0000000001299831

AUTHOR

Ewen Bodio

showing 58 related works from this author

New heteronuclear gold(I)-platinum(II) complexes with cytotoxic properties: are two metals better than one?

2014

A series of mono- and heterodinuclear gold(I) and platinum(II) complexes with a new bipyridylamine-phosphine ligand have been synthesized and characterized. The X-ray structures of the ligand precursor 4-iodo-N,N-di(pyridin-2-yl)benzamide, and of one gold derivative are reported. All the complexes display antiproliferative properties in vitro in human cancer cells in the range of cisplatin or higher, which appear to correlate with compounds' uptake. Interestingly, studies of the interactions of the compounds with models of DNA indicate different mechanisms of actions with respect to cisplatin. The biological activity study of these complexes provides useful information about the interest of…

Organoplatinum CompoundsStereochemistryCell SurvivalPhosphinesPyridinesthioglucoseGOLD COMPOUNDSchemistry.chemical_elementAntineoplastic AgentsPLATINUM COMPLEXESBiochemistryRutheniumInorganic Chemistrychemistry.chemical_compoundStructure-Activity RelationshipGold CompoundsCoordination ComplexesCell Line TumormedicineHumansDNA bindingBenzamideBIOLOGICAL-PROPERTIESCell ProliferationCisplatinheteronuclear complexDERIVATIVESChemistryLigandCytotoxinsBiological activityBiological TransportDNAPYRIDINEanticancer agentRutheniumHeteronuclear moleculepolymerizationBenzamidesLIGANDSCisplatinGold complexesPlatinumOrganogold Compoundsmedicine.drugPlasmidsJournal of inorganic biochemistry
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Towards the elaboration of new gold-based optical theranostics.

2014

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 CompoundsChemistryOptical ImagingNanotechnologyBiological TransportFluorescenceInorganic ChemistryNormal cellMicroscopy FluorescenceCell Line TumorBiophysicsOrganometallic CompoundsHumansBombesinGoldCancer cell linesCytotoxicityDalton transactions (Cambridge, England : 2003)
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BODIPYS and aza-BODIPY derivatives as promising fluorophores for in vivo molecular imaging and theranostic applications

2019

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…

In vivoChemistryAza-bodipyGeneral ChemistryMolecular imagingCombinatorial chemistryPreclinical imagingJournal of Porphyrins and Phthalocyanines
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Gold(I)-Coumarin-Caffeine-Based Complexes as New Potential Anti-Inflammatory and Anticancer Trackable Agents.

2018

Three new gold(I)-coumarin-based trackable therapeutic complexes and two non-trackable analogues have been synthesised and fully characterised. They all display anti-proliferative properties on several types of cancer cell lines, including those of colon, breast, and prostate. Two complexes displayed significant anti-inflammatory effects; one displayed pro-inflammatory behaviour; this highlights the impact of the position of the fluorophore on the caffeine scaffold. Additionally, the three coumarin derivatives could be visualised in vitro by two-photon microscopy.

Fluorophoremedicine.drug_classUltraviolet RaysAnti-Inflammatory AgentsAntineoplastic Agents010402 general chemistry01 natural sciencesBiochemistryAnti-inflammatoryFluorescencechemistry.chemical_compoundCoordination ComplexesCoumarinsCaffeineCell Line TumorDrug DiscoverymedicineHumansGeneral Pharmacology Toxicology and PharmaceuticsFluorescent DyesPharmacology010405 organic chemistryOrganic ChemistryCancerCoumarinmedicine.diseaseCombinatorial chemistryIn vitro0104 chemical sciencesHEK293 CellsMicroscopy Fluorescence MultiphotonchemistryMolecular MedicineGoldCancer cell linesCaffeineChemMedChem
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Aza-BODIPY: A New Vector for Enhanced Theranostic Boron Neutron Capture Therapy Applications

2020

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

Boron CompoundsBiodistributionboron compound[SDV.BIO]Life Sciences [q-bio]/BiotechnologyFluorophorein ovo modelAstrophysics::High Energy Astrophysical Phenomena[SDV]Life Sciences [q-bio]theranosticNuclear TheoryPhysics::Medical Physicsaza-BODIPY[SDV.CAN]Life Sciences [q-bio]/CancerBoron Neutron Capture Therapy010402 general chemistry01 natural sciencesSodium BorocaptateArticle03 medical and health scienceschemistry.chemical_compoundoptical imagingNIR-IMice0302 clinical medicine[SDV.CAN] Life Sciences [q-bio]/CancerPhysics::Atomic and Molecular ClustersAnimalsHumansNeutronNuclear Experiment10 B-BSHlcsh:QH301-705.5<sup>10</sup>B-BSHChemistryRadiochemistry10B-BSHGeneral MedicineFluorescence[SDV.BIO] Life Sciences [q-bio]/Biotechnology0104 chemical sciencesSWIR[SDV] Life Sciences [q-bio]Neutron capturelcsh:Biology (General)030220 oncology & carcinogenesisBNCTFemaleBODIPYEx vivoCells
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Near-infrared emitting fluorescent homobimetallic gold(I) complexes displaying promising in vitro and in vivo therapeutic properties

2021

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…

Boron Compoundsinorganic chemicalsCell SurvivalInfrared RaysAntineoplastic Agents01 natural sciencesMiceStructure-Activity Relationship03 medical and health sciencesOptical imagingCoordination ComplexesIn vivoDrug DiscoveryTumor Cells CulturedAza-bodipyAnimalsHumans[CHIM]Chemical SciencesNir fluorescenceComputingMilieux_MISCELLANEOUSCell ProliferationFluorescent Dyes030304 developmental biologyPharmacologyAza CompoundsMice Inbred BALB C0303 health sciencesDose-Response Relationship DrugMolecular Structure010405 organic chemistryChemistryOptical ImagingOrganic ChemistryNear-infrared spectroscopyNeoplasms ExperimentalGeneral MedicineFluorescenceIn vitro3. Good health0104 chemical sciencesBiophysicsGoldDrug Screening Assays AntitumorCancer cell lines
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New Gold(I) Organometallic Compounds with Biological Activity in Cancer Cells (Eur. J. Inorg. Chem. 27/2014)

2014

Inorganic Chemistrychemistry.chemical_classificationEnzymeChemistryStereochemistryCancer cellmedicineCancerBiological activitymedicine.diseaseGroup 2 organometallic chemistryEuropean Journal of Inorganic Chemistry
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Novel heterobimetallic radiotheranostic: preparation, activity, and biodistribution.

2014

A novel Ru(II) (arene) theranostic complex is presented. It is based on a 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid macrocycle bearing a triarylphosphine and can be tracked in vivo by using the γ emission of (153) Sm atoms. Notably, the heteroditopic ligand can be selectively metalated with ruthenium at the phosphorus atom despite the presence of other functionalities that are prone to metal coordination. Subsequent labeling with radionuclides such as (153) Sm can then be performed easily. The resulting heterobimetallic complex exhibits favorable solubility and stability properties in biologically relevant media. It also shows in vitro cytotoxicity in line with that expected …

BiodistributionStereochemistryCell SurvivalPhosphinesIn vitro cytotoxicitychemistry.chemical_elementBiochemistryRutheniumMetalHeterocyclic Compounds 1-RingMiceIn vivoCoordination ComplexesCell Line TumorDrug DiscoveryAnimalsHumansTissue DistributionGeneral Pharmacology Toxicology and PharmaceuticsSolubilityPharmacologyChemistryLigandOrganic ChemistryWaterRutheniumvisual_artPhosphorus atomIsotope Labelingvisual_art.visual_art_mediumMolecular MedicineRadiopharmaceuticalsChemMedChem
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BODIPY atropisomer interconversion, face discrimination, and superstructure appending

2016

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.

spectroscopybindingStereochemistryStackingAppend010402 general chemistryRing (chemistry)porphyrins01 natural sciencesbiomolecules[ CHIM ] Chemical SciencesCatalysischemistry.chemical_compounddimersMaterials Chemistryfluorophores[CHIM]Chemical SciencesAtropisomer010405 organic chemistryChemistryMetals and AlloysGeneral Chemistry0104 chemical sciencesSurfaces Coatings and FilmsElectronic Optical and Magnetic MaterialsFace discriminationCeramics and CompositescellsfluorescenceBODIPYprobesSuperstructure (condensed matter)moieties
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A Promising Family of Fluorescent Water-Soluble aza-BODIPY Dyes for in Vivo Molecular Imaging.

2019

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.

Boron CompoundsBiomedical EngineeringPharmaceutical ScienceQuantum yieldBioengineering02 engineering and technology01 natural sciencesMiceIn vivoCell Line TumorAza-bodipyAnimalsHumansFluorescent DyesPharmacologyMice Inbred BALB C010405 organic chemistryChemistryOrganic ChemistryWater021001 nanoscience & nanotechnologyCombinatorial chemistryFluorescenceIn vitro0104 chemical sciences3. Good healthMolecular ImagingWater solubleSolubilitySurface modificationHeterograftsMolecular imaging0210 nano-technologyBiotechnologyBioconjugate chemistry
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Atom Transfer Radical Addition Catalyzed by Ruthenium–Arene Complexes Bearing a Hybrid Phosphine–Diene Ligand

2018

International audience; The synthesis and characterization of a series of arene ruthenium complexes bearing either (3,5-cycloheptadienyl)diphenylphosphine or (cycloheptyl)-diphenylphosphine are reported. Upon irradiation or heating, all these complexes lose their arene ligand but then exhibit a different behavior depending on the nature of the phosphine ligand. (Cycloheptadienyl)phosphine complexes 1 and 3 give a cationic dinuclear Ru complex 5 for which the two Ru atoms are bridged by three chlorido ligands and flanked by two tridendate (cycloheptadienyl)phosphines. (Cycloheptyl)-diphenylphosphine complexes 2 and 4 undergo arene exchange when toluene is used as solvent or degrade in dithlo…

Dieneeffective core potentialsprecursorchemistry.chemical_element010402 general chemistrychemistry01 natural sciencesMedicinal chemistryAdductInorganic Chemistrychemistry.chemical_compoundMoiety[CHIM.COOR]Chemical Sciences/Coordination chemistryarylationPhysical and Theoretical ChemistryDiphenylphosphine010405 organic chemistryAtom-transfer radical-polymerizationLigand[CHIM.ORGA]Chemical Sciences/Organic chemistryOrganic Chemistry[CHIM.CATA]Chemical Sciences/Catalysismolecular calculations0104 chemical sciencesRutheniumkharasch reactionatrc reactionschemistrypolymerizationpincer complexesmetathesisPhosphine
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Phenoxyamidine Zn and Al Complexes: Synthesis, Characterization, and Use in the Ring-Opening Polymerization of Lactide

2019

International audience; Herein we report the synthesis of new ditopic ligands, which consist of a phenoxy group and N,N,N'trisubstituted amidines linked by a methylene spacer (L1-L4). Their coordination chemistry has been studied/investigated with Zn(II) and Al(III). Alkane elimination route between the phenol-amidine proligands (L1H-L4H) and Et2Zn led to dinuclear complexes [(L1-L4)ZnEt]2 (1a-4a) in which the Zn centers are chelated by phenoxyamidine ligands and bridged through the oxygen atom of the phenoxy groups. Salt metathesis reaction between two equivalents of the sodium amidine phenate L1Na and ZnCl2 led to a bis-chelate chiral spiro-complex (L12Zn) 1a'. Analogous alkane eliminatio…

STRUCTURAL-CHARACTERIZATIONchemistry.chemical_elementCATALYSTSZinc010402 general chemistryLIGANDS SYNTHESIS01 natural sciencesRing-opening polymerizationCoordination complexCatalysisInorganic Chemistrychemistry.chemical_compoundZINCIMINE LIGANDSGroup (periodic table)Polymer chemistry[CHIM.COOR]Chemical Sciences/Coordination chemistryPhysical and Theoretical ChemistryMethyleneCYCLIC ESTERSALUMINUM COMPLEXESchemistry.chemical_classificationEPSILON-CAPROLACTONELactide010405 organic chemistryOrganic ChemistryGROUP-4 METAL-COMPLEXES[CHIM.CATA]Chemical Sciences/CatalysisImine ligands0104 chemical scienceschemistryINITIATORSGROUP-4 METAL-COMPLEXES; ALUMINUM COMPLEXES; EPSILON-CAPROLACTONE; LIGANDS SYNTHESIS; IMINE LIGANDS; STRUCTURAL-CHARACTERIZATION; CYCLIC ESTERS; ZINC; CATALYSTS; INITIATORS
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Assessment of Catalysis by Arene‐Ruthenium Complexes Containing Phosphane or NHC Groups bearing Pendant Conjugated Diene Systems

2015

Two p-cymene-ruthenium complexes 1 and 2 were isolated in high yields by treating the [RuCl2(p-cymene)]2 dimer with new hybrid phosphane- or NHC-linked diene ligands. Both complexes were fully characterized by NMR spectroscopy, and the molecular structure of the ruthenium–p-cymene complex 1, containing the phosphane–diene ligand system, was determined by X-ray diffraction analysis. The catalytic activities of both compounds were probed in atom-transfer radical addition (ATRA) and polymerization (ATRP), in the cyclopropanation of olefins, in the ring-opening metathesis polymerization (ROMP) of norbornene, and in the synthesis of enol esters from hex-1-yne and 4-acetoxybenzoic acid.

Dienechemistry.chemical_elementHomogeneous catalysisROMPMetathesisEnolRutheniumInorganic Chemistrychemistry.chemical_compoundPolymerizationchemistryPolymer chemistryOrganic chemistryNorborneneEuropean Journal of Inorganic Chemistry
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Water-Soluble Aza-BODIPYs: Biocompatible Organic Dyes for High Contrast In Vivo NIR-II Imaging

2020

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.

Fluorophore[SDV]Life Sciences [q-bio]Biomedical EngineeringPharmaceutical ScienceBioengineering02 engineering and technology01 natural scienceschemistry.chemical_compoundIn vivoneoplasmsPharmacology[SDV.IB] Life Sciences [q-bio]/BioengineeringHigh contrast010405 organic chemistryOrganic Chemistrytechnology industry and agriculture021001 nanoscience & nanotechnologyBiocompatible materialequipment and suppliesFluorescenceIn vitro3. Good health0104 chemical sciences[SDV] Life Sciences [q-bio]Water solublesurgical procedures operativechemistryBiophysics[SDV.IB]Life Sciences [q-bio]/Bioengineering0210 nano-technologyPreclinical imagingBiotechnology
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Design of a multifunctionalizable BODIPY platform for the facile elaboration of a large series of gold(i)-based optical theranostics.

2018

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.

Materials science010405 organic chemistryLarge seriesNanotechnology010402 general chemistry01 natural sciences0104 chemical sciencesInorganic Chemistrychemistry.chemical_compoundchemistryConfocal imagingBODIPYCancer cell linesHigh potentialElaborationDalton transactions (Cambridge, England : 2003)
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Development of Trackable Anticancer Agents Based on Metal Complexes

2016

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 …

Fluorophoremedicine.diagnostic_test010405 organic chemistryChemistryStereochemistry010402 general chemistry01 natural sciencesPorphyrinFluorescenceCombinatorial chemistry0104 chemical scienceschemistry.chemical_compoundPositron emission tomographymedicinePhthalocyanineDOTAChelationBODIPY
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Synthesis and Characterization of a Stable Copper(I) Complex for Radiopharmaceutical Applications

2014

A highly stable copper(I) complex was obtained starting from a copper(II) salt. This compound was characterized by a combination of several analytical techniques (UV/Vis spectroscopy, energy-dispersive X-ray spectroscopy, electrochemistry, and X-ray photoelectron spectroscopy) and was shown to present an N4Cu structure. These results were confirmed by a density functional calculations study of the binding energy and the electronic structure of model ligand and copper complexes. Preliminary tests of complexation showed a high ability of the corresponding ligand to chelate 64Cu in very diluted medium, which is of interest for developing new positron emission tomography imaging agents. The sta…

BioconjugationX-ray photoelectron spectroscopyChemistryLigandInorganic chemistrychemistry.chemical_elementChelationGeneral ChemistryElectrochemistrySpectroscopyCopperRedoxChemPlusChem
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Coumarin-Phosphine-Based Smart Probes for Tracking Biologically Relevant Metal Complexes: From Theoretical to Biological Investigations

2016

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…

ab-initiotheranosticschemistry.chemical_element010402 general chemistryPhotochemistry01 natural sciences[ CHIM ] Chemical SciencesQuantitative Biology::Cell BehaviorBioinorganic chemistryInorganic Chemistrychemistry.chemical_compound[CHIM]Chemical SciencesOsmiumSinglet statePhosphoniumtherapyAntitumor agents010405 organic chemistryChemistryLigandFluorescence0104 chemical sciencesRutheniumP ligandsagentsTheranostic agentsExcited stateFluorescent probesporphyrinPhosphine
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Development of trackable metal-based drugs: new generation of therapeutic agents

2016

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.

Diagnostic ImagingExploitTheranostic NanomedicineComputer scienceNanotechnologyphosphine-porphyrinpotential anticancer agents[CHIM.INOR]Chemical Sciences/Inorganic chemistry010402 general chemistry01 natural sciencesin-vivo[ CHIM ] Chemical SciencesTheranostic NanomedicineInorganic Chemistrytheranostic agentsplatinum(ii) complexesorganometallic compoundsAnimals[CHIM]Chemical Sciences010405 organic chemistry[ CHIM.INOR ] Chemical Sciences/Inorganic chemistry0104 chemical sciences3. Good healthcancer-cellsRisk analysis (engineering)photodynamic therapycytotoxic propertiesDrug Designheterocyclic carbene complexes
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Development of an Easily Bioconjugatable Water-Soluble Single-Photon Emission-Computed Tomography/Optical Imaging Bimodal Imaging Probe Based on the …

2021

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…

Boron CompoundsFluorescence-lifetime imaging microscopyFluorophoreMice NudeQuantum yieldBreast Neoplasms01 natural sciencesMiceStructure-Activity Relationship03 medical and health scienceschemistry.chemical_compound0302 clinical medicineNuclear magnetic resonanceDrug DevelopmentIn vivoDrug DiscoveryAnimalsHumansFluorescent DyesTomography Emission-Computed Single-PhotonBioconjugationDose-Response Relationship DrugMolecular Structure010405 organic chemistryOptical ImagingNear-infrared spectroscopyAntibodies MonoclonalMammary Neoplasms ExperimentalWaterHep G2 CellsFluorescenceImaging agent0104 chemical sciences3. Good healthSolubilitychemistry030220 oncology & carcinogenesisMolecular MedicineFemaleJournal of Medicinal Chemistry
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Ruthenium and Osmium Complexes of Phosphine-Porphyrin Derivatives as Potential Bimetallic Theranostics: Photophysical Studies

2015

A series of (η6-p-cymene)ruthenium(II)- and osmium(II) complexes of porphyrin-phosphane derivatives have been synthesized as potential bimetallic theranostic candidates. The photophysical and electrochemical properties were investigated, and these species desirably exhibit no or almost no photoinduced intramolecular atom, energy, and electron transfer between the dye and the metallic fragment. These favorable features are mostly associated with the presence of their long chain (i.e., ∼ 1 nm) separating the two functional units. Interestingly, a decrease in emission intensity and lifetimes (up to 35-fold) has been observed, which was ascribed to a small heavy atom effect. This effect is poss…

Organic Chemistrychemistry.chemical_elementPhotochemistryPorphyrinRutheniumInorganic ChemistryMetalchemistry.chemical_compoundElectron transferchemistryvisual_artIntramolecular forcevisual_art.visual_art_mediumOsmiumPhysical and Theoretical ChemistryBimetallic stripPhosphineOrganometallics
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(Cycloheptadienyl)diphenylphosphine: A Versatile Hybrid Ligand

2012

(3,5-Cycloheptadienyl)diphenylphosphine is easily synthesized from the reaction of diphenylphosphine with 1,3,5-cycloheptatriene. This new phosphine-diene has been coordinated as a monodentate P ligand with Pt, Pd, Au, Ni, and Ru; as a bidentate (P, olefin) ligand with Pt and Pd; and as a tridentate (P, diene) ligand with Rh. Fluxional properties of several complexes have been studied via NMR experiments and theoretical consideration.

Inorganic Chemistrychemistry.chemical_compoundOlefin fiberDenticityDiphenylphosphinechemistryDieneLigandOrganic ChemistryPhysical and Theoretical ChemistryMedicinal chemistryOrganometallics
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“Early–Late” Heterobimetallic Catalysis and Beyond

2015

By combining an ever-increasing number of catalysts or catalytic functions, cooperative catalysis is a research area that grows fast. In the field, “early–late” heterobimetallic complexes are rather old objects but they still continue to fascinate chemists because of their latent reactivity. After a brief and concise overview of cooperative catalysis, this review focuses on “early–late” heterobimetallic complexes that were used in catalysis over the last decades. Examples of dual catalysis using early and late metal partners are also described. This chapter ends with an opening towards therapeutic applications of “early–late” heterobimetallic complexes.

ChemistryReactivity (chemistry)Combinatorial chemistryCatalysis
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BODIPY-phosphane as a versatile tool for easy access to new metal-based theranostics

2012

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.

Boron Compoundsinorganic chemicalsCell SurvivalPhosphinesINHIBITIONchemistry.chemical_elementGOLD COMPOUNDSRutheniumInorganic ChemistryMetalchemistry.chemical_compoundGold CompoundsPOLYPYRIDINE COMPLEXESCoordination ComplexesCHEMISTRYCell Line TumorFluorescence microscopeHumansOrganic chemistryOsmiumCytotoxicityAGENTSMicroscopy ConfocalChemistryOsmiumCombinatorial chemistryRutheniumMetalsvisual_artPHOTOPHYSICAL PROPERTIESCancer cellvisual_art.visual_art_mediumMODESGoldBODIPYDYESBEHAVIOR
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New Gold(I) Organometallic Compounds with Biological Activity in Cancer Cells

2014

N-Heterocyclic carbene gold(I) complexes bearing a fluorescent coumarin ligand were synthesized and characterized by various techniques. The compounds were examined for their antiproliferative effects in normal and tumor cells in vitro; they demonstrated moderate activity and a certain degree of selectivity. The compounds were also shown to efficiently inhibit the selenoenzyme thioredoxin reductase (TrxR), whereas they were poorly effective towards the glutathione reductase (GR) and glutathione peroxidase enzymes. Notably, {3-[(7-methoxy-2-oxo-2H-chromen-4-yl) methyl]-1-methylimidazol-2-ylidene}(tetra-O-acetyl-1-thio-beta-D-glucopyranosido) gold(I) (3) showed a pronounced inhibition of TrxR…

Thioredoxin reductaseGlutathione reductaseMECHANISMSInorganic Chemistrychemistry.chemical_compoundCoumarinsCHEMISTRYTARGETSN-HETEROCYCLIC CARBENESCancerchemistry.chemical_classificationSelenocysteineGlutathione peroxidaseGold; carbenes; coumarins; enzyme; CancerBiological activityLigand (biochemistry)EnzymesenzymechemistryBiochemistryCancer cellIodoacetamideCarbenesANTICANCER AGENTSCOMPLEXESGold
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Highly antiproliferative neutral Ru(ii)-arene phosphine complexes

2018

Six ruthenium(II)- and four gold(I)-phosphine based complexes were synthesized and fully characterized. Some of them displayed strong antiproliferative properties for several types of cancer including colon, breast, and lung. Notably, two of the Ru(II) complexes displayed an IC50 of around 2 μM, which is exceptional for these types of complexes. The dramatic impact of the nature of the arene coordinated on the ruthenium center was clearly evidenced.

010405 organic chemistrychemistry.chemical_elementCancerGeneral Chemistry010402 general chemistrymedicine.disease01 natural sciencesMedicinal chemistryCatalysis0104 chemical sciencesRutheniumchemistry.chemical_compoundchemistryMaterials ChemistrymedicinePhosphineNew Journal of Chemistry
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Anticancer Agents: Does a Phosphonium Behave Like a Gold(I) Phosphine Complex? Let a “Smart” Probe Answer!

2015

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. …

Models MolecularBiodistributionAuranofinPhosphinesStereochemistryAntineoplastic AgentsLigandsStructure-Activity Relationshipchemistry.chemical_compoundAuranofinNeoplasmsDrug DiscoveryTumor Cells CulturedZebrafish larvaemedicineAnimalsHumansTissue DistributionPhosphoniumZebrafishCell ProliferationMolecular StructureChemistryLigandProdrugAntirheumatic AgentsLarvaMolecular MedicineGoldPhosphineDerivative (chemistry)medicine.drugJournal of Medicinal Chemistry
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Gold( i )–BODIPY–imidazole bimetallic complexes as new potential anti-inflammatory and anticancer trackable agents

2017

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.

Boron Compoundsmedicine.drug_classStereochemistryAnti-Inflammatory AgentsAntineoplastic Agents[SDV.CAN]Life Sciences [q-bio]/Cancer010402 general chemistry01 natural sciences[ CHIM ] Chemical SciencesAnti-inflammatorylaw.invention[ SDV.CAN ] Life Sciences [q-bio]/CancerInorganic Chemistrychemistry.chemical_compoundConfocal microscopylawCoordination ComplexesCell Line TumorDrug DiscoverymedicineImidazoleHumans[CHIM]Chemical SciencesBimetallic stripCell ProliferationFluorescent Dyes010405 organic chemistryChemistryDrug discoveryImidazolesIn vitro0104 chemical sciences3. Good healthGoldBODIPY
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CCDC 1868748: Experimental Crystal Structure Determination

2019

Related Article: Florian Chotard, Rosita Lapenta, Anaëlle Bolley, Audrey Trommenschlager, Cédric Balan, Jérôme Bayardon, Raluca Malacea-Kabbara, Quentin Bonnin, Ewen Bodio, Hélène Cattey, Philippe Richard, Stefano Milione, Alfonso Grassi, Samuel Dagorne, Pierre Le Gendre|2019|Organometallics|38|4147|doi:10.1021/acs.organomet.9b00501

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parametersbis(2-({[(dimethylamino)(phenyl)methylidene]amino}methyl)phenolato)-zinc(ii)Experimental 3D Coordinates
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CCDC 1578513: Experimental Crystal Structure Determination

2018

Related Article: Florian Chotard, Raluca Malacea-Kabbara, Cédric Balan, Ewen Bodio, Michel Picquet, Philippe Richard, Miguel Ponce-Vargas, Paul Fleurat-Lessard, Pierre Le Gendre|2018|Organometallics|37|812|doi:10.1021/acs.organomet.7b00851

Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinatesdichloro-(cycloheptyl(diphenyl)phosphane)-(1-methyl-4-(propan-2-yl)benzene)-ruthenium(ii)
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CCDC 1578514: Experimental Crystal Structure Determination

2018

Related Article: Florian Chotard, Raluca Malacea-Kabbara, Cédric Balan, Ewen Bodio, Michel Picquet, Philippe Richard, Miguel Ponce-Vargas, Paul Fleurat-Lessard, Pierre Le Gendre|2018|Organometallics|37|812|doi:10.1021/acs.organomet.7b00851

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methyl 4-(37-dichloro-55-difluoro-5H-4lambda55lambda5-dipyrrolo[12-c:2'1'-f][132]diazaborinin-10-yl)benzoateSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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Space GroupCrystallographyCrystal SystemCrystal Structure4-(37-dichloro-55-difluoro-5H-4lambda55lambda5-dipyrrolo[12-c:2'1'-f][132]diazaborinin-10-yl)benzoic acidCell ParametersExperimental 3D Coordinates
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