Octadentate cages of Tb(III) 2-hydroxyisophthalamides: A new standard for luminescent lanthanide labels

Xu, Jide, Corneillie, Todd M., Moore, Evan G., Law, Ga-Lai, Butlin, Nathaniel G. and Raymond, Kenneth N. (2011) Octadentate cages of Tb(III) 2-hydroxyisophthalamides: A new standard for luminescent lanthanide labels. Journal of the American Chemical Society, 133 49: 19900-19910. doi:10.1021/ja2079898

Author Xu, Jide
Corneillie, Todd M.
Moore, Evan G.
Law, Ga-Lai
Butlin, Nathaniel G.
Raymond, Kenneth N.
Title Octadentate cages of Tb(III) 2-hydroxyisophthalamides: A new standard for luminescent lanthanide labels
Journal name Journal of the American Chemical Society   Check publisher's open access policy
ISSN 0002-7863
Publication date 2011-12-01
Sub-type Article (original research)
DOI 10.1021/ja2079898
Open Access Status Not yet assessed
Volume 133
Issue 49
Start page 19900
End page 19910
Total pages 11
Place of publication Washington, DC, United States
Publisher American Chemical Society
Language eng
Formatted abstract
The synthesis, structure, and photophysical properties of several Tb(III) complexes with octadentate, macrotricyclic ligands that feature a bicapped topology and 2-hydroxyisophthalamide (IAM) chelating units are reported. These Tb(III) complexes exhibit highly efficient emission (Φ total ≥ 50%), large extinction coefficients (ε max ≥ 20,000 M -1 cm -1), and long luminescence lifetimes (τH 2O ≥ 2.45 ms) at dilute concentrations in standard biological buffers. The structure of the methyl-protected ligand was determined by single-crystal X-ray diffraction and confirms the macrotricyclic structure of the parent ligand; the amide groups of the methyl-protected cage compound generate an anion binding cavity that complexes a chloride anion. Once the ligand is deprotected, a conformational change generates a similar cavity, formed by the phenolate and ortho amide oxygen groups that strongly bind lanthanide ions. The Tb(III) complexes thus formed display long-term stability, with little if any change in their spectral properties (including lifetime, quantum yield, and emission spectrum) over time or in different chemical environments. Procedures to prepare functionalized derivatives with terminal amine, carboxylate, and N-hydroxysuccinimide groups suitable for derivatization and protein bioconjugation have also been developed. These bifunctional ligands have been covalently attached to a number of different proteins, and the terbium complexes' exceptional photophysical properties are retained. These compounds establish a new aqueous stability and quantum yield standard for long-lifetime lanthanide reporters.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: School of Chemistry and Molecular Biosciences
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Created: Fri, 30 Aug 2013, 05:07:34 EST by Evan Moore on behalf of School of Chemistry & Molecular Biosciences