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A modular platform to develop peptoid-based selective fluorescent metal sensors

KnightThese authors contributed equally., Abigail S., Kulkarni, Rishikesh U., Zhou, Effie Y., Franke, Jenna M., Miller, Evan W., Francis, Matthew B.
Chemical communications 2017 v.53 no.24 pp. 3477-3480
N-substituted glycines, chelates, chemical reactions, colorimetry, fluorescence, fluorescent dyes, heavy metals, ligands, mercury, metal ions, moieties, toxicity
Despite the reduction in industrial use of toxic heavy metals, there remain contaminated natural water sources across the world. Herein we present a modular platform for developing selective sensors for toxic metal ions using N-substituted glycine, or peptoid, oligomers coupled to a fluorophore. As a preliminary evaluation of this strategy, structures based on previously identified metal-binding peptoids were synthesized with terminal pyrene moieties. Both derivatives of this initial design demonstrated a turn-off response in the presence of various metal ions. A colorimetric screen was designed to identify a peptoid ligand that chelates Hg(ii). Multiple ligands were identified that were able to deplete Hg(ii) from a solution selectively in the presence of an excess of competing ions. The C-terminal fluoropeptoid derivatives demonstrated similar selectivity to their label-free counterparts. This strategy could be applied to develop sensors for many different metal ions of interest using a variety of fluorophores, leading to a panel of sensors for identifying various water source contaminants.