Combinatorial design of multimeric chelating peptoids for selective metal coordination

Abel Ricano; Ilya Captain; Korey P Carter; Bryan P Nell; Gauthier J-P Deblonde; Rebecca J Abergel

doi:10.1039/c9sc01068h

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Combinatorial design of multimeric chelating peptoids for selective metal coordination

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Combinatorial design of multimeric chelating peptoids for selective metal coordination

Abel Ricano, Ilya Captain, Korey P Carter, Bryan P Nell, Gauthier J-P Deblonde and Rebecca J Abergel

Chemical science (Cambridge), Vol.10(28), pp.6834-6843

07/28/2019

DOI: 10.1039/c9sc01068h

PMCID: PMC6657411

PMID: 31391906

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Abstract

Current methods for metal chelation are generally based on multidentate organic ligands, which are generated through cumbersome multistep synthetic processes that lack flexibility for systematically varying metal-binding motifs. Octadentate ligands incorporating hydroxypyridinone or catecholamide binding moieties onto a spermine scaffold are known to display some of the highest affinities towards f-elements. Enhancing binding affinity for specific lanthanide or actinide ions however, necessitates ligand architectures that allow for modular and high throughput synthesis. Here we introduce a high-throughput combinatorial library of 16 tetrameric N-substituted glycine oligomers (peptoids) containing hydroxypyridinone or catecholamide chelating units linked via an ethylenediamine bridge and, for comparison, we also synthesized the corresponding mixed ligands derived from the spermine scaffold: 3,4,3-LI(1,2-HOPO)2(CAM)2 and 3,4,3-LI(CAM)2(1,2-HOPO)2. Coordination-based luminescence studies were carried out with Eu3+ and Tb3+ to begin probing the properties of the new ligand architecture and revealed higher sensitization efficiency with the spermine scaffold as well as different spectroscopic features among the structural peptoid isomers. Solution thermodynamic properties of selected ligands revealed different coordination properties between the spermine and peptoid analogues with Eu3+ stability constants log β110 ranging from 28.88 ± 3.45 to 43.97 ± 0.49. The general synthetic strategy presented here paves the way for precision design of new specific and versatile ligands, with a variety of applications tailored towards the use of f-elements, including separations, optical device optimization, and pharmaceutical development.

Details

Title: Subtitle: Combinatorial design of multimeric chelating peptoids for selective metal coordination
Creators: Abel Ricano - Chemical Sciences Division , Lawrence Berkeley National Laboratory , Berkeley , CA 94720 , USA . Email: abergel@berkeley.edu
Ilya Captain - Chemical Sciences Division , Lawrence Berkeley National Laboratory , Berkeley , CA 94720 , USA . Email: abergel@berkeley.edu
Korey P Carter - Chemical Sciences Division , Lawrence Berkeley National Laboratory , Berkeley , CA 94720 , USA . Email: abergel@berkeley.edu
Bryan P Nell - Chemical Sciences Division , Lawrence Berkeley National Laboratory , Berkeley , CA 94720 , USA . Email: abergel@berkeley.edu
Gauthier J-P Deblonde - Chemical Sciences Division , Lawrence Berkeley National Laboratory , Berkeley , CA 94720 , USA . Email: abergel@berkeley.edu
Rebecca J Abergel - Department of Nuclear Engineering , University of California , Berkeley , CA 94720 , USA
Resource Type: Journal article
Publication Details: Chemical science (Cambridge), Vol.10(28), pp.6834-6843
DOI: 10.1039/c9sc01068h
PMID: 31391906
PMCID: PMC6657411
NLM abbreviation: Chem Sci
ISSN: 2041-6520
eISSN: 2041-6539
Grant note: DOI: 10.13039/100006235, name: Lawrence Berkeley National Laboratory, award: DE-AC02-05CH11231
Language: English
Date published: 07/28/2019
Academic Unit: Chemistry
Record Identifier: 9984216597902771

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