Design of novel tripyridinophane-based Eu(III) complexes as efficient luminescent labels for bioassays applications
| Autor: | Pamela Faure, Claude Picard, Chantal Galaup, Nadine Leygue, Emmanuel Bourrier, Laurent J. Lamarque, Jurriaan M. Zwier |
|---|---|
| Přispěvatelé: | Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Cisbio Bioassays [Codolet, France] (Innovation Management / CbB) |
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Lanthanide
Pyridines Biotin chemistry.chemical_element Quantum yield 010402 general chemistry 01 natural sciences Biochemistry chemistry.chemical_compound Europium Coordination Complexes Pyridine [CHIM]Chemical Sciences Physical and Theoretical Chemistry Glutathione Transferase Bioconjugation Aqueous solution 010405 organic chemistry Organic Chemistry Combinatorial chemistry 0104 chemical sciences Sulfonate chemistry Yield (chemistry) Luminescent Measurements |
| Zdroj: | Organic and Biomolecular Chemistry Organic and Biomolecular Chemistry, Royal Society of Chemistry, In press, ⟨10.1039/D1OB02092G⟩ |
| ISSN: | 1477-0520 1477-0539 |
| Popis: | In this work, the development of high luminescent europium(III) complexes in water solution is reported, including their synthesis, analyses of their photophysical properties and applications in bioassays. The three Eu(III) complexes are derived from new ligands based on a tripyridinophane platform. There are four distinct sections in the structure of these ligands: an 18-membered polyaminocarboxylic macrocycle to bind efficiently lanthanide ion in aqueous solutions, three chromophoric subunits (4-(phenylethynyl)pyridine moieties) to effectively sensitize the emission of the metal, two peripheral moieties to solubilise the complex in aqueous media (sulfonate, sulfobetaine or glucose groups) and a free NH2 group available for grafting or bioconjugation. In our synthetic procedure, a pivotal macrocyclic platform is obtained with a high yield in the crucial macrocyclization step due to a metal template ion effect (74% yield). In Tris aqueous buffer (pH 7.4), the Eu(III) complexes display a maximum excitation wavelength at 320 nm, a suitable overall quantum yield (14%), a relatively long lifetime (0.80 ms) and a one-photon brightness in the range of 10000 M-1 cm-1. Importantly, these photophysical properties are retained at dilute concentrations, even in the presence of a very large excess of potentially competing species, such as EDTA or Mg2+ ions. Furthermore, we report the bioconjugation of a Eu(III) complex labelled by an N-hydroxysuccinimide ester reactive group with an antibody (anti-Glutathione-S-Transferase) and the successful application of the corresponding antibody conjugate in the detection of GST-biotin in a fluoroimmunoassay. These new complexes provide solution for high sensitivity in Homogenous Time-Resolved Fluorescence (HTRF®) bioassays. |
| Databáze: | OpenAIRE |
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