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 editors: Jurcek, Ondrej; Valkenier, Hennie; Puttreddy, Rakesh; Novák, Martin; Sparkes, Hazel; Marek, Radek; Rissanen, Kari; Davis, Anthony Peter
Journal or series: Chemistry: A European Journal
ISSN: 0947-6539
eISSN: 1521-3765
Publication year: 2018
Volume: 24
Issue number: 32
Pages range: 8178-8185
Publisher: Wiley-VCH.
Publication country: Germany
Publication language: English
DOI: https://doi.org/10.1002/chem.201800537
Publication open access: Not 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 keywords: anion recognition
Contributing organizations
Related projects
- Halogen bond: A strong and reliable alternative to coordination bond.
- Puttreddy, Rakesh
- Research Council of Finland
- Weak Interactions as Structural Elements in Self-assembling Molecular Systems
- Rissanen, Kari
- Research Council of Finland
- Weak Interactions as Structural Elements in Self-assembling Molecular Systems (research costs)
- Rissanen, Kari
- Research Council of Finland
Ministry reporting: Yes
Reporting Year: 2018
JUFO rating: 2