A1 Journal article (refereed)
Anion Recognition by a Bioactive Diureidodecalin Anionophore : Solid-State, Solution, and Computational Studies (2018)


Jurcek, O., Valkenier, H., Puttreddy, R., Novák, M., Sparkes, H., Marek, R., Rissanen, K., & Davis, A. P. (2018). Anion Recognition by a Bioactive Diureidodecalin Anionophore : Solid-State, Solution, and Computational Studies. Chemistry: A European Journal, 24(32), 8178-8185. https://doi.org/10.1002/chem.201800537


JYU authors or editors


Publication details

All authors or editorsJurcek, Ondrej; Valkenier, Hennie; Puttreddy, Rakesh; Novák, Martin; Sparkes, Hazel; Marek, Radek; Rissanen, Kari; Davis, Anthony Peter

Journal or seriesChemistry: A European Journal

ISSN0947-6539

eISSN1521-3765

Publication year2018

Volume24

Issue number32

Pages range8178-8185

PublisherWiley-VCH.

Publication countryGermany

Publication languageEnglish

DOIhttps://doi.org/10.1002/chem.201800537

Publication open accessNot open

Publication channel open access


Abstract

Recent work has identified a bis‐(p‐nitrophenyl)ureidodecalin anion carrier as a promising candidate for biomedical applications, showing good activity for chloride transport in cells yet almost no cytotoxicity. To underpin further development of this and related compounds, a detailed structural and binding investigation is reported. Crystal structures of the transporter as five solvates confirm the diaxial positioning of urea groups while revealing a degree of conformational flexibility. Structures of complexes with Cl−, Br−, NO3−, SO42− and AcO−, supported by computational studies, show how the binding site can adapt to accommodate these anions. 1H NMR binding studies revealed exceptionally high affinities for anions in DMSO, decreasing in the order SO42−>H2PO4−≈HCO3−≈AcO−≫HSO4−>Cl−>Br−>NO3−>I−. Analysis of the binding results suggests that selectivity is determined mainly by the H‐bond acceptor strength of different anions, but is also modulated by receptor geometry.


Free keywordsanion recognition


Contributing organizations


Related projects


Ministry reportingYes

Reporting Year2018

JUFO rating2


Last updated on 2023-18-12 at 13:18