High-affinity and selective detection of pyrophosphate in water by a resorcinarene salt receptor

Ngong Kodiah Beyeh; Isabel Díez; S. Maryamdokht Taimoory; Daniel Meister; Andrew I. Feig; John F. Trant; Robin H. A. Ras; Kari Rissanen

doi:10.1039/C7SC05167K

High-affinity and selective detection of pyrophosphate in water by a resorcinarene salt receptor†

Ngong Kodiah Beyeh,

*^ab Isabel Díez,^a S. Maryamdokht Taimoory,

^b Daniel Meister,^b Andrew I. Feig,

^d John F. Trant,

*^b Robin H. A. Ras

*^ac and Kari Rissanen

*^e

Author affiliations

* Corresponding authors

^a Aalto University, School of Science, Department of Applied Physics, Puumiehenkuja 2, Espoo, Finland
E-mail: tbeyeh@gmail.com, robin.ras@aalto.fi

^b University of Windsor, Department of Chemistry and Biochemistry, Windsor, ON N9B 3P4, Canada
E-mail: j.trant@uwindsor.ca

^c Aalto University, School of Chemical Engineering, Department of Bioproducts and Biosystems, Kemistintie 1, 02150 Espoo, Finland

^d Wayne State University, Department of Chemistry, 5101 Cass Ave., Detroit, MI, USA

^e University of Jyvaskyla, Department of Chemistry, P. O. Box 35, FI-40014 Jyväskylä, Finland
E-mail: kari.t.rissanen@jyu.fi

Abstract

Pyrophosphate (PPi) is a byproduct of DNA and RNA synthesis, and abnormal levels are indicative of disease. We report the high-affinity binding of PPi in water by N-alkyl ammonium resorcinarene chloride receptors. Experimental analysis using ¹H and ³¹P NMR, isothermal titration calorimetry, mass spectrometry, and UV-vis spectroscopy all support exceptional selectivity of these systems for PPi in water. The measured affinity of K₁ = 1.60 × 10⁷ M⁻¹ for PPi is three orders of magnitude larger than that observed for binding to another phosphate, ATP. This exceptional anion-binding affinity in water is explored through a detailed density functional theory computational study. These systems provide a promising avenue for the development of future innovative medical diagnostic tools.

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DOI: https://doi.org/10.1039/C7SC05167K
Article type: Edge Article
Submitted: 07 12 2017
Accepted: 15 12 2017
First published: 19 12 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2018,9, 1358-1367

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High-affinity and selective detection of pyrophosphate in water by a resorcinarene salt receptor

N. K. Beyeh, I. Díez, S. M. Taimoory, D. Meister, A. I. Feig, J. F. Trant, R. H. A. Ras and K. Rissanen, Chem. Sci., 2018, 9, 1358 DOI: 10.1039/C7SC05167K

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Chemical Science

High-affinity and selective detection of pyrophosphate in water by a resorcinarene salt receptor†

Abstract

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High-affinity and selective detection of pyrophosphate in water by a resorcinarene salt receptor

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