title: Aminopropargyl derivative of terpyridine-bis(methyl-enamine) tetraacetic acid chelate of europium (Eu (TMT)-AP3): a new reagent for fluorescent labelling of proteins and peptides.
abstract: The synthesis and photophysical properties of a new terpyridine-based europium(III) chelate (Eu (TMT)-AP3) designed for peptide and protein labelling in aqueous solution phase is described. In order to obtain a stable, easy to handle, versatile and efficient labelling agent, a reactive aminopropargyl arm has been introduced onto the terpyridine moiety. As preliminary biochemical applications the chelate has been 1) efficiently covalently attached onto a representative biomolecule-monoclonal antibody-and 2) converted into iodoacetamido and aldehyde derivatives, and the photoluminescent Eu (TMT)-AP3 was grafted onto cysteine and lysine amino acid residues respectively. These two different solution phase labelling methods yielded original fluorogenic FRET based probes suitable for "in vitro" detection of caspase-3 protease, a key mediator of apoptosis of mammalian cells.
authors.affiliation: IRCOF/LHO, Equipe de Chimie Bio-Organique, UMR 6014 CNRS, INSA de Rouen et Université de Rouen, 1, rue Lucien Tesnijres, FR-76131 Mont-Saint-Aignan Cedex, France.
authors.forename: Séverine
authors.initials: S
authors.lastname: Poupart
authors.forename: Cédric
authors.initials: C
authors.lastname: Boudou
authors.forename: Philippe
authors.initials: P
authors.lastname: Peixoto
authors.forename: Marc
authors.initials: M
authors.lastname: Massonneau
authors.forename: Pierre-Yves
authors.initials: PY
authors.lastname: Renard
authors.forename: Anthony
authors.initials: A
authors.lastname: Romieu
mesh_terms: D000345:Affinity Labels / Q000138:chemical synthesis / Q000737:chemistry; D002614:Chelating Agents / Q000138:chemical synthesis / Q000737:chemistry*; D005063:Europium / Q000737:chemistry*; D031541:Fluorescence Resonance Energy Transfer; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D010777:Photochemistry; D011506:Proteins / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D013237:Stereoisomerism; D013997:Time Factors
chemical_list: C518280:(4'-(3-amino-1-propynyl)phenyl-2,2',2''-terpyridine-bis(methylenamine)tetraacetic acid)europium(III); D000345:Affinity Labels; D002614:Chelating Agents; D005456:Fluorescent Dyes; D008024:Ligands; D009942:Organometallic Compounds; D010455:Peptides; D011506:Proteins; D011725:Pyridines; D005063:Europium