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Modulation of Luminescence Intensity of Lanthanide Complexes by Photoinduced Electron Transfer and Its Application to a Long-Lived Protease Probe

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Contribution from the Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, CREST, JST, 4-1-8 Honcho, Kawaguchi, Saitama, 332-0012, Japan, Department of Material and Life Science, Division of Advanced Science and Biotechnology, Graduate School of Engineering, Osaka University, 2-1 Yamada-oka, Suita, Osaka, 565-0871, Japan, Department of Internal Medicine, Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, and PRESTO, JST, 4-1-8 Honcho, Kawaguchi-shi, Saitama, 332-0012, Japan
Cite this: J. Am. Chem. Soc. 2006, 128, 21, 6938–6946
Publication Date (Web):May 6, 2006
https://doi.org/10.1021/ja060729t
Copyright © 2006 American Chemical Society
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    Luminescent lanthanide complexes (Tb3+, Eu3+, etc.) have excellent properties for biological applications, including extraordinarily long lifetimes and large Stokes shifts. However, there have been few reports of lanthanide-based functional probes, because of the difficulty in designing suitable complexes with a luminescent on/off switch. Here, we have synthesized a series of complexes which consist of three moieties:  a lanthanide chelate, an antenna, and a luminescence off/on switch. The antenna is an aromatic ring which absorbs light and transmits its energy to the metal, and the switch is a benzene derivative with a different HOMO level. If the HOMO level is higher than a certain threshold, the complex emits no luminescence at all, which indicates that the lanthanide luminescence can be modulated by photoinduced electron transfer (PeT) from the switch to the sensitizer. This approach to control lanthanide luminescence makes possible the rational design of functional lanthanide complexes, in which the luminescence property is altered by a biological reaction. To exemplify the utility of our approach to the design of lanthanide complexes with a switch, we have developed a novel protease probe, which undergoes a significant change in luminescence intensity upon enzymatic cleavage of the substrate peptide. This probe, combined with time-resolved measurements, was confirmed in model experiments to be useful for the screening of inhibitors, as well as for clinical diagnosis.

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    †

     Graduate School of Pharmaceutical Sciences, The University of Tokyo.

    ‡

     CREST, JST.

    §

     Osaka University.

    ‖

     Graduate School of Medicine, The University of Tokyo.

    ⊥

     PRESTO, JST.

    *

    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

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    Synthetic procedures of [Ln−X] (Ln = Tb, Eu) (X = 1−13); photophysical properties of the complexes; comparison of kinetic parameters; inhibition constants of LAP inhibitors; emission spectra of [Eu−8] and [Eu−1]; comparison of luminescence intensity before and after the enzymatic reaction; spectral change of [Ln−13] upon reaction with LAP; emission intensity of [Ln−X] after the addition of LAP or trypsin; HPLC chart of [Ln−X]; LAP reaction of [Tb−13] on 96-well plate; limit of detection of LAP using two probes; correlation between LAP activity measured by the two methods; serum LAP assay in the presence of amastatin; list of authors of ref 19b. This material is available free of charge via the Internet at http://pubs.acs.org.

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