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 af dette arbejde

15 Citationer (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.

Originalsprog	Engelsk
Tidsskrift	Angewandte Chemie International Edition
Vol/bind	58
Udgave nummer	13
Sider (fra-til)	4200-4204
Antal sider	5
ISSN	1433-7851
DOI	https://doi.org/10.1002/anie.201814149
Status	Udgivet - 22 mar. 2019

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10.1002/anie.201814149

Citationsformater

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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.",

author = "Plajer, {Alex J.} and Perc{\'a}stegui, {Edmundo G.} and Marco Santella and Rizzuto, {Felix J.} and Quan Gan and Laursen, {Bo W.} and Nitschke, {Jonathan R.}",

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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

M3 - Journal article

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JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 13

ER -

Fluorometric Recognition of Nucleotides within a Water-Soluble Tetrahedral Capsule

Abstract

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