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 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.
authors.affiliation: Monash Institute of Pharmaceutical Sciences, Monash University , Parkville VIC 3052, Australia.
authors.forename: William I
authors.initials: WI
authors.lastname: O'Malley
authors.affiliation: Research School of Chemistry, Australian National University , Canberra ACT 2601, Australia.
authors.forename: Elwy H
authors.initials: EH
authors.lastname: Abdelkader
authors.affiliation: School of Chemistry, Monash University , Clayton VIC 3800, Australia.
authors.forename: Margaret L
authors.initials: ML
authors.lastname: Aulsebrook
authors.affiliation: Department of Chemistry, University of Zurich , Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.
authors.forename: Riccardo
authors.initials: R
authors.lastname: Rubbiani
authors.affiliation: Research School of Chemistry, Australian National University , Canberra ACT 2601, Australia.
authors.forename: Choy-Theng
authors.initials: CT
authors.lastname: Loh
authors.affiliation: School of Chemistry, Monash University , Clayton VIC 3800, Australia.
authors.forename: Michael R
authors.initials: MR
authors.lastname: Grace
authors.affiliation: School of Chemistry, Monash University , Clayton VIC 3800, Australia.
authors.forename: Leone
authors.initials: L
authors.lastname: Spiccia
authors.affiliation: Department of Chemistry, University of Zurich , Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.
authors.forename: Gilles
authors.initials: G
authors.lastname: Gasser
authors.affiliation: Research School of Chemistry, Australian National University , Canberra ACT 2601, Australia.
authors.forename: Gottfried
authors.initials: G
authors.lastname: Otting
authors.affiliation: School of Chemistry, Monash University , Clayton VIC 3800, Australia.
authors.forename: Kellie L
authors.initials: KL
authors.lastname: Tuck
authors.affiliation: Monash Institute of Pharmaceutical Sciences, Monash University , Parkville VIC 3052, Australia.
authors.forename: Bim
authors.initials: B
authors.lastname: Graham
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D049449:Luminescence; D011506:Proteins / Q000737:chemistry*; D013725:Terbium / Q000737:chemistry*
chemical_list: D000480:Alkynes; D011506:Proteins; D013725:Terbium