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Anion Recognition by a Bioactive Diureidodecalin Anionophore: Solid-State, Solution, and Computational Studies.

Ondřej Jurček1,2,3, Hennie Valkenier2,4, Rakesh Puttreddy1

  • 1Department of Chemistry, University of Jyvaskyla, P.O. Box 35, 40014, Jyväskylä, Finland.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 1, 2018
PubMed
Summary

This study investigates a bis-(p-nitrophenyl)ureidodecalin anion carrier for biomedical uses. Structural and binding analyses reveal its adaptability and high anion affinities, crucial for developing new anion transporters.

Keywords:
anionshost-guest interactionshydrogen bondsreceptorssolid-state structures

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Area of Science:

  • Supramolecular Chemistry
  • Chemical Biology

Background:

  • Bis-(p-nitrophenyl)ureidodecalin derivatives show potential as anion carriers for biomedical applications.
  • These compounds exhibit efficient cellular chloride transport with minimal cytotoxicity.

Purpose of the Study:

  • To conduct a detailed structural and binding investigation of a bis-(p-nitrophenyl)ureidodecalin anion carrier.
  • To understand the structural basis for anion recognition and transport.

Main Methods:

  • X-ray crystallography to determine transporter structure in various solvates and anion complexes.
  • Computational studies to analyze anion binding modes.
  • Proton Nuclear Magnetic Resonance (¹H NMR) spectroscopy to quantify anion binding affinities in dimethyl sulfoxide (DMSO).

Main Results:

  • Crystal structures confirmed the diaxial urea positioning and revealed conformational flexibility.
  • The transporter's binding site adapts to accommodate various anions including chloride, bromide, nitrate, sulfate, and acetate.
  • NMR studies in DMSO showed exceptionally high affinities, ordered as sulfate > dihydrogen phosphate ≈ bicarbonate ≈ acetate ≫ hydrogen sulfate > chloride > bromide > nitrate > iodide.

Conclusions:

  • The bis-(p-nitrophenyl)ureidodecalin scaffold is structurally versatile and binds anions with high affinity.
  • Anion selectivity is primarily governed by hydrogen-bond acceptor strength, modulated by receptor geometry.
  • These findings support the further development of this class of anion transporters for biomedical applications.