Fluorometric Recognition of Nucleotides within a Water-Soluble Tetrahedral Capsule

Alex J. Plajer; Edmundo G. Percástegui; Marco Santella; Felix J. Rizzuto; Quan Gan; Bo W. Laursen; Jonathan R. Nitschke

doi:10.1002/anie.201814149

Fluorometric Recognition of Nucleotides within a Water-Soluble Tetrahedral Capsule

Alex J. Plajer, Edmundo G. Percástegui, Marco Santella, Felix J. Rizzuto, Quan Gan, Bo W. Laursen, Jonathan R. Nitschke^*

^*Corresponding author for this work

15 Citations (Scopus)

Abstract

The design of aqueous probes and binders for complex, biologically relevant anions presents a key challenge in supramolecular chemistry. Herein, a tetrahedral assembly with cationic faces and corners is reported that is capable of discriminating between anionic and neutral guests in water. Electrostatic repulsion between subcomponents can be overcome by the addition of an anionic template, or generating a robust covalent framework by incorporating tris(2-aminoethyl)amine (TREN). The resultant TREN-capped, water-soluble, fluorescent cage binds mono- and poly-phosphoric esters, including nucleotides. Its covalent skeleton renders it stable at micromolar concentrations in water, enabling the fluorometric detection of biologically relevant guests in an aqueous environment. Selective supramolecular encapsulants, such as 1, could enable new sensing applications, such as recognition of toxins and drugs, under biological conditions.

Original language	English
Journal	Angewandte Chemie International Edition
Volume	58
Issue number	13
Pages (from-to)	4200-4204
Number of pages	5
ISSN	1433-7851
DOIs	https://doi.org/10.1002/anie.201814149
Publication status	Published - 22 Mar 2019

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title = "Fluorometric Recognition of Nucleotides within a Water-Soluble Tetrahedral Capsule",

abstract = "The design of aqueous probes and binders for complex, biologically relevant anions presents a key challenge in supramolecular chemistry. Herein, a tetrahedral assembly with cationic faces and corners is reported that is capable of discriminating between anionic and neutral guests in water. Electrostatic repulsion between subcomponents can be overcome by the addition of an anionic template, or generating a robust covalent framework by incorporating tris(2-aminoethyl)amine (TREN). The resultant TREN-capped, water-soluble, fluorescent cage binds mono- and poly-phosphoric esters, including nucleotides. Its covalent skeleton renders it stable at micromolar concentrations in water, enabling the fluorometric detection of biologically relevant guests in an aqueous environment. Selective supramolecular encapsulants, such as 1, could enable new sensing applications, such as recognition of toxins and drugs, under biological conditions.",

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T1 - Fluorometric Recognition of Nucleotides within a Water-Soluble Tetrahedral Capsule

AU - Plajer, Alex J.

AU - Percástegui, Edmundo G.

AU - Santella, Marco

AU - Rizzuto, Felix J.

AU - Gan, Quan

AU - Laursen, Bo W.

AU - Nitschke, Jonathan R.

PY - 2019/3/22

Y1 - 2019/3/22

N2 - The design of aqueous probes and binders for complex, biologically relevant anions presents a key challenge in supramolecular chemistry. Herein, a tetrahedral assembly with cationic faces and corners is reported that is capable of discriminating between anionic and neutral guests in water. Electrostatic repulsion between subcomponents can be overcome by the addition of an anionic template, or generating a robust covalent framework by incorporating tris(2-aminoethyl)amine (TREN). The resultant TREN-capped, water-soluble, fluorescent cage binds mono- and poly-phosphoric esters, including nucleotides. Its covalent skeleton renders it stable at micromolar concentrations in water, enabling the fluorometric detection of biologically relevant guests in an aqueous environment. Selective supramolecular encapsulants, such as 1, could enable new sensing applications, such as recognition of toxins and drugs, under biological conditions.

AB - The design of aqueous probes and binders for complex, biologically relevant anions presents a key challenge in supramolecular chemistry. Herein, a tetrahedral assembly with cationic faces and corners is reported that is capable of discriminating between anionic and neutral guests in water. Electrostatic repulsion between subcomponents can be overcome by the addition of an anionic template, or generating a robust covalent framework by incorporating tris(2-aminoethyl)amine (TREN). The resultant TREN-capped, water-soluble, fluorescent cage binds mono- and poly-phosphoric esters, including nucleotides. Its covalent skeleton renders it stable at micromolar concentrations in water, enabling the fluorometric detection of biologically relevant guests in an aqueous environment. Selective supramolecular encapsulants, such as 1, could enable new sensing applications, such as recognition of toxins and drugs, under biological conditions.

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DO - 10.1002/anie.201814149

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JO - Angewandte Chemie International Edition

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Fluorometric Recognition of Nucleotides within a Water-Soluble Tetrahedral Capsule

Abstract

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