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Luminescent Lanthanide Complexes with Analyte-Triggered Antenna Formation
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
2012 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 134, no 24, 9832-9835 p.Article in journal (Refereed) Published
Abstract [en]

A new strategy for accessing analyte-responsive luminescent probes is presented. The lanthanide luminescence of Eu and Tb centers is switched on by the analyte-triggered formation of a sensitizing antenna from a nonsensitizing caged precursor. As the cage can be freely varied, an array of probes for different analytes (pd(0/2+), H2O2, F-, beta-galactosidase) can be created from the same core structure. The probe design affords nanomolar to micromolar detection limits, provides the capability to detect two analytes in parallel, and can be utilized to monitor enzymatic activity in live cells.

Place, publisher, year, edition, pages
2012. Vol. 134, no 24, 9832-9835 p.
National Category
Chemical Sciences
URN: urn:nbn:se:uu:diva-177592DOI: 10.1021/ja3004045ISI: 000305358900002OAI: oai:DiVA.org:uu-177592DiVA: diva2:541219
Available from: 2012-07-16 Created: 2012-07-16 Last updated: 2015-02-03Bibliographically approved
In thesis
1. Development and Multicolor Imaging Applications of Lanthanide-Based Luminescent Probes
Open this publication in new window or tab >>Development and Multicolor Imaging Applications of Lanthanide-Based Luminescent Probes
2014 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The study of biological analytes in their native environment is a major challenge for biochemistry and molecular biology.  Luminesce spectroscopy is well suited for this task due to its non-invasiveness, high spatial and temporal resolution, and high signal to noise ratio. This thesis describes the development and applications of Ln-based luminescent probes for detecting small molecules and enzymes.  Specifically the probes presented are based on coumarin sensitizers coupled to a DO3A chelated LnIII center. The 1st generation of these probes employ 7-OH coumarins, caged at the 7-O position (Chapter 2). By use of p-pinacolatoboron benzyl or p-methoxybenzyl cages, this design allowed the construction of ratiometric EuIII-based probes capable of detecting the reactive oxygen species H2O2, NO and ONOO.

The second and third part of the thesis describes a further improvement of the design (Chapters 3 and 4). By employing caged coumarin precursors EuIII and TbIII-based probes were developed for a variety of different analytes (F, Pd0, H2O2, β-galactosidase, β-glucosidase, α-mannosidase and phosphatase). Most of these probes displayed excellent turn-on responses when treated with their respective analytes. Furthermore they could be used for detecting multiple analytes simultaneously (Chapter 4). By use of one Eu-based and another Tb-based probe, the simultaneous detection of two analytes was possible. This could further be extended to simultaneous three analyte detection by the additional employment of an organic coumarin-based probe.

The last part of the thesis (Chapter 5) describes protocols for the rapid and efficient access to triazole-linked lanthanide-antenna complexes by use of the copper-catalyzed azide-alkyne cycloaddition reaction. For robust substrates, microwave heating at 100 °C enabled rapid (15-60 min) access to various lanthanide complexes, which could be isolated via simple precipitation. Using these conditions pure bi- and tri-homometallic lanthanide complexes could be prepared. A second protocol, for substrates carrying sensitive functionalities was also developed. The application of catalytic amounts of CuOAc, BimPy2 ligand, and a large excess of NaAsc afforded a variety of lanthanide complexes, among them caged responsive probes, in moderate to good yields.


Place, publisher, year, edition, pages
Acta Universitatis Upsaliensis, 2014. 76 p.
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 1208
Lanthanide, luminescent probe, multicolor
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
urn:nbn:se:uu:diva-236760 (URN)978-91-554-9112-3 (ISBN)
Public defence
2015-01-28, Magnelisalen, Stockholm University, Svante Arrhenius väg 16, Stockholm, 10:00 (English)
Available from: 2014-12-22 Created: 2014-11-22 Last updated: 2015-02-03

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