title: Synthesis and optical properties of macrocyclic lanthanide(III) chelates as new reagents for luminescent biolabeling.
abstract: The convenient and efficient synthesis of two macrocyclic ligands (15- and 18-membered) based on a dipyrido-6,7,8,9-tetrahydrophenazine (dpqc) or 2,2':6',2''-terpyridine (tpy) heterocycle and a DTTA (diethylenetriaminetriacetic acid) skeleton is described. In these ligands the DTTA skeleton contains an additional extracyclic functionality (NH(2) group) suitable for covalent attachment to bioactive molecules. These octa- and nonadentate ligands form very stable and luminescent neutral lanthanide complexes in aqueous solutions at physiological pH. The corresponding Eu(III) and Tb(III) complexes are characterized by a maximum absorption wavelength compatible with nitrogen laser excitation (337 nm) and attractive lifetimes and quantum yields. Further introduction of a maleimide bioconjugatable handle in the Eu(III) complexes was investigated and a valuable luminescence brightness above 1500 dm(3) mol(-1) cm(-1) at 337 nm was obtained with the corresponding Eu(III) tpy-derivative. Finally, these two luminescent chelates were grafted onto thiol residues of a model antibody (Mab GSS11) without loss of their luminescent properties.
authors.affiliation: Cisbio Bioassays, Parc Marcel Boiteux, BP 84175 30200, Codolet, France.
authors.forename: Sébastien
authors.initials: S
authors.lastname: Deslandes
authors.forename: Chantal
authors.initials: C
authors.lastname: Galaup
authors.forename: Robert
authors.initials: R
authors.lastname: Poole
authors.forename: Béatrice
authors.initials: B
authors.lastname: Mestre-Voegtlé
authors.forename: Stéphanie
authors.initials: S
authors.lastname: Soldevila
authors.forename: Nadine
authors.initials: N
authors.lastname: Leygue
authors.forename: Hervé
authors.initials: H
authors.lastname: Bazin
authors.forename: Laurent
authors.initials: L
authors.lastname: Lamarque
authors.forename: Claude
authors.initials: C
authors.lastname: Picard
mesh_terms: D000911:Antibodies, Monoclonal / Q000737:chemistry; D002614:Chelating Agents / Q000138:chemical synthesis / Q000737:chemistry*; D028581:Lanthanoid Series Elements / Q000138:chemical synthesis / Q000737:chemistry*; D049408:Luminescent Agents / Q000138:chemical synthesis / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D008301:Maleimides / Q000138:chemical synthesis / Q000737:chemistry; D004369:Pentetic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D010619:Phenazines / Q000138:chemical synthesis / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C517923:(2,2'-6',2'')-terpyridine; D000911:Antibodies, Monoclonal; D002614:Chelating Agents; D028581:Lanthanoid Series Elements; D049408:Luminescent Agents; D047028:Macrocyclic Compounds; D008301:Maleimides; D010619:Phenazines; D011725:Pyridines; C060068:diethylenetriaminetetraacetic acid; C043592:maleimide; D004369:Pentetic Acid