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

William I. O'Malley; Elwy H. Abdelkader; Margaret L. Aulsebrook; Riccardo Rubbiani; Choy Theng Loh; Michael R. Grace; Leone Spiccia; Gilles Gasser; Gottfried Otting; Kellie L. Tuck; Bim Graham

doi:10.1021/acs.inorgchem.5b02605

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

William I. O'Malley, Elwy H. Abdelkader, Margaret L. Aulsebrook, Riccardo Rubbiani, Choy Theng Loh, Michael R. Grace, Leone Spiccia, Gilles Gasser, Gottfried Otting, Kellie L. Tuck^*, Bim Graham

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

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 λ_max 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.

Original language	English
Pages (from-to)	1674-1682
Number of pages	9
Journal	Inorganic Chemistry
Volume	55
Issue number	4
DOIs	https://doi.org/10.1021/acs.inorgchem.5b02605
Publication status	Published - 15 Feb 2016

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

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.",

author = "O'Malley, {William I.} and Abdelkader, {Elwy H.} and Aulsebrook, {Margaret L.} and Riccardo Rubbiani and Loh, {Choy Theng} and Grace, {Michael R.} and Leone Spiccia and Gilles Gasser and Gottfried Otting and Tuck, {Kellie L.} and Bim Graham",

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doi = "10.1021/acs.inorgchem.5b02605",

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T1 - Luminescent Alkyne-Bearing Terbium(III) Complexes and Their Application to Bioorthogonal Protein Labeling

AU - O'Malley, William I.

AU - Abdelkader, Elwy H.

AU - Aulsebrook, Margaret L.

AU - Rubbiani, Riccardo

AU - Loh, Choy Theng

AU - Grace, Michael R.

AU - Spiccia, Leone

AU - Gasser, Gilles

AU - Otting, Gottfried

AU - Tuck, Kellie L.

AU - Graham, Bim

PY - 2016/2/15

Y1 - 2016/2/15

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AB - 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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DO - 10.1021/acs.inorgchem.5b02605

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JO - Inorganic Chemistry

JF - Inorganic Chemistry

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ER -

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

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