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

    Research output: Contribution to journalArticle

    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.

    Original languageEnglish (US)
    Pages (from-to)6834-6843
    Number of pages10
    JournalChemical Science
    Volume10
    Issue number28
    DOIs
    StatePublished - Jan 1 2019

    Fingerprint

    Peptoids
    Chelation
    Metals
    Ligands
    Spermine
    Scaffolds
    ethylenediamine
    Computer aided manufacturing
    N-substituted Glycines
    Actinoid Series Elements
    Throughput
    Lanthanoid Series Elements
    Optical devices
    Oligomers
    Isomers
    Luminescence
    Thermodynamic properties
    Ions

    Cite this

    Ricano, A., Captain, I., Carter, K. P., Nell, B. P., Deblonde, G. J. P., & Abergel, R. J. (2019). Combinatorial design of multimeric chelating peptoids for selective metal coordination. Chemical Science, 10(28), 6834-6843. https://doi.org/10.1039/c9sc01068h

    Combinatorial design of multimeric chelating peptoids for selective metal coordination. / Ricano, Abel; Captain, Ilya; Carter, Korey P.; Nell, Bryan P.; Deblonde, Gauthier J.P.; Abergel, Rebecca J.

    In: Chemical Science, Vol. 10, No. 28, 01.01.2019, p. 6834-6843.

    Research output: Contribution to journalArticle

    Ricano, A, Captain, I, Carter, KP, Nell, BP, Deblonde, GJP & Abergel, RJ 2019, 'Combinatorial design of multimeric chelating peptoids for selective metal coordination', Chemical Science, vol. 10, no. 28, pp. 6834-6843. https://doi.org/10.1039/c9sc01068h
    Ricano A, Captain I, Carter KP, Nell BP, Deblonde GJP, Abergel RJ. Combinatorial design of multimeric chelating peptoids for selective metal coordination. Chemical Science. 2019 Jan 1;10(28):6834-6843. https://doi.org/10.1039/c9sc01068h
    Ricano, Abel ; Captain, Ilya ; Carter, Korey P. ; Nell, Bryan P. ; Deblonde, Gauthier J.P. ; Abergel, Rebecca J. / Combinatorial design of multimeric chelating peptoids for selective metal coordination. In: Chemical Science. 2019 ; Vol. 10, No. 28. pp. 6834-6843.
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