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Luminescent Alkyne-Bearing Terbium(III) Complexes and Their Application to Bioorthogonal Protein Labeling


O’Malley, William I; Abdelkader, Elwy H; Aulsebrook, Margaret L; Rubbiani, Riccardo; Loh, Choy-Theng; Grace, Michael R; Spiccia, Leone; Gasser, Gilles; Otting, Gottfried; Tuck, Kellie L; Graham, Bim (2016). Luminescent Alkyne-Bearing Terbium(III) Complexes and Their Application to Bioorthogonal Protein Labeling. Inorganic Chemistry, 55(4):1674-1682.

Abstract

Two new bifunctional macrocyclic chelate ligands that form luminescent terbium(III) complexes featuring an alkyne group for conjugation to (bio)molecules via the Cu(I)-catalyzed “click” reaction were synthesized. Upon ligation, the complexes exhibit a significant luminescent enhancement when excited at the λmax of the “clicked” products. To demonstrate the utility of the complexes for luminescent labeling, they were conjugated in vitro to E. coli aspartate/glutamate-binding protein incorporating a genetically encoded p-azido-l-phenylalanine or p-(azidomethyl)-l-phenylalanine residue. The complexes may prove useful for time-gated assay applications.

Abstract

Two new bifunctional macrocyclic chelate ligands that form luminescent terbium(III) complexes featuring an alkyne group for conjugation to (bio)molecules via the Cu(I)-catalyzed “click” reaction were synthesized. Upon ligation, the complexes exhibit a significant luminescent enhancement when excited at the λmax of the “clicked” products. To demonstrate the utility of the complexes for luminescent labeling, they were conjugated in vitro to E. coli aspartate/glutamate-binding protein incorporating a genetically encoded p-azido-l-phenylalanine or p-(azidomethyl)-l-phenylalanine residue. The complexes may prove useful for time-gated assay applications.

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3 citations in Web of Science®
1 citation in Scopus®
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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2016
Deposited On:09 Feb 2017 14:01
Last Modified:09 Feb 2017 14:03
Publisher:American Chemical Society (ACS)
ISSN:0020-1669
Publisher DOI:https://doi.org/10.1021/acs.inorgchem.5b02605

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