagnostic Purposes.

International audience; Improved bifunctional chelating agents (BFC) are required for indium-111 radiolabeling of monoclonal antibodies (mAbs) under mild conditions to yield stable, target-specific agents. 2,2',2″-(10-(2,6-Dioxotetrahydro-2H-pyran-3-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid (DOTAGA-anhydride) was evaluated for mAb conjugation and labeling with indium-111. The DOTA analogue was synthesized and conjugated to trastuzumab-which targets the HER2/neu receptor-in mild conditions (PBS pH 7.4, 25 °C, 30 min) and gave a mean degree of conjugation of 2.6 macrocycle per antibody. Labeling of this immunoconjugate with indium-111 was performed in 75% yield after 1 h a…

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…

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.

The Scope of Application of Macrocyclic Polyamines Beyond Metal Chelation

Recent advances in the use of radiometals for both imaging and therapy has spurred on the development of an original chemistry that endows radionuclide-chelating molecular cages with ever sharper physicochemical properties. Macrocyclic polyamines (MPAs) such as cyclen and DOTA are among the most frequently encountered cages for the design of new radiotracers, owing to their versatile chemistry that makes them customizable molecular tools. The idea of using MPAs for alternative purposes has recently emerged, with an eye towards benefiting from their unique topology, versatility, symmetry and water-solubility. This review summarizes strategies that have been recently implemented in which MPAs…

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…

Minor changes in the macrocyclic ligands but major consequences on the efficiency of gold nanoparticles designed for radiosensitization

International audience; Many studies have been devoted to adapting the design of gold nanoparticles to efficiently exploit their promising capability to enhance the effects of radiotherapy. In particular, the addition of magnetic resonance imaging modality constitutes an attractive strategy for enhancing the selectivity of radiotherapy since it allows the determination of the most suited delay between the injection of nanoparticles and irradiation. This requires the functionalization of the gold core by an organic shell composed of thiolated gadolinium chelates. The risk of nephrogenic systemic fibrosis induced by the release of gadolinium ions should encourage the use of macrocyclic chelat…

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.

Ultrasmall Rigid Particles as Multimodal Probes for Medical Applications

International audience; Ultrasmall but multifunctional: Rigid imaging particles that are smaller than 5 nm in size can be obtained in a top-down process starting from a core–shell structure (core=gadolinium oxide; shell=polysiloxane). They represent the first multifunctional silica-based particles that are sufficiently small to escape hepatic clearance and enable animal imaging by four complementary techniques.

Abstract 4082: Preclinical assessment of external or targeted radiotherapy in combination with immunotherapies and co-development of companion imaging diagnostic

Abstract Immunotherapies have proven to be highly efficient for cancer treatments and combination with either internal vectorized or external radiotherapies can enhance this efficacy through notably increasing tumor immune infiltrate. The clinical evaluation of such combination therapies requires expertise and exquisite processes in multiple fields, immunotherapy, radiotherapy and nuclear medicine. Similarly, this applies into preclinical settings for assessing proof of concept of novel combinations. Herein, we will present our preclinical evaluation process to combine external or internal (i.e. lutetium-177 radiolabeled molecule) radiotherapy with immunotherapies that include radiochemistr…

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…

A New pH-Dependent Macrocyclic Rhodamine B-Based Fluorescent Probe for Copper Detection in White Wine

For efficiently measuring copper (II) ions in the acidic media of white wine, a new chemosensor based on rhodamine B coupled to a tetraazamacrocyclic ring (13aneN4CH2NH2) was designed and synthesized by a one-pot reaction using ethanol as a green solvent. The obtained chemosensor was characterized via NMR, UV and fluorescent spectra. It was marked with no color emission under neutral pH conditions, with a pink color emission under acidic conditions, and a magenta color emission under acidic conditions where copper (II) ions were present. The sensitivity towards copper (II) ions was tested and verified over Ca2+, Ag+, Zn2+, Mg2+, Co2+, Ni2+, Fe2+, Pb2+, Cd2+, Fe3+, and Mn2+, with a detection…

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.

The Scope of Application of Macrocyclic Polyamines Beyond Metal Chelation

International audience; Recent advances in the use of radiometals for both imaging and therapy has spurred on the development of an original chemistry that endows radionuclide-chelating molecular cages with ever sharper physicochemical properties. Macrocyclic polyamines (MPAs) such as cyclen and DOTA are among the most frequently encountered cages for the design of new radiotracers, owing to their versatile chemistry that makes them customizable molecular tools. The idea of using MPAs for alternative purposes has recently emerged, with an eye towards benefiting from their unique topology, versatility, symmetry and water-solubility. This review summarizes strategies that have been recently i…

Site-Specific Dual Labeling of Proteins on Cysteine Residues with Chlorotetrazines

International audience; Dual-labeled biomolecules constitute a new generation of bioconjugates with promising applications in therapy and diagnosis. Unfortunately, the development of these new families of biologics is hampered by the technical difficulties associated with their construction. In particular, the site specificity of the conjugation is critical as the number and position of payloads can have a dramatic impact on the pharmacokinetics of the bioconjugate. Herein, we introduce dichlorotetrazine as a trivalent platform for the selective double modification of proteins on cysteine residues. This strategy is applied to the dual labeling of albumin with a macrocyclic chelator for nucl…

Front Cover: The Scope of Application of Macrocyclic Polyamines Beyond Metal Chelation (Eur. J. Org. Chem. 36/2019)

International audience

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…

Thermal and Chemical Stability of Thiol Bonding on Gold Nanostars

The stability of thiol bonding on the surface of star-shaped gold nanoparticles was studied as a function of temperature in water and in a set of biologically relevant conditions. The stability was evaluated by monitoring the release of a model fluorescent dye, Bodipy-thiol (BDP-SH), from gold nanostars (GNSs) cocoated with poly(ethylene glycol) thiol (PEG-SH). The increase in the BDP-SH fluorescence emission, quenched when bound to the GNSs, was exploited to this purpose. A maximum 15% dye release in aqueous solution was found when the bulk temperature of gold nanostars solutions was increased to T = 42 °C, the maximum physiological temperature. This fraction reduces 3-5% for temperatures …

Gold nanostars co-coated with the Cu(II) complex of a tetraazamacrocyclic ligand

The twelve-membered tetraazamacrocyclic ligand L1 bears an appended lipoic acid unit, whose disulphide ring is an efficient grafting moiety for the surface of gold nanostars (GNS). The GNS that were used featured a localized surface plasmon resonance (LSPR) absorption at ∼800 nm, i.e. in the near infrared (NIR). We investigated different approaches for coating them with the Cu(2+) complex of L1. While the direct reaction of [CuL1](2+) with as-prepared GNS led to aggregation, an initial coating step with polyethyleneglycol-thiol (PEG-SH) was found to be advantageous. Displacement reactions were carried out on pegylated GNS either with [CuL1](2+), directly generating [Cun(L1@GNS)](2n+), or wi…

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…

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.

Bridge-Clamp Bis(tetrazine)s with [N] 8 π-Stacking Interactions and Azido- s -Aryl Tetrazines: Two Classes of Doubly Clickable Tetrazines

Click chemistry at a tetrazine core is useful for bioorthogonal labeling and crosslinking. Introduced here are two new classes of doubly clickable s-aryl tetrazines synthesized by Cu-catalyzed cross-coupling. Homocoupling of o-brominated s-aryl tetrazines leads to bis(tetrazine)s structurally characterized by tetrazine cores arranged face-to-face. [N]8 π-stacking interactions are essential to the conformation. Upon inverse electron demand Diels-Alder (iEDDA) cycloaddition, the bis(tetrazine)s produce a unique staple structure. The o-azidation of s-aryl tetrazines introduces a second proximal intermolecular clickable function that leads to double click chemistry opportunities. The stepwise i…

CCDC 1828692: Experimental Crystal Structure Determination

Related Article: Clève D. Mboyi, Delphine Vivier, Ahmad Daher, Paul Fleurat-Lessard, Hélène Cattey, Charles H. Devillers, Claire Bernhard, Franck Denat, Julien Roger, Jean-Cyrille Hierso|2020|Angew.Chem.,Int.Ed.|59|1149|doi:10.1002/anie.201911947

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 1908608: Experimental Crystal Structure Determination

Related Article: Clève D. Mboyi, Delphine Vivier, Ahmad Daher, Paul Fleurat-Lessard, Hélène Cattey, Charles H. Devillers, Claire Bernhard, Franck Denat, Julien Roger, Jean-Cyrille Hierso|2020|Angew.Chem.,Int.Ed.|59|1149|doi:10.1002/anie.201911947

CCDC 1908609: Experimental Crystal Structure Determination

Related Article: Clève D. Mboyi, Delphine Vivier, Ahmad Daher, Paul Fleurat-Lessard, Hélène Cattey, Charles H. Devillers, Claire Bernhard, Franck Denat, Julien Roger, Jean-Cyrille Hierso|2020|Angew.Chem.,Int.Ed.|59|1149|doi:10.1002/anie.201911947

CCDC 1828690: Experimental Crystal Structure Determination

Related Article: Clève D. Mboyi, Delphine Vivier, Ahmad Daher, Paul Fleurat-Lessard, Hélène Cattey, Charles H. Devillers, Claire Bernhard, Franck Denat, Julien Roger, Jean-Cyrille Hierso|2020|Angew.Chem.,Int.Ed.|59|1149|doi:10.1002/anie.201911947

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 1908612: Experimental Crystal Structure Determination

Related Article: Clève D. Mboyi, Delphine Vivier, Ahmad Daher, Paul Fleurat-Lessard, Hélène Cattey, Charles H. Devillers, Claire Bernhard, Franck Denat, Julien Roger, Jean-Cyrille Hierso|2020|Angew.Chem.,Int.Ed.|59|1149|doi:10.1002/anie.201911947

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 1828691: Experimental Crystal Structure Determination

Related Article: Clève D. Mboyi, Delphine Vivier, Ahmad Daher, Paul Fleurat-Lessard, Hélène Cattey, Charles H. Devillers, Claire Bernhard, Franck Denat, Julien Roger, Jean-Cyrille Hierso|2020|Angew.Chem.,Int.Ed.|59|1149|doi:10.1002/anie.201911947

CCDC 1583209: 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 1908611: Experimental Crystal Structure Determination

Related Article: Clève D. Mboyi, Delphine Vivier, Ahmad Daher, Paul Fleurat-Lessard, Hélène Cattey, Charles H. Devillers, Claire Bernhard, Franck Denat, Julien Roger, Jean-Cyrille Hierso|2020|Angew.Chem.,Int.Ed.|59|1149|doi:10.1002/anie.201911947

CCDC 1908610: Experimental Crystal Structure Determination

Related Article: Clève D. Mboyi, Delphine Vivier, Ahmad Daher, Paul Fleurat-Lessard, Hélène Cattey, Charles H. Devillers, Claire Bernhard, Franck Denat, Julien Roger, Jean-Cyrille Hierso|2020|Angew.Chem.,Int.Ed.|59|1149|doi:10.1002/anie.201911947

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 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 1908606: Experimental Crystal Structure Determination

Related Article: Clève D. Mboyi, Delphine Vivier, Ahmad Daher, Paul Fleurat-Lessard, Hélène Cattey, Charles H. Devillers, Claire Bernhard, Franck Denat, Julien Roger, Jean-Cyrille Hierso|2020|Angew.Chem.,Int.Ed.|59|1149|doi:10.1002/anie.201911947

CCDC 1583208: 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 1908607: Experimental Crystal Structure Determination

Related Article: Clève D. Mboyi, Delphine Vivier, Ahmad Daher, Paul Fleurat-Lessard, Hélène Cattey, Charles H. Devillers, Claire Bernhard, Franck Denat, Julien Roger, Jean-Cyrille Hierso|2020|Angew.Chem.,Int.Ed.|59|1149|doi:10.1002/anie.201911947

CCDC 1439079: 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 1828689: Experimental Crystal Structure Determination

Related Article: Clève D. Mboyi, Delphine Vivier, Ahmad Daher, Paul Fleurat-Lessard, Hélène Cattey, Charles H. Devillers, Claire Bernhard, Franck Denat, Julien Roger, Jean-Cyrille Hierso|2020|Angew.Chem.,Int.Ed.|59|1149|doi:10.1002/anie.201911947

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 931678: Experimental Crystal Structure Determination

Related Article: Bertrand Brizet, Claire Bernhard, Yulia Volkova, Yoann Rousselin, Pierre D. Harvey, Christine Goze, Franck Denat|2013|Org.Biomol.Chem.|11|7729|doi:10.1039/C3OB41370E

CCDC 960361: Experimental Crystal Structure Determination

Related Article: Pauline Désogère, Yoann Rousselin, Sophie Poty, Claire Bernhard, Christine Goze, Frédéric Boschetti, Franck Denat|2014|Eur.J.Org.Chem.|2014|7831|doi:10.1002/ejoc.201402708

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

CCDC 1476681: 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 960359: Experimental Crystal Structure Determination

Related Article: Pauline Désogère, Yoann Rousselin, Sophie Poty, Claire Bernhard, Christine Goze, Frédéric Boschetti, Franck Denat|2014|Eur.J.Org.Chem.|2014|7831|doi:10.1002/ejoc.201402708

CCDC 1583213: 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 960360: Experimental Crystal Structure Determination

Related Article: Pauline Désogère, Yoann Rousselin, Sophie Poty, Claire Bernhard, Christine Goze, Frédéric Boschetti, Franck Denat|2014|Eur.J.Org.Chem.|2014|7831|doi:10.1002/ejoc.201402708