English version

Equipe Marquage par le 14C

Frédéric TARAN
CEA Saclay/Bât. 547

Tél: (+33) 1 69 08 26 85
frederic.taran@cea.fr


Le groupe s’intéresse à l’identification de nouveaux catalyseurs et de nouvelles réactions chimiques en utilisant des méthodes de criblage à haut débit innovantes.


Moyens humains
Frédéric TARAN, Chercheur
Sophie DEZARD, Chercheur-Ingénieur
Dominique GEORGIN, Chercheur-Ingénieur
Olivier LOREAU, Chercheur-Ingénieur
Sandra GABILLET, Technicienne supérieure
Evelia AUDISIO, Post-doctorante
Mélanie FERRIE, Post-doctorante
Simon SPEKLIN, Post-doctorant
Sergii KOLODYCH, Doctorant


Thèmes de recherche

Notre équipe s’intéresse à l’identification, par l’utilisation de techniques de criblage à haut débit originales, de nouveaux catalyseurs ou de nouvelles réactions chimiques. En particulier, une technique de criblage à haut débit basée sur une détection par tests immunologiques a été mise au point et utilisée en collaboration avec une équipe d’immunologistes. Notre équipe mène également une recherche active dont l’objectif est de mettre au point de nouveaux chélates puissants et sélectifs de métaux pour diverses applications allant de la détection à la décontamination. Enfin, l’équipe développe de nouvelles méthodologies permettant d’introduire des isotopes du carbone (13C et 14C) dans des molécules biologiquement actives ou dans certaines nanoparticules pour faciliter l’étude de leur métabolisme et biodistribution.


Mots-clés
catalyse, carbone 14, complexants de métaux, chélates, criblage à haut-débit


Publications

Loreau O, Marlière P. (2013). Straightforward preparation of labeled potassium cyanate by ozonation and application to the synthesis of [13C] or [14C]ureidocarboxylic acids. J. Label. Compd. Radiopharm., 56, 347-350.

Trotier-Faurion A, Dézard S, Taran F, Valayannopoulos V, De Lonlay P, Mabondzo A. (2013). Synthesis and biological evaluation of new creatine Fatty esters revealed dodecyl creatine ester as a promising drug candidate for the treatment of the creatine transporter deficiency. J. Med. Chem., 56, 5173-5181.

Chtchigrovsky M, Lin Y, Ouchaou K, Chaumontet M, Robitzer M, Quignard F, Taran F. (2012). Dramatic Effect of the Gelling Cation on the Catalytic Performances of Alginate-Supported Palladium Nanoparticles for the Suzuki-Miyaura Reaction. Chem Mat. 24, 1505-1510.

Cortial S, Chaignon P, Sergent D, Dézard S, Ouazzani J. (2012). Dehydrogenation, oxidative denitration and ring contraction of N,N-dinnethyl-5-nitrouracil by a Bacillus nitroreductase Nfr-A1. J Mol Catal B-Enzym. 76, 1-8.

Kotera N, Tassali N, Leonce E, Boutin C, Berthault P, Brotin T, Dutasta JP, Delacour L, Traore DA, Taran F, Coudert S, Rousseau B. (2012). A Sensitive Zinc-Activated 129Xe MRI Probe Angew Chem-Int Edit. 51, 4100-4103.

Macovei C, Vicennati P, Quinton J, Nevers M C, Volland H, Créminon C, Taran F. (2012). Polyclonal antibodies: a cheap and efficient tool for screening of enantioselective catalysts. Chem Commun. 48, 4411-4413.

Obsen T, Faergeman NJ, Chung S, Martinez K, Gobern S, Loreau O, Wabitsch M, Mandrup S, McIntosh M. (2012). Trans-10, cis-12 conjugated linoleic acid decreases de novo lipid synthesis in human adipocytes. Journal of Nutritional Biochemistry. 23, 580-590.

Varenne F, Bourdillon M, Meyer M, Lin Y, Brellier M, Baati R, Charbonniere L J, Wagner A, Doris E, Taran F, Hagege A. (2012). Capillary electrophoresis-inductively coupled plasma-mass spectrometry hyphenation for the determination at the nanogram scale of metal affinities and binding constants of phosphorylated ligands. J Chromatogr A. 1229, 280-287.

Leydier A, Lin Y, Arrachart G, Turgis R, Lecercle D, Favre-Reguillon A, Taran F, Lemaire M, Pellet-Rostaing S. (2012). EDTA and DTPA modified ligands as sequestering agents for uranyl decorporation. Tetrahedron. 68, 1163-1170.

Le Roux A, Josset E, Benzina S, Nadal B, Desage-El Murr M, Heurtaux B, Taran F, Denis J M, Le Gall T, Meunier S, Bischoff P. (2012). Evaluation of the Radioprotective Potential of the Polyphenol Norbadione A. Lett Drug Des Discov. 9, 48-53.

Quinton J, Kolodych S, Chaumonet M, Bevilacqua V, Nevers MC, Volland H, Gabillet S, Thuery P, Créminon C, Taran F. (2012). Reaction Discovery by Using a Sandwich Immunoassay. Angew. Chem.-Int. Edit. 51, 6144-6148.

Yan LH, Dagorn F, Gravel E, Seon-Meniel B, Poupon E. (2012). Synthesis and reactivity of pelletierine-derived building blocks and pelletierine analogs. Tetrahedron. 68, 6276-6283.

Du Z Y, Degrace P, Gresti J, Loreau O, Clouet P. (2011). Vaccenic and Elaidic Acid Equally Esterify into Triacylglycerols, but Differently into Phospholipids of Fed Rat Liver Cells. Lipids. 46, 647-657.

Leydier A, Lecercle D, Pellet-Rostaing S, Favre-Reguillon A, Taran F, Lemaire M. (2011). Sequestering agent for uranyl chelation: new binaphtyl ligands. Tetrahedron Lett. 52, 3973-3977

Averseng O, Hagege A, Taran F, Vidaud C. (2010). Surface Plasmon Resonance for Rapid Screening of Uranyl Affine Proteins. Anal Chem. 82, 9797-9802.

Du Z Y, Degrace P, Gresti J, Loreau O, Clouet P. (2010). Dissimilar Properties of Vaccenic Versus Elaidic Acid in beta-Oxidation Activities and Gene Regulation in Rat Liver Cells. Lipids. 45, 581-591.

Francois-Endelmond C, Carlin T, Thuery P, Loreau O, Taran F. (2010). A Phosphine-Mediated Construction of 1,4-Oxazepines and 1,3-Oxazines. Org Lett. 12, 40-42.

Malpuech-Brugere C, Mensink R P, Loreau O, Maret A, Fernie C E, Lassel T S, Chardigny J M, Scrimgeour C M, Sebedio J L, Beaufrere B. (2010). Comparison of Postprandial Oleic Acid, 9c,11t CLA and 10t,12c in Healthy Moderately Overweight Subjects. Lipids. 45, 1047-1051.

Ogier J, Arnauld T, Carrot G, Lhumeau A, Delbos J M, Boursier C, Loreau O, Lefoulon F, Doris E. (2010). Enhanced drug loading in polymerized micellar cargo. Org Biomol Chem. 8, 3902-3907.

Ouchaou K, Georgin D, Taran F. (2010). Straightforward Conversion of Arene Carboxylic Acids into Aryl Nitriles by Palladium-Catalyzed Decarboxylative Cyanation Reaction. Synlett. 2083-2086.

Quinton J, Charruault L, Nevers M C, Volland H, Dognon J P, Créminon C, Taran F. (2010). Toward the Limits of Sandwich Immunoassay of Very Low Molecular Weight Molecules. Anal Chem. 82, 2536-2540.

Ansoborlo E, Taran F, Benech H, Fattal E, Tsapis N, Menetrier F, Deverre JR, Burgada R. (2009). Research on new therapeutics. Biofutur. 295, 41-43

Chtchigrovsky M, Primo A, Gonzalez P, Molvinger K, Robitzer M, Quignard F, Taran F. (2009). Functionalized Chitosan as a Green, Recyclable, Biopolymer-Supported Catalyst for the [3+2] Huisgen Cycloaddition. Angew Chem-Int Edit. 48, 5916-5920.

Louit G, Hanedanian M, Taran F, Coffigny H, Renault JP, Pin S. (2009). Determination of hydroxyl rate constants by a high-throughput fluorimetric assay: towards a unified reactivity scale for antioxidants. Analyst. 134, 250-255.

Migianu-Griffoni E, Mbemba C, Burgada R, Lecercle D, Taran F, Lecouvey M. (2009). Design and synthesis of new polyphosphorylated upper-rim modified calix[4]arenes as potential and selectivechelating agents of uranyl ion. Tetrahedron. 65, 1517-1523.

Siby A, Loreau O, Taran F. (2009). Phosphine-Catalyzed Reaction of Cyanohydrins with Activated Alkynes. Synthesis-Stuttgart. 14, 2365-2369.

Carboni M, Gomis JM, Loreau O, Taran F. (2008). Synthesis of Thiohydantoins by Phosphine-Catalyzed Reaction of Thioureas with Aryl propiolates. Synthesis. 3, 417-424.

Lecerclé D, Gabillet S, Gomis JM, Taran F. (2008). A facile synthesis of aminomethylene bisphosphonates through rhodium carbenoid mediated N–H insertion reaction. Application to the preparation of powerful uranyl ligands. Tetrahedron Lett. 49, 2083-2087.

Leydier A, Lecerclé D, Pellet-Rostaing S, Favre-Reguillon A, Taran F, Lemaire M. (2008). Sequestering agents for uranyl chelation: new calixarene ligands. Tetrahedron. 64, 6662-6669.

Leydier A, Lecerclé D, Pellet-Rostaing S, Favre-Reguillon A, Taran F, Lemaire M. (2008). Sequestering agent for uranyl chelation: a new family of CAMS ligands. Tetrahedron. 64, 11319-11324.

Pouvreau JB, Moranc¸ais M, Taran F, Rosa P, Dufosse´ L, Gue´rard F, Pin S, Fleurence J, Pondaven P. (2008). Antioxidant and Free Radical Scavenging Properties of Marennine, a Blue-Green Polyphenolic Pigment from the Diatom Haslea ostrearia (Gaillon/Bory) Simonsen Responsible for the Natural Greening of Cultured Oysters. J Agric Food Chem. 56, 6278-86.

Sawicki M, Lecerclé D, Grillon G, Le Gall B, Sérandour AL, Poncy JL, Bailly T, Burgada R, Lecouvey M, Challeix V, Leydier A, Pellet-Rostaing S, Ansoborlo E, Taran F. (2008). Bisphosphonate Sequestering Agents. Synthesis and Preliminary Evaluation for in vitro and in vivo Uranium(VI) Chelation. Eur J Med Chem. 43, 2768-77.

Ansoborlo E, Amekraz B, Moulin C, Moulin V, Taran F, Bailly T, Burgada R, Hengé-Napoli MH, Jeanson A, Den Auwer C, Bonin L, Moisy P. (2007). Review of actinide decorporation with chelating agents. Comptes Rendus Chimie. 1-10

Carboni M, Gomis JM, Loreau O, Taran F. (2007).Synthesis of Thiohydantoins by Phosphine-Catalyzed Reaction of Thioureas with Aryl propiolates. Synthesis. 3, 417-424

Gabillet S, Lecerclé D, Loreau O, Carboni M, Dézard S, Gomis JM, Taran F. (2007). Phosphine-Catalyzed Construction of Sulfur Heterocycles. Org Lett. 9, 3925-3927.

Gabillet S, Lecerclé D, Loreau O, Dézard S, Gomis JM, Taran F. (2007). Phosphine-Catalyzed Tandem a-O-Addition and Transesterification of Oxgen Pronucleophiles on Arylpropiolates: A New Route to Dioxygenated Heterocyles Synthesis. 4, 515-522.

Kim HR, Andrieux K, Delomenie C, Chacun H, Appel M, Desmaële D, Taran F, Georgin D, Couvreur P, Taverna M. (2007). Analysis of plasma protein adsorption onto PEGylated nanoparticles by complementary methods: 2-DE, CE and Protein Lab-on-chip system. Electrophoresis. 28, 2252-61.

Kim HR, Gil S, Andrieux K, Nicolas V, Appel M, Chacun H, Desmaele D, Taran F, Georgin D, Couvreur P. (2007). Low-density lipoprotein receptor-mediated endocytosis of PEGylated nanoparticles in rat brain endothelial cells. Cell Mol Life Sci. 64, 356-364.

Kim HR, Andrieux K, Gil S, Taverna M, Chacun H, Desmaele D, Taran F, Georgin D, Couvreur P. (2007). Translocation of Poly(ethylene glycol-co-hexadecyl)cyanoacrylate Nanoparticles into Rat Brain Endothelial Cells: Role of Apolipoproteins in Receptor-Mediated Endocytosis. Biomacromolecules. 8, 793-799.

Lecerclé D, Mothes C, Taran F. (2007). A Straightforward Synthesis of 2-aryl-1-alkynylphosphonates and arylpropiolates. Synth. Commun. 37, 1301-1311.

Lecerclé D, Taran F. (2007). A Facile Anchoring of the Bis-phosphonate Moiety into Alcohols and Phenols Through Copper-Carbenoid Mediated O-H Insertion Reaction. SynLett 12, 1863-186.

Bretillon L, Loreau O, Sébédio JL, Taran F. (2006). In vivo oxidation of [9-14C] cyclic fatty acids derived from linolenic acid in the rat Reprod Nutr Dev. 46, 189-193.

Doussin S, Birlirakis N, Georgin D, Taran F, Berthault P. (2006). Novel zwitterionic reverse micelles for encapsulation of proteins in low-viscosity media. Chem Eur J. 12, 1470-4175.

Le Gall B, Taran F, Renault D, Wilk JC, Ansoborlo E. (2006). Comparison of Prussian blue and apple-pectin efficacy on 137Cs decorporation in rats Biochimie. 88, 1837-1841.

Lecerclé D, Sawicki M, Taran F. (2006). Phosphine-catalyzed alpha-P-addition on activated alkynes: A new route to P-C-P backbones. Org Lett. 8, 4283-4285.

Garcia-Garcia E, Andrieux K, Gil S, Ryoung Kim H, Le Doan T, Desmaële D, d’Angelo J, Taran F, Georgin D, Couvreur P. (2005). A methodology to study intracellular distribution of nanoparticles in brain endothelial cells. Int J Pharm. 298, 310-314.

Garcia-Garcia E, Gil S, Andrieux K, Desmaele D, Nicolas V, Taran F, Georgin D, Andreux JP, Roux F, Couvreur P. (2005). A relevant in vitro rat model for the evaluation of blood-brain barrier translocation of nanoparticles. Cell Mol Life Sci. 62, 1400-1408.

Hanédanian M, Loreau O, Sawicki M, Taran F. (2005). Tributylphosphine as a superior catalyst for the a-C-addition of 1,3-dicarbonyl compounds to electron-deficient alkynes. Tetrahedron. 61, 2287-2294.

Louit G, Foley S, Cabillic J, Coffigny H, Taran F, Valleix A, Renault JP, Pin S. (2005). The reaction of coumarin with the OH radical revisited: Hydroxylation product analysis determined by fluorescence and chromatography. Radiat Phys Chem. 72, 119-124.

Meunier S, Hanedanian M, Desage-El Murr M, Nowaczyk S, Le Gall T, Pin S, Renault JP, Boquet D, Creminon C, Mioskowski C, Taran F. (2005). High-Throughput Evaluation of Antioxidant and Pro-oxidant Activities of Polyphenols with Thymidine Protection Assays. Chembiochem. 6, 1234-1241.

Meunier S, Cristau P, Taran F. (2005). New Nitrilotriacetic Acid and Ethylenediaminetetraacetic Acid Nitro Derivatives for the Synthesis of Bifunctional and Trifunctional Chelating Agents. Synth Commun. 35, 2415-2425.

Sawicki M, Siaugue JM, Jacopin C, Moulin C, Bailly T, Burgada R, Meunier S, Baret P, Pierre JL, Taran F. (2005). Discovery of Powerful Uranyl Ligands from Efficient Synthesis and Screening. Chem Eur J. 11, 3689-3697.

Vicennati P, Bensel N, Wagner A, Creminon C, Taran F. (2005). Sandwich Immunoassay as a High-Throughput Screening Method for Cross-Coupling Reactions. Angew Chem Int Ed Engl. 44, 6863-6866.

Broustal G, Loreau O. (2004). Stereocontrolled synthesis of (7E,9Z)-[9,10-2H]-conjugated linoleic acid. J Labelled Compd Rad. 47, 875-880.

Hanédanian M, Loreau O, Taran F, Mioskowski C. (2004). a-Addition of activated methylenes to alkynoates. A straightforward synthesis of multifunctional compounds. Tetrahedron Lett. 45, 7035-7038.

Joffre F, Roy A, Bretillon L, Pasquis B, Sergiel JP, Loreau O, Chardigny JM, Sébédio JL. (2004). In vivo oxidation of carboxyl-labelled cyclic fatty acids formed from linoleic and linolenic acids in the rat. Reprod Nutr Dev. 44, 123-130.

Meunier S, Desage-El Murr M, Nowaczyk S, Le Gall T, Pin S, Renault JP, Boquet D, Creminon C, Saint-Aman E, Valleix A, Taran F, Mioskowski C. (2004). A powerful antiradiation compound revealed by a new high-throughput screening method. Chembiochem. 5, 832-840.

Roy U, Loreau O, Balazy M. (2004). Cytochrome P450/NADPH-dependent formation of trans epoxides from trans-arachidonic acids. Bioorg Med Chem Lett. 14, 1019-1022.

Volland H, Pradelles P, Taran F, Buscarlet L, Créminon C. (2004). Recent developments for SPIE-IA, a new sandwich immunoassay format for very small molecules. J Pharm Biomed Anal. 34, 737-752.

Chardigny JM, Masson E, Sergiel JP, Dairbois M, Loreau O, Noël JP, Sebedio JL. (2003). The position of rumenic acid on triacylglycerols alters its bioavailability in rats. J Nutr. 133, 4212-4214.

Georgin D, Taran F, Mioskowski C. (2003). A divergent synthesis of (1-14C)-mono-E isomers of fatty acids. Chem Phys Lipids. 125, 83-91.

Gruffat D, De La Torre A, Chardigny JM, Durand D, Loreau O, Sebedio JL, Bauchart D. (2003). In vitro comparison of hepatic metabolism of 9cis-11 trans and 10trans-12cis isomers of CLA in the rat. Lipids. 38, 157-163.

Jacopin C, Sawicki M, Plancque G, Doizi D, Taran F, Ansoborlo E, Amekraz B, Moulin C. (2003). Investigation of the interaction between 1-hydroxyethane-1,1'-diphosphonic acid (HEDP) and uranium(VI). Inorg Chem. 42, 5015-5022.

Loiseau N, Gomis JM, Santolini J, Delaforge M, André F. (2003). Predicting the conformational states of cyclic tetrapeptides. Biopolymers. 69, 363-385.

Loreau O, Chardigny JM, Sebedio JL, Noël JP. (2003). Stereoselective synthesis of (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid, (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid, and their [1-14C]-radiolabeled analogs. Chem Phys Lipids. 124, 135-145.

Meunier S, Siaugue JM, Sawicki M, Calbour F, Dezard S, Taran F, Mioskowski C. (2003). Modular liquid-phase parallel synthesis of a highly diverse ligand library. J Comb Chem. 5, 201-204.