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Clickable Pyclen-Based Luminescent Lanthanide Complexes: Application to Two-Photon Microscopy.

Baptiste Chartier¹, Nadège Hamon², Dina Akl³

¹Univ. Grenoble Alpes, CNRS, CEA, IRIG, LCBM (UMR 5249), Grenoble, F-38000, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|July 24, 2025

Summary

New lanthanide luminescent bioprobes were synthesized for biological imaging. These probes, functionalized using click chemistry, enable efficient cellular imaging with europium (Eu³⁺) and samarium (Sm³⁺) complexes.

Keywords:

cell imaging click chemistry lanthanide microscopy peptide

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Synthesis of Core-shell Lanthanide-doped Upconversion Nanocrystals for Cellular Applications

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Published on: November 10, 2017

Area of Science:

Coordination Chemistry
Bioconjugation Chemistry
Bioimaging and Biosensing

Background:

Lanthanide luminescent bioprobes are crucial for advanced biological imaging and sensing.
Functionalization of biomolecules using click chemistry offers a straightforward route to smart luminescent tools.
Developing novel probes with enhanced photophysical properties and efficient cellular uptake is essential.

Purpose of the Study:

To synthesize and characterize novel lanthanide complexes with a reactive alkyne group for click chemistry functionalization.
To evaluate the photophysical properties, specifically two-photon absorption and emission, of the synthesized europium (Eu³⁺) and samarium (Sm³⁺) complexes.
To demonstrate the utility of these complexes as bioprobes for live-cell imaging via conjugation to cell-penetrating peptides.

Main Methods:

Synthesis of pyclen-based lanthanide complexes featuring a terminal alkyne group and a 4-(4-alkylthiophenyl)picolinate sensitizer.
Copper-catalyzed azide-alkyne cycloaddition (click chemistry) for conjugating lanthanide complexes to azide-functionalized cell-penetrating peptides.
Two-photon microscopy imaging of live HeLa cells using the synthesized lanthanide-peptide conjugates.

Main Results:

The synthesized Eu³⁺ and Sm³⁺ complexes exhibited excellent two-photon absorption and emission properties.
Conjugation to cell-penetrating peptides via click chemistry did not significantly alter the luminescence properties of the complexes.
Efficient delivery and detection of Eu³⁺ luminescence in live HeLa cells at low concentrations (50 nM), and high-quality imaging with the Sm³⁺ complex were achieved.

Conclusions:

The developed lanthanide complexes are versatile building blocks for creating smart luminescent bioprobes.
Click chemistry provides an efficient method for conjugating these probes to biomolecules for biological applications.
These novel bioprobes demonstrate significant potential for advanced live-cell imaging and sensing applications.