0000000000265992

AUTHOR

Pauline Désogère

showing 18 related works from this author

Efficient Synthesis of Multifunctional Chelating Agents Based on Tetraazacycloalkanes

2018

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.

Primary (chemistry)010405 organic chemistryLigandChemistryOrganic ChemistryCarbon skeletonRegioselectivity010402 general chemistry01 natural sciencesCombinatorial chemistry0104 chemical sciencesAmine gas treatingChelationPhysical and Theoretical ChemistryEuropean Journal of Organic Chemistry
researchProduct

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

2010

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…

Inorganic ChemistryCrystallographychemistry.chemical_compoundAqueous solutionCyclenLigandHydrogen bondChemistryInorganic chemistryCryptandPotentiometric titrationMoietyProtonationDalton transactions (Cambridge, England : 2003)
researchProduct

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

2013

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…

Models MolecularMacrocyclic CompoundsStereochemistrychemistry.chemical_elementAcetatesCrystallography X-RayCyclamsInorganic Chemistrychemistry.chemical_compoundCyclenCoordination ComplexesHeterocyclic CompoundsPolymer chemistryMoietyChelationPhysical and Theoretical ChemistryBenzofuransChelating AgentsChemistryPhenyl EthersSpectrum AnalysisDiphenyl etherCopperDibenzofuranThermodynamicsCopperInorganic Chemistry
researchProduct

Selectively Functionalized Constrained Polyazamacrocycles: Building Blocks for Multifunctional Chelating Agents

2013

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.

chemistry.chemical_compoundChemistryOrganic ChemistryCarbon skeletonRegioselectivityOrganic chemistryChelationPhysical and Theoretical ChemistryBifunctionalCombinatorial chemistryEuropean Journal of Organic Chemistry
researchProduct

Efficient Synthesis of 1,4,7-Triazacyclononane and 1,4,7-Triazacyclononane-Based Bifunctional Chelators for Bioconjugation (Eur. J. Org. Chem. 35/201…

2014

chemistry.chemical_compoundBioconjugationChemistryOrganic ChemistryOrganic chemistryChelationPhysical and Theoretical ChemistryBifunctionalEuropean Journal of Organic Chemistry
researchProduct

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

2014

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…

chemistry.chemical_compoundBioconjugationchemistryBicyclic moleculeOrganic ChemistryDiethylenetriamineAminalOrganic chemistryChloroacetaldehydeChelationPhysical and Theoretical ChemistryBifunctionalCatalysisEuropean Journal of Organic Chemistry
researchProduct

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

2016

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 …

0301 basic medicineBenzylaminesReceptors CXCR4Biomedical EngineeringPharmaceutical ScienceGallium Radioisotopes[SDV.CAN]Life Sciences [q-bio]/CancerBioengineeringPharmacologyCyclamsCXCR4[ CHIM ] Chemical Sciences[ SDV.CAN ] Life Sciences [q-bio]/Cancer03 medical and health scienceschemistry.chemical_compound0302 clinical medicineHeterocyclic CompoundsIn vivoCyclamHumans[CHIM]Chemical SciencesMoietyReceptorG protein-coupled receptorPharmacologyCXCR4CXCR4 antagonistChemistryOrganic Chemistry3. Good health030104 developmental biology030220 oncology & carcinogenesisCancer researchStem cellBiotechnology
researchProduct

CCDC 1583210: Experimental Crystal Structure Determination

2018

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

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters1-(anthracen-9-yl)-N-[(9b9c-dimethyldecahydro-5H-2a4a7a9a-tetraazacyclopenta[cd]phenalen-1-yl)methyl]methanamineExperimental 3D Coordinates
researchProduct

CCDC 1583212: Experimental Crystal Structure Determination

2018

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

Space GroupCrystallographyCrystal SystemCrystal Structure{1-(9b9c-dimethyldecahydro-5H-2a4a7a9a-tetraazacyclopenta[cd]phenalen-1-yl)-N-[(pyren-1-yl)methyl]methanamine}(trihydrido)boronCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1583211: Experimental Crystal Structure Determination

2018

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

Space GroupCrystallography{1-(anthracen-9-yl)-N-[(9b9c-dimethyldecahydro-5H-2a4a7a9a-tetraazacyclopenta[cd]phenalen-1-yl)methyl]methanamine}(trihydrido)boronCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1583209: Experimental Crystal Structure Determination

2018

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

Space GroupCrystallographyCrystal SystemN-[(9b9c-dimethyldecahydro-5H-2a4a7a9a-tetraazacyclopenta[cd]phenalen-1-yl)methyl]-1-(pyren-1-yl)methanimineCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 924316: Experimental Crystal Structure Determination

2013

Related Article: Catarina V. Esteves, Pedro Lamosa, Rita Delgado, Judite Costa, Pauline Désogère, Yoann Rousselin, Christine Goze, and Franck Denat|2013|Inorg.Chem.|52|5138|doi:10.1021/ic400015v

(22'-(9-Oxa-1172025-tetraazatetracyclo[15.5.5.0^38^.0^1015^]heptacosa-357101214-hexaene-2025-diyl)diacetato)-copper(ii) hydrateSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1583208: Experimental Crystal Structure Determination

2018

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

Space GroupCrystallography1-(anthracen-9-yl)-N-[(9b9c-dimethyldecahydro-5H-2a4a7a9a-tetraazacyclopenta[cd]phenalen-1-yl)methyl]methanimineCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 907927: Experimental Crystal Structure Determination

2013

Related Article: Catarina V. Esteves, Pedro Lamosa, Rita Delgado, Judite Costa, Pauline Désogère, Yoann Rousselin, Christine Goze, and Franck Denat|2013|Inorg.Chem.|52|5138|doi:10.1021/ic400015v

Space GroupCrystallographyCrystal SystemCrystal Structure(22'-(9-Oxa-1172025-tetraazapentacyclo[15.5.5.0^38^.0^711^.0^1015^]heptacosa-357101214-hexaene-2025-diyl)diacetic acid)-copper(ii) diperchlorateCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 960361: Experimental Crystal Structure Determination

2014

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

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters2-(ammoniomethyl)-147-triazonanetriium tetrachloride monohydrateExperimental 3D Coordinates
researchProduct

CCDC 960359: Experimental Crystal Structure Determination

2014

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

Space GroupCrystallography147-tribenzyl-147-triazonane-14-diium dichloride trihydrateCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1583213: Experimental Crystal Structure Determination

2018

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

Space GroupCrystallographyCrystal SystemCrystal StructureN-[(anthracen-9-yl)methyl]-N-[(9b9c-dimethyldecahydro-5H-2a4a7a9a-tetraazacyclopenta[cd]phenalen-1-yl)methyl]prop-2-yn-1-amine cyclohexane solvateCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 960360: Experimental Crystal Structure Determination

2014

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

Space GroupCrystallography6-(ammoniomethyl)-147-tribenzyl-147-triazonane-14-diium oxonium tetrachloride monohydrateCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct