Using Native Chemical Ligation for Site-Specific Synthesis of Hetero-bis-lanthanide Peptide Conjugates: Application to Ratiometric Visible or Near-Infrared Detection of Zn2.

Céline Cepeda, Laurent Raibaut, Guillaume Fremy, Svetlana V Eliseeva, Anthony Romieu, Jacques Pécaut, Didier Boturyn, Stéphane Petoud, Olivier Sénèque

Chemistry (Weinheim an der Bergstrasse, Germany) 2020 Oct 21

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The interest in ratiometric luminescent probes that detect and quantify a specific analyte is growing. Owing to their special luminescence properties, lanthanide(III) cations offer attractive opportunities for the design of dual-color ratiometric probes. Here, the design principle of hetero-bis-lanthanide peptide conjugates by using native chemical ligation is described for perfect control of the localization of each lanthanide cation within the molecule. Two zinc-responsive probes, r-LZF1Tb|Cs124|Eu and r-LZF1Eu|Cs124|Tb are described on the basis of a zinc finger peptide and two DOTA (DOTA=1,4,7,10-tetraaza-cyclododecane-1,4,7,10-tetraacetic acid) complexes of terbium and europium. Both display dual-color ratiometric emission in response to the presence of Zn2+ . By using a screening approach, anthracene was identified for the sensitization of the luminescence of two near-infrared-emitting lanthanides, Yb3+ and Nd3+ . Thus, two novel zinc-responsive hetero-bis-lanthanide probes, r-LZF3Yb|Anthra|Nd and r-LZF3Nd|Anthra|Yb were assembled, the former offering a neat ratiometric response to Zn2+ with emission in the near-infrared around 1000 nm, which is unprecedented. © 2020 Wiley-VCH GmbH.

Citation

Céline Cepeda, Laurent Raibaut, Guillaume Fremy, Svetlana V Eliseeva, Anthony Romieu, Jacques Pécaut, Didier Boturyn, Stéphane Petoud, Olivier Sénèque. Using Native Chemical Ligation for Site-Specific Synthesis of Hetero-bis-lanthanide Peptide Conjugates: Application to Ratiometric Visible or Near-Infrared Detection of Zn2. Chemistry (Weinheim an der Bergstrasse, Germany). 2020 Oct 21;26(59):13476-13483